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New visnagin-9-sulfonamide derivatives 3 and 4a−c were synthesized through the reaction of visnagin-9-sulfonyl chloride 2 with amino compounds. Acetylation of compounds 4b and 4c gave the monoacetyl and diacetyl derivatives 5 and 6, respectively. Diazotization reaction of compound 4b afforded the corresponding benzotriazole derivative 8. Pyrazole and thiopyrimidine derivatives 9 and 10 were obtained via the opening of pyrone ring upon reaction of compound 3 with hydrazine hydrate and thiourea, respectively. In addition, hydrolysis of compound 3 with potassium hydroxide furnished the visnaginone derivative 11 which used as starting material for synthesize benzofuran derivatives 12−14 and bergaptene derivatives 15−17. The synthesized compounds were tested for antimicrobial activity. Furochromone derivatives 3, 4a−c, 5, 6 and 8 (visnagin-9-sulfonamide derivatives) demonstrate moderate antibacterial and antifungal activities compared with the antibacterial and antifungal activites of the standard drugs. Benzofuran derivatives 11−14 (visnaginone derivatives) showed the lowest antimicrobial activity among all the compounds investigated in this study. Furocoumarin derivatives 15a,b, 16 and 17 (furobenzopyransulfonamide [bergaptensulfonamides]) are moderately active against all the tested strains.

A novel series of thiazolo[5,4‐b]pyridine, polysubstituted pyridines, pyrazolo [3,4‐b] pyridine‐5‐carbonitriles, and polyhydroquinoline were synthesized via one‐pot reaction of 2‐iminothiazolidin‐5‐one, acetyl pyridine, pyrazolone, and/or cyclohexanone with various aldehydes, some active methylene and ammonium acetate in the presence of ceric ammonium nitrate (CAN). The resulting compounds were generated in high yields in a short amount of time, and the structures of the novel compounds were confirmed using IR, 1H NMR, 13C‐NMR, and mass spectra. The cytotoxic activity of 15 substances was tested in vitro against HePG‐2 and Caco‐2 cell lines. The results of antitumor assay confirmed that quinoline 12d compounds possess higher cytotoxic activity against two cell lines closed to doxorubicin, which is used as a standard anticancer drug. Also, 12c compounds are more efficient antitumor against the 2‐cell lines. While compounds 1 showed moderate activity toward Caco‐2. On the other hand, most of the tested compounds exhibited moderate to low cytotoxic activity toward the two cell lines. Based on the results, some of the newly synthesized derivatives showed excellent antitumor activity that qualified them for biomedical applications.

Design and synthesis a novel of 2-oxo-pyridine and 1′H-spiro-pyridine derivatives as a new apoptotic inducers agents.