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

Molecules

Sobhi M. Gomha¹  Yasser H. Zaki²  Abdou O. Abdelhamid¹ 

[1] Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt;Department of Chemistry, Faculty of Science, Beni-Suef University, Beni-Suef 62514, Egypt;

关键词: pyrazolo[1;    5-a]pyrimidine;    tetrazolo[1;    5-a]pyrimidine;    1;    3;    4-thiadiazoles;    thiazoles;    hydrazonoyl halides;    hydroximoyl chlorides;    antitumor activity;   

DOI  :  10.3390/molecules201219803

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.