New groups of antimycobacterial agents: 6-chloro-3-phenyl-4-thioxo-2 H -1,3-benzoxazine-2(3 H )-ones and 6-chloro-3-phenyl-2 H -1,3-benzoxazine-2,4(3 H )-dithiones

来自 NCBI

阅读量：

作者：

Karel Waisser a，Jií Gregor a，Lenka Kubicová a，Věra Klimeová a，Jií Kune a b，Milo Macháek a，Jarmila Kaustová c

展开

摘要：

A series of 6-chloro-3-phenyl-4-thioxo-2H-1,3-benzoxazine-2(3H)-ones 3 and a series of 6-chloro-3-phenyl-2H-1,3-benzoxazine-2,4(3H)-dithiones 4 were synthesized by melting 6-chloro-3-phenyl-2H-1,3-benzoxazine-2,4(3H)-dione and its derivatives substituted on the phenyl ring 2 with tetraphosphorus decasulfide. Compounds 2c–e, 3 and 4 exhibited in vitro activity against Mycobacterium tuberculosis, M.kansasii (two strains) and M.avium better than or comparable to that of isoniazid. Replacement of the oxo group by a thioxo group at position 4 led to improvement in activity against M.tuberculosis and M.kansasii. The Free-Wilson method and procedure developed by the authors were used to analyse the structure–activity and structure–antimycobacterial profile relationships, respectively.

展开

关键词：

1,3-benzoxazine-2,4-diones 1,3-benzoxazine-2,4-dithiones 4-thioxo-1,3-benzoxazine-2-ones antimycobacterial activity quantitative structure–activity relationship cosine coefficient

DOI：

10.1016/S0223-5234(00)00174-4

被引量：

209

年份：

2000