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Facile synthesis of benzonitrile/nicotinonitrile based s-triazines as new potential antimycobacterial agents
European Journal of Medicinal Chemistry ( IF 6.0 ) Pub Date : 2014-04-01 , DOI: 10.1016/j.ejmech.2014.03.085
Amit B. Patel , Kishor H. Chikhalia , Premlata Kumari

A common strategy to synthesize 4/6-(4-(4-methylpiperazin-1-yl)-6-(4-(4-oxo-2-phenylthiazolidin-3-yl)phenyl)-1,3,5-triazin-2-yloxy)benzonitriles/nicotinonitriles was developed by applying an efficient palladium-catalyzed C–C Suzuki coupling. Moreover, the synthesized compounds were also tested for their in vitro antimycobacterial activity against Mycobacterium tuberculosis H37Rv using BACTEC MGIT and Lowenstein–Jensen MIC methods. Several compounds displayed profound antimycobacterial activity in combination with low toxicity towards mammalian cells. The best results were observed amongst the nicotinonitrile substituted s-triazine analogs and it could be a potential starting point to develop new lead compounds in the fight against M. tuberculosis H37Rv. The newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR, MS and elemental analysis.



中文翻译:

轻松合成基于苯甲腈/烟腈的s-三嗪作为新的潜在抗分枝杆菌药

合成4 / 6-(4-(4-甲基哌嗪-1-基)-6-(4-(4-氧-2-苯基噻唑烷-3-基)苯基)-1,3,5-三嗪的通用策略通过应用有效的钯催化的CC Suzuki偶联剂开发了-2-基氧基)苄腈/烟腈。此外,还使用BACTEC MGIT和Lowenstein-Jensen MIC方法测试了合成的化合物对结核分枝杆菌H 37 Rv的体外分枝杆菌活性。几种化合物具有很强的抗分枝杆菌活性,并且对哺乳动物细胞的毒性低。在烟腈取代的s-三嗪类似物中观察到了最好的结果,这可能是在抗结核药物中开发新的先导化合物的潜在起点。结核分枝杆菌H 37 Rv。通过IR,1 H NMR,13 C NMR,MS和元素分析对新合成的化合物进行表征。

更新日期:2014-04-01
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