Synthesis, crystal structure, and density functional theory study of a new compound 4-(2-chlorobenzyl)-1-(5-fluoro-2-hydroxy-3-(thiomorpholinomethyl)phenyl [1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one,Journal of Heterocyclic Chemistry

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Synthesis, crystal structure, and density functional theory study of a new compound 4-(2-chlorobenzyl)-1-(5-fluoro-2-hydroxy-3-(thiomorpholinomethyl)phenyl [1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2021-06-28 , DOI: 10.1002/jhet.4333
Weiyin Hu _{1,

2,

3} , Tianhui Liao _{1,

3} , Liyuan Deng _{2,

3} , Hong Sun _{1,

3} , Zhixu Zhou _{1,

2} , Huifang Chai ₄ , Chunshen Zhao _{1,

2,

4}

Affiliation

In this paper, a novel SHP244 derivative 4-(2-chlorobenzyl)-1- (5-fluoro-2-hydroxy-3- [thiomorph-olinomethyl] phenyl)- [1,2,4]triazolo [4,3-a] quinazolin-5(4H)-one was synthesized through five steps. The single crystals were grown in a suitable solvent system (dichloromethane and methanol). Its structure was confirmed by ¹H NMR, ¹³C NMR spectroscopy, ESI-MS, m/z: 534.12[M-H] (MS), FT-IR, and X-ray single crystal diffraction. The crystal structure of the title compound was optimized by density functional theory (DFT) calculation. The crystal structure after X-ray single crystal diffraction was compared with the structure optimized by DFT calculation, and the result shows that the two structures are consistent. In order to explore certain physical and chemical properties, the frontier molecular orbital and molecular electrostatic potential of the title compound were analyzed. In addition, the docking of the title compound to the target protein was studied to understand the docking effect of the compound with the target protein.

中文翻译：

一种新化合物4-(2-氯苄基)-1-(5-氟-2-羟基-3-(硫代吗啉甲基)苯基[1,2,4]三唑并[4, 3-a]喹唑啉-5(4H)-one

在本文中，一种新型SHP244衍生物4-(2-氯苄基)-1-(5-氟-2-羟基-3-[硫代吗啉甲基]苯基)-[1,2,4]三唑并[4,3- a] quinazolin-5(4H)-one 通过五个步骤合成。单晶在合适的溶剂系统（二氯甲烷和甲醇）中生长。其结构经¹ H NMR、¹³C NMR 光谱、ESI-MS、m/z：534.12[MH] (MS)、FT-IR 和 X 射线单晶衍射。通过密度泛函理论 (DFT) 计算优化了标题化合物的晶体结构。将X射线单晶衍射后的晶体结构与DFT计算优化后的结构进行比较，结果表明两者结构一致。为了探究某些理化性质，对标题化合物的前沿分子轨道和分子静电势进行了分析。此外，研究了标题化合物与目标蛋白的对接，以了解化合物与目标蛋白的对接效果。

更新日期：2021-06-28

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