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醋酸锌催化、超声辐射下绿色高效合成呫吨衍生物：X射线晶体学分析与研究

Zinc acetate-catalyzed, green and efficient synthesis of xanthene derivatives under ultrasound irradiation: X-ray crystallographic analysis and study.

作者信息

Sayad Rayene, Bouzina Abdeslem, Bouone Yousra Ouafa, Beldjezzia Dounia, Djemel Abdelhak, Ibrahim-Ouali Malika, Aouf Nour-Eddine, Aouf Zineb

机构信息

Laboratory of Applied Organic Chemistry, Bioorganic Chemistry Group, Sciences Faculty, Chemistry Department, Badji Mokhtar-Annaba University Box 12 23000 Annaba Algeria

Research Unit in Medicinal Plants, URPM, Attached to Research Center of Biotechnology, CRBt 3000 Laghouat 25000 Constantine Algeria.

出版信息

RSC Adv. 2024 Aug 6;14(34):24585-24603. doi: 10.1039/d4ra04135f. eCollection 2024 Aug 5.

DOI:10.1039/d4ra04135f
PMID:39108949
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11301142/
Abstract

A simple, one-pot method using zinc acetate and ultrasound irradiation has been developed to synthesize xanthene derivatives from cyclic diketones and aromatic aldehydes, yielding good to excellent results. This method offers advantages like mild conditions, high atom economy, easy isolation, and a recyclable catalyst. All xanthene derivatives, including two new molecules, were confirmed using standard spectroscopic methods, with X-ray crystallographic data provided for compound 3r. The synthesized molecules were shown to inhibit the VEGFR-2 enzyme, confirmed by molecular docking studies. A 200 ns molecular dynamics simulation validated these findings, showing significant stability for the 3e-VEGFR-2 complex after 1 ns and the 3p-VEGFR-2 complex for 8 ns. DFT calculations were used to analyze electronic and geometric properties, including HOMO and LUMO bandgap energies and molecular electrostatic potential surfaces. Additionally, the absorption, distribution, metabolism, and excretion (ADME) properties of the synthesis compounds were assessed.

摘要

已开发出一种使用醋酸锌和超声辐射的简单一锅法，用于从环状二酮和芳香醛合成呫吨衍生物，取得了良好到优异的结果。该方法具有条件温和、原子经济性高、易于分离和催化剂可循环利用等优点。所有呫吨衍生物，包括两个新分子，均使用标准光谱方法进行了确认，并提供了化合物3r的X射线晶体学数据。分子对接研究证实，合成的分子可抑制VEGFR-2酶。200纳秒的分子动力学模拟验证了这些发现，显示3e-VEGFR-2复合物在1纳秒后以及3p-VEGFR-2复合物在8纳秒后具有显著稳定性。使用密度泛函理论（DFT）计算分析了电子和几何性质，包括最高占据分子轨道（HOMO）和最低未占据分子轨道（LUMO）带隙能量以及分子静电势表面。此外，还评估了合成化合物的吸收、分布、代谢和排泄（ADME）性质。

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