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一些嘧啶并六氢喹啉候选物：合成、密度泛函理论、细胞毒性活性评估、分子对接及研究

Some pyrimidohexahydroquinoline candidates: synthesis, DFT, cytotoxic activity evaluation, molecular docking, and studies.

作者信息

Ramadan Sayed K, Abd-Rabboh Hisham S M, Abdel Hafez Amal A, Abou-Elmagd Wael S I

机构信息

Chemistry Department, Faculty of Science, Ain Shams University Cairo 11566 Egypt

Chemistry Department, College of Science, King Khalid University P. O. Box 9004 Abha 62223 Saudi Arabia.

出版信息

RSC Adv. 2024 May 22;14(23):16584-16599. doi: 10.1039/d4ra02271h. eCollection 2024 May 15.

DOI:10.1039/d4ra02271h
PMID:38779387
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11109844/
Abstract

Some hexahydroquinoline candidates were prepared by reacting 2-amino-3-cyano-1-cyclohexylhexahydroquinoline with oxalyl chloride and triethyl orthoformate. The computational chemical approach agreed with the product-testing results. The produced substances were examined for their antiproliferative activity against liver carcinoma (HepG2), breast adenocarcinoma (MCF7), prostate cancer (PC3), and colon cancer (HCT116) cell lines. The highest potency against the four cell lines was exhibited by hydrazide, thiosemicarbazide, and thiazolidinone derivatives. The best docking score was presented by thiosemicarbazide and thiazolidinone derivatives as they showed the highest binding to the Mcl-1 enzyme with binding energies of -8.97 and -8.90 kcal mol, respectively, which were higher than that of the co-crystallized ligand (LC3) with a binding energy of -8.74 kcal mol. Besides, the modeling pharmacokinetics disclosed their desirable drug-likeness and oral bioavailability characteristics.

摘要

通过使2-氨基-3-氰基-1-环己基六氢喹啉与草酰氯和原甲酸三乙酯反应制备了一些六氢喹啉候选物。计算化学方法与产物测试结果一致。检测了所产生的物质对肝癌（HepG2）、乳腺腺癌（MCF7）、前列腺癌（PC3）和结肠癌（HCT116）细胞系的抗增殖活性。酰肼、氨基硫脲和噻唑烷酮衍生物对这四种细胞系表现出最高的效力。氨基硫脲和噻唑烷酮衍生物呈现出最佳的对接分数，因为它们与Mcl-1酶的结合力最高，结合能分别为-8.97和-8.90 kcal/mol，高于共结晶配体（LC3）的结合能-8.74 kcal/mol。此外，建模的药代动力学揭示了它们理想的类药物性质和口服生物利用度特征。

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