Characterization of Novel Aminobenzylcantharidinimides and Related Imides by Proton NMR Spectra and Their Effects on NO Induction
作者:Ing-Jy Tseng、Pen-Yuan Lin、Shiow-Yunn Sheu、Wan-Ni Tung、Ching-Tung Lin、Mei-Hsiang Lin
DOI:10.1002/jccs.201400228
日期:2015.1
0032) to produce cantharidinimides and their analogues in good yields. The para‐aminobenzylic imides showed greater inhibition of nitric oxide (NO) synthesis by NO synthase (NOS) than did ortho‐ and meta‐aminobenzylic imides. Compound 3fp, para‐aminobenzylic norbonane‐imide, had the most potent effect on inducible NOS among the tested compounds and showed 35% inhibition.
通过与氨基苄胺和三乙胺反应,将包括邻th啶在内的各种酸酐转变为相应的氨基苄基邻ari啶亚胺3a和类似的酰亚胺3b〜k(在邻位,间位和对位)。邻苯二甲酰亚胺3ao,3am和3ap的两个甲基侧链以及相关的酰亚胺具有两个以上的手性中心。当苄胺的氨基在邻位时,氢的孤电子对在H-NMR光谱中显示出不同的化学位移和耦合常数位置。这些邻苯二甲酰亚胺具有母体苯胺,吡啶和萘的平面结构,伯胺的亲核性和碱性可能反映了感应电子对化学位移的负面影响。我们通过将反应物Cantharidin 1a,脂族和芳族酸酐,伯苄基胺和苯胺衍生物加热到大约17.5 ℃,制备了cantharidinimides 。在高压密封管(Buchi glasuster 0032)中,用3 mL干甲苯和1-2 mL三乙胺在200°C的条件下以高收率生产邻苯二甲酰亚胺和类似物。的对位-aminobenzylic酰亚胺表明一氧化氮(NO)合成的更大