Synthesis and in vitro antimicrobial activity of benzo[b][1,4]thiazin-3(4H)-ones via smiles rearrangement
2011
Yang, Hao | Fang, Liang | Li, Zhu-Bo | Ren, Fang-Kui | Wang, Liying | Tian, Xiao | Shin, Dong-Soo | Zuo, Hua
New benzo[b][1,4]thiazin-3(4H)-one derivatives (compounds 12a-p) were synthesized via Smiles rearrangement and assayed in vitro for their antimicrobial activity against Gram-positive, Gram-negative bacteria and fungi. The antimicrobial activity of the benzo[b][1,4]thiazin-3(4H)-ones showed, on the whole, potent toward all tested Gram-positive and Gram-negative microorganism (minimal inhibitory concentration ranging from 16 to 64 μg/ml), whereas weak effectiveness was exhibited against fungi. Data obtained suggested that 12g, 12i, and 12o exerted the best antibacterial activity against Gram-positive bacteria and compound 12b demonstrated the best inhibition of Gram-negative bacteria. These observations provide some predictions to design further antimicrobial active compounds prior to their synthesis following with molecular modeling studies.
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