Chu D T, Fernandes P B, Pernet A G
J Med Chem. 1986 Aug;29(8):1531-4. doi: 10.1021/jm00158a037.
A new class of heterocyclic compounds with potent antibacterial activity, namely, 2-substituted amino-3-fluoro-5,12-dihydro-5-oxobenzothiazolo[3, 2-a]quinoline-6-carboxylic acids, is described. The compounds are conformationally restricted analogues of 7-substituted amino-6-fluoro-1-aryl-1, 4-dihydro-4-oxoquinoline-3-carboxylic acids. Compounds 7 and 10, having a 4-methylpiperazinyl and a piperazinyl substitution at the 2-position, respectively, possess in vitro antibacterial activities comparable to norfloxacin (15). Compound 8, which has a 4-acetylpiperazinyl substitution at the 2-position, is active against Gram-positive organisms and nearly inactive against Gram-negative organisms. An efficient and short synthesis of this novel heterocyclic system via an intramolecular nucleophilic displacement cyclization reaction is reported.
描述了一类具有强效抗菌活性的新型杂环化合物，即2-取代氨基-3-氟-5,12-二氢-5-氧代苯并噻唑并[3,2-a]喹啉-6-羧酸。这些化合物是7-取代氨基-6-氟-1-芳基-1,4-二氢-4-氧代喹啉-3-羧酸的构象受限类似物。化合物7和10分别在2位具有4-甲基哌嗪基和哌嗪基取代，其体外抗菌活性与诺氟沙星相当(15)。化合物8在2位具有4-乙酰哌嗪基取代，对革兰氏阳性菌有活性，而对革兰氏阴性菌几乎无活性。报道了通过分子内亲核取代环化反应高效、简短地合成这种新型杂环体系的方法。
