Synthesis of some new pyrazole-based 1,3-thiazoles and 1,3,4-thiadiazoles as anticancer agents
| Autor: | Peter Metz, Heba S.A. El-Zahabi, Taha M. A. Eldebss, Mahmoud H. Yousef, Kamal M. Dawood |
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| Rok vydání: | 2013 |
| Předmět: |
Antineoplastic Agents
Pyrazole Medicinal chemistry Structure-Activity Relationship chemistry.chemical_compound Thiadiazoles Cell Line Tumor Drug Discovery medicine Humans Organic chemistry Ethyl chloroacetate Cell Proliferation Pharmacology Dose-Response Relationship Drug Molecular Structure Chemistry Human lung cancer Organic Chemistry Cancer Hep G2 Cells General Medicine medicine.disease Thiazoles MCF-7 Cells Pyrazoles Drug Screening Assays Antitumor Human breast Hepatocelluar carcinoma |
| Zdroj: | European Journal of Medicinal Chemistry. 70:740-749 |
| ISSN: | 0223-5234 |
| DOI: | 10.1016/j.ejmech.2013.10.042 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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