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Synthesis of some new pyrazole-based 1,3-thiazoles and 1,3,4-thiadiazoles as anticancer agents. | LitMetric

Synthesis of some new pyrazole-based 1,3-thiazoles and 1,3,4-thiadiazoles as anticancer agents.

Eur J Med Chem

Department of Chemistry, Faculty of Science, University of Cairo, Giza 12613, Egypt. Electronic address:

Published: September 2014

AI Article Synopsis

  • A compound called N-(4-(Pyrazol-4-yl)thiazol-2-yl)-N'-phenylthiourea was synthesized and reacted with different hydrazonoyl chlorides to create several derivatives with potential anticancer properties.
  • The synthesis also involved reactions with ethyl chloroacetate and a specific diketone, leading to the formation of thiazolidin-4-one and 1,3-thiazole derivatives.
  • Testing of these newly synthesized compounds against various cancer cell lines revealed that many exhibited moderate to high anticancer activity, with effectiveness influenced by the presence of different chemical groups.

Article Abstract

N-(4-(Pyrazol-4-yl)thiazol-2-yl)-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.

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Source
http://dx.doi.org/10.1016/j.ejmech.2013.10.042DOI Listing

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