顺/反-1,2,4-噁二唑衍生物的结构确证
#共同第一作者
收稿日期: 2025-10-20
网络出版日期: 2026-01-27
基金资助
国家自然科学基金资助项目(22567024)
Structure Elucidation of cis- and trans-1,2,4-Oxadiazol Derivatives
Received date: 2025-10-20
Online published: 2026-01-27
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．
高源 , 刘心月 , 王思宏 , 胡伟 . 顺/反-1,2,4-噁二唑衍生物的结构确证[J]. 波谱学杂志, 2026 , 43(2) : 164 -174 . DOI: 10.11938/cjmr20253184
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.
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