Gomha Sobhi M, Zaki Yasser H, Abdelhamid Abdou O
Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt.
Department of Chemistry, Faculty of Science, Beni-Suef University, Beni-Suef 62514, Egypt.
Molecules. 2015 Dec 4;20(12):21826-39. doi: 10.3390/molecules201219803.
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.
含有吡唑并[1,5 - a]嘧啶、四唑并[1,5 - a]嘧啶、咪唑并[1,2 - a]嘧啶、吡唑并[3,4 - d]嘧啶、1,3,4 - 噻二唑和噻唑的香豆素衍生物由6 - 溴 - 3 - (3 - (二甲基氨基)丙烯酰基)-2H - 色烯 - 2 - 酮、2 - (1 - (6 - 溴 - 2 - 氧代 - 2H - 色烯 - 3 - 基)亚乙基)肼基二硫代甲酸甲酯、2 - (1 - (6 - 溴 - 2 - 氧代 - 2H - 色烯 - 3 - 基)亚乙基)肼基硫代甲酰胺与各种杂环胺、肼基酰氯和肟基酰氯合成。新合成化合物的结构在元素分析、光谱数据以及尽可能采用的替代合成路线的基础上得以阐明。此外，对选定的新合成产物针对肝癌细胞系(HEPG2 - 1)进行了抗肿瘤活性评估。结果显示，吡唑并[1,5 - a]嘧啶7c、噻唑23g和1,3,4 - 噻二唑18a(IC50分别为2.70±0.28、3.50±0.23和4.90±0.69 μM)对肝癌(HEPG2 - 1)具有有前景的抗肿瘤活性，而大多数测试化合物表现出中等活性。
