Badithapuram Vinitha, Nukala Satheesh Kumar, Thirukovela Narasimha Swamy, Dasari Gouthami, Manchal Ravinder, Bandari Srinivas
Department of Chemistry, Chaitanya (Deemed to be University), 506001 Warangal, Telangana, India.
Russ J Bioorg Chem. 2022;48(3):565-575. doi: 10.1134/S1068162022030220. Epub 2022 Jun 21.
The synthesis of some new quinoxaline derivatives (-) and their structure determination using H NMR, C NMR and mass spectral analysis was described herein. The in vitro anti-cancer activity of the these compounds () revealed that the compound1-((1-(4-bromophenyl)-1-1,2,3-triazol-4-yl)methyl)-2-(tetrazolo[1,5-]quinoxalin-4-yl)pyrazolidine-3,5-dione () has shown promising activity, whereas, compounds 1-((1-phenyl-1-1,2,3-triazol-4-yl)methyl)-2-(tetrazolo[1,5-]quinoxalin-4-yl)pyrazolidine-3,5-dione (), 1-(tetrazolo[1,5-]quinoxalin-4-yl)-2-((1-(-tolyl)-1-1,2,3-triazol-4-yl)methyl)pyrazolidine-3,5-dione (), 1-((1-(3,5-dimethoxyphenyl)-1-1,2,3-triazol-4-yl)methyl)-2-(tetrazolo[1,5-]quinoxalin-4-yl)pyrazolidine-3,5-dione () and 1-((1-(4-nitrophenyl)-1-1,2,3-triazol-4-yl)methyl)-2-(tetrazolo[1,5-]quinoxalin-4-yl)pyrazolidine-3,5-dione () exhibited good to moderate activity against four human cancer cell lines such as HeLa, MCF-7, HEK 293T, and A549 as compared to the doxorubicin. Predominantly, the compound displayed excellent activity over HeLa, MCF-7, HEK 293T, and A549 with IC values of 3.20 ± 1.32, 4.19 ± 1.87, 3.59 ± 1.34, and 5.29 ± 1.34 μM, respectively. Moreover, molecular docking studies of derivatives (-) on EGFR receptor suggested that the most potent compound strongly binds to protein EGFR (pdbid:4HJO) and the energy calculations of in silico studies were also in good agreement with the obtained IC values.
The online version contains supplementary material available at 10.1134/S1068162022030220.
本文描述了一些新的喹喔啉衍生物（-）的合成及其通过氢核磁共振、碳核磁共振和质谱分析进行的结构测定。这些化合物（）的体外抗癌活性表明，化合物1-((1-(4-溴苯基)-1H-1,2,3-三唑-4-基)甲基)-2-(四唑并[1,5-a]喹喔啉-4-基)吡唑烷-3,5-二酮（）显示出有前景的活性，而化合物1-((1-苯基-1H-1,2,3-三唑-4-基)甲基)-2-(四唑并[1,5-a]喹喔啉-4-基)吡唑烷-3,5-二酮（）、1-(四唑并[1,5-a]喹喔啉-4-基)-2-((1-(对甲苯基)-1H-1,2,3-三唑-4-基)甲基)吡唑烷-3,5-二酮（）、1-((1-(3,5-二甲氧基苯基)-1H-1,2,3-三唑-4-基)甲基)-2-(四唑并[1,5-a]喹喔啉-4-基)吡唑烷-3,5-二酮（）和1-((1-(4-硝基苯基)-1H-1,2,3-三唑-4-基)甲基)-2-(四唑并[1,5-a]喹喔啉-4-基)吡唑烷-3,5-二酮（）与阿霉素相比，对四种人类癌细胞系如HeLa、MCF-7、HEK 293T和A549表现出良好至中等的活性。主要地，该化合物对HeLa、MCF-7、HEK 293T和A549表现出优异的活性，IC值分别为3.20±1.32、4.19±1.87、3.59±1.34和5.29±1.34μM。此外，衍生物（-）对表皮生长因子受体的分子对接研究表明，最有效的化合物与蛋白质表皮生长因子受体（pdbid:4HJO）强烈结合，并且计算机模拟研究的能量计算也与获得的IC值高度一致。
在线版本包含可在10.1134/S1068162022030220获取的补充材料。
