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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. 1995

Z Brzozowski
Department of Drug Technology, Faculty of Pharmacy, School of Medicine, Gdańsk, Poland.

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.

UI MeSH Term Description Entries
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000970 Antineoplastic Agents Substances that inhibit or prevent the proliferation of NEOPLASMS. Anticancer Agent,Antineoplastic,Antineoplastic Agent,Antineoplastic Drug,Antitumor Agent,Antitumor Drug,Cancer Chemotherapy Agent,Cancer Chemotherapy Drug,Anticancer Agents,Antineoplastic Drugs,Antineoplastics,Antitumor Agents,Antitumor Drugs,Cancer Chemotherapy Agents,Cancer Chemotherapy Drugs,Chemotherapeutic Anticancer Agents,Chemotherapeutic Anticancer Drug,Agent, Anticancer,Agent, Antineoplastic,Agent, Antitumor,Agent, Cancer Chemotherapy,Agents, Anticancer,Agents, Antineoplastic,Agents, Antitumor,Agents, Cancer Chemotherapy,Agents, Chemotherapeutic Anticancer,Chemotherapy Agent, Cancer,Chemotherapy Agents, Cancer,Chemotherapy Drug, Cancer,Chemotherapy Drugs, Cancer,Drug, Antineoplastic,Drug, Antitumor,Drug, Cancer Chemotherapy,Drug, Chemotherapeutic Anticancer,Drugs, Antineoplastic,Drugs, Antitumor,Drugs, Cancer Chemotherapy
D013449 Sulfonamides A group of compounds that contain the structure SO2NH2. Sulfonamide,Sulfonamide Mixture,Sulfonamide Mixtures,Mixture, Sulfonamide,Mixtures, Sulfonamide
D014407 Tumor Cells, Cultured Cells grown in vitro from neoplastic tissue. If they can be established as a TUMOR CELL LINE, they can be propagated in cell culture indefinitely. Cultured Tumor Cells,Neoplastic Cells, Cultured,Cultured Neoplastic Cells,Cell, Cultured Neoplastic,Cell, Cultured Tumor,Cells, Cultured Neoplastic,Cells, Cultured Tumor,Cultured Neoplastic Cell,Cultured Tumor Cell,Neoplastic Cell, Cultured,Tumor Cell, Cultured
D019380 Anti-HIV Agents Agents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS. AIDS Drug,AIDS Drugs,Anti-AIDS Agents,Anti-AIDS Drug,Anti-HIV Agent,Anti-HIV Drug,Anti-AIDS Drugs,Anti-HIV Drugs,Agent, Anti-HIV,Agents, Anti-AIDS,Agents, Anti-HIV,Anti AIDS Agents,Anti AIDS Drug,Anti AIDS Drugs,Anti HIV Agent,Anti HIV Agents,Anti HIV Drug,Anti HIV Drugs,Drug, AIDS,Drug, Anti-AIDS,Drug, Anti-HIV,Drugs, AIDS,Drugs, Anti-AIDS,Drugs, Anti-HIV

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