新型苯并咪唑氨基酸酯的合成及其抗分枝杆菌活性评估
Synthesis and evaluation of antimycobacterial activity of new benzimidazole aminoesters.
作者信息
Yoon Yeong Keng, Ali Mohamed Ashraf, Wei Ang Chee, Choon Tan Soo, Ismail Rusli
机构信息
Institute for Research in Molecular Medicine, Universiti Sains Malaysia, Minden 11800, Penang, Malaysia.
Institute for Research in Molecular Medicine, Universiti Sains Malaysia, Minden 11800, Penang, Malaysia; New Drug Discovery Research, Department of Medicinal Chemistry, Alwar Pharmacy College, Alwar, Rajasthan 301030, India; New Drug Discovery Research, Department of Medicinal Chemistry, Sunrise University, Alwar, Rajasthan 301030, India.
出版信息
Eur J Med Chem. 2015 Mar 26;93:614-24. doi: 10.1016/j.ejmech.2013.06.025. Epub 2013 Jun 22.
A total of 51 novel benzimidazoles were synthesized by a 4-step reaction starting from basic compound 4-fluoro-3-nitrobenzoic acid under relatively mild reaction conditions. The structure of the novel benzimidazoles was confirmed by mass spectra as well as (1)H NMR spectroscopic data. Out of the 51 novel synthesized compounds, 42 of them were screened for their antimycobacterial activity against Mycobacterium tuberculosis H37Rv strain using BacTiter-Glo™ Microbial Cell Viability (BTG) method. Results of activity screened using Alamar Blue method was also provided for comparison purposes. Two of the novel benzimidazoles synthesized showed moderately good activity with IC50 of less than 15 μM. Compound 5g, ethyl 2-(4-(trifluoromethyl)phenyl)-1-(2-morpholinoethyl)-1H-benzo[d]imidazole-5-carboxylate, was found to be the most active with IC50 of 11.52 μM.
以碱性化合物4-氟-3-硝基苯甲酸为起始原料，通过4步反应，在相对温和的反应条件下总共合成了51种新型苯并咪唑。新型苯并咪唑的结构通过质谱以及¹H NMR光谱数据得以确证。在合成的51种新型化合物中，使用BacTiter-Glo™微生物细胞活力（BTG）方法对其中42种化合物针对结核分枝杆菌H37Rv菌株的抗分枝杆菌活性进行了筛选。为作比较，还提供了使用阿拉玛蓝法进行活性筛选的结果。合成的两种新型苯并咪唑显示出中等良好的活性，IC50小于15 μM。发现化合物5g，即2-(4-(三氟甲基)phenyl)-1-(2-吗啉代乙基)-1H-苯并[d]咪唑-5-羧酸乙酯，活性最强，IC50为11.52 μM。
Zotero 插件