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Synthesis and biological evaluation of novel hybrid compounds derived from gallic acid and the 2-aminothiophene derivatives
Journal of the Iranian Chemical Society ( IF 2.2 ) Pub Date : 2019-11-16 , DOI: 10.1007/s13738-019-01813-0
Behnam Mahdavi , Seyed Mahmood Hosseyni-Tabar , Esmail Rezaei-Seresht , Hasan Rezaei-Seresht , Farahnaz Falanji

Abstract

Gallic acid (GA) and its benzamide derivatives have a wide variety of biological activities, such as antimicrobial, antioxidant, anticancer. In this study, we have reported the synthesis of some new hybrid compounds comprised of the 2-aminothiophene and GA moieties and evaluation of their cytotoxic activities against HeLa (cervical cancer), HCT116 (human colon cancer), and FT (fibroblast) cell lines as well as antimicrobial activities against some Gram-positive and Gram-negative bacteria. The reaction of some 2-aminothiophene derivatives (previously prepared from the Gewald reaction) with galloyl chloride having the acetylated hydroxyl groups and the subsequent deprotection of the hydroxyl groups gave the desired hybrid compounds. Then, the antimicrobial activity of the compounds was evaluated using disc diffusion and minimum inhibitory concentration assays. Finally, the MTT assay was carried out to evaluate the cytotoxicity of the synthesized compounds on the mentioned cell lines. The structure of the synthesized compounds was elucidated by conventional spectroscopic methods such as NMR, FT-IR, and UV–Vis spectroscopy. All compounds prevented the growth of Staphylococcus coagulase more than the positive control of chloramphenicol, and one compound was more sensitive to the growth of Klebsiella pneumonia compared to the standard antibiotic. All compounds showed acceptable activity against cancer cells. The highest activity was observed against HeLa with an IC50 value of 3.2 μg/mL for compound 3d and against HCT116 with IC50 of 59.4 μg/mL for 3b. The high anticancer activity of compound 3d against HeLa allows us to consider it as a good lead compound for the development of new potent anticancer agents for the treatment of cervical cancer.

Graphic abstract



中文翻译:

没食子酸和2-氨基噻吩衍生物的新型杂化化合物的合成与生物学评价

摘要

没食子酸(GA)及其苯甲酰胺衍生物具有广泛的生物活性,例如抗微生物剂,抗氧化剂,抗癌剂。在这项研究中,我们报告了一些合成的新型杂合化合物,它们由2-氨基噻吩和GA部分组成,并评估了它们对HeLa(子宫颈癌),HCT116(人结肠癌)和FT(成纤维细胞)细胞系的细胞毒活性。以及对某些革兰氏阳性和革兰氏阴性细菌的抗菌活性。一些2-氨基噻吩衍生物(先前由Gewald反应制备)与具有乙酰化羟基的没食子酰氯反应,随后使羟基脱保护,得到所需的杂化化合物。然后,使用圆盘扩散法和最小抑菌浓度测定法评估化合物的抗菌活性。最后,进行MTT测定以评估合成的化合物对所述细胞系的细胞毒性。合成化合物的结构通过常规光谱方法(例如NMR,FT-IR和UV-Vis光谱)进行了阐明。所有化合物均阻止了金黄色葡萄球菌凝固酶比氯霉素的阳性对照更多,并且与标准抗生素相比,一种化合物对肺炎克雷伯菌的生长更敏感。所有化合物均显示出可接受的抗癌细胞活性。化合物3d的抗HeLa活性最高,IC 50值为3.2μg/ mL,3b的抗HCT116活性最高,IC 50为59.4μg/ mL 。化合物3d对HeLa的高抗癌活性使我们可以将其视为开发用于治疗子宫颈癌的新型有效抗癌药的良好先导化合物。

图形摘要

更新日期:2019-11-16
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