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This paper presents the photophysical investigations of two organic compounds synthesised directly by the aminolysis depolymerisation of the waste poly(ethylene terephthalate) (rPET) with aromatic amines, i.e., aniline and 3-amino-N-hexyl-1,8-naphthalimide without use of a catalyst. The chemical structure was confirmed by 1H-NMR and 13C-NMR, as well as FT-IR. The thermal, electrochemical and optical studies of the obtained derivatives were performed. The presented compounds were thermally stable up to 360 °C, and the glass transition temperature (Tg) occurred for the compound with the 1,8-naphthalimide units. The electrochemical investigations of the synthesised compounds have revealed one oxidation process and two reduction processes for the compound with the 1,8-naphthalimide fragments. The tested derivatives were characterised by a low-lying highest occupied molecular orbital (HOMO) level (below –6.09 eV) and an energy-band gap (Eg) below 3.10 eV. The obtained molecules were absorbed in the range of 204 nm - 445 nm and emitted light from a purple to a green spectral region deepened on the used solvent with low quantum yields. The blends with poly(3-hexylthiophene-2,5-diyl) (P3HT), which is used as a donor in the bulk heterojunction solar cells (BHJ), and amide derivative with 1,8-naphthalimide fragments were made, and the emission quenching of poly(3-hexylthiophene-2,5-diyl) (P3HT) was recorded. The presented results of the photophysical investigations have opened new possibilities for obtaining functional materials from recycled poly(ethylene terephthalate) (rPET). [ABSTRACT FROM AUTHOR]

A facile intramolecular [1,5] hydride transfer reaction in a Dihydroquinazolin‐4(1H)‐one moiety synthesized from anthranilamide, glutaraldehyde, and aromatic amines is described in isopropanol medium in the presence of catalytic HCl. Based on that, we have designed a simple, efficient strategy for conjugating quinazolinone, a pharmaceutically active moiety, with an aromatic amine through an aliphatic spacer. The use of isopropanol as a reaction medium at RT and isolation of the product without rigorous column purification make the process a step ahead towards sustainability. One of the synthesized compounds was evaluated as a small molecule DNA binder. Detailed binding properties were investigated by the multispectroscopy methods. [ABSTRACT FROM AUTHOR]

Seven new thiophene hydrazide derivatives were prepared through the coupling of active methylene of 2-cyano-N'-(thiophen-2-ylmethylene)acetohydrazide with diazonium salts of aromatic amines, and heterocyclic amines at 0–5°C in pyridine. The new hydrazonothiophene derivatives could exist in two possible tautomeric forms, which are the enol and keto tautomer. The optimized molecular structures and calculation of the total energies of both tautomers revealed that the enol tautomer is energetically lower than its corresponding keto form. A prediction study for the biological activities of the newly synthesized thiophene hydrazide derivatives were performed via using PASS online software, which displayed promising activities in the treatment of posttraumatic stress disorder, as phosphodiesterase X inhibitor, and as sarcosine oxidase inhibitor. In addition, DFT calculations showed that the new hydrazonothiophene derivatives containing CH3, OCH3, and COOH groups have chemical activity among all the newly synthesized compounds due to their lower band gaps. [ABSTRACT FROM AUTHOR]

New amides of 3-O-acetyl-18β-H-glycyrrhetic acid with several aromatic and heterocyclic amines were synthesized. The chemical structures of the synthesized compounds were elucidated by UV, IR and NMR spectroscopic and mass spectrometric methods. [ABSTRACT FROM AUTHOR]

5-Amino-substituted 3-bromo-1-(1,1-dioxothietan-3-yl)-4-nitro-1H-pyrazoles were synthesized via the reactions of 3,5-dibromo-1-(1,1-dioxothietan-3-yl)-4-nitro-1H-pyrazole with aliphatic, aromatic, and heterocyclic amines. The structures of the synthesized compounds were confirmed by IR, PMR, and 13C NMR spectroscopy and mass spectrometry. According to in silico calculations, they were predicted to have no toxic risks (mutagenicity, tumorigenicity, reproductive effects, irritating effects), low toxicity (class IV-V), and acceptable oral bioavailability (based on the topological polar surface area indicator). All synthesized compounds, regardless of the amine structure, showed significant antidepressant activity after a single intraperitoneal injection to male mice in the forced swimming test that was comparable to that of amitriptyline, while 1-[3-bromo-1-(1,1-dioxothietan-3-yl)-4-nitro-1H-pyrazol-5-yl]-4-methylpiperazine (compound IIi) had a significant sedative effect in the open field test. The results of a comprehensive assessment of the biological activity of the synthesized compounds in vivo/in silico indicated that the class of 5-amino-substituted pyrazole derivatives was promising for further research. [ABSTRACT FROM AUTHOR]

A series of new N-(1,3-dioxoisoindolin-4-yl)acetamide derivatives were designed and synthesized via a condensation reaction between N-(1,3-dioxo1,3-dihydro isobenzofuran-4-yl)acetamide and various aliphatic and aromatic amines in water as an environmentally friendly solvent. All synthesized compounds (NPD 1--14) molecular structure was confirmed by their FTIR, ¹H NMR, 13C NMR, and mass spectroscopy. The final target compounds were screened for their in vitro antiproliferative activity by taking 5-Fluorouracil (5-FU) as a reference drug. Among 14 newly synthesized compounds, five compounds were shown to be effectively cytotoxic against the MCF7 cells. In comparison to the standard medication drug 5-FU (CC50 = 11.219 ± 0.847), the synthesized compounds NPD-8 (CC50 = 16.14 ± 2.08 μM) and NPD-12 (CC50 = 11.26 ± 1.158 μM) demonstrated the most active against the MCF7 cells. Furthermore, in silico study was performed to find molecular level interaction of active compounds with anticancer drug target enzyme NUDT5 inhibitors block hormone signaling in breast cancer cells. The compound NPD-12 showed the highest molecular binding energy -8.3 kcal/mol which interacted more effectively than the reference drug 5-FU binding energy -4.6 kcal/mol. These synthesized N-(1,3-dioxoisoindolin-4-yl) acetamide derivatives have been identified as a potential class of chemicals for further research as plausible new anticancer entities. [ABSTRACT FROM AUTHOR]

The reaction of (1,3‐diphenyl‐1H‐pyrazole‐4‐carbaldehyde) with different aromatic amines and triethylphosphite in the presence of magnesium perchlorate as a catalyst resulted in high yields of new α‐aminophosphonates containing pyrazole moiety. The structures of the newly prepared α‐aminophosphonates were confirmed using IR, elemental analysis, 1H NMR, and 13C NMR spectra. The antibacterial analysis of the prepared compounds showed potential inhibitory effects against the selected bacterial strains with minimal inhibitory concentrations (MIC) ranging from 12.5 to 3.125 mg/mL compared to the start compound. Some compounds have exhibited higher DPPH scavenging activity. Further, the molecular docking studies illustrated that the synthesized compounds have an inhibitory effect against topoisomerase II, which targets many approved drugs. The best modified α‐aminophosphonates compound had the highest binding affinity, with a value of −7.57 kcal/mol. Modified α‐aminophosphonates can be employed as a feasible starting point for generating new antimicrobial and anticancer agents and incorporating new reducing agents into therapeutic formulations. [ABSTRACT FROM AUTHOR]

In this research, a set of novel mercaptobenzenesulfonamides were synthesized and evaluated as potential antibacterial agents. These novel sulfonamides were synthesized in three steps, including acylation of 2-aminothiophenol, chlorosulfonation of the obtained 2-mercaptophenyl acetamide, and finally the reaction of aromatic amines with 4-acetamide-3-mercaptobenzene-1-sulfonyl chloride. The chemical structure of the prepared sulfonamides was verified by IR, 1H-NMR, and 13C-NMR spectroscopy. The antibacterial activity of the synthesized compounds was also analyzed by the agar diffusion method against Staphylococcus aureus and Escherichia coli bacteria. Furthermore, computational ducking calculation and Pharmacophoric studies of sulfonamides were conducted by AutoDock Vina software and ZINCPharmer methods, respectively. According to the in vitro antibacterial evaluation as well as the computational results, mercaptobenzenesulfonamides with methoxy, hydroxy, and chloro substituents showed the highest antibacterial activity compared to other synthesized sulfonamides. [ABSTRACT FROM AUTHOR]

In the present work, a library of 120 compounds was prepared using various aliphatic and aromatic amines. Finally, 10 compounds were selected through in silico screening carrying 4‐aminobenzoyl‐l‐glutamic acid and 1,3,5‐triazine moiety. The docking results of compounds 4d16 and 4d38 revealed higher binding interaction with amino acids Asp54 (−537.96 kcal/mol) and Asp54, Phe116 (−618.22 kcal/mol) against wild (1J3I) and quadruple mutant (1J3K) type of Pf‐DHFR inhibitors and were comparable to standard WR99210. These compounds were developed by facile and microwave‐assisted synthesis via nucleophilic substitution reaction and characterized by different spectroscopic methods. In vitro antimalarial assay results also suggested that these two compounds were having higher antimalarial activity against chloroquine‐sensitive (3D7) and chloroquine‐resistant (Dd2) strain out of the ten synthesized compounds with IC50 13.25 μM and 14.72 μM, respectively. These hybrid scaffolds might be useful in the lead discovery of a new class of Pf‐DHFR inhibitors. [ABSTRACT FROM AUTHOR]

A series of Schiff bases of indole-3-carbaldehyde were synthesized by the condensation reaction of indole-3-carbaldehyde with different aryl amines. The reaction of indole-3-carbaldehyde with different aryl amines was carried out in the presence of glacial acetic acid. All the synthesized compounds were characterized with microanalytical data 1H and 13C NMR, FT-IR spectroscopy and Mass spectrometry and screened for their in vitro microbial activity against bacterial strain Dickeya species as well as fungal culture Fusarium oxysporum using agar well diffusion method. The standard used for bacterial and fungal cultures were Carbendazim and Gentamicin, respectively. The results revealed that the synthesized Schiff base N‑((indol-1H-3-yl)methylene)-4-nitrobenzenamine exhibited the maximum activity against both bacteria (MIC = 2000 µg/mL) as well as fungus (MFC = 5000 µg/mL) cultures as compared with all other synthesized compounds. [ABSTRACT FROM AUTHOR]

A simple and efficient iodine‐promoted synthesis has been developed for the synthesis of isoxazolyl aryl thiazole amines (3) from easily available isoxazolyl aryl ethanones (1) and thiourea (2) in good yields. Furthermore, isoxazolyl aryl thiazole amines (3) are utilized as building blocks for the synthesis of novel isoxazolyl imidazo[2,1‐b]thiazole libraries 6. All the synthesized compounds were characterized by IR, 1H NMR, 13C NMR, and Mass spectral data. The title compounds 6a‐ah were evaluated for their antimicrobial activity. Compounds 6d, 6 g, 6p, 6q, 6r, 6 s, 6u, 6v, 6w, and 6x exhibited significant antimicrobial activity as that of standard drugs. [ABSTRACT FROM AUTHOR]

Seven mono-, di-and tri-substituted derivatives of s-triazine were synthesized by condensation reaction of s-triazine with different aromatic amines at different temperature conditions. The synthesized compounds were characterized by various spectral techniques, i.e. 1HNMR, 1HNMR-D2O, 13CNMR, elemental analysis and mass spectrometry and screened for their antifungal activity against Helminthosporium oryzae, Rhizoctonia solani and Alternaria brassicae. Among all the synthesized triazine derivatives; compounds (5c), (7b) and (5a) were found to be the most effective with ED50 values 4, 7 and 9 pg/ml against H. oryzae, R. solani and A. brassicae, respectively. [ABSTRACT FROM AUTHOR]

A facile and convenient greener route has been introduced for the synthesis of novel 2‐phenyl‐2,3,5,6‐tetraazaaceanthrylene‐1,4(2H,5H)‐dione derivatives via one pot three component reaction of barbituric acid, substituted aryl amines and isatin with ethanol as solvent. The synthesized compounds were characterized by FT‐IR, 1H NMR and 13C NMR techniques. The remarkable features of this method are catalyst‐free, short reaction time, good yields and simple purification techniques. The effect of inhibition and possibilities of interaction of 1GQN enzyme on Salmonella typhi with synthesized compounds was explored through molecular docking approach. Pharmacokinetics profile of the synthesized compounds was explored by ADME technique. All the synthesized compounds have also been evaluated for their antibacterial activity against Gram positive and Gram‐negative bacterial strains. The compounds 4a and 4d exhibited significant effect against four human pathogenic bacterial strains with the maximum inhibition zone. [ABSTRACT FROM AUTHOR]

The present work emphasizes the utility of 2,4‐dichloro‐5‐methylbenzo[h][1,6]naphthyridine as starting precursors. The reaction of 2,4‐dichloro‐5‐methylbenzo[h][1,6]naphthyridine with a variety of aliphatic and aromatic amines yielded 2‐amino substituted 2,4‐dichlorobenzo[h]naphthyridines. All the compounds were examined for their in vitro anticancer activity against six human cancer lines and docked with PDK1 inhibitors. The structure‐activity relationship studies are revealed that the compounds holding aminocarbazole moiety and triazole amine moiety improve the activity profile. All the structures of synthesized compounds were optimized at B3LYP‐D3/6‐31G(d) level in the water. Furthermore, the electronic properties and biological reactivity of the synthesized compounds are explored using computational techniques. [ABSTRACT FROM AUTHOR]

The study investigates the synthesis of fused pyridine and pyrimidine derivatives known for their diverse biological activities and structural versatility which serve as pivotal building blocks in organic synthesis. A series of indole-substituted cyanamide derivatives were synthesized by one-pot three-component cyclo-condensation between Indole-3-carboxaldehyde, malononitrile, and electron-rich aromatic and heterocyclic amines by employing several methods such as grinding, microwave irradiation and conventional reflux in the presence of ceric ammonium nitrate and DMF. The nuclei differ concerning the heterocyclic amines such as pyridine, pyrimidine, pyrazine, thiazole, and tetrazole. The newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR, and Mass spectra. The reaction proceeds via Knoevenagel condensation, Michael addition, and intramolecular cyclization. The employed methodology offers the convenient advantages of cascade one-pot condensation, easy isolation, short reaction time, and excellent yield (83–95%). [Display omitted] [ABSTRACT FROM AUTHOR]

A sequence of functionalized 1′H-spiro-[indoline-3,5′-pyrimido[4,5-b]quinoline] − 2,2′,4′ (3′H,10′H)-trione derivatives have been synthesized by a catalyst-free three-component reaction of barbituric acid with arylamines and isatin under aqueous conditions. Neutral reaction conditions, high yields, and operational simplicity are the important features of the present protocol. The molecular docking studies of all the synthesized compounds were performed with jackbean urease (PDB ID: 3LA4). The results suggest that the compounds 4a-4j showed good binding affinities with the active site of jackbean urease having an inhibition constant Ki = 76.26 nm. This study offers the first example of the exhibition of urease inhibitory potential by spiro indoline derivatives paying route to develop more potent anti-urease compounds of medicinal and agricultural interest. The selected compounds 4a and 4j were evaluated for antimicrobial studies. [ABSTRACT FROM AUTHOR]

New series of diazenylschiff's bases of salicylaldehydes were synthesized. The new diazenylschiff's bases were synthesized by condensation reaction of 5-(3-bromophenyldiazo)salicylaldehyde with various amines such as aromatic amines, sulfa drugs, naphthalenes, aminoantipyrine and aminothaizoles. The antimicrobial activity for the synthesized diazenylschiff's bases was screened against various Gram-positive and Gram-negative bacteria as well as fungal strains. The mean values of the obtained inhibition zone diameter for the synthesized compounds suggested that most of the Schiff's bases possess significant antifungal activity against Aspergillus fumigatus. Most of the Schiff's bases possess moderate activity against Bacillus subtilis and Candida albicans. [ABSTRACT FROM AUTHOR]

In the present research work, a new series of N-(substituted-phenyl)-3-(4-phenyl-1-piperazinyl)propanamides were synthesized. The synthesis was initiated by the coupling of different aromatic amines with 3-bromopropanoyl chloride in aqueous basic medium, to synthesize different electrophiles with good yields. These electrophiles were further reacted with 1-phenylpiperazine to yield the desired compounds, N-(substituted-phenyl)-3-(4-phenyl-1-piperazinyl)propanamides as depicted in scheme 1. The structural confirmation of all the synthesized compounds was corroborated by IR, 1H NMR, 13C NMR, HMBC and CHN analysis data. The in vitro inhibitory potential of these propanamides was evaluated against alkaline phosphatase enzyme and it was explored that all these molecules exhibit potent inhibition relative to the standard used. The Kinetics mechanism analyzed by Lineweaver-Burk plots which exposed that N-(4-ethylphenyl)-3-(4-phenyl-1-piperazinyl)propanamide inhibited this enzyme competitively by forming an enzyme-inhibitor complex. Moreover, these compounds were studied for cytotoxic behaviour by hemolytic activity, whereby it was avowed that nearly all these propanamides disclosed low cytotoxicity. In addition, kinetic analysis were also carried out to understand the mode of inhibition for these compounds. The in silico investigation of these compounds was also in agreement with the in vitro results. So, it was envisaged that these derivatives might lead to further research gateways for obtaining better and safe as nontoxic medicinal scaffolds for dealing with the alkaline phasphatase related ailments such as bone diseases, diabetes, prostatic cancer and liver dysfunction. [ABSTRACT FROM AUTHOR]

The behaviour of 2‐benzyl‐4H‐3,1‐benzoxazin‐4‐one towards nitrogen nucleophiles namely, amino acids, aromatic amines, sodium azide, and secondary amines has been investigated. Also the reaction of 3‐amino‐2‐benzylquinazolin‐4(3H)‐one and 2‐[2‐benzyl‐4‐oxoquinazolin‐3(4H)‐yl]acetohydrazide with carbon electrophiles has been discussed. As well as The novel synthesized compounds were evaluated as chemosensor for detecting formyl, carbonyl group and revealed high‐selectivity and specificity to detect metals ions in water samples and, agricultural crops. Qualitative and quantitative assays indicated appreciable selectivity of novel compounds 13 and 15 as a chemo sensor for Optical detection of Hg2+and Cr2+ respectively. [ABSTRACT FROM AUTHOR]

Imidazolones are potent for their intense antimicrobial and mitigating exercises wherein, an assortment of imidazolone analogs 4-aryl-1-(4-chloro-3-fluorophenyl)-2-phenyl-1H-imidazol-5(4H)-ones (2a-o) and 4-aryl-2-phenyl-1-(4-(trifluoromethyl) phenyl)-1H-imidazol-5(4H)-ones (3a-o) were studied amalgamating them by using oxazolones and various aryl amines. Newly synthesized compounds were screened for in vitro activity towards bacterial as well as fungal pathogenic microscopic organisms. Among the synthesized imidazolone derivatives, compound 2f, 2g, 2i, 3b, 3h, and 3k showed moderate antibacterial action while 2d, 2j, 2m, 2n, 3e, 3g, and 3f furnished earmarked antifungal action. In-silico docking of all structures was performed for fungal and bacterial targets. Out of all novel imidazolones, the compounds 2e, 2o and 3o exhibited superior affinity against fungal target 14α-demethylase when compared with other compounds. [ABSTRACT FROM AUTHOR]

In the present work, reaction of 3‐nitrophthalic anhydride with anthranilic acid to afford the corresponding anthranil that is treated with acetic anhydride that yielded the 2‐benzoxazinonyl‐5‐nitrobenzoic acid (BNBA) could be isomerized to the stereogenic 9‐nitrobenzoxazinone[2,3‐a]isoindolinone acetate (NBIA) via basic reaction conditions. A reaction of the BNBA→NBIA was allowed with series of nitrogen nucleophiles such as formamide and hydrazine derivatives, for example, hydrazine hydrate, hydroxyl amine, acetic hydrazide, thiosemicarbazide, thiocarboihydrazide, and some amino acid, for example, glycine, alanine, and some aliphatic amine, for example, octyl amine, decyl amine, and aromatic amine, for example, aniline, o‐toluidine, 4‐aminobenzoic acid, and carbon nucleophiles such as malononitrile and diethylmalonate. The basicity of previous nucleophiles and thermal stability of the products can be controlled on the course of reaction. The chemical structure of the synthesized compounds can be confirmed by micro‐analytical, spectral data, and they are optimized by quantum chemical parameters (DFT study) to identify the thermal stability of the products. The data obtained from the molecular modeling were correlated with those obtained from the biological screening. A novel sequence of quinazoline derivatives were synthesized, evaluated for their algaecides activity against compounds 1, 2b, and 6 that showed the highest algaecides activities of this series with relatively low toxicity in the median lethal dose test. The obtained results proved that the most active compounds could be useful models for future design, adaptation, and investigation to construct more active analogs. [ABSTRACT FROM AUTHOR]

An expedient strategy is reported for the synthesis of novel bis(thiazolidinones). This strategy involves a one-pot, multi-component reaction of bis-aldehydes, aromatic amines and thioglycolic acid in benzene at reflux. A two-steps approach to the synthesis of target compounds has also been studied. Anticancer activity of the synthesized compounds against some cancer cell lines was assessed. [ABSTRACT FROM AUTHOR]

Fluoroquinolones are extensively used in clinical applications as a crucial class of antibacterial medicine and have shown high potential for the treatment of several other diseases. This study is based on synthesis, structure elucidation and biological evaluation of various fluoroquinolone (enoxacin) analogues with electrophilic substitution of aromatic amine moiety of central enoxacin nucleus by benzyl halides. The synthesized derivatives were characterized on the basis of different chemical and physical measurements and structures were elucidated by various spectroscopic techniques (NMR, EI‐MS), including elemental (CHN), and X‐ray diffraction analysis. Furthermore these compounds were investigated for their potential α‐glucosidase inhibition activities and all synthesized analogues of fluoroquinolones were found to exhibit promising inhibition potential of 45.8±0.2 to 74.5±0.2 μM in comparison to IC50 value of 425.6±1.3 μM for standard inhibitor of α‐glucosidase1‐deoxynojirimycin. Further, docking of synthetic compounds were carried out by using α‐glucosidase I enzyme of Saccharomyces cerevisiaeas a target. The study provided an insight of the molecular interactions of fluoroquinolone derivatives with the enzyme that are in good agreement with the inhibitory activity of synthesized compounds and can be considered as a valuable tool for designing new drugs. [ABSTRACT FROM AUTHOR]

Green and sustainable synthesis of chemicals using biocatalysis is emerging as an alternative to the traditional chemical methods. Here, we reported the establishment of two artificial enzymatic cascades for the synthesis of benzylamine, 2‐phenylethylamine and their analogues from renewable feedstocks via whole‐cell biocatalysis approach. A five‐step enzymatic cascade containing L‐amino acid deaminase (LAAD), hydroxymandelate synthase (HmaS), (S)‐mandelate dehydrogenase (SMDH), benzoylformate decarboxylase (BFD) and ω‐transaminase (ω‐TA) was developed to produce benzylamine from L‐phenylalanine. We also obtained p‐hydroxybenzylamine and m‐fluorobenzylamine with >98 % conversion from L‐tyrosine and m‐fluoro‐phenylalanine. In addition, a three‐step enzymatic cascade comprising LAAD, α‐keto acid decarboxylase (KDC) and ω‐TA was designed for the synthesis of 2‐phenylethylamine, tyramine and m‐fluorophenylethylamine. In summary, we have developed one‐pot whole‐cell biocatalysis system for benzylamine and 2‐phenylethylamine synthesis, which might be amendable for synthesizing other amine compounds in a green and sustainable manner. [ABSTRACT FROM AUTHOR]

Isatin (1H-indole-2,3-dione) and its analogs are an important class of heterocyclic compounds. N-benzyl isatins and Schiff bases of isatin analogs have been reported to demonstrate a variety of biological activities. This work illustrates the synthesis of new N-benzylisatin Schiff bases and studies their biological activity. Firstly, Isatin and its analogs; 5-methoxyisatin, 5-fluoroisatin reacted with benzyl iodide to obtain N- benzylated derivatives of isatins 2(a-c). Secondly, these compounds were reacted with different amines (sulphanilamide and 4- methyl sulphonyl aniline) separately, to obtain Schiff bases compounds 3(a-c) and 4(a-c), respectively. The synthesized compounds were characterized by using FT-IR and 1HNMR spectroscopy. The synthesized Schiff bases 3(a-c) and 4(a-c) were examined for their in vitro antimicrobial activity using different Gram-positive bacteria, Gram-negative bacteria, and Candida albicans as fungi. The obtained results were compared with standard drugs: amoxicillin, ciprofloxacin, and fluconazole. All the compounds show no antifungal activity at any concentrations used, while most of them show moderate antibacterial activity at concentration 5mg/mL toward most bacteria except Klebsiella pneumonia. [ABSTRACT FROM AUTHOR]

N‐Acetyltransferases play critical roles in the deactivation and clearance of xenobiotics, including clinical drugs. NAT2 has been classified as an arylamine N‐acetyltransferase that mainly converts aromatic amines, hydroxylamines, and hydrazines. Herein, we demonstrate that the human arylamine N‐acetyltransferase NAT2 also acetylates aliphatic endogenous amines. Metabolomic analysis and chemical synthesis revealed increased intracellular concentrations of mono‐ and diacetylated spermidine in human cell lines expressing the rapid compared to the slow acetylator NAT2 phenotype. The regioselective N8‐acetylation of monoacetylated spermidine by NAT2 answers the long‐standing question of the source of diacetylspermidine. We also identified selective acetylation of structurally diverse alkylamine‐containing drugs by NAT2, which may contribute to variations in patient responses. The results demonstrate a previously unknown functionality and potential regulatory role for NAT2, and we suggest that this enzyme should be considered for re‐classification. [ABSTRACT FROM AUTHOR]

[Display omitted] • Synthesis and Investigation of some novel bis furamides and corresponding their quinazolinone derivatives. • In vitro anticancer activity of all bis quinazolinones. • In vitro antibacterial and anti-fungal activity of synthesized compounds. • DPPH radical scavenging activity. • Molecular Docking study of synthesized compounds. • In silico pharmacokinetics, ADMET profiles and HOMO-LUMO energies have been reported. Novel derivatives of bisquinazolinones and bisfuramides were synthesized and tested for their efficiency in this work. Within short reaction times (1–10 min), bisfuramide derivatives were synthesized through the interaction of the ring opening of bis benzoxazin-4-one with primary aromatic amines. FT-IR, 1H NMR, 13C NMR, MS spectral data were used to characterize the structures of newly synthesized compounds. These compounds were screened in vitro antimicrobial activity. The inhibition zone of the synthesized compounds against various bacteria (S. aureus, E. coli) and fungus (C. albicans) was measured by using well and disc diffusion assay. The novel bisquinazolinones were screened for their anti-cancer activity against MCF-7 cell lines, the obtained results clearly reveal moderate to excellent anti-proliferative activity, anti-oxidant activity was performed by using DPPH method. Furthermore, molecular docking analysis revealed a favorable binding contact with the Kinase inhibitor (PDB ID: 1XKK). DFT calculations with B3LYP/6–31 + G (d) level were used to analyze the electronic and geometric characteristics deduced from the stable structure of the compounds. The electron affinity (EA), ionization potential (IP), energy gap (Egap), electronegativity (χ), electrophilicity (ω), hardness (η), softness (S) and electrophilicity index (ωi) were computed and discussed. Furthermore, in silico ADMET (i.e. Absorption, distribution, metabolism, and excretion) calculations were performed on all synthesized compounds that showed potency in comparison to conventional azithromycin. [ABSTRACT FROM AUTHOR]

[Display omitted] • Synthesis of new substituted thiadiazine thiones. • Anti-nociceptive activity of the synthesized compounds. • Major inflammatory enzymes, COX-2 and 5-LOX was examined. • Molecular docking COX-2 and 5-LOX was performed. A series of new thiadiazine derivatives including 2-(5-alkyl/aryl-6-thioxo-1,3,5-thiadiazinan-3-yl) propanoic acids (a) and 4-methyl-2-(5-alkyl/aryl-6-thioxo-1,3,5-thiadiazinan-3-yl) pentanoic acids (b) were synthesized by reacting primary alkyl/aryl amines with CS 2 , followed by reaction with formaldehyde and amino acids. The chemical structures of synthesized compounds were confirmed by 13C- NMR and 1H- NMR techniques. The inhibitory potential of major inflammatory enzymes, COX-2 and 5-LOX was examined. Moreover, anti-nociceptive and anti-inflammatory activities were evaluated in the in vivo thermally induced nociceptive, and carrageenan induced paw edema models in mice. The in-vitro results reflect that these compounds exhibited concentration dependent inhibition of COX-2 and 5-LOX. The tested compounds at 50 mg/kg showed significant effect on thermally induced pain, and reduced latency time (seconds) as compared to the vehicle treated animals. Moreover, tested compounds exhibited percent inhibition of paw edema in the carrageenan induced paw edema model in mice. Furthermore, the binding modes of the most active COX-2 and 5-LOX inhibitors were determined through computational methods. The computational study reflects that the docked compounds have high binding affinities for COX-2 and 5-LOX enzymes, which leads to inhibition of these enzymes. [ABSTRACT FROM AUTHOR]

1-Substituted 5-oxopyrrolidine-3-carboxylic acids were prepared via cyclization of 2-methylenesuccinic acid with aliphatic, aromatic, and heterocyclic amines. The synthesized compounds possessed analgesic and antihypoxic effects of varying strength. The analgesic activity was slightly greater for compounds with an aromatic or heterocyclic radical in the 1-position. [ABSTRACT FROM AUTHOR]

Graphical abstract Highlights • Metal-free conversion of alkynes into secondary amines. • One-pot three-step process. • Atom-, step-economy. Abstract A metal-free one-pot synthesis of secondary amines from aryl alkynes via hydration-condensation-reduction three-step process in the presence of TfOH and B 2 (OH) 4 has been developed. A series of secondary amines were obtained with good functional group tolerance and satisfied yields. [ABSTRACT FROM AUTHOR]

Despite the large number of methods for the synthesis of amides, formation of the amide bond from aromatic amines has always been a challenge for organic chemists due to their weak nucleophile character. We describe here a new efficient method of amide formation from N‐Acyl‐Benzotriazoles and Aromatic Amines (ABAA reaction) including aniline derivatives, in acidic conditions. This reaction is selective for aromatic amines, since aliphatic amines did not react under the same experimental conditions. Using the ABAA reaction, we have synthesized a series of aromatic amide compounds including labelled enzyme substrates, in excellent yield. The ABAA reaction also allowed the one‐pot synthesis of Nordiazepam, which is a precursor of the anxiolytic Diazepam (Valium®). This procedure opens new ways of synthesis of amides from aromatic amines, as well as of heterocyclic structures. A simple and practical approach for the synthesis of aromatic amides has been developed using N‐Acyl‐Benzotriazole derivatives and aromatic amines including anilines (ABAA reaction). The reaction is performed in acidic medium, is selective for the coupling of aromatic amines vs. aliphatic amines, and features broad functional group tolerance. [ABSTRACT FROM AUTHOR]

Synthesis of some novel tricyclic compounds bearing thienodipyrimidine moiety by the reaction of ethyl 6-amino-1,3-dimethyl- 2,4-dioxo-1,2,3,4-tetrahydrothieno[3,2-d]pyrimidine-7-carboxylate (1) with different types of aromatic amines to give the corresponding carboxamide derivatives 2-;11, which cyclized with triethyl orthoformate in acetic anhydride to afford thieno[2,3-d:4,5-d']dipyrimidine derivatives 12-;15 is described. Similarly, thieno[2,3-d:4,5-d']dipyrimidine derivative 17 was also prepared via the reaction of carboxamide derivative 2 with chloroacetyl chloride in chloroform to give thieno[3,2-d]pyrimidine-7-carboxamide derivative 16, followed by a cyclization in boiling acetic anhydride. The structure of these compounds was confirmed on the basis of their spectral and analytical data such as IR, 1H-NMR, 13C-NMR spectroscopy and mass spectral data. The synthesized compounds were screened for their cytotoxic activity. [ABSTRACT FROM AUTHOR]

An iodine‐promoted one‐pot synthesis of functionally diverse and highly substituted 4‐aminopyrroles directly from aryl methyl ketones, arylamines, and enamines was developed. The reaction involves in‐situ oxidation of aryl methyl ketone to glyoxal, subsequent imine formation by aniline, followed by nucleophilic addition of enamine, and cyclization to afford highly substituted 4‐aminopyrroles. This reaction involved the formation of two C−N bonds and one C−C bond by a formal [1+1+3] annulation approach. The present method provides an interesting framework of two 4‐aminopyrrole units directly attached to a biphenyl core by the reaction of 4,4′‐diacyl biphenyl, amine, and enamine groups. This Hantzsch‐type one‐pot reaction provides diverse 4‐aminopyrroles, which could be useful in medicinal/material chemistry. [ABSTRACT FROM AUTHOR]

• New heterocyclic disperse dyes were synthesized. • Solvatochromic attributes were investigated in different organic solvents. • pH sensitivity was explored in detail. • The synthesized dyes were applied on polyester fabric and their fastness parameters were completely studied. In current research exploration, novel heterocyclic disperse dyes were synthesized, using 8-aminonaphthalen-2-ol as a coupling component and different heterocyclic aromatic amines e.g. sulfadiazine, sulfamethazine, sulfathiazole sodium salt, 2-aminobenzothiazole and 2-amino-6-methoxybenzothiazol as a diazonium component. Different analytical techniques including FT-IR, 1H-NMR, UV-Visible, FAB-LRMS and FAB-HRMS were used for the structural elucidation of the synthesized disperse dyes. The melting point of the synthesized compounds were also determined. The solvatochromism of these dyes was examined in six organic solvents possessing different polarity and the sensitivity of the absorption maxima (λ max) to acidic and basic pH were evaluated in methanol. Bathochromic shift was observed with increase in solvent polarity and under acidic pH. The fluorescence studies all the dyes were performed in four different solvents. The obtained chromophores were applied on polyester fabric observing different parameters like build-up profile, perspiration fastness, rubbing fastness, wash fastness, light fastness and sublimation fastness. All the dyes exhibited good to very good color yield and excellent fastness properties. [Display omitted] [ABSTRACT FROM AUTHOR]

One-pot tandem synthesis was developed for substituted quinolines (in up to 97% yields) involving a selective catalytic oxidation of primary amines to aldehydes and their condensation with arylamines under the action of a dispersion of Fe(CrO2)2 and water solution of H2O2 at room temperature. The stage of catalytic oxidation of alcohols was accelerated by photoactivation. A presumable mechanism of the photoactivated tandem synthesis of 2-methylquinoline was suggested. Catalyst Fe(CrO2)2 was prepared by photochemical synthesis. [ABSTRACT FROM AUTHOR]

A series of N ′-phenyl- N -hydroxyureas has been prepared by reacting hydroxylamine with aromatic isocyanates. These compounds were investigated as inhibitors of human carbonic anhydrases (hCAs, EC 4.2.1.1), considering four physiologically relevant isoforms, the cytosolic isoforms hCA I and II, and tumor associated, transmembrane isoforms hCA IX and XII. The new compounds reported here did not inhibit the widespread cytosolic isoforms hCA I and II, but they inhibited the tumor associated isoforms with interesting potencies. The most effective inhibitors showed K I s ranging between 72.8 and 78.9 nM against hCA IX and between 6.9 and 7.2 against hCA XII, making them of interest as candidates for antitumor studies. [ABSTRACT FROM AUTHOR]

Abstract: Despite significant recent progress in copper‐catalyzed enantioselective hydroamination chemistry, the synthesis of chiral N‐arylamines, which are frequently found in natural products and pharmaceuticals, has not been realized. Initial experiments with N‐arylhydroxylamine ester electrophiles were unsuccessful and, instead, their reduction in the presence of copper hydride (CuH) catalysts was observed. Herein, we report key modifications to our previously reported hydroamination methods that lead to broadly applicable conditions for the enantioselective net addition of secondary anilines across the double bond of styrenes, 1,1‐disubstituted olefins, and terminal alkenes. NMR studies suggest that suppression of the undesired reduction pathway is the basis for the dramatic improvements in yield under the reported method. [ABSTRACT FROM AUTHOR]

Abstract: Among various alkali (Na, K) and alkaline-earth (Ca, Mg, Sr, Ba) chlorides, calcium(II) chloride was found to be a cost-effective Lewis acid catalyst for solvent-free synthesis of pyrroles from primary aromatic and aliphatic amines under open-vessel focused microwave irradiation. The salient features of this environmentally benign method are high to quantitative conversion, short reaction time, safe and clean reaction profile, possibility of scale-up to multigram quantities, and use of a low-cost, widely available, nontoxic catalyst.Graphical abstract: [ABSTRACT FROM AUTHOR]

Bio-resourced non-isocyanate polyurethane (NIPU) network was synthesized to valorize a sustainable natural product (i.e., tannic acid, TA) toward biomaterials. Thus, a glycerol-based epichlorohydrin was glycidylated to form epoxidized TA (ETA). Facile chemical fixation of CO 2 onto ETA was used to prepare carbonated TA (CTA) under normal conditions. Both aliphatic and aromatic amines were then used to convert CTA to NIPU networks. The networks were analyzed spectrally and thermally by FTIR, CP/MAS 13C NMR, and DSC, respectively. The amine-curing kinetics of CTA was evaluated based on Vyazovkin's advanced isoconversional method. The approach revealed different activation energies comparing to its epoxy counterpart, ETA. The TA-based NIPU possessed remarkable thermo-oxidation stability in comparison with its petroleum-based counterpart (OIT 2.38 vs. 0.12 min). The L929 fibroblast cells viability was used to evaluate the cytotoxicity and biocompatibility of the TA-based NIPU which proved its biocompatibility. Finally, the antioxidizing property of this polymer was ascertained by DPPH radical scavenging analysis. It was concluded that the value-added NIPU networks may be considered as good candidates for biomaterials. [ABSTRACT FROM AUTHOR]

An efficient and catalyst-free for the synthesis of 1,2,4,5-tetrasubstituted imidazoles has been developed using a one-pot, two-step reaction of arylamins, benzonitriles, arylglyoxals, and Meldrum’s acid. All the products were obtained in good to excellent yields and their structures were established from their spectroscopic data. [ABSTRACT FROM AUTHOR]

We describe herein the first examples of Povarov reaction of tetrasubstituted cyclopentadienones in the preparation of quinoline compounds. Polycyclic compounds bearing tetrahydro‐3H‐cyclopenta[c]quinoline and dihydro‐1H‐cyclopenta[c]naphtha[2,3‐h]quinoline moieties have been synthesized by one pot reaction of tetrasubstituted cyclopentadienones with N‐arylamines and formaldehyde in the presence of trifluoroacetic acid. The control of the regioselectivity was total as well with symmetrical and non symmetrical cyclopentadienones. The X‐ray structures of new quinolines were reported. [ABSTRACT FROM AUTHOR]

A one-pot four-component reaction of aldehyde, aromatic amine, and two equivalents of piperidine-2,4-dione was treated in ionic liquids of [BMIm]Br catalyzed by TsOH (p-toluenesulfonic acid), and gave a series of 5,10-diarylpyrido[4,3-b][1,6]naphthyridine derivatives in good yields. This procedure has the advantages of mild reaction conditions, good yields, one-pot, and environmentally benign. [ABSTRACT FROM AUTHOR]

A new class of 2-arylamino-dihydroxyindenopyrroles were prepared by the one-pot multicomponent reaction of ninhydrin, N -methyl-1-(methylthio)-2-nitroethenamine and aromatic amines in EtOH at room temperature. The advantages of this procedure are short reaction times, good to high yields, easy separation of products and good functional group tolerance. [ABSTRACT FROM AUTHOR]

Abstract: We have developed a unified strategy for preparing a variety of imidazo‐fused N‐heteroaromatic compounds through regiospecific electrochemical (3+2) annulation reaction of heteroarylamines with tethered internal alkynes. The electrosynthesis employs a novel tetraarylhydrazine as the catalyst, has a broad substrate scope, and obviates the need for transition‐metal catalysts and oxidizing reagents. [ABSTRACT FROM AUTHOR]

Aniline, heterocyclic aromatic amines, and arylamines are known carcinogens. Recently aniline mustard has come into prominence as a novel anticancer agent. In this project, microwave irradiation has been used to synthesize an optically active alkylated aniline namely 2,6-dimethyl-4-(1-(p-tolyl)ethyl)aniline (abbreviated DMPA). The presence of quartet and doublet peaks in NMR and a single chromatogram in HPLC verified that the final product DMPA, prepared from the synthesis reactions, had no major impurities. By using a Lux chiral column in HPLC, two peaks have been detected in the chromatogram, which correspond to two enantiomers of the chiral aniline derivative. Fluorescence spectroscopic measurements on DMPA indicated conspicuous dependence of its emission behavior on the polarity (in terms of the empirical polarity parameter E T (30)) of the homogeneous solvents used, a property important for an optical sensor. The nature of the emission profiles, along with the relevant parameter namely wavelength at emission maximum ( λ em max ) is used to infer the distribution, binding and microenvironment of the DMPA molecules in human serum albumin protein (HSA). DMPA is weakly fluorescent in aqueous buffer medium, with a dramatic enhancement in the fluorescence emission in the presence of HSA. Molecular modeling studies have been carried out on the two enantiomers (R and S) of DMPA with HSA. The implications of these findings are examined in relation to the potentialities of DMPA as a novel fluorescence sensor for biological systems. [ABSTRACT FROM AUTHOR]

Arylamines constitute the core structure of many therapeutic agents, agrochemicals, and organic materials. The development of methods for the efficient and selective construction of these structural motifs from simple building blocks is desirable but still challenging. We demonstrate that protonated electron-poor O-aryl hydroxylamines give aminium radicals in the presence of Ru(bpy)3Cl2. These highly electrophilic species undergo polarized radical addition to aromatic compounds in high yield and selectivity. We successfully applied this method to the late-stage modification of chiral catalyst templates, therapeutic agents, and natural products. [ABSTRACT FROM AUTHOR]

A new one-pot, four-component reaction of phenylglyoxal or ethylglyoxalate, 1,3-dicarbonyls, N, N-dimethylbarbituric acid, and aromatic amines for the synthesis of highly substituted pyrroles or dihydro-1 H-pyrrole containing barbituric acid in moderate-to-good yields is described. Short reaction time, mild reaction condition, use of simple experimental procedure, and prompt isolation of the products are some advantages of this protocol. [ABSTRACT FROM AUTHOR]

Reactions of methyl 3,4,6-trioxoalkanoates (3,4-dihydroxy-6-oxo-2,4-alkadienoates) with a mixture of arylamines and aromatic aldehydes or with the corresponding arylidenearylamines lead to the formation of methyl (4- alkanoyl-3-hydroxy-1,5-diaryl-1 H-pyrrol-2-yl)acetates. Structure of the synthesized compounds is discussed basing on IR, H NMR spectroscopy, mass spectrometry, and X-ray diffraction data. [ABSTRACT FROM AUTHOR]

Reactions of methyl 3,4,6-trioxoalkanoates (3,4-dihydroxy-6-oxo-2,4-alkadienoates) with mixtures of aromatic aldehydes and arylamines or with the corresponding N-(arylmethylidene)anilines afforded methyl (4-alkanoyl-1,5-diaryl-2-hydroxy-3-oxo-2,3-dihydro-1 H-pyrrol-2-yl)acetates. The product structure was discussed on the basis of their IR, H NMR, and mass spectra and X-ray diffraction data, and their antimicrobial activity against Staphylococcus aureus P-209 and Escherichia coli M was evaluated. [ABSTRACT FROM AUTHOR]

A Cu(OAc) 2 -catalyzed synthesis of 2-arylquinoline N -oxides with easily available arylamines is described. The main features of this reaction are mild reaction conditions, high functional-group tolerance, excellent regioselectivity, and good to excellent yields. This procedure is mild, operationally simple, and constitutes a greener approach to the arylation of quinoline N -oxides. [ABSTRACT FROM AUTHOR]