POTENTIAL ANTILEUKEMIC AND IMMUNOSUPPRESSIVE DRUGS . PREPARATION AND IN VITRO PHARMACOLOGICAL ACTIVITY OF SOME BENZO-2,1,3-OXADIAZOLES (BENZOFURAZANS) AND THEIR N-OXIDES (BENZOFUROXANS)

被引：151

作者：

GHOSH, PB

WHITEHOUSE, MW

机构：

[1] Departments of Medical Chemistry and Experimental Pathology, John Curtin School of Medical Research, Australian National University, Canberra, A.C.T

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 1968年 / 11卷 / 02期

关键词：

D O I：

10.1021/jm00308a027

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Eight methods for synthesizing various benzo-2,1,3-oxadiazoles (benzofurazans) and their N-oxides (benzofuroxans) are described. The activity of benzofurazans and benzofuroxans as in vitro inhibitors of RNA synthesis in sheep lymphocytes is given. Optimal drug activity in vitro was exhibited by 4-nitrobenzofurazan and 4-nitrobenzofuroxan and their 7-thio or 7-phenoxy derivatives. These compounds readily formed Meisenheimer complexes with nucleophiles and their drug action was abolished by preincubation with aliphatic thiols, e.g., glutathione. It is concluded that the most active compounds reacted with key intracellular thiol groups. The 4-nitro group and furazan ring were essential for optimal drug activity. © 1968, American Chemical Society. All rights reserved.

引用

页码：305 / +

页数：1

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