319 results on '"Giancarlo Fabrizi"'
Search Results
2. Palladium-Catalyzed Tsuji–Trost-Type Reaction of 3-Indolylmethylacetates with O, and S Soft Nucleophiles
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Antonia Iazzetti, Antonio Arcadi, Marco Chiarini, Giancarlo Fabrizi, Antonella Goggiamani, Federico Marrone, Andrea Serraiocco, and Roberta Zoppoli
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3-carbinol ,Tsuji–Trost-type reaction ,O and S soft nucleophiles ,renewable sources ,Organic chemistry ,QD241-441 - Abstract
The chemical valorization of widespread molecules in renewable sources is a field of research widely investigated in the last decades. In this context, we envisaged that indole-3-carbinol, present in different Cruciferae plants, could be a readily available building block for the synthesis of various classes of indoles through a palladium-catalyzed Tsuji–Trost-type reaction with O and S soft nucleophiles. The regiochemical outcome of this high-yielding functionalization shows that the nucleophilic substitution occurs only at the benzylic position. Interestingly, with this protocol, the sulfonyl unit could be appended to the indole nucleus, providing convenient access to new classes of molecules with potential bioactivity. more...
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- 2024
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3. Valorisation of Side Stream Products through Green Approaches: The Rapeseed Meal Case
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Francesco Cairone, Dario Allevi, Stefania Cesa, Giancarlo Fabrizi, Antonella Goggiamani, Domiziana Masci, and Antonia Iazzetti
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rapeseed meal ,sinapic acid ,supercritical fluid extraction ,polyphenols ,green methods ,Chemical technology ,TP1-1185 - Abstract
Rapeseed meal (RSM) is a by-product of rapeseed oil extraction and is a rich source of bioactive compounds, including proteins and antioxidants. This study compared two methods for extracting antioxidants from RSM: conventional ethanol Soxhlet extraction and supercritical CO2 extraction. These procedures were applied to both native RSM and RSM after protein removal to evaluate their bio-compound composition and potential applications. HPLC-DAD, NMR, and GC/MS analyses revealed a rich polyphenolic profile in the extracts, including the presence of sinapic acid. The concentration of sinapic acid varied depending on the extraction method used. The anti-radical activity of the extracts was also analysed using the DPPH assay, which confirmed the potential of RSM as a source of antioxidants for use in cosmetics, food, and pharmaceutical formulations. more...
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- 2023
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4. Synthesis of Functionalized 3H-pyrrolo-[1,2,3-de] Quinoxalines via Gold-Catalyzed Intramolecular Hydroamination of Alkynes
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Antonia Iazzetti, Giancarlo Fabrizi, Antonella Goggiamani, Federico Marrone, Alessio Sferrazza, and Karim Ullah
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3H-pyrrolo-[1,2,3-de] quinoxalines ,gold catalysis ,quinoxalines ,hydroamination ,Organic chemistry ,QD241-441 - Abstract
A gold-catalyzed protocol to obtain functionalized 3H-pyrrolo [1,2,3-de] quinoxalines from suitable substituted N-alkynyl indoles has been proposed. The mild reaction conditions were revealed to be compatible with different functional groups, including halogen, alkoxyl, cyano, ketone, and ester, allowing the isolation of title compounds with yields from good to high. A reaction mechanism has been proposed, and theoretical calculations have been provided to rationalize the final step of the hypothesized reaction mechanism. As quinoxaline-containing polycyclic compounds, this class of molecules may represent a valuable template in medicinal chemistry and material science. more...
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- 2023
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5. Self-assembling ferritin-dendrimer nanoparticles for targeted delivery of nucleic acids to myeloid leukemia cells
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Federica Palombarini, Silvia Masciarelli, Alessio Incocciati, Francesca Liccardo, Elisa Di Fabio, Antonia Iazzetti, Giancarlo Fabrizi, Francesco Fazi, Alberto Macone, Alessandra Bonamore, and Alberto Boffi more...
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Ferritin ,Protein nanoparticles ,Self-assembly ,Targeted delivery ,Dendrimers ,PAMAM ,Biotechnology ,TP248.13-248.65 ,Medical technology ,R855-855.5 - Abstract
Abstract Background In recent years, the use of ferritins as nano-vehicles for drug delivery is taking center stage. Compared to other similar nanocarriers, Archaeoglobus fulgidus ferritin is particularly interesting due to its unique ability to assemble-disassemble under very mild conditions. Recently this ferritin was engineered to get a chimeric protein targeted to human CD71 receptor, typically overexpressed in cancer cells. Results Archaeoglobus fulgidus chimeric ferritin was used to generate a self-assembling hybrid nanoparticle hosting an aminic dendrimer together with a small nucleic acid. The positively charged dendrimer can indeed establish electrostatic interactions with the chimeric ferritin internal surface, allowing the formation of a protein-dendrimer binary system. The 4 large triangular openings on the ferritin shell represent a gate for negatively charged small RNAs, which access the internal cavity attracted by the dense positive charge of the dendrimer. This ternary protein-dendrimer-RNA system is efficiently uptaken by acute myeloid leukemia cells, typically difficult to transfect. As a proof of concept, we used a microRNA whose cellular delivery and induced phenotypic effects can be easily detected. In this article we have demonstrated that this hybrid nanoparticle successfully delivers a pre-miRNA to leukemia cells. Once delivered, the nucleic acid is released into the cytosol and processed to mature miRNA, thus eliciting phenotypic effects and morphological changes similar to the initial stages of granulocyte differentiation. Conclusion The results here presented pave the way for the design of a new family of protein-based transfecting agents that can specifically target a wide range of diseased cells. Graphic abstract more...
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- 2021
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6. Diaryl-Pyrano-Chromenes Atropisomers: Stereodynamics and Conformational Studies
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Alessia Ciogli, Andrea Fochetti, Andrea Sorato, Giancarlo Fabrizi, Nunzio Matera, Andrea Mazzanti, and Michele Mancinelli
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aryls-pyrano-chromenes ,atropisomer ,Dynamic-NMR ,Dynamic-HPLC ,ECD ,DFT ,Organic chemistry ,QD241-441 - Abstract
The dynamic scenario of di-aryls-pyrano-chromenes was investigated using DFT calculations. The symmetry of the chromene scaffold and the presence of two ortho-substituted aryls substituents can generate two syn/anti diastereoisomers and conformational enantiomers with different rotational barriers. The relative conformations and configurations were derived using NOESY-1D experiments. Depending on the energies related to the conformational exchange, the experimental energy barriers were determined through Dynamic NMR, Dynamic HPLC or kinetic studies. The atropisomeric pairs were resolved in the latter scenario, and their absolute configuration was assigned using the ECD/TD-DFT method. more...
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- 2023
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7. In-Depth Chemical Characterization of Punica granatum L. Seed Oil
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Francesco Cairone, Chiara Salvitti, Antonia Iazzetti, Giancarlo Fabrizi, Anna Troiani, Federico Pepi, and Stefania Cesa
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pomegranate seed oil ,HPLC-DAD analysis ,AP-MALDI-MS analysis ,1H and 13C-NMR analysis ,Chemical technology ,TP1-1185 - Abstract
Fruit seeds belonging to the pomegranate cultivar “Granata” were subjected to extraction and oily component analysis, with the aim of obtaining information about their composition. The presence of conjugated isomers of linolenic acid (CLNA isomers) in the oily phase extracted from the seeds gives a high added value to this part of the fruit, which is too often considered and treated as waste. The separated seeds were subjected to a classic Soxhlet extraction with n-hexane or extraction with supercritical CO2, assisted by ethanol. The resulting oils were evaluated by 1H and 13C-NMR and AP-MALDI-MS techniques. Differences in the triacylglycerols composition, with particular regard to punicic acid and other CLNA content, were studied in depth. Results showed the prevalence of punicic acid in the triacylglycerol mixture up to the 75%, with clear preponderance in the extract by supercritical fluids. Consequently, other CLNA isomers are, altogether, two-fold less represented in the supercritical extract than in the Soxhlet one. The two oily residues were subjected to solid phase extraction (SPE) and to HPLC-DAD analysis for the polyphenolic isolation and characterization. In addition to HPLC analysis, which showed different content and composition, DPPH analysis to evaluate the antiradical potential showed that the extract obtained with supercritical CO2 was much more active. more...
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- 2023
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8. Highly Efficient and Mild Gold (I) Catalyzed Synthesis of 3,8-Diarylidene-2,7-dioxaspiro[4.4]nonane-1,6-diones
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Antonia Iazzetti, Dario Allevi, Andrea Calcaterra, Giancarlo Fabrizi, Antonella Goggiamani, Giulia Mazzoccanti, Alessio Sferrazza, Rosanna Verdiglione, and Valeria Vergine
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spirobislactone ,spirolactone ,spiro compounds ,Au(I)-catalyzed cyclization ,alkyne activation ,heterocyclization ,Organic chemistry ,QD241-441 - Abstract
The gold-catalyzed cyclization of 2,2-bis(3-arylprop-2-yn1-yl)malonic acid has been proposed as an efficient approach to substituted 3,8-dibenzyl-2,7-dioxaspiro[4.4]nonane-1,6-diones. The reaction proceeds smoothly in mild reaction conditions to give the desired products in quantitative yields in the presence of variously substituted starting materials. In addition, the synthesis of γ-arylidene spirobislactone bearing different substituents on the two aromatic rings has been achieved. This kind of compound could be of great interest in pharmaceutical science given the widespread presence of this scaffold in bioactive natural and synthetic products. more...
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- 2022
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9. Valorization of By-Products from Biofuel Biorefineries: Extraction and Purification of Bioactive Molecules from Post-Fermentation Corn Oil
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Francesco Cairone, Stefania Cesa, Alessia Ciogli, Giancarlo Fabrizi, Antonella Goggiamani, Antonia Iazzetti, Gabriella Di Lena, Jose Sanchez del Pulgar, Massimo Lucarini, Luca Cantò, Gokhan Zengin, and Petra Ondrejíčková more...
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post-fermentation corn oil ,phenolics ,carotenoids ,bioactive molecules ,valorization of industrial side streams ,antioxidant activity ,Chemical technology ,TP1-1185 - Abstract
The aim of this work was to develop innovative and sustainable extraction, concentration, and purification technologies aimed to recover target substances from corn oil, obtained as side stream product of biomass refineries. Residues of bioactive compounds such as carotenoids, phytosterols, tocopherols, and polyphenols could be extracted from this matrix and applied as ingredients for food and feeds, nutraceuticals, pharmaceuticals, and cosmetic products. These molecules are well known for their antioxidant and antiradical capacity, besides other specific biological activities, generically involved in the prevention of chronic and degenerative diseases. The project involved the development of methods for the selective extraction of these minor components, using as suitable extraction technique solid phase extraction. All the extracted and purified fractions were evaluated by NMR spectroscopic analyses and UV–Vis spectrophotometric techniques and characterized by quali-quantitative HPLC analyses. TPC (total phenolic content) and TFC (total flavonoid content) were also determined. DPPH and ABTS radical were used to evaluate radical quenching abilities. Acetylcholinesterase (AChE), amylase, glucosidase, and tyrosinase were selected as enzymes in the enzyme inhibitory assays. The obtained results showed the presence of a complex group of interesting molecules with strong potential in market applications according to circular economy principles. more...
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- 2022
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10. Synthesis of indolo[1,2-c]quinazolines from 2-alkynylaniline derivatives through Pd-catalyzed indole formation/cyclization with N,N-dimethylformamide dimethyl acetal
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Antonio Arcadi, Sandro Cacchi, Giancarlo Fabrizi, Francesca Ghirga, Antonella Goggiamani, Antonia Iazzetti, and Fabio Marinelli
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arylboronic acids ,DMFDMA ,indoles ,indoloquinazolines ,quinazolines ,Science ,Organic chemistry ,QD241-441 - Abstract
An efficient strategy for the synthesis of 6-unsubstituted indolo[1,2-c]quinazolines is described. The Pd-catalyzed reaction of o-(o-aminophenylethynyl) trifluoroacetanilides with Ar–B(OH)2 afforded 2-(o-aminophenyl)-3-arylindoles, that were converted to 12-arylindolo[1,2-c]quinazolines by adding dimethylformamide dimethyl acetal (DMFDMA) to the reaction mixture after extractive work-up. This reaction outcome is different from the previously reported Pd-catalyzed sequential reaction of the same substrates with Ar–I, Ar–Br and ArN2+BF4−, that afforded 12-arylindolo[1,2-c]quinazolin-6(5H)-ones. Moreover, 12-unsubstituted indolo[1,2-c]quinazolines can be obtained both by reacting 2-(o-aminophenyl)indoles with DMFDMA or by sequential Pd-catalyzed reaction of o-(o-aminophenylethynyl)aniline with DMFDMA. more...
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- 2018
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11. Synthesis of 4-Substituted-1,2-Dihydroquinolines by Means of Gold-Catalyzed Intramolecular Hydroarylation Reaction of N-Ethoxycarbonyl-N-Propargylanilines
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Antonio Arcadi, Andrea Calcaterra, Giancarlo Fabrizi, Andrea Fochetti, Antonella Goggiamani, Antonia Iazzetti, Federico Marrone, Vincenzo Marsicano, Giulia Mazzoccanti, and Andrea Serraiocco
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gold catalysis ,intramolecular hydroarylation ,1,2-dihydroquinolines ,Organic chemistry ,QD241-441 - Abstract
An alternative Au(I)-catalyzed synthetic route to functionalized 1,2-dihydroquinolines is reported. This novel approach is based on the use of N-ethoxycarbonyl protected-N-propargylanilines as building blocks that rapidly undergo the IMHA reaction affording the 6-endo cyclization product in good to high yields. In the presence of N-ethoxycarbonyl-N-propargyl-meta-substituted anilines, the regiodivergent cyclization at the ortho-/para-position is achieved by the means of catalyst fine tuning. more...
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- 2021
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12. Phytocomplex Characterization and Biological Evaluation of Powdered Fruits and Leaves from Elaeagnus angustifolia
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Simone Carradori, Francesco Cairone, Stefania Garzoli, Giancarlo Fabrizi, Antonia Iazzetti, Anna Maria Giusti, Luigi Menghini, Sengul Uysal, Gunes Ak, Gokhan Zengin, and Stefania Cesa
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Elaeagnus angustifolia ,MW-assisted extraction ,scCO2-assisted extraction ,pigments ,polyphenols ,HS-GC/MS ,Organic chemistry ,QD241-441 - Abstract
Fully ripe fruits and mature leaves of Elaeagnus angustifolia were harvested and analyzed by means of analytical and biological tests to better comprehend the chemical composition and therapeutic/nutraceutical potential of this plant. Fruits and leaves were dried and the obtained powders were analyzed to study their color character and (via headspace gas chromatography) describe the chemical profile. Subsequently, they were submitted to a chloroform–methanol extraction, to a hydroalcoholic extraction procedure assisted or not by microwaves, and to an extraction with supercritical CO2, assisted or not by ethanol as the co-solvent, to detect the polyphenolic and the volatile content. The resulting extracts were evaluated in terms of chlorophyll and carotenoid content, polyphenolic content, volatile fraction, total phenolic content, total flavonoid content, antioxidant activity, radical scavenging activity, and enzymatic inhibition activity. The results confirmed the correlation between the chemical composition and the high antioxidant potential of leaf extracts compared to the fruit extracts in terms of the phenolic and pigment content. A promising effect against tyrosinase emerged for all the extracts, suggesting a therapeutic/nutraceutical use for this plant. Conversely, the volatile content from both natural matrices was similar. more...
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- 2020
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13. Phosphine ligands and nitrogen bases in the solvent-free Heck reaction of butenone with aryl iodides. A highly selective synthesis of benzalacetones
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Sandro Cacchi, Giancarlo Fabrizi, and Antonella Goggiamani
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Organic chemistry ,QD241-441 - Published
- 2003
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14. Synthesis of 3-substituted 2,3-dihydropyrazino[1,2-a]indol-4(1H)-ones by sequential reactions of 2-indolylmethyl acetates with α-amino acids
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Antonella Goggiamani, Antonio Arcadi, Alessia Ciogli, Martina De Angelis, Stefano Dessalvi, Giancarlo Fabrizi, Federica Iavarone, Antonia Iazzetti, Alessio Sferrazza, and Roberta Zoppoli
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Sequential Reactions. Annulation Reactions. Indole-2-ylmethylacetates. 2 ,Sequential Reactions. Annulation Reactions. Indole-2-ylmethylacetates. 2,3-Dihydropyrazino[1,2-a]indol-4(1H)-ones ,General Chemical Engineering ,General Chemistry ,2-a]indol-4(1H)-ones ,3-Dihydropyrazino[1 - Abstract
The synthesis of 2,3-dihydropyrazino[1,2-a]indol-4(1H)-ones through the in situ generation of 2-methide-2H-indole intermediate I starting from 2-indolylmethyl acetates under basic conditions/nucleophilic Michael addition/cyclization cascade reaction. more...
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- 2023
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15. Diaryl-Pyrano-Chromenes Atropisomers: Stereodynamics and Conformational Studies
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Mancinelli, Alessia Ciogli, Andrea Fochetti, Andrea Sorato, Giancarlo Fabrizi, Nunzio Matera, Andrea Mazzanti, and Michele
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aryls-pyrano-chromenes ,atropisomer ,Dynamic-NMR ,Dynamic-HPLC ,ECD ,DFT ,TD-DFT - Abstract
The dynamic scenario of di-aryls-pyrano-chromenes was investigated using DFT calculations. The symmetry of the chromene scaffold and the presence of two ortho-substituted aryls substituents can generate two syn/anti diastereoisomers and conformational enantiomers with different rotational barriers. The relative conformations and configurations were derived using NOESY-1D experiments. Depending on the energies related to the conformational exchange, the experimental energy barriers were determined through Dynamic NMR, Dynamic HPLC or kinetic studies. The atropisomeric pairs were resolved in the latter scenario, and their absolute configuration was assigned using the ECD/TD-DFT method. more...
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- 2023
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16. Direct Regioselective Hydro(hetero)arylation/Cyclocondensation Reactions of β-(2-Aminophenyl)-α,β-ynones by Means of Transition-Metal Catalysis/Brønsted Acid Synergism: Experimental Results and Computational Insights
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Vincenzo Marsicano, Antonio Arcadi, Massimiliano Aschi, Marco Chiarini, Giancarlo Fabrizi, Antonella Goggiamani, Fabio Marinelli, and Antonia Iazzetti
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FRIEDEL-CRAFTS ALKENYLATION ,ARENES ACTIVATION ,SILVER ,Organic Chemistry ,INDOLES ,HYDROARYLATION ,ALKYNES ,C-H FUNCTIONALIZATION - Published
- 2023
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17. Synthesis of Indole/Benzofuran-Containing Diarylmethanes through Palladium-Catalyzed Reaction of Indolylmethyl or Benzofuranylmethyl Acetates with Boronic Acids
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Andrea Calcaterra, Antonia Iazzetti, Vincenzo Marsicano, Giancarlo Fabrizi, Antonella Goggiamani, Andrea Serraiocco, Andrea Fochetti, Federico Marrone, Antonio Arcadi, and Marco Chiarini
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Indole test ,benzofurans ,boronic acids ,diarylmethanes ,indoles ,palladium ,suzuki-miyaura reaction ,Chemistry ,Settore CHIM/06 - CHIMICA ORGANICA ,Organic Chemistry ,chemistry.chemical_element ,Combinatorial chemistry ,palladium, boronic acids, Suzuki–Miyaura reaction, indoles, benzofurans, diarylmethanes ,Catalysis ,Suzuki–Miyaura reaction ,chemistry.chemical_compound ,XPhos ,Benzofuran ,Palladium - Abstract
The palladium-catalyzed synthesis of indole/benzofuran-containing diarylmethanes starting from indolylmethyl or benzofuranylmethyl acetates with boronic acids has been investigated. The success of the reaction is influenced by the choice of precatalyst: with indolylmethyl acetates the reaction works well with [Pd(η3-C3H5)Cl]2/XPhos while with benzofuranylmethyl acetates Pd2(dba)3/XPhos is more efficient. The good to high yields and the simplicity of the experimental procedure make this protocol a versatile synthetic tool for the preparation of 2- and 3-substituted indoles and 2-benzo[b]furans. The methodology can be advantageously extended to the preparation of a key precursor of Zafirlukast. more...
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- 2021
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18. Synthesis of Polycyclic Chromene Cores through Gold (I)‐Catalyzed Intramolecular Hydroarylation Reaction (IMHA)
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Antonia Iazzetti, Antonio Arcadi, Roberta Franzini, Francesca Ghirga, Giancarlo Fabrizi, Antonella Goggiamani, Andrea Serraiocco, Andrea Fochetti, and Federico Marrone
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Annulation ,Gold catalysis ,Hydroarylation ,Annulation · Gold catalysis · Hydroarylation ,Chemistry ,Settore CHIM/06 - CHIMICA ORGANICA ,Intramolecular force ,Organic Chemistry ,Physical and Theoretical Chemistry ,Medicinal chemistry ,Catalysis - Published
- 2021
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19. Immobilization of
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Elisa, Di Fabio, Antonia, Iazzetti, Alessio, Incocciati, Valentina, Caseli, Giancarlo, Fabrizi, Alberto, Boffi, Alessandra, Bonamore, and Alberto, Macone
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Aldehydes ,Lathyrus ,Magnetic Phenomena ,Biocatalysis ,Humans ,Amines ,Enzymes, Immobilized ,Oxidoreductases ,Monoamine Oxidase - Abstract
Amine oxidases are enzymes belonging to the class of oxidoreductases that are widespread, from bacteria to humans. The amine oxidase from
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- 2022
20. One-pot synthesis of dihydroquinolones by sequential reactions of
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Antonio, Arcadi, Andrea, Calcaterra, Giancarlo, Fabrizi, Andrea, Fochetti, Antonella, Goggiamani, Antonia, Iazzetti, Federico, Marrone, Giulia, Mazzoccanti, and Andrea, Serraiocco
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Dioxanes ,Cyclization - Abstract
The functionalized 3,4-dihydroquinolin-2-one nucleus has been assembled in good to high yields through the sequential reaction of readily available
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- 2022
21. One-pot synthesis of dihydroquinolones by sequential reactions of o-aminobenzyl alcohol derivatives with Meldrum's acids
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Antonio Arcadi, Andrea Calcaterra, Giancarlo Fabrizi, Andrea Fochetti, Antonella Goggiamani, Antonia Iazzetti, Federico Marrone, Giulia Mazzoccanti, and Andrea Serraiocco
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Dioxanes ,Dihydroquinolones ,Cyclization ,Settore CHIM/06 - CHIMICA ORGANICA ,Organic Chemistry ,Sequential Reactions. Dihydroquinolones. Aza-o-quinone methides ,Physical and Theoretical Chemistry ,Biochemistry - Abstract
The functionalized 3,4-dihydroquinolin-2-one nucleus has been assembled in good to high yields through the sequential reaction of readily available N-Ts-o-aminobenzyl alcohols with Meldrum's acid derivatives under mild basic conditions. more...
- Published
- 2022
22. Immobilization of Lathyrus cicera Amine Oxidase on Magnetic Microparticles for Biocatalytic Applications
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Elisa Di Fabio, Antonia Iazzetti, Alessio Incocciati, Valentina Caseli, Giancarlo Fabrizi, Alberto Boffi, Alessandra Bonamore, and Alberto Macone
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magnetic particles ,enzyme immobilization ,amine oxidase ,aldehydes ,biocatalysis ,oxidative deamination ,primary amines ,Settore CHIM/06 - CHIMICA ORGANICA ,Organic Chemistry ,General Medicine ,Catalysis ,Computer Science Applications ,Inorganic Chemistry ,Physical and Theoretical Chemistry ,Molecular Biology ,Settore BIO/10 - BIOCHIMICA ,Spectroscopy - Abstract
Amine oxidases are enzymes belonging to the class of oxidoreductases that are widespread, from bacteria to humans. The amine oxidase from Lathyrus cicera has recently appeared in the landscape of biocatalysis, showing good potential in the green synthesis of aldehydes. This enzyme catalyzes the oxidative deamination of a wide range of primary amines into the corresponding aldehydes but its use as a biocatalyst is challenging due to the possible inactivation that might occur at high product concentrations. Here, we show that the enzyme’s performance can be greatly improved by immobilization on solid supports. The best results are achieved using amino-functionalized magnetic microparticles: the immobilized enzyme retains its activity, greatly improves its thermostability (4 h at 75 °C), and can be recycled up to 8 times with a set of aromatic ethylamines. After the last reaction cycle, the overall conversion is about 90% for all tested substrates, with an aldehyde production ranging between 100 and 270 mg depending on the substrate used. As a proof concept, one of the aldehydes thus produced was successfully used for the biomimetic synthesis of a non-natural benzylisoquinoline alkaloid. more...
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- 2022
23. Reactivity of Indolylmethylacetates with N, O, and S Soft Nucleophiles: Evidence of 2-Alkylideneindolenines and 3-Alkylideneindoleninium Generation by ESI-MS and IRMPD Spectroscopy
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Antonio Arcadi, Giel Berden, Alessia Ciogli, Davide Corinti, Maria Elisa Crestoni, Martina De Angelis, Giancarlo Fabrizi, Antonella Goggiamani, Antonia Iazzetti, Federico Marrone, Vincenzo Marsicano, Jos Oomens, and Andrea Serraiocco more...
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FELIX Molecular Structure and Dynamics ,Carbinols ,Synthetic methods ,Indole-2-methides ,Settore CHIM/06 - CHIMICA ORGANICA ,Nitrogen heterocycles ,Organic Chemistry ,IRMPD ,Physical and Theoretical Chemistry - Abstract
Contains fulltext : 284404.pdf (Publisher’s version ) (Closed access)
- Published
- 2022
24. Synthesis of Polysubstituted 1,2-Dihydro-3H-pyrrolo[1,2-a]indol-3-ones through Domino Palladium-Catalyzed Reactions of Indol-2-ylmethyl Acetates with 1,3-Dicarbonyl Derivatives
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Antonia Iazzetti, Antonio Arcadi, Stefano Dessalvi, Giancarlo Fabrizi, Antonella Goggiamani, Federico Marrone, Andrea Serraiocco, Alessio Sferrazza, and Karim Ullah
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2-dihydro-3H-pyrrolo[1 ,1,2-dihydro-3H-pyrrolo[1,2-a]indol-3-ones ,indolyl methides ,palladium catalysis ,domino reactions ,Settore CHIM/06 - CHIMICA ORGANICA ,2-a]indol-3-ones ,Physical and Theoretical Chemistry ,Catalysis ,General Environmental Science - Abstract
A straightforward assembly of polysubstituted 1,2-dihydro-3H-pyrrolo[1,2-a]indol-3-ones through a domino palladium-catalyzed reaction of indol-2-ylmethyl acetates with 1,3-dicarbonyl derivatives is described. The key role of the features of the 1,3-dicarbonyls on the reaction outcome has been explored. The employment of 2-methylcyclohexan-1,3-dione as the dicarbonyl source could allow further challenging indole nucleus functionalizations. more...
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- 2022
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25. Stereo- and regioselective gold(<scp>i</scp>)-catalyzed hydroamination of 2-(arylethynyl)pyridines with anilines
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Giancarlo Fabrizi, Antonia Iazzetti, Sandro Cacchi, Francesca Ghirga, Antonella Goggiamani, and Andrea Fochetti
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Trifluoromethyl ,010405 organic chemistry ,Settore CHIM/06 - CHIMICA ORGANICA ,Organic Chemistry ,stereo and regio-selective reaction ,Regioselectivity ,Ether ,010402 general chemistry ,01 natural sciences ,Biochemistry ,Medicinal chemistry ,0104 chemical sciences ,Catalysis ,hydroamination ,chemistry.chemical_compound ,chemistry ,gold-catalysis ,Hydroamination ,Physical and Theoretical Chemistry ,Selectivity ,biochemistry ,physical and theoretical chemistry ,organic chemistry - Abstract
The gold-catalyzed hydroamination of 2-(arylethynyl)pyridines with anilines affords stereoselectively Z-enamine products with excellent regioselectivity. The reaction proceeds with moderate to excellent yields and accommodates a diverse range of functional groups on alkynes (ether, bromo, trifluoromethyl, acetyl, and carbomethoxy) and anilines (ether, bromo, chloro, and carbethoxy). The stereochemistry of the obtained enamines is complementary to that reported in previous studies. A plausible explanation for the observed selectivity was attained by means of NMR experiments. more...
- Published
- 2019
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26. Synthesis of 4-Substituted-1,2-Dihydroquinolines by Means of Gold-Catalyzed Intramolecular Hydroarylation Reaction of N-Ethoxycarbonyl-N-Propargylanilines
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Giulia Mazzoccanti, Andrea Fochetti, Andrea Calcaterra, Vincenzo Marsicano, Antonia Iazzetti, Federico Marrone, Antonio Arcadi, Antonella Goggiamani, Andrea Serraiocco, and Giancarlo Fabrizi
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Settore CHIM/06 - CHIMICA ORGANICA ,CHROMENES ,Pharmaceutical Science ,Organic chemistry ,Article ,1,2-dihydroquinolines ,Analytical Chemistry ,Catalysis ,QD241-441 ,intramolecular hydroarylation ,Drug Discovery ,gold catalysis ,QUINOLINE DERIVATIVES ,ALKYNES ,Physical and Theoretical Chemistry ,Chemistry ,intramolecular hydroarylation reaction ,Combinatorial chemistry ,2-dihydroquinolines ,Chemistry (miscellaneous) ,Product (mathematics) ,Intramolecular force ,Molecular Medicine ,Gold catalysis ,Intramolecular hydroarylation - Abstract
An alternative Au(I)-catalyzed synthetic route to functionalized 1,2-dihydroquinolines is reported. This novel approach is based on the use of N-ethoxycarbonyl protected-N-propargylanilines as building blocks that rapidly undergo the IMHA reaction affording the 6-endo cyclization product in good to high yields. In the presence of N-ethoxycarbonyl-N-propargyl-meta-substituted anilines, the regiodivergent cyclization at the ortho-/para-position is achieved by the means of catalyst fine tuning. more...
- Published
- 2021
27. Sequential condensation/biannulation reactions of β-(2-aminophenyl)-α,β-ynones with 1,3-dicarbonyls
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Antonia Iazzetti, Vincenzo Marsicano, Antonella Goggiamani, Giancarlo Fabrizi, Marco Chiarini, and Antonio Arcadi
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PYRANOQUINOLINONES ,Settore CHIM/06 - CHIMICA ORGANICA ,BIOLOGICAL-ACTIVITIES ,Alcohol ,Biochemistry ,Medicinal chemistry ,CYCLIZATION ,Catalysis ,chemistry.chemical_compound ,Physical and Theoretical Chemistry ,CONJUGATE ADDITION ,Sequential reactions ,Ethanol ,SAMOQUASINE ,Solvent molecule ,4H-pyrano[3 ,Organic Chemistry ,Condensation ,Quinoline ,NUCLEOPHILES ,4-c]quinoline core ,QUINOLINE ,4H-pyrano[3,4-c]quinoline core ,chemistry ,MULTICOMPONENT REACTIONS ,NATURAL-PRODUCT SYNTHESIS ,DOMINO REACTIONS - Abstract
A divergent domino condensation/biannulation reaction of β-(2-aminophenyl) α,β-ynones with 1,3-dicarbonyls to construct a polycyclic 4H-pyrano[3,4-c]quinoline core has been developed. The p-TsOH·H2O catalyzed reaction of β-(2-aminophenyl) α,β-ynones with β-ketoesters in ethanol proceeds with good to excellent yields to provide a simple and effective method for the synthesis of functionalized 4H-pyrano[3,4-c]quinolinones. Further elaboration of these latter derivatives with an excess of 20% NH4OH in EtOH at 50 °C helps achieve the synthesis of the perlodinine analogues benzo[c][2,7]naphthyridin-4(3H)-one derivatives in high yields. Moreover, the p-TsOH·H2O mediated reaction of β-(2-aminophenyl) α,β-ynones with β-di-ketones leads to the formation of a variety of structurally diverse 4H-pyrano[3,4-c]quinoline polycyclic ketals by the incorporation of an alcohol solvent molecule in a cascade fashion. more...
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- 2021
28. Convergent total synthesis of (±)-kuwanol E
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Juan Jose Guevara, Bruno Botta, Giancarlo Fabrizi, and Andrea Calcaterra
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- 2021
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29. Self-Assembling Ferritin-Dendrimer Nanoparticles for Targeted Delivery of Nucleic Acids to Myeloid Leukemia Cells
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Antonia Iazzetti, Federica Palombarini, Francesco Fazi, Alberto Macone, Alberto Boffi, Alessio Incocciati, Elisa Di Fabio, Francesca Liccardo, Silvia Masciarelli, Alessandra Bonamore, and Giancarlo Fabrizi more...
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Myeloid ,Pharmaceutical Science ,Medicine (miscellaneous) ,PAMAM ,Applied Microbiology and Biotechnology ,Protein nanoparticles ,Drug Delivery Systems ,Nucleic Acids ,Receptors ,Tumor ,Leukemia ,biology ,Chemistry ,Transferrin ,Myeloid leukemia ,Self-assembly ,Transfection ,CD ,Cell biology ,Leukemia, Myeloid ,Archaeoglobus fulgidus ,Drug delivery ,Molecular Medicine ,Biotechnology ,Dendrimers ,Biomedical Engineering ,Bioengineering ,Cell Line ,Antigens, CD ,Cell Line, Tumor ,Dendrimer ,Receptors, Transferrin ,Medical technology ,Humans ,R855-855.5 ,Antigens ,dendrimers ,ferritin ,miRNA ,protein nanoparticles ,self-assembly ,targeted delivery ,Settore BIO/10 - BIOCHIMICA ,Ferritin ,Research ,Fusion protein ,MicroRNAs ,Ferritins ,Nucleic acid ,biology.protein ,Nanoparticles ,Targeted delivery ,Nanocarriers ,TP248.13-248.65 - Abstract
Background In recent years, the use of ferritins as nano-vehicles for drug delivery is taking center stage. Compared to other similar nanocarriers, Archaeoglobus fulgidus ferritin is particularly interesting due to its unique ability to assemble-disassemble under very mild conditions. Recently this ferritin was engineered to get a chimeric protein targeted to human CD71 receptor, typically overexpressed in cancer cells. Results Archaeoglobus fulgidus chimeric ferritin was used to generate a self-assembling hybrid nanoparticle hosting an aminic dendrimer together with a small nucleic acid. The positively charged dendrimer can indeed establish electrostatic interactions with the chimeric ferritin internal surface, allowing the formation of a protein-dendrimer binary system. The 4 large triangular openings on the ferritin shell represent a gate for negatively charged small RNAs, which access the internal cavity attracted by the dense positive charge of the dendrimer. This ternary protein-dendrimer-RNA system is efficiently uptaken by acute myeloid leukemia cells, typically difficult to transfect. As a proof of concept, we used a microRNA whose cellular delivery and induced phenotypic effects can be easily detected. In this article we have demonstrated that this hybrid nanoparticle successfully delivers a pre-miRNA to leukemia cells. Once delivered, the nucleic acid is released into the cytosol and processed to mature miRNA, thus eliciting phenotypic effects and morphological changes similar to the initial stages of granulocyte differentiation. Conclusion The results here presented pave the way for the design of a new family of protein-based transfecting agents that can specifically target a wide range of diseased cells. Graphic abstract more...
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- 2021
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30. Synthesis of functionalised 2,3-dihydroquinolin-4(1: H)-ones vs. quinoline or N -alkenylindole derivatives through sequential reactions of 2-alkynylanilines with ketones
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Giancarlo Fabrizi, Antonio Arcadi, Antonia Iazzetti, Marco Chiarini, Vincenzo Marsicano, and Antonella Goggiamani
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Reaction conditions ,quinolines ,Settore CHIM/06 - CHIMICA ORGANICA ,Diversity-oriented synthesis. Sequential reactions. Catalysis ,Organic Chemistry ,Quinoline ,Biochemistry ,Medicinal chemistry ,Toluene ,Catalysis ,chemistry.chemical_compound ,N-alkenylindole ,chemistry ,Functional group ,Lewis acids and bases ,quinolones ,Physical and Theoretical Chemistry ,Brønsted–Lowry acid–base theory ,diversity-oriented synthesis ,N-alkenylindole, quinolines, quinolones, diversity-oriented synthesis - Abstract
This study describes diversity-oriented synthesis of 2,2,3-substituted-2,3-dihydroquinolin-4(1H)-ones vs. functionalised quinoline or N-alkenylindole derivatives through Bronsted acid mediated or Lewis acid catalyzed sequential reactions of 2-alkynylanilines with ketones. In particular, a series of challenging quinolin-4-one derivatives are prepared with good functional group tolerance in an atom-economical fashion by using p-toluenesulfonic acid monohydrate as a promoter of the reaction of ketones with 2-alkynylanilines in EtOH at reflux, while the same starting materials give the corresponding 4-substituted quinolines in toluene at 110 °C both in the presence of p-toluenesulfonic acid monohydrate as the promoter and FeCl3 as the catalyst. The divergent formation of N-alkenylindole derivatives occurs by switching to the use of ZnBr2 as the catalyst under the same reaction conditions. Conversely, only 4-methylsubstituted quinoline derivatives were isolated by reacting 2-ethynylanilines and/or 2-trimethylsylilanilines with ketones in all examined cases. more...
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- 2021
31. Palladium-catalyzed Tsuji–Trost-type reaction of benzofuran-2-ylmethyl acetates with nucleophiles
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Andrea Fochetti, Giancarlo Fabrizi, Antonio Arcadi, Federico Marrone, Andrea Serraiocco, Antonella Goggiamani, Antonia Iazzetti, Giulia Mazzoccanti, and Francesca Ghirga
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General Chemical Engineering ,Settore CHIM/06 - CHIMICA ORGANICA ,chemistry.chemical_element ,Benzofuran ,palladium catalysis ,Tsuji–Trost-type reaction ,organic synthesis ,General Chemistry ,Sulfur ,Medicinal chemistry ,Benzofurans ,Catalysis ,Palladium ,chemistry.chemical_compound ,Palladium catalysis, Tsuji–Trost-type reaction ,benzofurans ,chemistry ,Nucleophile ,XPhos ,Nucleophilic substitution - Abstract
The palladium-catalyzed benzylic-like nucleophilic substitution of benzofuran-2-ylmethyl acetate with N, S, O and C soft nucleophiles has been investigated. The success of the reaction is dramatically influenced by the choice of catalytic system: with nitrogen based nucleophiles the reaction works well with Pd2(dba)3/dppf, while with sulfur, oxygen and carbo-nucleophiles [Pd(η3-C3H5)Cl]2/XPhos is more efficient. The regiochemical outcome shows that the nucleophilic substitution occurs only on the benzylic position of the η3-(benzofuryl)methyl complex. The high to excellent yields and the simplicity of the experimental procedure make this protocol a versatile synthetic tool for the preparation of 2-substituted benzo[b]furans. more...
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- 2021
32. Synthesis of functionalised 2,3-dihydroquinolin-4(1
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Vincenzo, Marsicano, Antonio, Arcadi, Marco, Chiarini, Giancarlo, Fabrizi, Antonella, Goggiamani, and Antonia, Iazzetti
- Abstract
This study describes diversity-oriented synthesis of 2,2,3-substituted-2,3-dihydroquinolin-4(1H)-ones vs. functionalised quinoline or N-alkenylindole derivatives through Brønsted acid mediated or Lewis acid catalyzed sequential reactions of 2-alkynylanilines with ketones. In particular, a series of challenging quinolin-4-one derivatives are prepared with good functional group tolerance in an atom-economical fashion by using p-toluenesulfonic acid monohydrate as a promoter of the reaction of ketones with 2-alkynylanilines in EtOH at reflux, while the same starting materials give the corresponding 4-substituted quinolines in toluene at 110 °C both in the presence of p-toluenesulfonic acid monohydrate as the promoter and FeCl3 as the catalyst. The divergent formation of N-alkenylindole derivatives occurs by switching to the use of ZnBr2 as the catalyst under the same reaction conditions. Conversely, only 4-methylsubstituted quinoline derivatives were isolated by reacting 2-ethynylanilines and/or 2-trimethylsylilanilines with ketones in all examined cases. more...
- Published
- 2020
33. Phytocomplex Characterization and Biological Evaluation of Powdered Fruits and Leaves from Elaeagnus angustifolia
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Gunes Ak, Stefania Garzoli, Antonia Iazzetti, Sengul Uysal, Luigi Menghini, Gokhan Zengin, Stefania Cesa, Anna Maria Giusti, Francesco Cairone, Simone Carradori, and Giancarlo Fabrizi
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Pigments ,Chlorophyll ,Antioxidant ,Magnetic Resonance Spectroscopy ,medicine.medical_treatment ,Flavonoid ,Pharmaceutical Science ,HPLC-DAD ,01 natural sciences ,Antioxidants ,Mass Spectrometry ,Analytical Chemistry ,chemistry.chemical_compound ,antioxidant activity ,elaeagnus angustifolia ,enzyme inhibition activity ,hplc-dad ,hs-gc/ms ,mw-assisted extraction ,pigments ,polyphenols ,scco ,2 ,assisted extraction ,Drug Discovery ,Food science ,Microwaves ,Carotenoid ,Chemical composition ,Chromatography, High Pressure Liquid ,chemistry.chemical_classification ,0303 health sciences ,Chromatography ,Elaeagnaceae ,Monophenol Monooxygenase ,food and beverages ,Chemistry (miscellaneous) ,Gas ,High Pressure Liquid ,Molecular Medicine ,Chloroform ,Powders ,Chromatography, Gas ,Settore CHIM/06 - CHIMICA ORGANICA ,Color ,lcsh:QD241-441 ,03 medical and health sciences ,Nutraceutical ,lcsh:Organic chemistry ,Antioxidant activity ,Phenols ,Elaeagnus angustifolia ,medicine ,MW-assisted extraction ,Physical and Theoretical Chemistry ,Settore CHIM/10 - CHIMICA DEGLI ALIMENTI ,ScCO ,030304 developmental biology ,Flavonoids ,Enzyme inhibition activity ,010405 organic chemistry ,Plant Extracts ,Methanol ,Organic Chemistry ,Extraction (chemistry) ,Polyphenols ,Carotenoids ,0104 chemical sciences ,Plant Leaves ,chemistry ,Polyphenol ,Fruit ,Solvents ,scCO2-assisted extraction ,HS-GC/MS - Abstract
Fully ripe fruits and mature leaves of Elaeagnus angustifolia were harvested and analyzed by means of analytical and biological tests to better comprehend the chemical composition and therapeutic/nutraceutical potential of this plant. Fruits and leaves were dried and the obtained powders were analyzed to study their color character and (via headspace gas chromatography) describe the chemical profile. Subsequently, they were submitted to a chloroform&ndash, methanol extraction, to a hydroalcoholic extraction procedure assisted or not by microwaves, and to an extraction with supercritical CO2, assisted or not by ethanol as the co-solvent, to detect the polyphenolic and the volatile content. The resulting extracts were evaluated in terms of chlorophyll and carotenoid content, polyphenolic content, volatile fraction, total phenolic content, total flavonoid content, antioxidant activity, radical scavenging activity, and enzymatic inhibition activity. The results confirmed the correlation between the chemical composition and the high antioxidant potential of leaf extracts compared to the fruit extracts in terms of the phenolic and pigment content. A promising effect against tyrosinase emerged for all the extracts, suggesting a therapeutic/nutraceutical use for this plant. Conversely, the volatile content from both natural matrices was similar. more...
- Published
- 2020
34. Synthesis of indolo[1,2-c]quinazolines from 2-alkynylaniline derivatives through Pd-catalyzed indole formation/cyclization with N,N-dimethylformamide dimethyl acetal
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Sandro Cacchi, Giancarlo Fabrizi, Antonella Goggiamani, Francesca Ghirga, Antonio Arcadi, Antonia Iazzetti, and Fabio Marinelli
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Indole formation ,Indoles ,Settore CHIM/06 - CHIMICA ORGANICA ,Arylboronic acids ,DMFDMA ,Indoloquinazolines ,Quinazolines ,Organic Chemistry ,010402 general chemistry ,01 natural sciences ,Medicinal chemistry ,Catalysis ,lcsh:QD241-441 ,Dimethyl acetal ,chemistry.chemical_compound ,Aniline ,lcsh:Organic chemistry ,lcsh:Science ,010405 organic chemistry ,0104 chemical sciences ,arylboronic acids ,indoles ,indoloquinazolines ,quinazolines ,chemistry ,N dimethylformamide ,Dimethylformamide ,lcsh:Q - Abstract
An efficient strategy for the synthesis of 6-unsubstituted indolo[1,2-c]quinazolines is described. The Pd-catalyzed reaction of o-(o-aminophenylethynyl) trifluoroacetanilides with Ar–B(OH)2 afforded 2-(o-aminophenyl)-3-arylindoles, that were converted to 12-arylindolo[1,2-c]quinazolines by adding dimethylformamide dimethyl acetal (DMFDMA) to the reaction mixture after extractive work-up. This reaction outcome is different from the previously reported Pd-catalyzed sequential reaction of the same substrates with Ar–I, Ar–Br and ArN2+BF4−, that afforded 12-arylindolo[1,2-c]quinazolin-6(5H)-ones. Moreover, 12-unsubstituted indolo[1,2-c]quinazolines can be obtained both by reacting 2-(o-aminophenyl)indoles with DMFDMA or by sequential Pd-catalyzed reaction of o-(o-aminophenylethynyl)aniline with DMFDMA. more...
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- 2018
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35. Chimica organica essenziale (seconda edizione)
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Maria Emanuela Amato, Giovanni Battista Appendino, Stefano Banfi, Paola Maria Bonaccorsi, Bruno Botta, Sandro Cacchi, Enrico Caruso, Ilaria D’Acquarica, Leonardo Degennaro, Giancarlo Fabrizi, Luca Forti, Concetta Imperatore, Renzo Luisi, Fabio Mantellini, Marialuisa Menna, Marco Pierini, Barbara Richichi, Maurizio Taddei, Giovanni Zappia, Maria Emanuela Amato, Giovanni Battista Appendino, Stefano Banfi, Paola Maria Bonaccorsi, Bruno Botta, Sandro Cacchi, Enrico Caruso, Ilaria D’Acquarica, Leonardo Degennaro, Giancarlo Fabrizi, Luca Forti, Concetta Imperatore, Renzo Luisi, Fabio Mantellini, Marialuisa Menna, Marco Pierini, Barbara Richichi, Maurizio Taddei, Giovanni Zappia, Bruno Botta, Emanuela Amato, Maria, Battista Appendino, Giovanni, Banfi, Stefano, Maria Bonaccorsi, Paola, Botta, Bruno, Cacchi, Sandro, Caruso, Enrico, D’Acquarica, Ilaria, Degennaro, Leonardo, Fabrizi, Giancarlo, Forti, Luca, Imperatore, Concetta, Luisi, Renzo, Mantellini, Fabio, Menna, Marialuisa, Pierini, Marco, Richichi, Barbara, Taddei, Maurizio, and Zappia, Giovanni more...
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- 2018
36. 2-(Aminomethyl)-3-arylindoles from 3-(o-Trifluoroacetamidoaryl)-1-propargylic Alcohols, Aryl Halides, and Amines: A Domino Palladium-Catalyzed Three-Component Approach
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Antonia Iazzetti, Sandro Cacchi, Antonella Goggiamani, Rosanna Verdiglione, and Giancarlo Fabrizi
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cyclization ,multicomponent reaction ,3-(o -trifluoroacetamidoaryl)-1-propargylic alcohols ,010405 organic chemistry ,Chemistry ,Settore CHIM/06 - CHIMICA ORGANICA ,Aryl ,Organic Chemistry ,Halide ,chemistry.chemical_element ,palladium ,010402 general chemistry ,01 natural sciences ,Catalysis ,Domino ,0104 chemical sciences ,chemistry.chemical_compound ,Cascade reaction ,domino reaction ,2-(aminomethyl)indoles ,Organic chemistry ,Palladium - Abstract
A simple, straightforward palladium-catalyzed approach to 2-(aminomethyl)-3-arylindoles from 3-(o-trifluoroacetamidoaryl)-1-propargylic alcohols, amines, and aryl iodides has been developed.
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- 2017
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37. Identification of novel quinazoline derivatives as potent antiplasmodial agents
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Johan Schultz, Dany Pechalrieu, Sergio Valente, Anne Bouchut, Tina S. Skinner-Adams, Giancarlo Fabrizi, Paola B. Arimondo, Urban Hoglund, Katherine T. Andrews, Roberta Mazzone, Sophia Lafitte, Antonello Mai, Alessia Lucidi, Christine Pierrot, Ming Jang Chua, Jamal Khalife, Dante Rotili, Institut Pasteur de Lille, Università degli Studi di Roma 'La Sapienza' = Sapienza University [Rome] [UNIROMA], Pharmacochimie de la Régulation Epigénétique du Cancer [ETaC], Réseau International des Instituts Pasteur (RIIP), Università degli Studi di Roma 'La Sapienza' = Sapienza University [Rome], Kancera AB [Sweden], Adlego Biomedical AB [Sweden], Pharmacochimie de la Régulation Epigénétique du Cancer (ETaC), PIERRE FABRE-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS), GRIFFITH UNIVERSITY AUS, Partenaires IRSTEA, Institut national de recherche en sciences et technologies pour l'environnement et l'agriculture (IRSTEA)-Institut national de recherche en sciences et technologies pour l'environnement et l'agriculture (IRSTEA), This work was supported by the Australian National Health and Medical Research Council (APP1074016 to K.T.A.), Italian PRIN 2016 (prot. 20152TE5PK to A.M.), AIRC 2016 (n. 19162 to A.M.), NIH (n. R01GM114306 to A.M.), Progetto Ateneo Sapienza 2017 (to D.R.), the A-ParaDDisE program funded under the European Union's Seventh Framework Programme (grant agreement no. 602080 to A.B., C.P., S.L., A.M., D.R., S.V., J.S., U.H., K.T.A. and J.K.) and Griffith University (GUIPRS and GUPRS scholarships to M.J.C.). We thank Mary Clarke (Griffith University) for technical assistance. We also thank the BioImaging Center Lille Facility for access to the BD FACSCanto II cytometer., European Project: 602080,EC:FP7:HEALTH,FP7-HEALTH-2013-INNOVATION-1,A-PARADDISE(2014), Università degli Studi di Roma 'La Sapienza' = Sapienza University [Rome] (UNIROMA), Griffith University [Brisbane], Centre d’Infection et d’Immunité de Lille (CIIL) - INSERM U1019 - UMR 9017 (CIIL), Université de Lille-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre Hospitalier Régional Universitaire [Lille] (CHRU Lille)-Centre National de la Recherche Scientifique (CNRS)-Institut Pasteur de Lille, Réseau International des Instituts Pasteur (RIIP)-Réseau International des Instituts Pasteur (RIIP), Università degli Studi di Roma 'La Sapienza' [Rome], and PIERRE FABRE-Centre National de la Recherche Scientifique (CNRS) more...
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Plasmodium berghei ,Molecular Conformation ,Pharmacology ,MESH: Parasitic Sensitivity Tests ,01 natural sciences ,Antimalarial agents ,MESH: Dose-Response Relationship, Drug ,Mice ,MESH: Structure-Activity Relationship ,Parasitic Sensitivity Tests ,PK studies ,Histone deacetylase inhibitors ,Drug Discovery ,P. berghei mouse model ,MESH: Animals ,Antimalarial Agent ,DNA methyltransferase inhibitors ,Artemisinin ,MESH: Plasmodium falciparum ,media_common ,0303 health sciences ,Mice, Inbred BALB C ,biology ,Chemistry ,General Medicine ,3. Good health ,MESH: Quinazolines ,[SDV.MP]Life Sciences [q-bio]/Microbiology and Parasitology ,medicine.drug ,Drug ,antimalarial agents ,histone deacetylase inhibitors ,media_common.quotation_subject ,Plasmodium falciparum ,MESH: Mice, Inbred BALB C ,Context (language use) ,03 medical and health sciences ,Antimalarials ,Structure-Activity Relationship ,In vivo ,parasitic diseases ,medicine ,MESH: Plasmodium berghei ,[CHIM]Chemical Sciences ,Animals ,Humans ,MESH: Mice ,030304 developmental biology ,MESH: Molecular Conformation ,MESH: Humans ,Dose-Response Relationship, Drug ,010405 organic chemistry ,Organic Chemistry ,Fibroblasts ,biology.organism_classification ,medicine.disease ,MESH: Antimalarials ,0104 chemical sciences ,MESH: Fibroblasts ,Quinazolines ,[SDV.SPEE]Life Sciences [q-bio]/Santé publique et épidémiologie ,Malaria - Abstract
International audience; Despite the recent reductions in the global burden of malaria, this disease remains a devastating cause of death in tropical and subtropical regions. As there is no broadly effective vaccine for malaria, prevention and treatment still rely on chemotherapy. Unfortunately, emerging resistance to the gold standard artemisinin combination therapies means that new drugs with novel modes of action are urgently needed. In this context, Plasmodium histone modifying enzymes have emerged as potential drug targets, prompting us to develop and optimize compounds directed against such epigenetic targets. A panel of 51 compounds designed to target different epigenetic enzymes were screened for activity against Plasmodium falciparum parasites. Based on in vitro activity against drug susceptible and drug-resistant P. falciparum lines, selectivity index criterion and favorable pharmacokinetic properties, four compounds, one HDAC inhibitor (1) and three DNMT inhibitors (37, 43 and 45), were selected for preclinical studies in a mouse model of malaria. In vivo data showed that 37, 43 and 45 exhibited oral efficacy in the mouse model of Plasmodium berghei infection. These compounds represent promising starting points for the development of novel antimalarial drugs. more...
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- 2019
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38. Chalcones and Chalcone-mimetic Derivatives as Notch Inhibitors in a Model of T-cell Acute Lymphoblastic Leukemia
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Giancarlo Fabrizi, Daniele Passarella, Viviana Cuartas, Gloria Tobajas, Isabella Screpanti, Francesca Ghirga, Michael S. Christodoulou, Eva-María Priego, Marta Gargantilla, Bruno Botta, Mattia Mori, Deborah Quaglio, Silvia Balducci, Álvaro Carmona Pestaña, Rocco Palermo, María-Jesús Pérez-Pérez, Nadezda Zhdanovskaya, European Commission, Sapienza Università di Roma, and Ministerio de Economía y Competitividad (España) more...
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Chalcone ,T cell ,Lymphoblastic Leukemia ,Notch inhibitors ,01 natural sciences ,Biochemistry ,chemistry.chemical_compound ,Drug Discovery ,Notch inhibitors, T-ALL ,medicine ,cancer ,Cancer ,tetrahydronaphthalene scaffold ,010405 organic chemistry ,Chemistry ,T-ALL ,Organic Chemistry ,0104 chemical sciences ,010404 medicinal & biomolecular chemistry ,medicine.anatomical_structure ,Cell culture ,Chemical diversity ,Cancer research ,Antiproliferative effect ,Tetrahydronaphthalene scaffold - Abstract
Based on hit-likeness and chemical diversity, a number of chalcones and chalcone-mimetic compounds were selected as putative Notch inhibitors. The evaluation of the antiproliferative effect combined with the inhibition of Notch1 expression in KOPTK1 cell line identified compound 18, featuring a tetrahydronaphthalene-based scaffold, as a new promising Notch-blocking agent., The authors acknowledge networking contribution by the COST Action CM1407 “Challenging organic syntheses inspired by nature - from natural products chemistry to drug discovery”. V.C. thanks the Universidad del Valle (CIAM- 2017) and the Science, Technology and Innovation Fund- General Royalties System (FCTeI-SGR) under contract BPIN 2013000100007 for a predoctoral fellowship. This work has been supported by Italian Ministry of Education, University and Research - Dipartimenti di Eccellenza - L. 232/2016. This work has been partially supported by a grant from MINECO/ FEDER SAF2015-64629-C2-1-R (to M-J.P.-P and E-M.P), MIUR PNR 2015−2020 (ARS01_00432) (to I.S.), and Sapienza University 2016 Project number RG116154E2- C7A6FB (to I.S.). more...
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- 2019
39. Palladium-Catalyzed C12-Selective Direct Arylation of [1,2-c]Quinazolin-6(5H)-ones
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Sandro Cacchi, Fabio Marinelli, Giancarlo Fabrizi, Francesca Ghirga, Antonio Arcadi, Antonella Goggiamani, Antonia Iazzetti, and Andrea Fochetti
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polycycles ,010405 organic chemistry ,quinazolinones ,Settore CHIM/06 - CHIMICA ORGANICA ,Aryl ,Organic Chemistry ,chemistry.chemical_element ,Halide ,indoles ,010402 general chemistry ,palladium ,arylation ,policycles ,01 natural sciences ,Combinatorial chemistry ,Catalysis ,0104 chemical sciences ,chemistry.chemical_compound ,chemistry ,indoles, quinazolinones, palladium, arylation, polycycles ,Palladium - Abstract
A straightforward approach to the synthesis of the challenging 12-arylindolo[1,2-c]quinazolin-6(5H)-ones through the palladium-catalyzed direct arylation of N-benzyl and NH-free [1,2-c]quinazolin-6(5H)-ones with aryl halides is described. more...
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- 2019
40. Development of alkyl glycerone phosphate synthase inhibitors: Structure-activity relationship and effects on ether lipids and epithelial-mesenchymal transition in cancer cells
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Giulia Stazi, Sharon M. Louie, Sara Marchese, Giancarlo Fabrizi, Andrea Mattevi, Roberto Cirilli, Valentina Piano, Monica Viviano, Rino Ragno, Alexandros Patsilinakos, Cecilia Battistelli, Alessia Ciogli, Raffaele Strippoli, Antonello Mai, Lorenzo Antonini, Marco Tripodi, Alessandra Marchetti, Roberta Mazzone, Daniel K. Nomura, Biagina Marrocco, Gianluca Sbardella, Clemens Zwergel, and Sergio Valente more...
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Epithelial-Mesenchymal Transition ,Motility ,01 natural sciences ,Cell Line ,03 medical and health sciences ,Structure-Activity Relationship ,Cell Movement ,Cell Line, Tumor ,Neoplasms ,Drug Discovery ,medicine ,AGPS inhibitors ,Cancer ,E-cadherin ,Ether lipids ,Snail ,Humans ,Epithelial–mesenchymal transition ,030304 developmental biology ,Cell Proliferation ,Pharmacology ,0303 health sciences ,Alkyl and Aryl Transferases ,010405 organic chemistry ,Cell growth ,Chemistry ,Organic Chemistry ,Lipid metabolism ,Cell migration ,General Medicine ,medicine.disease ,Cadherins ,Lipid Metabolism ,0104 chemical sciences ,Cell biology ,Cell culture ,Cancer cell ,Matrix Metalloproteinase 2 ,Snail Family Transcription Factors - Abstract
In aggressive tumors, alkylglyceronephosphate synthase (AGPS) controls cellular ether phospholipid utilization and metabolism to promote cancer cell proliferation and motility. SAR studies on the first-in-class AGPS inhibitor 1, discovered by our group, led to the 2,6-difluoro analog 2i which showed higher binding affinity than 1 in vitro. In 231MFP cancer cells, 2i reduced ether lipids levels and cell migration rate. When tested in PC-3 and MDA-MB-231 cancer cells, 2i specifically impaired epithelial to mesenchymal transition (EMT) by modulating E-cadherin, Snail and MMP2 expression levels. Moreover, the combination of siRNAs against AGPS and 2i provided no additive effect, confirming that the modulation of 2i on EMT specifically relies on AGPS inhibition. Finally, this compound also affected cancer cell proliferation especially in MDA-MB-231 cells expressing higher AGPS level, whereas it provided negligible effects on MeT5A, a non-tumorigenic cell line, thus showing cancer specificity. more...
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- 2018
41. Synthesis of indolo[1,2
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Antonio, Arcadi, Sandro, Cacchi, Giancarlo, Fabrizi, Francesca, Ghirga, Antonella, Goggiamani, Antonia, Iazzetti, and Fabio, Marinelli
- Abstract
An efficient strategy for the synthesis of 6-unsubstituted indolo[1,2
- Published
- 2018
42. Palladium-Catalyzed Cascade Approach to 12-(Aryl)indolo[1,2- c ]quinÂazolin-6(5 H )-ones
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Fabio Marinelli, Sandro Cacchi, Antonio Arcadi, Francesca Ghirga, Giancarlo Fabrizi, Antonia Iazzetti, and Antonella Goggiamani
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polycycles ,quinazolinones ,Settore CHIM/06 - CHIMICA ORGANICA ,chemistry.chemical_element ,elimination ,indoles ,palladium ,trifluoromethane ,catalysis ,organic chemistry ,010402 general chemistry ,01 natural sciences ,Medicinal chemistry ,trifluoromethane elimination ,Catalysis ,chemistry.chemical_compound ,Indole test ,010405 organic chemistry ,Chemistry ,Aryl ,Triple bond ,0104 chemical sciences ,Cascade ,Palladium - Abstract
A straightforward one-pot approach to the synthesis of challenging 12-arylindolo[1,2-c]quinazolin-6(5H)-ones is described. Starting from readily available o-(o-aminophenylethynyl)trifluoroacetanilides, palladium-catalyzed aminoarylation of the triple bond with ArI, ArBr, and ArN2 +BF4 – is followed by cyclization of the resulting N-trifluoroacetyl-2-(o-aminophenyl)-3-aryl indole. This sequential reaction provides the title compounds by means of a rare elimination of trifluoromethane. more...
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- 2018
43. Copper-catalyzed C-N bond formation via C-H functionalization: facile synthesis of multisubstituted imidazo[1,2- a ]pyridines from N -(2-pyridinyl)enaminones
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Antonella Goggiamani, Giancarlo Fabrizi, Sandro Cacchi, Nicola Demitri, Francesca Ghirga, Doriano Lamba, Antonia Iazzetti, and Alessia Ciogli
- Subjects
cyclization ,Settore CHIM/06 - CHIMICA ORGANICA ,chemistry.chemical_element ,C-H functionalization ,C-N bond formation ,copper ,enaminones ,imidazo[1,2- a ]pyridines ,Catalysis ,Organic Chemistry ,02 engineering and technology ,imidazo[1 ,01 natural sciences ,Medicinal chemistry ,chemistry.chemical_compound ,Pyridine ,010405 organic chemistry ,Chemistry ,Bond formation ,021001 nanoscience & nanotechnology ,Copper ,0104 chemical sciences ,2- a ]pyridines ,Copper catalyzed ,Surface modification ,0210 nano-technology - Abstract
An efficient, new copper-catalyzed approach to the construction of the multisubstituted imidazo[1,2-a]pyridine skeleton from N-(2-pyridinyl)enaminones has been developed.
- Published
- 2018
- Full Text
- View/download PDF
44. A facile palladium-catalyzed route to 2,5,7-trisubstituted indoles
- Author
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Antonella Goggiamani, Antonia Iazzetti, Giancarlo Fabrizi, Rosanna Verdiglione, and Sandro Cacchi
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Indole test ,One-pot reactions ,Settore CHIM/06 - CHIMICA ORGANICA ,Organic Chemistry ,cross-coupling ,one-pot reactions ,palladium ,polysubstituted indoles ,biochemistry ,organic chemistry ,drug discovery3003 pharmaceutical science ,Substituent ,Sonogashira coupling ,chemistry.chemical_element ,Polysubstituted indoles ,Biochemistry ,Combinatorial chemistry ,Catalysis ,chemistry.chemical_compound ,chemistry ,Drug Discovery ,Cross-coupling ,Surface modification ,Organic chemistry ,Palladium - Abstract
A facile and general approach to the synthesis of 2,5,7-trisubstituted indoles from readily available 2-bromo-6-iodo-4-substituted and 2-bromo-4-chloro-6-iodoanilines is reported. The assembly of the indole rings is accomplished via a one-pot Sonogashira cross-coupling with terminal alkynes followed by a palladium-catalyzed cyclization step. The functionalization at C7 and at C5 (with indoles bearing a chloro substituent at C5) is carried out by alkynylations, Suzuki–Miyaura cross-couplings, and Buchwald-Hartwig C–N bond forming reactions. One-pot protocols for the synthesis of 2,5,7-trisubstituted indoles from 2-aryl-7-bromo-5-chloroindoles as well as from 2-bromo-4-chloro-6-iodoaniline are also described. more...
- Published
- 2015
- Full Text
- View/download PDF
45. Palladium-Catalyzed Nucleophilic Substitution of Propargylic Carbonates and Meldrum's Acid Derivatives
- Author
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Ilaria Ambrogio, Giancarlo Fabrizi, Sandro Cacchi, Antonia Iazzetti, and Antonella Goggiamani
- Subjects
Substitution reaction ,Chemistry ,Organic Chemistry ,chemistry.chemical_element ,Homogeneous catalysis ,Meldrum's acid ,Catalysis ,chemistry.chemical_compound ,Nucleophilic substitution ,Organic chemistry ,Acid hydrolysis ,Stereoselectivity ,Physical and Theoretical Chemistry ,Palladium - Abstract
The palladium-catalyzed reaction of propargylic carbonates with Meldrum's acid derivatives proceeds smoothly in the presence of Pd(OAc)2 and P(2-furyl)3 in THF at 80 °C to give substitution products. The substitution products can be useful intermediates for the stereoselective synthesis of functionalized (Z)-γ-alkylidene-γ-butyrolactones. more...
- Published
- 2015
- Full Text
- View/download PDF
46. Palladium-Catalyzed Synthesis of 2-(Aminomethyl)indoles from 3-(o-Trifluoroacetamidoaryl)-1-propargylic Alcohols and Amines
- Author
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Sandro Cacchi, Carmela Molinaro, Antonella Goggiamani, Giancarlo Fabrizi, and Rosanna Verdiglione
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Indoles ,Molecular Structure ,Propanols ,Chemistry ,Organic Chemistry ,chemistry.chemical_element ,Stereoisomerism ,Catalysis ,Alkynes ,Molecule ,Organic chemistry ,Palladium - Abstract
A novel palladium-catalyzed approach to 2-(aminomethyl)indoles from 3-(o-trifluoroacetamidoaryl)-1-propargylic alcohols and amines has been developed.
- Published
- 2013
- Full Text
- View/download PDF
47. Sequential alkylation/cyclization/isomerization of ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic esters: a new route to 2-acyl- and 2-ethoxycarbonyl-3-alkenyl indoles
- Author
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Ilaria Ambrogio, Giancarlo Fabrizi, Antonella Goggiamani, Sandro Cacchi, Antonio Arcadi, and Fabio Marinelli
- Subjects
Propargylic carbonates ,Sequential reactions ,Indoles ,cyclization ,Chemistry ,indoles sequential reactions ,Organic Chemistry ,Ethyl iodoacetate ,Alkylation ,Biochemistry ,indoles ,intramolecular sn2′ ,propargylic carbonates ,sequential reactions ,chemistry.chemical_compound ,Drug Discovery ,Organic chemistry ,Isomerization - Abstract
The reaction of ethyl 3-(o-trifluoroacetamidoaryl)-1-propargylic esters with ethyl iodoacetate or α-bromoacetophenone in the presence of K2CO3 in DMSO provides a new simple access to 2-acyl- and 2-ethoxycarbonyl-3-alkenyl indoles. more...
- Published
- 2013
- Full Text
- View/download PDF
48. Copper-Catalyzed Oxidation of Deoxybenzoins to Benzils under Aerobic Conditions
- Author
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Antonia Iazzetti, Giancarlo Fabrizi, Antonella Goggiamani, Rosanna Verdiglione, and Sandro Cacchi
- Subjects
oxidation ,Settore CHIM/06 - CHIMICA ORGANICA ,Organic Chemistry ,chemistry.chemical_element ,benzils ,catalysis ,copper ,deoxybenzoins ,Copper ,Catalysis ,chemistry ,Copper catalyzed ,Organic chemistry ,heterocyclic compounds - Abstract
A novel copper-catalyzed approach to benzils from readily available deoxybenzoins under neutral conditions using air as the oxidant has been developed. The reaction tolerates a variety of useful substituents including chloro, bromo, iodo, keto, ester, and cyano groups. more...
- Published
- 2013
- Full Text
- View/download PDF
49. ChemInform Abstract: Construction of the 1,5-Benzodiazepine Skeleton from o-Phenylendiamine and Propargylic Alcohols via a Domino Gold-Catalyzed Hydroamination/Cyclization Process
- Author
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Sandro Cacchi, Giancarlo Fabrizi, Antonella Goggiamani, and Antonia Iazzetti
- Subjects
Chemistry ,Scientific method ,General Medicine ,Hydroamination ,Combinatorial chemistry ,Domino ,Catalysis - Abstract
The gold-catalyzed reaction of o-phenylendiamine with propargylic alcohols affords 1,5-benzodiazepines bearing different substituents on the 2 and 4 positions. The method allows even for the selective preparation of 4-substituted 1,5-benzodiazepine derivatives. more...
- Published
- 2016
- Full Text
- View/download PDF
50. Total Synthesis of (±)-Kuwanol E
- Author
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Andrea Calcaterra, Bruno Botta, Irene Benni, Ilaria D'Acquarica, Rocchina Sabia, Valentina Iovine, and Giancarlo Fabrizi
- Subjects
Models, Molecular ,Stereochemistry ,Cyclohexene ,Pharmaceutical Science ,Ether ,010402 general chemistry ,01 natural sciences ,Analytical Chemistry ,Adduct ,Stereocenter ,chemistry.chemical_compound ,Chalcones ,Drug Discovery ,Cyclohexenes ,Pharmacology ,Flavonoids ,Molecular Structure ,010405 organic chemistry ,Organic Chemistry ,Intermolecular force ,Temperature ,Total synthesis ,Stereoisomerism ,Cycloaddition ,0104 chemical sciences ,Complementary and alternative medicine ,chemistry ,Molecular Medicine ,Derivative (chemistry) - Abstract
The total synthesis of the Diels–Alder-type adducts (±)-kuwanol E and the heptamethyl ether derivative of (±)-kuwanon Y has been accomplished via a convergent strategy involving 2′-hydroxychalcone 6 or 9 and dehydroprenylstilbene 7, in nine steps. The synthesis features, as a key step, a Lewis acid-mediated biomimetic intermolecular Diels–Alder [4+2] cycloaddition for the construction of the cyclohexene skeleton with three stereogenic centers. Notably, the endo/exo diastereoselectivity of the reaction proved to be temperature-controlled. more...
- Published
- 2016
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