Synthesis, anticancer evaluation, and docking studies of some novel azo chromene derivatives,Journal of the Chinese Chemical Society

当前位置： X-MOL 学术 › J. Chin. Chem. Soc. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Synthesis, anticancer evaluation, and docking studies of some novel azo chromene derivatives
Journal of the Chinese Chemical Society ( IF 1.6 ) Pub Date : 2020-05-06 , DOI: 10.1002/jccs.201900481
Kaliyan Bhuvaneswari ₁ , Paramasivam Sivaguru ₂ , Appaswami Lalitha ₁

Affiliation

We have described a simple, convenient, and high‐yielding one‐pot synthesis of novel azo chromene derivatives via a three‐component reaction of various azo aldehydes with dimedone and malononitrile using 10 mol% of 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) as catalyst and ethanol as solvent at reflux condition. All the synthesized compounds have been characterized using Fourier‐transform infrared spectroscopy (FT‐IR), ¹H NMR, ¹³C NMR, and HR‐MS spectra and molecular docking was performed to explore new inhibitors of human placental aromatase cytochrome P450 and cyclooxygenase‐2 enzymes. Of all the compounds docked, compound (E)‐2‐amino‐4‐(4,4‐dimethyl‐2,6‐dioxocyclohexyl)‐6‐((3‐methoxyphenyl)diazenyl‐4H‐chromene‐3‐carbonitrile (4o) showed good binding affinity with the active site of human placental aromatase cytochrome P450 enzyme (PDB: 3EQM) with inhibition constant (Ki) 1.66 nM and compound 4o also showed good binding affinity with the active site of cyclooxygenase‐2 enzyme (PDB: 6COX) with inhibition constant (Ki) 367.17 pM. In vitro anti‐cancer activity studies against MCF‐7 cells were also performed for compounds 4o, anastrozole and celecoxib. Compound 4o showed an effective cytotoxicity at 19.8 μg/ml compared to anastrozole and celecoxib (24.7 and 26.2 μg/ml).

中文翻译：

某些新型偶氮苯并噻吩衍生物的合成，抗癌评估和对接研究

我们已经描述了使用10 mol％的1,8-二氮杂双环[3.4.0]通过各种偶氮醛与二甲酮和丙二腈的三组分反应，简单，方便且高收率的新型偶氮苯二烯衍生物的一锅法合成[5.4.0]在回流条件下，十一碳烯（DBU）作为催化剂，乙醇作为溶剂。所有合成的化合物均使用傅里叶变换红外光谱（FT-IR），¹ H NMR，¹³ C NMR和HR-MS光谱进行了表征，并进行了分子对接以探索人类胎盘芳香化酶细胞色素P450和环氧合酶的新型抑制剂。 2种酶。在所有对接的化合物中，化合物（E）-2-氨基-4-（4,4-二甲基-2,6-二氧代环己基）-6-（（3-甲氧基苯基）二氮烯基4 H-色烯-3-腈（4度）与抑制因子（Ki）为1.66 nM的人胎盘芳香化酶细胞色素P450酶（PDB：3EQM）的活性位点具有良好的结合亲和力，化合物4o也与环氧合酶2酶的活性位点（PDB：6COX）具有良好的结合力抑制常数（Ki）为367.17 pM。还针对化合物4o，阿那曲唑和塞来昔布对MCF-7细胞进行了体外抗癌活性研究。与阿那曲唑和塞来昔布（24.7和26.2μg/ ml）相比，化合物4o在19.8μg/ ml处显示有效的细胞毒性。

更新日期：2020-05-06

点击分享查看原文

点击收藏

阅读更多本刊最新论文本刊介绍/投稿指南11