Characterization of Novel Aminobenzylcantharidinimides and Related Imides by Proton NMR Spectra and Their Effects on NO Induction
Tseng, I; Lin, P; Sheu, SY; Tung, W; Lin, CT; Lin, M
| HERO ID | 2841037 |
|---|---|
| In Press | No |
| Year | 2015 |
| Title | Characterization of Novel Aminobenzylcantharidinimides and Related Imides by Proton NMR Spectra and Their Effects on NO Induction |
| Authors | Tseng, I; Lin, P; Sheu, SY; Tung, W; Lin, CT; Lin, M |
| Journal | Journal of the Chinese Chemical Society |
| Volume | 62 |
| Issue | 1 |
| Page Numbers | 59-63 |
| Abstract | Various acidic anhydrides including cantharidin were converted into corresponding aminobenzylcantharidinimide 3a and analogous imides 3b similar to k (at the ortho, meta, and para positions) with 35 similar to 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 la, aliphatic and aromatic acid anhydrides, primary benzylic amines, and aniline derivatives to ca. 200 degrees 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. Thepara-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. |
| Doi | 10.1002/jccs.201400228 |
| Wosid | WOS:000348005400010 |
| Url | <Go to ISI>://WOS:000348005400010 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |
| Keyword | Cantharidin; Cantharidinimide; Aminobenzylamine; iNOS |