顺/反-1,2,4-噁二唑衍生物的结构确证OA
Structure Elucidation of cis- and trans-1,2,4-Oxadiazol Derivatives
顺反异构体的几何构型差异可导致其生物活性显著不同,对异构体进行分离与构型鉴定是评估其药效的关键.本研究合成了一对顺/反-1,2,4-噁二唑衍生物异构体即顺/反-4-[2-(3-((1H-吲哚-3-基)甲基)-1,2,4-噁二唑-5-基)乙烯基]-N,N-二甲基苯胺,并综合利用核磁共振(NMR)、傅里叶变换红外光谱(FT-IR)、高分辨质谱(HRMS)及理论计算,成功实现了这一对异构体的明确指认与区分.抗弓形虫活性评价表明,顺式异构体(化合物 2,选择性指数 SI=1.50)的活性优于其反式异构体(化合物 1,SI=0.92)及阳性对照药螺旋霉素(SI=0.98),充分体现了构型分离与鉴定在药物研究中的价值.本研究深化了对构型-活性关系的理解,为高选择性抗弓形虫药物的开发提供了新思路.
The geometric configuration of cis-trans isomers critically influences their biological activities,making the separation and configurational identification essential for efficacy evaluation.In this study,cis/trans-1,2,4-oxadiazole derivatives were synthesized and comprehensively characterized by nuclear magnetic resonance(NMR),Fourier transform infrared spectroscopy(FT-IR),high-resolution mass spectrometry(HRMS),and theoretical calculations.This approach enabled unambiguous identification and distinction of a pair of isomers,including cis-4-[2-(3-((1H-indol-3-yl)methyl)-1,2,4-oxadiazol-5-yl)vinyl]-N,N-dimethylaniline and its trans-configuration analogue.Anti-Toxoplasma gondii activity assessment revealed that the cis-isomer(compound 2,selectivity index SI=1.50)exhibited higher activity than the trans-isomer(compound 1,SI=0.92)and the positive control spiramycin(SI=0.98),highlighting the value of configurational separation and identification in pharmaceutical research.This study deepens the understanding of configuration-activity relationships and provides new insights for developing highly selective anti-Toxoplasma agents.
高源;刘心月;王思宏;胡伟
长白山天然药物研究教育部重点实验室,延边大学,吉林 延吉 133002长白山天然药物研究教育部重点实验室,延边大学,吉林 延吉 133002延边大学分析测试中心,吉林 延吉 133002松山湖材料实验室,广东 东莞 523008
数理科学
1,2,4-噁二唑抗寄生虫药结构解析顺式构型核磁共振
1,2,4-oxadiazoleantiparasitic agentsstructural elucidationcis-configurationNMR
《波谱学杂志》 2026 (2)
164-174,11
国家自然科学基金资助项目(22567024).
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