Chavan Ameya A, Pai Nandini R
Department of Organic Chemistry, D.G.Ruparel College, Senapati Bapat Marg, Mahim, Mumbai-400016, India.
Molecules. 2007 Nov 12;12(11):2467-77. doi: 10.3390/12112467.
2-Aminobenzothiazole-6-carboxylic acid (1), on condensation with chloroacetyl chloride yielded 2-(2-chloroacetylamino)benzothiazole-6-carboxylic acid (2), which on amination with hydrazine hydrate yielded in turn 2-(2-hydrazinoacetylamino)benzo-thiazole-6-carboxylic acid (3). Compound 3, on condensation with various aromatic aldehydes afforded a series of 2-{2-[N'-(arylidene)hydrazino]acetylamino}benzothiazole-6-carboxylic acids 4a-h, which upon dehydrative annulation in the presence of chloroacetyl chloride and triethylamine yielded 2-{2-[3-chloro-2-(aryl)-4-oxoazetidin-1-ylamino]-acetylamino}benzothiazole-6-carboxylic acids 5a-h. The synthesized compounds 4a-h and 5a-h were screened for their antibacterial activity against four microorganisms: Staphylococcus aureus (Gram positive), Bacillus subtilis (Gram positive), Psuedomonas aeruginosa (Gram negative) and Escherichia coli (Gram negative). They were found to exhibit good to moderate antibacterial activity. The antifungal activity of these compounds were also tested against three different fungal species. None of them were active against the species tested.
2-氨基苯并噻唑-6-羧酸（1）与氯乙酰氯缩合得到2-（2-氯乙酰氨基）苯并噻唑-6-羧酸（2），2-（2-氯乙酰氨基）苯并噻唑-6-羧酸（2）再与水合肼胺化得到2-（2-肼基乙酰氨基）苯并噻唑-6-羧酸（3）。化合物3与各种芳香醛缩合得到一系列2-{2-[N'-(亚芳基)肼基]乙酰氨基}苯并噻唑-6-羧酸4a-h，4a-h在氯乙酰氯和三乙胺存在下进行脱水环化反应得到2-{2-[3-氯-2-(芳基)-4-氧代氮杂环丁烷-1-基氨基]-乙酰氨基}苯并噻唑-6-羧酸5a-h。对合成的化合物4a-h和5a-h针对四种微生物进行了抗菌活性筛选：金黄色葡萄球菌（革兰氏阳性）、枯草芽孢杆菌（革兰氏阳性）、铜绿假单胞菌（革兰氏阴性）和大肠杆菌（革兰氏阴性）。发现它们表现出良好至中等的抗菌活性。还针对三种不同的真菌物种测试了这些化合物的抗真菌活性。它们对测试的物种均无活性。
