Synthesis, Antiproliferative, and Antioxidant Evaluation of 2-Pentylquinazolin-4(3H)-one(thione) Derivatives with DFT Study
Synthesis, Antiproliferative, and Antioxidant Evaluation of 2-Pentylquinazolin-4(3H)-one(thione) Derivatives with DFT Study
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DOI：
10.3390/molecules24203787
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发表时间：
2019-10-01
期刊：
影响因子：
4.6
通讯作者：
Naglah, Ahmed M.
中科院分区：
文献类型：
--
作者：
El-Sayed, Amira A.;Ismail, Mahmoud F.;Naglah, Ahmed M.
本研究主要研究了一些新型喹唑烷酮(硫酮)衍生物6-14的抗增殖和抗氧化活性。本工作主要集中在两个方面：第一，比较了喹唑烷酮类化合物和喹唑硫酮类化合物。鉴于所研究化合物的抗增殖活性(对两种细胞系HepG2和MCF-7)和抗氧化活性(ABTS和DPPH两种方法)，最好的喹唑硫酮衍生物为6和14，分别表现出与喹唑烷酮衍生物5和9相当的良好效力。其次，我们比较了四个系列的席夫碱的活性，其中包括喹唑烷酮(11a-d)。此外，还研究了不同芳醛肼类化合物(11a-d)的抗增殖活性和抗氧化活性。由于共轭体系的扩展，化合物的活性随着p-位(OH>；OME>；Cl)上给电子基的增加而增强。值得注意的是，所测试化合物的大多数抗增殖和抗氧化活性结果与密度泛函理论计算结果一致。
The current study was chiefly designed to examine the antiproliferative and antioxidant activities of some novel quinazolinone(thione) derivatives 6-14. The present work focused on two main points; firstly, comparing between quinazolinone and quinazolinthione derivatives. Whereas, antiproliferative (against two cell lines namely, HepG2 and MCF-7) and antioxidant (by two methods; ABTS and DPPH) activities of the investigated compounds, the best quinazolinthione derivatives were 6 and 14, which exhibited excellent potencies comparable to quinazolinone derivatives 5 and 9, respectively. Secondly, we compared the activity of four series of Schiff bases which included the quinazolinone moiety (11a-d). In addition, the antiproliferative and antioxidant activities of the compounds with various aryl aldehyde hydrazone derivatives (11a-d) analogs were studied. The compounds exhibited potency that increased with increasing electron donating group in p-position (OH > OMe > Cl) due to extended conjugated systems. Noteworthy, most of antiproliferative and antioxidant activities results for the tested compounds are consistent with the DFT calculations.