Synthesis of some new pyrazole-based 1,3-thiazoles and 1,3,4-thiadiazoles as anticancer agents
Synthesis of some new pyrazole-based 1,3-thiazoles and 1,3,4-thiadiazoles as anticancer agents
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DOI：
10.1016/j.ejmech.2013.10.042
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发表时间：
2013-12-01
影响因子：
6.7
通讯作者：
Metz, Peter
中科院分区：
文献类型：
--
作者：
Dawood, Kamal M.;Eldebss, Taha M. A.;Metz, Peter
合成了N-(4-(Pyrazol-4-yl)thiazol-2-y1)-N‘-phenylthiourea衍生物2，然后在碱性条件下与不同的酰氯肼反应，得到相应的2-(4-(pyrazol-4-yl)thiazol-2-ylimino)-1，3，4-thiadiazole衍生物6、10a-e和17a-e。2与氯乙酸乙酯和3-氯-2，4-戊二酮反应，分别得到噻唑烷-4-酮22和1，3-噻唑25衍生物。噻唑烷-4-酮22与醛的缩合反应得到它们的5-亚芳基衍生物23a-f。大部分合成的化合物对人肝癌HepG2、人乳腺癌MCF-7和人肺癌A549具有抗癌活性。研究了电子供给基和电子引退基团的电子因素对其SAR的不同影响。许多被测试的化合物显示出中等到高度的抗癌活性。(C)2013年爱思唯尔·马森公司。版权所有。
N-(4-(Pyrazol-4-yl)thiazol-2-y1)-N'-phenylthiourea derivative 2 was synthesized and then treated with variety of hydrazonoyl chlorides under basic condition at reflux to afford the corresponding 2-(4-(pyrazol-4-yl)thiazol-2-ylimino)-1,3,4-thiadiazole derivatives 6, 10a-e and 17a-e. Reaction of 2 with ethyl chloroacetate and with 3-chloro-2,4-pentanedione gave the thiazolidin-4-one 22 and 1,3-thiazole 25 derivatives, respectively. Condensation of thiazolidin-4-one 22 with aldehydes gave their 5-arylidene derivatives 23a-f. Most of the synthesized compounds were tested for anticancer activity against human hepatocelluar carcinoma HepG2, human breast cancer MCF-7 and human lung cancer A549. Their SAR was studied and variously affected by the electronic factor of electron donating and withdrawing groups. Many of the tested compounds showed moderate to high anticancer activity. (C) 2013 Elsevier Masson SAS. All rights reserved.