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2-巯基-N-（唑基）苯磺酰胺。I. N-（1,1-二氧代-1,4,2-苯并二硫嗪-3-基）胍的合成及其向具有潜在抗HIV或抗癌活性的2-巯基-N-（5-氨基-1,2,4-三唑-3-基）苯磺酰胺衍生物的转化。

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.

作者信息

Brzozowski Z

机构信息

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

出版信息

Acta Pol Pharm. 1995 Mar-Apr;52(2):91-101.

PMID:8960241
Abstract

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.

摘要

N-(1,1-二氧代-1,4,2-苯并二噻嗪-3-基)-N'-R3-胍[IIa-IIo]由相应的3-甲硫基-1,4,2-苯并二噻嗪1,1-二氧化物衍生物[Ia-Id]制备。根据R3取代基的电子效应，苯并二噻嗪基胍[II]的肼解反应以良好的产率得到以下衍生物：要么是2-巯基-N-(5-氨基-1,2,4-三唑-3-基)苯磺酰胺[IIIa-IIIc](R3 = H、Bu和Bzl时产率为82-90%)，要么是2-巯基-N-[5-(R3-氨基)-1,2,4-三唑-3-基]苯磺酰胺[IIIa-IIIm](R3 = Ph或取代苯基时产率为42-80%)。已提出反应机理。初步筛选数据表明，化合物[IIId、IIIf-IIIi、IIIk]表现出中等的抗HIV-1活性，化合物[IIIe、IIIj、III l]表现出抗癌活性。

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