2-(3'-Indolyl)-N-arylthiazole-4-carboxamides: Synthesis and evaluation of antibacterial and anticancer activities.
2-(3'-Indolyl)-N-arylthiazole-4-carboxamides: Synthesis and evaluation of antibacterial and anticancer activities.
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2-(3-吲哚基)-N-芳基噻唑-4-甲酰胺：抗菌和抗癌活性的合成和评价。
DOI：
10.1016/j.bmcl.2015.07.105
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发表时间：
2015
影响因子：
2.7
通讯作者：
Kumar,Dalip
中科院分区：
文献类型：
--
作者：
Tantak,MukundP;Wang,Jing;Singh,RajnishPrakash;Kumar,Anil;Shah,Kavita;Kumar,Dalip
设计并合成了一系列新的2-（3′-吲哚基）-N-芳基噻唑-4-甲酰胺17 a-p。利用容易获得的硫代酰胺15与溴代丁二酸在室温下反应生成不同的噻唑羧酸16，然后用EDCI·HCl和HOBt与芳胺偶联，得到不同的芳基噻唑-4-甲酰胺17 a-pin，产率78-87%。对革兰氏阳性和革兰氏阴性细菌菌株的抗菌活性评价导致化合物17 i-k和17 o作为有效的和选择性的（革兰氏阴性）抗菌剂。噻唑甲酰胺17 a-p的细胞毒性也在一组人癌细胞系上进行了评价。在测试的衍生物中，化合物17 i（IC 50 = 8.64 μM; HEK 293 T）和17 l（IC 50 = 3.41 μM; HeLa）被鉴定为该系列中最有效的类似物。噻唑甲酰胺17 i的初步作用机制研究表明，其对HeLa细胞的细胞毒性涉及通过凋亡诱导细胞死亡。
A new series of 2-(3′-indolyl)-N-arylthiazole-4-carboxamides17a–phas been designed and synthesized. Initial reaction of readily available thioamides15with bromopyruvic acid under refluxing conditions produced different thiazole carboxylic acids16which upon coupling with arylamines by using EDCI·HCl and HOBt afforded diverse arylthiazole-4-carboxamides17a–pin 78–87% yields. Antibacterial activity evaluation against Gram-positive and Gram-negative bacterial strains led to compounds17i–kand 17o as potent and selectively (Gram-negative) antibacterial agents. The cytotoxicity of thiazole carboxamides17a–pwas also evaluated on a panel of human cancer cell lines. Among the tested derivatives, compounds17i(IC50= 8.64 μM; HEK293T) and17l(IC50= 3.41 μM; HeLa) were identified as the most potent analogues of the series. Preliminary mechanism of action studies of thiazole carboxamide17isuggested that its cytotoxicity against HeLa cells involves the induction of cell death by apoptosis.