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Molecules 2015, 20(12), 21826-21839; doi:10.3390/molecules201219803

Utility of 3-Acetyl-6-bromo-2H-chromen-2-one for the Synthesis of New Heterocycles as Potential Antiproliferative Agents

1
Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt
2
Department of Chemistry, Faculty of Science, Beni-Suef University, Beni-Suef 62514, Egypt
*
Author to whom correspondence should be addressed.
Academic Editor: Richard A. Bunce
Received: 27 August 2015 / Revised: 25 November 2015 / Accepted: 26 November 2015 / Published: 4 December 2015
(This article belongs to the Collection Heterocyclic Compounds)
View Full-Text   |   Download PDF [900 KB, uploaded 4 December 2015]   |  

Abstract

Coumarin derivatives containing pyrazolo[1,5-a]pyrimidine, tetrazolo[1,5-a]pyrimidine, imidazo[1,2-a]pyrimidine, pyrazolo[3,4-d]pyrimidine, 1,3,4-thiadiazoles and thiazoles were synthesized from 6-bromo-3-(3-(dimethylamino)acryloyl)-2H-chromen-2-one, methyl 2-(1-(6-bromo-2-oxo-2H-chromen-3-yl)ethylidene)hydrazine carbodithioate, 2-(1-(6-bromo-2-oxo-2H-chromen-3-yl)ethylidene) hydrazine carbothioamide and each of heterocyclic amine, hydrazonoyl chlorides and hydroximoyl chlorides. The structures of the newly synthesized compounds were elucidated on the basis of elemental analysis, spectral data, and alternative synthetic routes whenever possible. Moreover, selected newly synthesized products were evaluated for their antitumor activity against a liver carcinoma cancer cell line (HEPG2-1). The results revealed that pyrazolo[1,5-a]pyrimidine 7c, thiazole 23g and 1,3,4-thiadiazole 18a (IC50 = 2.70 ± 0.28, 3.50 ± 0.23 and 4.90 ± 0.69 µM, respectively) have promising antitumor activity against liver carcinoma (HEPG2-1) while most of the tested compounds showed moderate activity. View Full-Text
Keywords: pyrazolo[1,5-a]pyrimidine; tetrazolo[1,5-a]pyrimidine; 1,3,4-thiadiazoles; thiazoles; hydrazonoyl halides; hydroximoyl chlorides; antitumor activity pyrazolo[1,5-a]pyrimidine; tetrazolo[1,5-a]pyrimidine; 1,3,4-thiadiazoles; thiazoles; hydrazonoyl halides; hydroximoyl chlorides; antitumor activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Gomha, S.M.; Zaki, Y.H.; Abdelhamid, A.O. Utility of 3-Acetyl-6-bromo-2H-chromen-2-one for the Synthesis of New Heterocycles as Potential Antiproliferative Agents. Molecules 2015, 20, 21826-21839.

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