2-Mercapto-N-(azolyl)benzenesulphonamides. I. Synthesis of N-(1,1-dioxo-1,4,2-benzodithiazin-3-yl)guanidines and their transformations into 2-mercapto-N-(5-amino-1,2,4-triazol-3-yl) benzenesulphonamide derivatives with potential anti-HIV or anticancer activity.
N-(1,1-Dioxo-1,4,2-benzodithiazin-3-yl)-N'-R3-guanidines [IIa-IIo] were prepared from the corresponding 3-methylthio-1,4,2-benzodithiazine 1,1-dioxide derivatives [Ia-Id]. Depending on electronic effects of R3 substituents, hydrazinolysis of the benzodithiazinylguanidines [II] afforded the following derivatives in good yields: either 2-mercapto-N-(5-amino-1,2,4-triazol-3-yl)benzenesulphonamides [IIIa-IIIc] (82-90% yields for R3 = H, Bu and Bzl) or 2-mercapto-N-[5-(R3-amino)-1,2,4-triazol-3-yl]benzenesulphonamides [IIIa-IIIm] (42-80% yields for R3 = Ph or substituted phenyl). The mechanism of the reaction has been suggested. Preliminary screening data indicated that compounds [IIId, IIIf-IIIi, IIIk] exhibit moderate anti-HIV-1 activity, and compounds [IIIe, IIIj, III l] anticancer activity.
Brzozowski
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Department of Drug Technology, Faculty of Pharmacy, School of Medicine, Gdańsk, Poland.
D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000494:pharmacology; D014407:Tumor Cells, Cultured
D019380:Anti-HIV Agents; D000970:Antineoplastic Agents; D013449:Sulfonamides