Characterization of novel aminobenzylcantharidinimides and related imides by proton NMR spectra and their effects on NO induction

Ing Jy Tseng, Pen Yuan Lin, Shiow Yunn Sheu, Wan Ni Tung, Ching Tung Lin, Mei Hsiang Lin

研究成果: 雜誌貢獻文章同行評審

2 引文 斯高帕斯(Scopus)

摘要

Various acidic anhydrides including cantharidin were converted into corresponding aminobenzylcantharidinimide 3a and analogous imides 3b∼k (at the ortho, meta, and para positions) with 35%∼87% yields by reacting with aminobenzylamines and triethylamine. The two methyl side chains of cantharidinimides 3ao, 3am, and 3ap, and related imides had more than two chiral centers; the lone pair of electrons of nitrogen displayed a different chemical shift and coupling constant in H-NMR spectra when the amino group of benzylamine was in the ortho position. These cantharidinimides had parent aniline, pyridine, and naphthalene plane structures, and the primary amine nucleophilicity and basicity might reflect the inductive electron's negative effect on chemical shifts. We prepared cantharidinimides by heating the reactants cantharidin 1a, aliphatic and aromatic acid anhydrides, primary benzylic amines, and aniline derivatives to ca. 200 °C with 3 mL of dry toluene, and 1∼2 mL of triethylamine in high-pressure sealed tubes (Buchi glasuster 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. Cantharidinimides and their analogue were prepared by heating the reactants cantharidin, aliphatic, aromatic acid anhydrides, and primary benzyl amines, aniline derivatives with 3 mL of dry toluene, and 1-2 mL of triethylamine in high-pressure sealed tube at 200 oC in good yields. The para-aminobenzylic imides showed greater inhibition of nitric oxide (NO) synthesis by NO synthase (NOS) than that of ortho- and meta-aminobenzylic imides did.

原文英語
頁(從 - 到)59-63
頁數5
期刊Journal of the Chinese Chemical Society
62
發行號1
DOIs
出版狀態已發佈 - 2015
對外發佈Yes

ASJC Scopus subject areas

  • Chemistry(all)

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