6-氟-4-羟基-3-氧代-3,4-二氢喹喔啉-1(2H)-羧酸叔丁酯的合成、晶体结构及抗肿瘤活性研究
Synthesis,Crystal Structure and Antitumor Activity of 6-Fluoro-4-Hydroxy-3-Oxo-3,4-Dihydroquinoxaline-1(2H)-Carboxylic Acid Tert-Butyl Ester
毛云虹 1赵春深1
作者信息
- 1. 贵州大学药学院,贵阳 550025;贵州省合成药物工程实验室,贵阳 550025
- 折叠
摘要
喹喔啉类化合物由于具有显著的生物活性而被广泛应用于医药、化工领域,特别是抗癌药物研发领域.本文通过四步反应法首次合成了 6-氟4-羟基-3-氧代-3,4-二氢喹喔啉-1(2H)-羧酸叔丁酯,经溶液结晶法获得其单晶体.晶体学分析表明,该化合物属单斜晶系,空间群C2/c,晶胞常数a=1.286 63(10)nm,b=2.252 49(17)nm,c=1.015 64(7)nm,Z=8,ρc=1.359 g·cm-3,R=0.053 8,Rw=0.140 6.在 B3LYP/6-311+G(2d,p)模式下使用密度泛函理论(DFT)计算了该化合物的最佳结构,与X射线单晶衍射确定的晶体结构基本一致.抗肿瘤活性研究表明其有良好的抗肿瘤作用.此外,通过DFT计算了分子的静电势和前沿分子轨道.
Abstract
Quinoxaline compounds are widely used in the fields of medicine and chemical industry,especially in the development of anticancer drugs,due to their significant biological activity.6-fluoro-4-hydroxy-3-oxo-3,4-dihydroquinoline-1(2H)-carboxylic acid tert-butyl ester was synthesized through a four-step reaction method in this paper,and its single crystal was obtained by solution crystallization method.Crystallographic analysis indicates that the compound belongs to monoclinic crystal system with space group C2/c,the unit cell dimensions are a=1.286 63(10)nm,b=2.252 49(17)nm,c=1.015 64(7)nm,Z=8,pc=1.359 g·cm-3,R=0.053 8,Rw=0.140 6.The optimal structure was calculated using density functional theory(DFT)in B3LYP/6-311+G(2d,p)mode.The results are basically consistent with those obtained by X-ray single crystal diffraction.The antitumor activity study shows that the compound has good antitumor effect.In addition,the electrostatic potential and frontier molecular orbitals of the molecules were calculated by DFT to further understand their physical and chemical properties.
关键词
喹喔啉类化合物/6-氟-4-羟基-3-氧代-3,4-二氢喹喔啉-1(2H)-羧酸叔丁酯/晶体结构/密度泛函理论/合成/抗肿瘤活性Key words
quinoxaline compound/6-fluoro-4-hydroxy-3-oxo-3,4-dihydroquinoxalin-1(2H)-carboxylic acid tert-butyl ester/crystal structure/density functional theory/synthesis/antitumor activity引用本文复制引用
出版年
2024
国家科技期刊平台
NSTL
万方数据