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Comprehensive Summary: The first catalytic asymmetric total synthesis of (+)‐propolisbenzofuran B, enabled by a highly enantioselective rhodium‐catalyzed hydrogenation of a tetrasubstituted olefin, was described. Other noteworthy aspects include the construction of the central hydrodibenzo[b,d]furan core through a sequence of Zn(II)‐mediated regioselective benzofuran formation and Dieckmann condensation, as well as C‐H oxidations, involving a visible light‐induced Fe(III)‐catalyzed benzylic C(sp3)‐H oxidation. Additionally, the absolute configuration was confirmed by X‐ray analysis of a carbonate intermediate. [ABSTRACT FROM AUTHOR]

Comprehensive Summary: The first catalytic asymmetric total synthesis of (+)‐propolisbenzofuran B, enabled by a highly enantioselective rhodium‐catalyzed hydrogenation of a tetrasubstituted olefin, was described. Other noteworthy aspects include the construction of the central hydrodibenzo[b,d]furan core through a sequence of Zn(II)‐mediated regioselective benzofuran formation and Dieckmann condensation, as well as C‐H oxidations, involving a visible light‐induced Fe(III)‐catalyzed benzylic C(sp3)‐H oxidation. Additionally, the absolute configuration was confirmed by X‐ray analysis of a carbonate intermediate. [ABSTRACT FROM AUTHOR]

MRSA, a resistant bacteria causing severe infections, is targeted by researchers developing new anti-resistance compounds. The study aimed to investigate the MRSA inhibitory activity of two series of benzofuran-pyrazolo[1,5-a]pyrimidines 1 and 2, attached to arene units via methylene or azo linkage, respectively. The desired products were prepared, in 82–92% yields, by reacting benzofuran-based enaminone 4 with the appropriate 1H-pyrazole-3,5-diamines 5 in pyridine at reflux for 5–6 h. The new hybrids showed a wide spectrum of antibacterial activity against different ATCC strains. Products with azo linkage and para-substituted arene units with electron-releasing groups demonstrated higher antibacterial activity. 3-((4-Methoxyphenyl)diazenyl)-linked pyrazolo[1,5-a]pyrimidine 2e demonstrates activity that exceeded the reference ciprofloxacin with MIC/MBC values of 1.8/3.6 µM against S. aureus and E. coli strains. Also, it demonstrated more effective MRSA inhibitory activity than the reference linezolid, with MIC/MBC values of 3.6/14.4 and 1.8/7.2 µM against MRSA ATCC:33591 and ATCC:43300 strains, respectively. [ABSTRACT FROM AUTHOR]

Following a request from the European Commission, EFSA was asked to deliver a scientific opinion on the assessment of the application for the renewal of authorisation of a preparation containing a smoke flavouring extract for cats and dogs. The applicant provided data demonstrating that the additive currently on the market does not fully comply with the conditions of authorisation, but with newly proposed specifications based on different analytical methods. Considering that the additive under assessment contains benzofuran and styrene, for which a potential concern for genotoxicity has been identified, and that the whole mixture raises a potential concern for genotoxicity, additional data would be needed to complete the assessment. Therefore, the FEEDAP Panel is not in the position to conclude on the safety for cats and dogs. The additive is authorised for use in feed for cats and dogs, and therefore, there is no need to perform an assessment of the safety for the consumer and the environment. Regarding user safety, the additive should be considered as irritant to skin and eyes, and as a dermal and respiratory sensitiser. When handling the additive, exposure of unprotected users to potential genotoxic substances may occur. Therefore, to reduce the risk, the exposure of the users should be minimised. There was no need for assessing the efficacy of the additive in the context of the renewal of the authorisation. [ABSTRACT FROM AUTHOR]

2-Chloropyridine-3-carbonitrile derivative 1 was utilized as a key precursor to build a series of linear and angular annulated pyridines linked to a 6-hydroxy-4,7-dimethoxybenzofuran moiety. Reaction of substrate 1 with various hydrazines afforded pyrazolo[3,4-b]pyridines. Treatment of substrate 1 with 1,3-N,N-binucleophiles including 3-amino-1,2,4-triazole, 5-amino-1H-tetrazole, 3-amino-6-methyl-1,2,4-triazin-5(4H)-one and 2-aminobenzimidazole produced the novel angular pyrido[3,2-e][1,2,4]triazolo[4,3-a]pyrimidine, pyrido[3,2-e][1,2,4]tetrazolo[1,5-a]pyrimidine, pyrido[3′,2′:5,6] pyrimido[2,1-c][1,2,4]triazine and benzo[4,5]imidazo[1,2-a]pyrido[3,2-e]pyrimidine, respectively. Reaction of substrate 1 with 1,3-C,N-binucleophiles including cyanoacetamides and 1H-benzimidazol-2-ylacetonitrile furnished 1,8-naphthyridines and benzoimidazonaphthyridine. Moreover, reacting substrate 1 with 5-aminopyrazoles gave pyrazolo[3,4-b][1,8]naphthyridines. Finally, reaction of compound 1 with 6-aminouracils as cyclic enamines yielded pyrimido[4,5-b][1,8]naphthyridines. Some of the synthesized products showed noteworthy antimicrobial efficiency against all types of microbial strains. Structures of the produced compounds were established using analytical and spectroscopic tools. [ABSTRACT FROM AUTHOR]

One undescribed benzofuran derivative (illiciumphenolicacid A, 1) and one new phenolic glycoside (illiciumphenolicacid B, 2), together with six known compounds (3–8) were isolated from the leaves of Illicium dunnianum Tutcher. Their structures were elucidated by detailed spectroscopic data (UV, IR, HR-ESI-MS, 1D and 2D NMR). In addition, we determined the α-glucosidase inhibitory activity of the isolates in vitro using spectrophotometric methods. Compared with the positive control acarbose (IC50 306.2 ± 4.1 μM), compounds 1–8 were shown to be moderate potential α-glucosidase inhibitory activity with IC50 values in the range 380–655 μM. [ABSTRACT FROM AUTHOR]

ABSTRACT A rapid and efficient protocol for synthesizing two series of benzofuran‐based hybrid polyheterocycles is presented: benzofuran‐isatin and benzofuran N‐acylhydrazones, and evaluation of their antibacterial activity both in vitro and in silico against two strains of Pseudomonas aeruginosa, PAO1 and PA14 were determined. Six of the tested compounds were shown to be active against the hypervirulent strain PA14. Docking studies were conducted using RNA polymerase sigmaS protein for P. aeruginosa PAO1 and PqsE protein for P. aeruginosa PA14 to provide additional insights into these results. A pharmacophore model was computed to suggest potential structural derivatives on the target molecules, offering further insights for future research. Finally, 40 novel compounds, including intermediates, were synthesized in a three‐step reaction. [ABSTRACT FROM AUTHOR]

A catalyst-free one-pot synthetic protocol is presented for the preparation of CF3-containing benzofuran, indolin, and benzothiophene derivatives using readily available aromatic aldehydes and ketones. 2-Bromo-3,3,3-trifluoropropene was employed as a non-corrosive and environmentally benign trifluoromethylacetylene synthon for incorporation of the CF3 group. The reaction proceeds via the formation of a suitably substituted 4,4,4-trifluoro-1-phenylbut-2-yn-1-ol intermediate, which undergoes 5-exo-dig cyclization, resulting in an exocyclic double bond with Z-configuration. The synthetic utility, substrate scope, tolerance to broader substrates are also presented. [ABSTRACT FROM AUTHOR]

Hydrazine, a compound known for its toxicity to human health and the environment, finds extensive use across various industries and potentially contributes to several diseases. Hence, the accurate measurement of hydrazine levels is paramount. This study introduces three new aggregation induced emissive luminogens (AIEgens) GBY-7, GBY-8, and GBY-9 crafted from benzofuran infused with a dicyanovinylidene group, tailored specifically for hydrazine monitoring. These probes feature a D–π–A core with a rotor, providing an optimal fluorescent base. Additionally, a potent electron-attracting nitrile group aids in the nucleophilic addition of N2H4 to form hydrazone, thereby blocking the intramolecular charge transfer (ICT) process and inducing optical signal modulation. Notably, luminogens GBY-8 and GBY-9 exhibit high selectivity in detecting hydrazine amidst competing amine-based compounds, showing detection limits of 0.00020 mM and 0.0043 mM, respectively. [ABSTRACT FROM AUTHOR]

Streptomyces aureofaciens widely produces the antibiotic tetracycline and many other compounds during fermentation. The compounds have yet to be known for their antibacterial potential. This work aims to determine new antibiotics or other possible antibacterial compounds produced by marine S.aureofaceiens A3 through an in silico molecular docking method. The ethyl acetate (EA) extracts from fermented marine S. aureofaciens A3 in ISP4 medium enriched with seawater components showed strong antibacterial activity. The antibacterial activity of EA extracts during 6-12 days of fermentation was carried out by the Kirby-Bauer method and the compounds of EA extracts were analyzed by GC/MS. Compounds identified by GC/MS were ligands for an in silico molecular docking study against four target proteins (DNA gyrase, topoisomerase IV, PBP 1a, and DHFR) of pathogenic bacteria. The drug-likeness of selected chemicals as antibacterial agents was assessed using Lipinski's Rule of Five. The results showed the prospective compounds as a narrow-spectrum antibacterial, including 3,5-di-tert-Butyl-4-hydroxyphenylpropionic acid against PBP 1a and Benzenepropanoic acid, and 3,5-bis (1,1-dimethyl ethyl)-4-hydroxy-, methyl esters against DHFR. Substances with broad-spectrum antibacterial activity, such as 3-Acetylphenanthrene and 3-(p-Ethoxyphenyl)-5-(O-tolyloxymethyl)-2-oxazolidone, against multitarget DNA gyrase B and DHFR, 7,9-Di-tert-butyl-1-oxaspiro (4,5) Deca-6,9-diene-2,8-dione against PBP1a and DHFR, and isobenzofuro [5,6-b] benzofuran-8-carboxylic acid, 1,3-dihydro-7,10-dimethoxy-9-methyl-1-oxo-, methyl ester against DNA gyrase B, PBP 1a, and DHFR. On the 12th day of fermentation, two compounds were identified: isobenzofuro[5,6-b] benzofuran-8-carboxylic acid, 1,3-dihydro-7,10-dimethoxy-9-methyl-1-oxo-, methyl ester, and 3-(p-Ethoxyphenyl)-5-(O-tolyl oxy methyl)-2-oxazolidone. This is the first report that these two compounds, known as potential drugs like antibiotics through in silico molecular docking, were first produced by Streptomyces species. [ABSTRACT FROM AUTHOR]

Natural compounds are important precursors for the synthesis of new drugs. The development of novel molecules that are useful for various diseases is the main goal of researchers, especially for the diagnosis and treatment of many diseases. Some pathologies need to be treated with radiopharmaceuticals, and, for this reason, radiopharmaceuticals that use the radiolabeling of natural derivates molecules are arousing more and more interest. Radiopharmaceuticals can be used for both diagnostic and therapeutic purposes depending on the radionuclide. β+- and gamma-emitting radionuclides are used for diagnostic use for PET or SPECT imaging techniques, while α- and β−-emitting radionuclides are used for in metabolic radiotherapy. Based on these assumptions, the purpose of this review is to highlight the studies carried out in the last ten years, to search for potentially useful radiopharmaceuticals for nuclear medicine that use molecules of natural origin as lead structures. In this context, the main radiolabeled compounds containing natural products as scaffolds are analyzed, in particular curcumin, stilbene, chalcone, and benzofuran. Studies on structural and chemical modifications are emphasized in order to obtain a collection of potential radiopharmaceuticals that exploit the biological properties of molecules of natural origin. The radionuclides used to label these compounds are 68Ga, 44Sc, 18F, 64Cu, 99mTc, and 125I for diagnostic imaging. [ABSTRACT FROM AUTHOR]

A highly diastereo‐ and enantioselective organocatalytic Michael addition of α‐aryl isocyanoacetates to aurone‐derived azadienes under mild conditions has been developed. This efficient methodology enables access to chiral α,α‐disubstituted α‐amino ester derivatives with two adjacent stereocenters, one of them quaternary, bearing a benzofuran scaffold in their structure in high yields and stereocontrol. Furthermore, the reaction product can be readily converted into an α,α‐disubstituted α‐amino acid in high yield via hydrolysis of the isocyano group without compromising enantioselectivity. [ABSTRACT FROM AUTHOR]

An efficient cascade cyclization strategy was developed to synthesize aminobenzofuran spiroindanone and spirobarbituric acid derivatives utilizing 2-bromo-1,3-indandione, 5-bromo-1,3-dimethylbarbituric acid, and ortho-hydroxy α-aminosulfones as substrates. Under the optimized reaction conditions, the corresponding products were obtained with high efficiency, exceeding 95% and 85% yields for the respective derivatives. This protocol demonstrates exceptional substrate versatility and robust scalability up to the Gram scale, establishing a stable platform for the synthesis of 3-aminobenzofuran derivative. The successful synthesis paves the way for further biological evaluations with potential implications in scientific research. [ABSTRACT FROM AUTHOR]

We report an unprecedented iron‐catalyzed C−H annulation using readily available 2‐vinylbenzofurans as the reaction pattern. The redox‐neutral strategy, based on cheap, non‐toxic, and earth‐abundant iron catalysts, exploits triazole assistance to promote a cascade C−H alkylation, benzofuran ring‐opening and insertion into a Fe−N bond, to form highly functionalized isoquinolones. Detailed mechanistic studies supported by DFT calculations fully disclosed the manifold of the iron catalysis. [ABSTRACT FROM AUTHOR]

Developing pragmatic strategies for accessing functional benzofuran‐2‐ones from 3‐([1,1′‐biphenyl]‐2‐yl)benzofuran remains an enduring challenge. Herein, we have achieved a highly discriminating electrochemical oxidative dearomative spiroannulation of 3‐([1,1′‐biphenyl]‐2‐yl)benzofuran, culminating in the synthesis of 2H‐spiro[benzofuran‐3,9′‐fluoren]‐2‐one derivatives. By harnessing the electrophilic intermediates of benzofuryl radical cations supported by DFT calculations, we attain exceptional regioselectivity while eliminating the need for stoichiometric oxidants. Mechanistic investigations reveal a sequence of events involving the benzofuran radical cation, encompassing the capture of H2O, nucleophilic arene attack, and subsequent deprotonation, ultimately yielding the final benzofuran‐2‐ones. [ABSTRACT FROM AUTHOR]

The benzofuran core inhibitors HCV-796, BMS-929075, MK-8876, compound 2, and compound 9B exhibit good pan-genotypic activity against various genotypes of NS5B polymerase. To elucidate their mechanism of action, multiple molecular simulation methods were used to investigate the complex systems of these inhibitors binding to GT1a, 1b, 2a, and 2b NS5B polymerases. The calculation results indicated that these five inhibitors can not only interact with the residues in the palm II subdomain of NS5B polymerase, but also with the residues in the palm I subdomain or the palm I/III overlap region. Interestingly, the binding of inhibitors with longer substituents at the C5 position (BMS-929075, MK-8876, compound 2, and compound 9B) to the GT1a and 2b NS5B polymerases exhibits different binding patterns compared to the binding to the GT1b and 2a NS5B polymerases. The interactions between the para-fluorophenyl groups at the C2 positions of the inhibitors and the residues at the binding pockets, together with the interactions between the substituents at the C5 positions and the residues at the reverse β-fold (residues 441–456), play a key role in recognition and the induction of the binding. The relevant studies could provide valuable information for further research and development of novel anti-HCV benzofuran core pan-genotypic inhibitors. [ABSTRACT FROM AUTHOR]

A class of novel chiral‐bridged biphenyl monophosphine ligands with a benzofuran moiety (He‐phos) has been successfully synthesized and reported. These ligands exhibited good performance in the gold‐catalyzed enantioselective cycloaddition reaction of 2‐(1‐alkynyl)‐2‐en‐1‐ones with nitrones, resulting in the successful preparation of a series of polyaryl‐substituted heterocyclic compounds with high enantioselectivities (up to 99% yield, 98% ee). The wide substrate adaptability (53 examples) and mild reaction conditions demonstrate the practicability of He‐phos in this reaction. [ABSTRACT FROM AUTHOR]

N,N‐dialkylbenzofuran‐ and N,N‐dialkylbenzothiophene‐2‐carboxamides were readily prepared from bare benzofuran and benzothiophene by deprotocupration followed by trapping with N,N‐dialkylcarbamoyl chlorides. They were reacted with 2‐benzofuryl‐ and 2‐benzothienyllithiums to form symmetrical and unsymmetrical diarylketones, or underwent deprotolithiation‐electrophilic trapping sequences at their 3 position. From 3‐iodinated derivatives, copper‐catalysed N‐arylation of azoles was performed, followed by lithium amide‐promoted cyclisation, to give 'tripentone' analogues. The diarylketones were also iodinated at their 3,3' positions and then engaged in the copper‐promoted double N‐arylation of anilines, giving rise to a family of original pentacyclic derivatives. A preliminary assessment of their electrochemical and biological properties was carried out, showing promising results against the proliferation of melanoma cells. [ABSTRACT FROM AUTHOR]

A new benzofuran, named as (2S, 3S)-5,6-dimethoxy-3-methyl-2-(3'-hydroxyphenyl)-2,3-dihydrobenzofuran (1), along with the six known isoflavonoids, 2'-hydroxy-4',7-dimethoxyisoflavone (2), 2' ²-methoxybiochanin A (3), tectorigenin (4), calycosin (5), 7-hydroxy-2',4',5'-trimethoxyisoflavone (6), orobol (7) were isolated from the heartwood of Dalbergia odorifera T.Chen. The structure of compounds was characterised by NMR spectroscopic data and comparisons with relevant literature data. The absolute structural configuration of compound 1 was determined through X-ray single crystal diffraction. Moreover, compounds 1-7 have no significant cytotoxic effects on H9c2 cells (IC50 > 200 μM). Compound 1-7 exhibit a significant protective effect against H/R (hypoxia/reoxygenation) induced H9c2 cell damage at 10~40, 5~40, 5~40, 5~40, 5~40, 5~40 and 5~10 μM (P≩0.05). [ABSTRACT FROM AUTHOR]

A series of new pyrazole‐alkyl phosphine ligands with varying cycloalkyl ring sizes that enable additive‐free regio‐ and chemoselective C─H arylation of heterocycles are reported. Excellent α/β selectivity of various heterocycles such as benzo[b]thiophene, thiophene, furan, benzofuran, and thiazole can be achieved using these ligands, along with excellent chemoselectivity of C─Cl over C─OTf of chloroaryl triflates. Mechanistic studies supported by both experimental findings and density functional theory calculations indicate that the pyrazole phosphine ligands with optimal ring sizes allow the reaction to proceed with a lower energy barrier via a concerted metalation–deprotonation pathway. [ABSTRACT FROM AUTHOR]

This article explores the synthesis of medium-sized lactones, which are important structural components in natural products and pharmaceuticals. The authors provide examples of specific lactones and their biological activities. They then discuss their own research on synthesizing benzannulated lactams and lactones using a specific starting material and different reaction conditions. The article includes a table summarizing their experimental results, demonstrating the formation of various lactones. The authors conclude by discussing the implications and potential applications of their findings. The study was supported by Evonik Industries, and the authors express gratitude to individuals who assisted in the laboratory. [Extracted from the article]

A concise and efficient synthetic protocol for the synthesis of furan-based bis-stilbene derivatives (BPBFCz1) was described, which is a very promising organic laser dye. Starting with 4,4'-diethynylbiphenyl, BPBFCz1 was prepared with a total yield of 40% through a three-step classical reaction of Sonogashira Coupling, intramolecular cyclization of 2-alkynyl phenol, and Buchwald Hartwig cross-coupling. The crystal structure of BPBFCz1 was presented for the first time. The synthesis strategy was applied to the synthesis of other three materials with similar structure and the yields of 28.6–36.6% were obtained. [ABSTRACT FROM AUTHOR]

Abstract Following a request from the European Commission, EFSA was asked to deliver a scientific opinion on the assessment of the application for the renewal of authorisation of a preparation containing a smoke flavouring extract for cats and dogs. The applicant provided data demonstrating that the additive currently on the market does not fully comply with the conditions of authorisation, but with newly proposed specifications based on different analytical methods. Considering that the additive under assessment contains benzofuran and styrene, for which a potential concern for genotoxicity has been identified, and that the whole mixture raises a potential concern for genotoxicity, additional data would be needed to complete the assessment. Therefore, the FEEDAP Panel is not in the position to conclude on the safety for cats and dogs. The additive is authorised for use in feed for cats and dogs, and therefore, there is no need to perform an assessment of the safety for the consumer and the environment. Regarding user safety, the additive should be considered as irritant to skin and eyes, and as a dermal and respiratory sensitiser. When handling the additive, exposure of unprotected users to potential genotoxic substances may occur. Therefore, to reduce the risk, the exposure of the users should be minimised. There was no need for assessing the efficacy of the additive in the context of the renewal of the authorisation.

2-Chloro-5-[(6-hydroxy-4,7-dimethoxy-1-benzofuran-5-yl)carbonyl]pyridine-3-carbonitrile (3) was synthesized and its chemical reactivity was investigated toward a diversity of binucleophiles. Treatment of compound 3 hydrazine hydrate and phenylhydrazine produced pyrazolo[3,4-b]pyridines while isoxazolo[5,4-b]pyridine was obtained from reacting compound 3 with hydroxylamine. A diversity of pyrido[2,3-d]pyrimidines was synthesized from treatment of staring substrate 3 with some 1,3-N,N-binucleophiles. Treating compound 3 with some 1,4-binucleophiles including ethylenediamine, o-phenylenediamine, 2-aminophenol and 2-aminothiophenol furnished pyrido[2,3-e][1,4]diazepine 12 and pyrido[2,3-b][1,5] benzodiazepine 13, pyrido[2,3-b][1,5]benzoxazepine 14 and pyrido[2,3-b][1,5] benzothiazepine 15, respectively. The synthesize compounds shown remarkable effect against yeast and fungus, while compounds 4 and 7–11 exhibit excellent efficacy against all types of Gram + and Gram - bacteria. Structures of the produced compounds were established using analytical and spectroscopic tools. [ABSTRACT FROM AUTHOR]

The fruit of Choerospondias axillaris (Anacardiaceae), known as south wild jujube in China, has been consumed widely in several regions of the world to produce fruit pastille and leathers, juice, jam, and candy. A comprehensive chemical study on the fresh fruits led to the isolation and identification of 18 compounds, including 7 new (1–7) and 11 known (8–18) comprised of 5 alkenyl (cyclohexenols and cyclohexenones) derivatives (1–5), 3 benzofuran derivatives (6–8), 6 flavonoids (9–14) and 4 lignans (15–18). Their structures were elucidated by extensive spectroscopic analysis. The known lignans 15–18 were isolated from the genus Choerospondias for the first time. Most of the isolates exhibited significant inhibitory activity on α-glucosidase with IC50 values from 2.26 ± 0.06 to 43.9 ± 0.96 μM. Molecular docking experiments strongly supported the potent α-glucosidase inhibitory activity. The results indicated that C. axillaris fruits could be an excellent source of functional foods that acquire potential hypoglycemic bioactive components. [ABSTRACT FROM AUTHOR]

Treatment of copper iodide with 1,1′-bis(diphenylphosphino)ferrocene in 1:1 equivalent ratio afforded centrosymmetric dimer product of composition [{Cu(µ-I)(dppf)}2] (1a). However, similar reactions of 1,1′-bis(diphenylchalcogenophosphoryl)ferrocene (dppfE2) (E = S, Se) with [Cu(CH3CN)4]+ in 1:2 equivalents yielded [{Cu(dppfS2)}n]+ (1b) and [{Cu2(dppfSe2)3}n]2+ (1c) compounds, respectively. These reported compounds have synthesized with slight modifications. All the mentioned complexes were characterized by Uv–Vis, IR, 1H, 31P{1H} NMR spectroscopy and Mass spectrometry. The molecular structure of complex [{Cu(µ-I)(dppf)}2] was established through single crystal X-ray analysis, which suggests distorted tetrahedral geometry around the copper metal center. All the synthesized complexes were studied as a catalyst for synthesis of benzofuran derivatives under an environmentally friendly approach. [ABSTRACT FROM AUTHOR]

This paper presents four one‐component Type II visible‐light‐absorbing chalcones (CY10‐13) that containing various fused aromatic rings as its π‐conjugated moiety, that is a 2‐naphthalene moiety for CY10, 1‐naphthalene for CY11, benzofuran for CY12, and benzothiophene for CY13. The absorption region changes significantly when introducing various fused aromatic rings. However, they all exhibit good absorption properties ranging from 300 to 450 nm that can be well‐matched under ultraviolet (UV), 365 and 405 nm light irradiations. Furthermore, the structure–reactivity relationship is also studied through thermal, photochemical, electrochemical, and computation properties. Finally, all the chalcones demonstrate photoinitiating ability without additive additional hydrogen donor in their systems. Both of the CY11 and CY12 based photoinitiating formulations initiate sufficiently upon UV and light‐emitting diode (LED)@405 nm light exposures. Furthermore, triphenylamine‐substituted chalcone analogous (CY8) is added for comparison. Although CY10‐13 compounds have lower light harvesting regions than CY8, some of those new chalcones exhibit better photoreactivity. Thus, a chalcone containing fuses aromatic ring featuring straightforward synthesis as well as versatile absorption region and photoinitiating performance, has great potential in photopolymerization applications. [ABSTRACT FROM AUTHOR]

In this paper, nickel (Ni)-tungsten (W) bimetallic carbide nanoparticles with different W : Ni ratios were prepared, and the catalytic deoxidation and hydrodeoxidation activities of the carbides were significantly improved by the modification and synergistic effect of the newly added second metal on the monometallic carbides. Pure phase Ni6W6C and W2C/Ni6W6C composites with different Ni contents were synthesized via organic and inorganic hybrid method. The structure and morphology of bimetallic carbides were characterized by XRD, XPS, BET, TEM, and SEM, and the Hydrodeoxygenation activity of bimetallic carbides was detected by hydrodeoxidationb reaction of benzofuran. Results showed that W2C and Ni–W bimetallic carbides had synergistic effects at certain W/Ni ratio. Even the formation of a small amount of Ni–W bimetallic carbides can significantly improve the catalytic activity. When the atomic ratio of W:Ni was 6 (the mass fraction of nickel is only 5%), the catalytic deoxidation activity and hydrogenation activity of Ni–W bimetallic carbides were 17 and 11 times higher than that of W2C, respectively. [ABSTRACT FROM AUTHOR]

An attractive approach for the preparation of spirocyclic benzofuran–furocoumarins has been developed through iodine-catalyzed cascade annulation of 4-hydroxycoumarins with aurones. The reaction involves Michael addition, iodination, and intramolecular nucleophilic substitution in a one-step process, and offers an efficient method for easy access to a series of valuable spirocyclic benzofuran–furocoumarins in good yields (up to 99%) with excellent stereoselectivity. Moreover, this unprecedented protocol provides several advantages, including readily available materials, an environmentally benign catalyst, a broad substrate scope, and a simple procedure. [ABSTRACT FROM AUTHOR]

In search of novel antimicrobial agents, new series of N-(arylsulfonyl)-l-proline-derived hybrids tethered with pharmacologically attractive cores as 1-(3-Methyl-1-phenyl-1H-pyrazol-5-yl)piperazine and 5-(Piperazin-1-yl)benzofuran-2-carboxamide were synthesized and evaluated for in vitro antimicrobial potential against six different representative human pathogenic strains. Among all, N-acetyl derivative 5e containing phenylpyrazolyl moiety displayed an appreciable inhibitory value (MIC: 107 µg/mL) with noteworthy binding energy (–6.65 kcal/mol) against S. aureus as compared to standard ampicillin (MIC: 250 µg/mL). The N-phenyl-pyrazolyl containing analogue 5b elicited comparable activity against E. coli and P. aeruginosa with MIC values of 104 µg/mL and 121 µg/mL, respectively. Moreover, 5b, 5d, and 6c showed appreciable antioxidant activity (IC50:19.25–20.69 µg/mL) as compared to butylated hydroxytoluene (BHT, IC50:16.47 μg/mL). Molecular docking studies against target tyrosyl-tRNA synthetase (TyrRS) of S. aureus (PDB: 1JIJ) revealed the potential binding mode of the ligands to the appropriate site of targets and their plausible mechanism of in vitro antibacterial activity. [ABSTRACT FROM AUTHOR]

Pd‐catalyzed cyclization of a fluorescent dimer in which two cores of the potent estrogenic estradiol are bridged by the 1,4‐diethynil benzene moiety led to a steroid dimer bearing the 1,4‐di(benzofuran‐2‐yl)benzene. The obtained compound showed an intense blue fluorescence characterized by a broad emission band between 350 and 550 nm, with four maxima at 384, 403, 435, and 456 nm. The benzofuran dimer showed an 18‐fold increased quantum yield compared with that of its synthetic precursor. [ABSTRACT FROM AUTHOR]

Malaria remains a severe infectious disease caused by Plasmodium parasites among the primarily afflicting impoverished populations. According to World Health Organization (WHO) report, there were an estimated 247 million malarial cases globally, resulting in approximately 6,19,000 fatalities. Particularly prevalent in tropical and subtropical regions, the development of drug resistance has exacerbated this public health challenge. Consequently, there has been a concrete effort to explore novel compounds with anti‐malarial properties. In continuation of our previous works, this review focuses on heterocyclic compounds documented in 2021 and 2022, including artemisinin, benzimidazole, benzofuran, β‐lactam, coumarin, furan, indole, morpholine, piperazine, pyrimidine, quinoline, triazole, etc. highlighting their efficacy, structural characteristics, in vitro and in vivo activities, among other relevant aspects for the broad interest of medicinal chemists working on the design and development of novel anti‐malarial agents. [ABSTRACT FROM AUTHOR]

Heteroacenes are considered as an important class of compounds for material applications due to their stability, electron‐richness and tunable properties. Mostly, four ring containing heteroacenes have found immense applications in organic electronic devices and some of them have been successfully commercialized. One such class of heteroacene are benzothienobenzofuran for which four different isomers are reported to date based on the position where the benzothiophene unit is fused to the benzofuran ring. The available literature claims different synthetic strategies towards the benzothienobenzofurans starting from multistep synthesis to tandem transformations, electrochemical synthesis and annulations. Different metal catalyzed transformations including Pd‐catalyzed dual C−H activations, Ullmann coupling, dual metal‐catalyzed one‐pot processes etc. are reported for the synthesis of different isomers of benzothienobenzofurans. The present review analyses all the synthetic methodologies reported for the preparation of the four isomers and examines the generality of each method by highlighting its advantages and disadvantages. We discuss all available mechanisms of the reactions for the benefit of the readers. Finally, the existing basic photophysical properties of benzothienobenzofurans and their limited applications in fabricating devices for organic light‐emitting diode (OLED), organic field‐effect transistor (OFET), and organic phototransistor (OPT) uses are deliberated [ABSTRACT FROM AUTHOR]

The reaction of a mixture of equimolar quantities of 2-acetylbenzofuran and (2,4,6-trichlorophenyl)hydrazine in ethanol containing concentrated hydrochloric acid (0.2 mL; 37%) as a catalyst under reflux for two hours yielded 1-(1-(benzofuran-2-yl)ethylidene)-2-(2,4,6-trichlorophenyl)hydrazine. The crude product was purified by crystallization using dimethylformamide to provide the title heterocycle in a 90% yield. The structure of the new heterocycle was confirmed through X-ray diffraction and spectral analyses. [ABSTRACT FROM AUTHOR]

2-Chloropyridine-3-carbonitrile derivative 1 was utilized as a key precursor to build a series of linear and angular annulated pyridines linked to a 6-hydroxy-4,7-dimethoxybenzofuran moiety. Reaction of substrate 1 with various hydrazines afforded pyrazolo[3,4-b]pyridines. Treatment of substrate 1 with 1,3-N,N-binucleophiles including 3-amino-1,2,4-triazole, 5-amino-1H-tetrazole, 3-amino-6-methyl-1,2,4-triazin-5(4H)-one and 2-aminobenzimidazole produced the novel angular pyrido[3,2-e][1,2,4]triazolo[4,3-a]pyrimidine, pyrido[3,2-e][1,2,4]tetrazolo[1,5-a]pyrimidine, pyrido[3′,2′:5,6] pyrimido[2,1-c][1,2,4]triazine and benzo[4,5]imidazo[1,2-a]pyrido[3,2-e]pyrimidine, respectively. Reaction of substrate 1 with 1,3-C,N-binucleophiles including cyanoacetamides and 1H-benzimidazol-2-ylacetonitrile furnished 1,8-naphthyridines and benzoimidazonaphthyridine. Moreover, reacting substrate 1 with 5-aminopyrazoles gave pyrazolo[3,4-b][1,8]naphthyridines. Finally, reaction of compound 1 with 6-aminouracils as cyclic enamines yielded pyrimido[4,5-b][1,8]naphthyridines. Some of the synthesized products showed noteworthy antimicrobial efficiency against all types of microbial strains. Structures of the produced compounds were established using analytical and spectroscopic tools.

Rationale: Phenylethylamines are one of the most common types of new psychoactive substances, following synthetic cannabinoids and synthetic cathinones. They are regulated in many countries because of their strong hallucinogenic effects, which can cause serious nerve damage. There is a wide variety of phenylethylamines, exhibiting rapid renewal and extremely similar structures, therefore accurate qualitative analysis of isomers is a difficult problem in current drug analysis. Methods: The dissociation pathways of the position isomers 2‐(2‐methylaminoprolyl)benzofuran (2‐MAPB) and 5‐(2‐methylaminopropyl)benzofuran (5‐MAPB) were investigated by gas chromatography–mass spectrometry and liquid chromatography coupled to high‐resolution quadrupole Orbitrap MS. The dissociation patterns of the phenethylamine‐based designer drugs 2‐MAPB and 5‐MAPB were explored and extended in this work based on MS combined with density functional theory studies. Results: For electron ionization mass spectrometry (EI‐MS) analysis, the dissociation patterns of 2‐MAPB were similar to those of 5‐MAPB. For electrospray ionization mass spectrometry (ESI‐MSn) analysis, the hydrogen atom on amino group was facile to form a intramolecular hydrogen bond with the oxygen atom on the parent nucleus of benzofuran in the structure of 2‐MAPB, leading to higher abundance of the product ion at m/z 58. However, there was a conjugated system between the positive charge formed by the cleavage of the 5‐MAPB side chain and the benzofuran ring, enabling the 5‐MAPB to generate a product ion at m/z 131. Computational study showed that energy barrier and spin density difference distribution jointly control the selective dissociation in EI‐MS, while different types of orbital interaction induced by intramolecular hydrogen bond led to different dissociation results in ESI‐MSn. Conclusions: These different dissociation patterns could be used to distinguish 2‐MAPB from 5‐MAPB. This could assist forensic laboratories in the differentiation and characterization of potential isomers in these kinds of compounds, especially in mixtures. [ABSTRACT FROM AUTHOR]

An ideal DNA‐encoded library (DEL) selection requires the library to consist of diverse core skeletons and cover chemical space as much as possible. However, the lack of efficient on‐DNA synthetic approaches toward core skeletons has greatly restricted the diversity of DEL. To mitigate this issue, this work disclosed a "Mask & Release" strategy to streamline the challenging on‐DNA core skeleton synthesis. N‐phenoxyacetamide is used as a masked phenol and versatile directing group to mediate diversified DNA‐compatible C‐H functionalization, introducing the 1st‐dimensional diversity at a defined site, and simultaneously releasing the phenol functionality, which can facilitate the introduction of the 2nd diversity. This work not only provides a set of efficient syntheses toward DNA‐conjugated drug‐like core skeletons such as ortho‐alkenyl/sulfiliminyl/cyclopropyl phenol, benzofuran, dihydrobenzofuran but also provides a paradigm for on‐DNA core skeleton synthetic method development. [ABSTRACT FROM AUTHOR]

The cycloaddition of nitrile oxides with ethynyl‐B(dan) (dan=naphthalene‐1,8‐diaminato) allowed the facile preparation of diverse isoxazolyl‐B(dan) compounds, all of which displayed excellent protodeborylation‐resistant properties. The dan‐installation on the boron center proves vital to the high stability of the products as well as the perfect regioselectivity arising from hydrogen bond‐directed orientation in the cycloaddition. The diminished boron‐Lewis acidity of ethynyl‐B(dan) also renders it amenable to azide‐alkyne cycloaddition, Larock indole synthesis and related heteroannulations. The obtained boron‐containing triazole, indoles, benzofuran and indenone exhibit sufficient resistance toward protodeborylation. Despite the commonly accepted transmetalation‐inactive property derived from the diminished Lewis acidity, the synthesized heteroaryl‐B(dan) compound was still found to be convertible to the oligoarene via sequential Suzuki‐Miyaura coupling. [ABSTRACT FROM AUTHOR]

The epidermal growth factor receptor (EGFR), also known as ErbB1 and HER1, belongs to the receptor tyrosine kinase family. EGFR serves as the primary driver in non-small-cell lung cancer (NSCLC) and is a promising therapeutic target for NSCLC. In this study, we synthesized a novel chemical library based on a benzofuran–indole hybrid scaffold and identified 8aa as a potent and selective EGFR inhibitor. Interestingly, 8aa not only showed selective anticancer effects against NSCLC cell lines, PC9, and A549, but it also showed significant inhibitory effects against the double mutant L858R/T790M EGFR, which frequently occurs in NSCLC. In addition, in PC9 and A549 cells, 8aa potently blocked the EGFR signaling pathway, cell viability, and cell migration. These findings suggest that 8aa, a benzofuran–indole hybrid derivative, is a novel EGFR inhibitor that may be a potential candidate for the treatment of NSCLC patients with EGFR mutations. [ABSTRACT FROM AUTHOR]

Functionalized benzofurans are attractive chemical motifs with various pharmacological and physiological applications, therefore chemists are constantly working to develop new and superior methods for their synthesis. During the past decade, significant upsurge of interest can be found in the application of visible-light-mediated chemical reactions for the synthesis of a variety of molecules, including benzofuran derivatives. This would be the first comprehensive review generalizing synthetic methodologies toward functionalized benzofurans under visible-light-assisted conditions. The review will describe different possible visible-light-mediated synthesis and briefly describe the mechanisms of the reactions. [ABSTRACT FROM AUTHOR]

A catalyst-free and atom-economical [4 þ 3] cycloaddition of azadienes with C,N-cyclic azomethine imines has been developed, providing an efficient and environmentally benign access to 1,2,4-triazepines with high diastereoselectivities and yields. This reaction can be performed in 2-methyltetrahydrofuran under mild conditions smoothly. [ABSTRACT FROM AUTHOR]

The phytochemical investigation of Cortex Mori Radicis led to the isolation and identification of a new prenylated benzofuranone (1) and four ring-opening derivatives (2–5) named albaphenol A–E, as well as nigranol A (6), together with ten 2-arylbenzofuran derivatives (7–16). The characterization of the structures of the new compounds and the structural revision of nigranol A (6) were conducted using the comprehensive analysis of spectroscopic data (1D/2D NMR, HRESIMS, CD, and XRD). Compounds 1–16 were tested for their inhibitory effects on acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Compounds 1 and 4 showed weak BChE-inhibitory activity (IC50 45.5 and 61.0 μM); six 2-arylbenzofuran derivatives showed more-potent BChE-inhibitory activity (IC50 2.5–32.8 μM) than the positive control galantamine (IC50 35.3 μM), while being inactive or weakly inhibitory toward AChE. Cathafuran C (14) exhibited the most potent and selective inhibitory activity against BChE in a competitive manner, with a Ki value of 1.7 μM. The structure–activity relationships of the benzofuran-type stilbenes were discussed. Furthermore, molecular docking and dynamic simulations were performed to clarify the interactions of the inhibitor–enzyme complex. [ABSTRACT FROM AUTHOR]

We have developed a new scaffold that exhibits an efficient intramolecular through-space charge transfer (CT). In this design, electron-rich benzofuran and electron-deficient ynone groups are placed strategically in proximity via a naphthalene spacer. Charge transfer is supported by distinct CT bands in the visible region (>500 nm) in their UV-vis absorption and emission spectra. [ABSTRACT FROM AUTHOR]

The given text is a collection of scientific documents discussing the synthesis and characterization of various compounds. The compounds mentioned include vinblastine analogues, indoles, Benzofuran 12, compound 12, benzofuran 13, compounds 13 and 14, compounds 15 and 27, the second diastereomer of compound 15, compound 16, compound 17, and compounds 18 and 19. The documents provide detailed procedures for the synthesis of these compounds, as well as information about their physical properties and spectroscopic data. The information presented can be useful for researchers studying these compounds and their properties. [Extracted from the article]

In this investigation, a novel group of compounds, 2-mercapto-benzofuro-pyrimidine derivatives, were synthesized from 2-hydroxy-5-nitro-1-benzonitrile (1) as the starting material. This was treated with various haloketones to provide the corresponding 1-(3-amino-5-nitro-1-benzofuran-2-yl) ethan-1-one (2a-d), which was then treated with ammonium thiocyanate and acetyl chloride to yield N-[(2-acetyl-5-nitro-1-benzofuran-yl) carbamothioyl]acetamide (3a-d). Further, it was reflux with sodium hydroxide yields 4-methyl/aryl-8-nitro[1] benzofuro[3,2-d]pyrimidine-2-thiol(4a-d). To obtain the appropriate acids, continue stirring compounds (4ad) with chloroacetic acid to obtain [(4-methyl-8-nitro[1]benzofuro[3,2-d]pyrimidin-2-yl)sulfanyl]acetic acid (5a-d). The structures of all the newly synthesized compounds have been established by spectral studies such as Fourier-transform infrared, Proton nuclear magnetic resonance and Mass spectra. Furthermore, all the new compounds were screened antibacterial and antifungal activity against human pathogenic viz. gram +Ve and gram -Ve organisms by agar well diffusion method. In addition, molecular docking was performed for all synthesized compounds using high inhibition organisms selected protein of both genetic and non-genetic algorithm techniques, where result are demonstrate in an excellent docking energy. [ABSTRACT FROM AUTHOR]

Benzofuran‐ and benzopyran‐fused polycyclic acetals are found in a variety of biologically active natural products. The synthetic methods toward this class of polycyclic heterocycles have fascinated one of the most intensive pursuits in total synthesis. Nevertheless, stereoselective methods towards the rapid construction of such skeletons still remain challenging for organic chemists. Significant progress has been made in this research area in recent years, however, literature on enantioselective approaches to construct these molecules has not fully reviewed. Driven by their intriguing and complex scaffolds with potential usefulness, we compose the recent advances in this review covering all the important works in this field. We hope this review will promote future research in this area. [ABSTRACT FROM AUTHOR]

This article discusses the synthesis of flavone, quinolone, and benzofuran derivatives, which have diverse pharmacological applications. The authors introduce a new synthetic methodology using designed transition-metal complexes. The study focuses on the cyclization of 2'-hydroxychalcones using different transition-metal catalysts and explores the effects of different substituents on the phenyl rings. The article also discusses the synthesis and characterization of catalysts and provides information on the synthesis and characterization of various compounds, including 2-phenylquinolin-4(1H)-ones and benzofurochromenone compounds. The compounds were synthesized, characterized, and analyzed using various spectroscopic techniques. The document also mentions the detection of hydrogen peroxide during the catalytic reactions and acknowledges the funding and support received for the research. [Extracted from the article]

Benzo‐fused five‐membered N/O/S heterocyclic compounds, such as indole, benzofuran, and benzothiophene, possessing a single heteroatom, have important applications in medicinal chemistry, agrochemistry, and material chemistry. Metal‐catalysed reactions are well‐established synthetic pathways for the formation of C−X bonds, enabling the direct synthesis of heterocycles. This approach offers advantages over traditional methods, such as fewer steps, increased atom economy, low catalyst loading, regioselectivity, and stereoselectivity. Due to their widespread use in the pharmaceutical industry, the formation of C−N, C−O, and C−S bonds has gained significant attention. This article focusses on the metal‐catalysed synthesis and corresponding mechanistic approaches for N/O/S‐heterocycles, particularly indole, benzofuran, and benzothiophene, reviewing the progress of the past five years and discussing unexplored future opportunities. [ABSTRACT FROM AUTHOR]

A possibility of using the reductive intramolecular Heck–Matsuda reaction of a sterically hindered substituted allylic ether in the synthesis of 3-(adamantan-1-yl)-3-methyl-2,3-dihydrobenzofuran was demonstrated for the first time. [ABSTRACT FROM AUTHOR]