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p-Fluorophenacyl chloride (1) was used as a building block for the preparation of new tetra-substituted thiophene derivatives. The basic-catalyzed reaction of 1 with various thiocarbamoyl compounds such as 2-acetyl-2-substituted-thioacetanilides 2a,b, 3-arylazo-4-mercapto-4-phenylamino-buten-2-ones 5a–c, ethyl 2-arylazo-3-mercapto-3-phenylamino-acrylates 8a–c, N-aryl-2-cyano-3-mercapto-3-phenylamino-acrylamides 11a–c, N-aryl-2-(mercapto(phenylamino)methylene)-3-oxo-butanamides 14a–c, and 2-mercapto-4,6-dimethylnicotinonitrile 17 led to the production of their corresponding substituted thiophene compounds 4a–b, 7a–c, 10a–c, 13a–c, 16a–c, and 19 in moderate yields. The newly synthesized thiophene compounds were deduced according to FTIR, 1H NMR, 13C NMR, 19F NMR, and mass analyses along with micro-analytical data. The synthesized thiophene compounds were tested to evaluate their antibacterial and antioxidant activities. The majority of the synthesized thiophenes showed good to moderate anti-bacterial and antioxidant activities. The hydroxythiophene compound 4a showed extremely high antibacterial activity with inhibition zones 15–21 mm (from 60 to 87.5% activity indices). It inhibits bacterial growth and approaches the activity of Ampicillin, which inhibits bacteria with areas of inhibition from 23 to 25 mm. The hydroxythiophene compound 4a showed excellent antioxidant properties (85.9%) relative to the reference, Ascorbic acid (88.0%). [ABSTRACT FROM AUTHOR]

A new series of chromeno[4,3-b]pyridine derivatives has been designed, synthesized via reaction of 4-amino-2-oxo-2H-chromene-3-carboxaldehyde (1) with activated methylene compounds as (3-acetyl-2H-chromen-2-one, 1-(10H-phenothiazin-2-yl)ethan-1-one 2-(1H-benzo[d]imidazol-2-yl)acetonitrile, quincilidin-3-one hydrochloride, 2-oxo-3-phenylpropanoic acid, thiazolidine-2,4-dione, 1,2-iminothiazolidin-4-one, 1,3-diphenylimidazolidine-2,4-dione,2-methyl-2-phenyl-1,3-oxothiazolan-5-one). These compounds were screened for computational ADME and Lipinski's analysis followed by molecular docking and binding energy. The anticancer activities of the synthesized compounds were studied in breast (MCF-7). The molecular docking studies were found the oxolone moiety is a required common feature for good interaction and we found that compounds 2a, 2b, and 3 showed the highest activity toward breast cancer cell line. The structures of the new synthesized compounds were confirmed by 1H-NMR, 13C-NMR, IR, and MS spectroscopic methods. [ABSTRACT FROM AUTHOR]

A novel binary compounds as 3-(1,3-diphenyl-1H-pyrazol-4-yl)-2-phenyl-2H-benzo[f]indazole-4,9-dione (10) and fused compounds as 2-hydroxy-3-(4-hydroxy-7-methoxy-2-oxo-1,2-dihydroquinolin-3-yl)naphthalene-1,4-dione (7) and naphtho[2,3-b]furan-3,4,9(2H)-trione (6) based on lawsone 'that plays as important precursor' was synthesized by reaction with 1,3-diphenyl-1H-pyrazole-4-carbaldehyde and halo-compounds, such as 2-chloroacetyl chloride or 3-bromo-4-hydroxy-7-methoxyquinolin-2(1H)-one. Spectra and elemental analysis of newly synthesized compounds were investigated. The target molecules were showed easy access to antioxidant (calorimetrical measurement) and antitumor (Ehrlich ascites carcinoma [EAC] cells) activities. Geometrical isomers (enol, Keto conformers, and syn, anti-conformers) were achieved by density functional theory (DFT) that conformed to the spectral analysis of the investigated compounds. Supplemental data for this article is available online at here. [ABSTRACT FROM AUTHOR]

The aim of this study involves the synthesis of novel heterocyclic scaffolds containing quinoline moiety and studying their role as antimicrobial agents. 4‐hydroxy‐6‐phenyl‐2H‐pyrano[3,2‐c]quinoline‐2,5(6H))‐dione (1) was utilized as a precursor for the construction of new polyheterocyclic ring systems. It reacted with three aryl and (heteroaryl) aldehydes to furnish the corresponding arylidenes 2a‐c. The nucleophilic cyclization of compound 2 with hydrazine hydrate to give pyrazolyl quinolinone 3. Moreover, the reaction of 1 with HCHO/morpholine led to the formation of the adduct 7. The synthesized N‐(5–3‐formyl‐4‐hydroxy‐6‐phenyl‐2,5‐dioxo‐5,6‐dihydro‐2H‐pyrano [3,2‐c] quinoline (10) was utilized for the synthesis of 3‐(([aryl]amino)methylene)‐6‐phenyl‐2H‐pyrano[3,2‐c]quinoline‐2,4,5 (3H,6H)‐trione 11a‐c via its treatment with three types of amines. Treatment of 1 with POCl3/Et3N afforded the corresponding 4‐chloro derivative 20. Which upon treatment with thiourea lead to the formation of the corresponding 4‐mercapto derivative 21. The latter 21 was alkylated using ethylbromo acetate giving 22. All freshly synthesized scaffolds were elucidated by considering the data of both elemental and spectral analyses. The synthesized scaffolds were screened for antimicrobial activities also showed promising results. The p‐chlorobenzylidene pyrazolylquinolone derivative 3 has excellent antimicrobial properties against Proteus vulgaris compared to its mild activity against Staph aureus. While 4‐Chloro‐6‐phenyl‐2H‐pyrano[3,2‐c]quinoline‐2,5(6H)‐dione (20) exhibited good activates against Staph aureus surpassing the activity of reference antibiotic. Also, compounds 21 showed excellent antifungal activity against Candida albicans higher than fluconazole. [ABSTRACT FROM AUTHOR]

One-pot condensation of malononitrile 1, furan-2-carbaldehyde 2, butan-2-one 3, and ammonium acetate in ethanol, followed by cyanoacetylation of the formed nicotinonitrile 4 with 3-(3,5-dimethyl-1 H-pyrazol-1-yl)-3-oxopropanenitrile 5 afforded the cyanoacetamide 6. Compound 6 was used as a key for synthesis of nicotinonitriles via reaction with different reagents. [ABSTRACT FROM AUTHOR]

This review describes the synthesis and reactions of 2-aminothiophene-3-carboxamides as building blocks for the syntheses of polyfunctionalized heterocyclic compounds. [ABSTRACT FROM AUTHOR]