Polycyclic Aromatic Compounds ( IF 2.4 ) Pub Date : 2020-12-29 , DOI: 10.1080/10406638.2020.1866035 Amira Atef Ghoneim 1, 2 , Abeer Gahffer Ali Hassan 3
Abstract
In this research, we aimed to synthesize a new series of C-glycosides that have thiazole-4, 5-diamine base. C-glycosides 8 was prepared by coupling compound 7 with D-glucose in the presence of iodine used as an oxidant/promoter dissolved in acetic acid and stirring at room temperature. Compound 8 was protected by reaction with acetic anhydride in the presence of pyridine gave compound 9. Furthermore, cyclization compound 7 with hydrazine hydrate and D-glucose gave the cyclic glycosides analogs 10. The compound 7 was condensed with phenyl hydrazine hydrochloride and D-xylose gave C-glycoside 11. The anticancer activity of the newly synthesized compounds was tested in vitro for their anticancer activities against human colorectal carcinoma (HCT-116), human prostate adenocarcinoma (PC-3), and human liver hepatocellular carcinoma (HepG-2) cell lines.
中文翻译:
具有预期抗癌活性的噻唑并[4, 5-b]吡嗪和咪唑并[4,5-d]噻唑无环C-糖苷的有效合成方法
摘要
在这项研究中,我们旨在合成一系列具有 thiazole-4, 5-diamine 碱基的C-糖苷。C-糖苷8通过在溶解于乙酸中的用作氧化剂/促进剂的碘存在下将化合物7与D-葡萄糖偶联并在室温下搅拌来制备。通过在吡啶存在下与乙酸酐反应保护化合物8,得到化合物9。此外,水合肼和D-葡萄糖的环化化合物7得到环状糖苷类似物10。化合物7与苯肼盐酸盐缩合,D-木糖得到C-糖苷11。新合成化合物的抗癌活性在体外测试了它们对人结肠直肠癌 (HCT-116)、人前列腺腺癌 (PC-3) 和人肝细胞癌 (HepG-2) 细胞系的抗癌活性。