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2-(1H-苯并[d]咪唑-2-基硫代)-N-(取代的4-氧代噻唑烷-3-基)乙酰胺的合成、表征、生物学评价及分子对接研究

Synthesis, characterization, biological evaluation and molecular docking studies of 2-(1H-benzo[d]imidazol-2-ylthio)-N-(substituted 4-oxothiazolidin-3-yl) acetamides.

作者信息

Yadav Snehlata, Narasimhan Balasubramanian, Lim Siong M, Ramasamy Kalavathy, Vasudevan Mani, Shah Syed Adnan Ali, Selvaraj Manikandan

机构信息

Department of Pharmaceutical Sciences, Maharshi Dayanand University, Rohtak, 124001, India.

Faculty of Pharmaceutical Sciences, Maharshi Dayanand University, Rohtak, 124001, India.

出版信息

Chem Cent J. 2017 Dec 22;11(1):137. doi: 10.1186/s13065-017-0361-6.

DOI:10.1186/s13065-017-0361-6
PMID:29274036
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5741571/
Abstract

BACKGROUND

A series of 2-(1H-benzo[d]imidazol-2-ylthio)-N-(substituted 4-oxothiazolidin-3-yl) acetamides was synthesized and characterized by physicochemical and spectral means. The synthesized compounds were evaluated for their in vitro antimicrobial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Candida albicans and Aspergillus niger by tube dilution method. The in vitro cytotoxicity study of the compounds was carried out against human colorectal (HCT116) cell line. The most promising anticancer derivatives (5l, 5k, 5i and 5p) were further docked to study their binding efficacy to the active site of the cyclin-dependent kinase-8.

RESULTS

All the compounds possessed significant antimicrobial activity with MIC in the range of 0.007 and 0.061 µM/ml. The cytotoxicity study revealed that almost all the derivatives were potent in inhibiting the growth of HCT116 cell line in comparison to the standard drug 5-fluorouracil. Compounds 5l and 5k (IC = 0.00005 and 0.00012 µM/ml, respectively) were highly cytotoxic towards HCT116 cell line in comparison to 5-fluorouracil (IC = 0.00615 µM/ml) taken as standard drug.

CONCLUSION

The molecular docking studies of potent anticancer compounds 5l, 5k, 5i and 5p showed their putative binding mode and significant interactions with cyclin-dependent kinase-8 as prospective agents for treating colon cancer.

摘要

背景

合成了一系列2-(1H-苯并[d]咪唑-2-基硫代)-N-(取代的4-氧代噻唑烷-3-基)乙酰胺，并通过物理化学和光谱手段对其进行了表征。采用试管稀释法对合成的化合物进行了体外抗金黄色葡萄球菌、枯草芽孢杆菌、大肠杆菌、白色念珠菌和黑曲霉的抗菌活性评价。对这些化合物进行了针对人结肠直肠癌(HCT116)细胞系的体外细胞毒性研究。对最有前景的抗癌衍生物(5l、5k、5i和5p)进行了进一步的对接研究，以研究它们与细胞周期蛋白依赖性激酶-8活性位点的结合效力。

结果

所有化合物均具有显著的抗菌活性，最低抑菌浓度(MIC)在0.007至0.061μM/ml范围内。细胞毒性研究表明，与标准药物5-氟尿嘧啶相比，几乎所有衍生物都能有效抑制HCT116细胞系的生长。与作为标准药物的5-氟尿嘧啶(IC = 0.00615μM/ml)相比，化合物5l和5k(IC分别为0.00005和0.00012μM/ml)对HCT116细胞系具有高度细胞毒性。

结论

对强效抗癌化合物5l、5k、5i和5p的分子对接研究表明了它们与细胞周期蛋白依赖性激酶-8的假定结合模式和显著相互作用，有望成为治疗结肠癌的药物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/518c/5741571/f82319abc53b/13065_2017_361_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/518c/5741571/ac7d5cc6d3b2/13065_2017_361_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/518c/5741571/fb14af52755e/13065_2017_361_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/518c/5741571/f82319abc53b/13065_2017_361_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/518c/5741571/ac7d5cc6d3b2/13065_2017_361_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/518c/5741571/fb14af52755e/13065_2017_361_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/518c/5741571/f82319abc53b/13065_2017_361_Fig2_HTML.jpg

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