一些新型6-甲基咪唑并[2,1-b]噻唑-5-碳酰肼衍生物的合成及其抗菌活性。

Synthesis of some new 6-methylimidazo[2,1-b]thiazole-5-carbohydrazide derivatives and their antimicrobial activities.

作者信息

Ur Füsun, Cesur Nesrin, Birteksöz Seher, Otük Gülten

机构信息

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Istanbul University, Istanbul, Turkey.

出版信息

Arzneimittelforschung. 2004;54(2):125-9. doi: 10.1055/s-0031-1296947.

DOI:10.1055/s-0031-1296947

PMID:15038463

Abstract

In this study, 14 new compounds having 6-methyl-N2-(alkylidene/cycloalkylidene)imidazo[2,1-b]thiazole-5-carbohydrazide (3a-g), 3-[[(6-methylimidazo[2,1-b]thiazole-5-yl)carbonyl]amino]-4-thiazolidinone (4a-d) and 4-[[(6-methylimidazo[2,1-b]thiazole-5-yl)carbonyl]amino]-1-thia-4-azaspiro[4.4]nonan/[4.5]decan-3-one (4e-g) structures were synthesized. The structures of the compounds were elucidated by UV, IR, 1H-NMR, 13C-NMR, 1H-13C-COSY, mass spectra and elemental analysis. All compounds synthesized were tested for antimicrobial activity against Staphylococcus aureus ATCC 6538, Staphylococcus epidermidis ATCC 12228, Escherichia coli ATCC 8739, Klebsiella pneumoniae ATCC 4352, Pseudomonas aeruginosa ATCC 1539, Salmonella typhi, Shigella flexneri, Proteus mirabilis ATCC 14153, Candida albicans ATCC 10231 and Mycobacterium tuberculosis H37Rv. Only 4d and 4f demonstrated antimicrobial activity against S. epidermidis ATCC 12228 (MIC: 19.5 microg/ml and 39 microg/ml, respectively).

摘要

在本研究中，合成了14种具有6-甲基-N2-（亚烷基/亚环烷基）咪唑并[2,1-b]噻唑-5-碳酰肼（3a-g）、3-[[（6-甲基咪唑并[2,1-b]噻唑-5-基）羰基]氨基]-4-噻唑烷酮（4a-d）和4-[[（6-甲基咪唑并[2,1-b]噻唑-5-基）羰基]氨基]-1-硫杂-4-氮杂螺[4.4]壬烷/[4.5]癸烷-3-酮（4e-g）结构的新化合物。通过紫外光谱、红外光谱、1H-核磁共振、13C-核磁共振、1H-13C-COSY、质谱和元素分析对这些化合物的结构进行了阐明。对合成的所有化合物针对金黄色葡萄球菌ATCC 6538、表皮葡萄球菌ATCC 12228、大肠杆菌ATCC 8739、肺炎克雷伯菌ATCC 4352、铜绿假单胞菌ATCC 1539、伤寒沙门菌、福氏志贺菌、奇异变形杆菌ATCC 14153、白色念珠菌ATCC 10231和结核分枝杆菌H37Rv进行了抗菌活性测试。只有4d和4f对表皮葡萄球菌ATCC 12228表现出抗菌活性（最低抑菌浓度分别为19.5微克/毫升和39微克/毫升）。