Synthesis and antimicrobial activities of novel quinoline derivatives carrying 1,2,4-triazole moiety
Synthesis and antimicrobial activities of novel quinoline derivatives carrying 1,2,4-triazole moiety
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DOI：
10.1016/j.ejmech.2009.06.031
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发表时间：
2009-11-01
影响因子：
6.7
通讯作者：
Shetty, N. Suchetha
中科院分区：
文献类型：
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作者：
Eswaran, Sumesh;Adhikari, Airody Vasudeva;Shetty, N. Suchetha
以4-羟基-8-三氟甲基喹啉-3-碳酰肼4为原料，经多步反应合成了一类新的含1，2，4-三唑基的喹罗啉衍生物。化合物4用取代的异硫氰酸酯处理，得到喹啉-氨基硫脲5a-c，其在碱性介质中方便地环化为（5-巯基-4H-三唑-3-基）-喹啉-4-醇6a-c。然后通过用三氯氧磷处理将这些中间体转化为它们各自的氯代衍生物7a-c，其进一步与不同的生物活性稀有胺反应，以良好的产率得到目标化合物8a-g、9a-h和10a-h。最后一步，涉及亲核取代反应是通过微波诱导技术实现的，与常规加热相比，该技术大大缩短了反应时间，并提高了产率。新合成的最终化合物进行了评价，其在体外抗菌和抗真菌活性对四个菌株。初步结果表明，大多数化合物表现出非常好的抗菌活性，与一线标准药物相当。最有效的化合物在6.25 μ g/mL的MIC下表现出活性。(C)2009年Elsevier Masson SAS。All rights reserved.
A new class of quirroline derivatives containing 1,2,4-triazole moiety were synthesized from derivatives of 4-hydroxy-8-(trifluoromethyl)quinoline-3-carbohydrazide 4 through multi-step reactions. The compound 4, on treatment with substituted Isothiocyanates yielded quinoline-thiosemicarbazides 5a-c, which were conveniently cyclized to (5-mercapto-4H-triazol-3-yl)-quinolin-4-ols 6a-c in basic medium. These intermediates were then transformed to their respective chloro derivatives 7a-c by treatment with phosphorus oxychloride, which on further reaction with different biologically active rare amines yielded the target compounds 8a-g, 9a-h and 10a-h in good yield. The ultimate step, involving nucleophilic substitution reaction was achieved by microwave-induced technique, which has reduced the reaction time drastically as well as improved the yield when compared to conventional heating. The newly synthesized final compounds were evaluated for their in vitro antibacterial and antifungal activities against four strains each. Preliminary results indicated that most of the compounds demonstrated very good antimicrobial activity, comparable to the first line standard drugs. The most effective compounds have exhibited activity at MIC of 6.25 mu g/mL. (C) 2009 Elsevier Masson SAS. All rights reserved.