首页|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

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

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  • 国家科技期刊平台
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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.
Synthesis,Crystal Structure and Antitumor Activity of 6-Fluoro-4-Hydroxy-3-Oxo-3,4-Dihydroquinoxaline-1(2H)-Carboxylic Acid Tert-Butyl Ester
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.

quinoxaline compound6-fluoro-4-hydroxy-3-oxo-3,4-dihydroquinoxalin-1(2H)-carboxylic acid tert-butyl estercrystal structuredensity functional theorysynthesisantitumor activity

毛云虹、赵春深

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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

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

2024

人工晶体学报
中材人工晶体研究院

人工晶体学报

CSTPCD北大核心
影响因子：0.554
ISSN：1000-985X
年,卷(期)：2024.53(7)
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