Synthesis and Anti-HIV-1 Activity of One Schiff Base Derivative with Glucosamine of Gossypol
- VernacularTitle:一种氨基葡萄糖棉酚Schiff碱衍生物的制备及其抗HIV-1病毒活性
- Author:
Jian YANG
;
Wei ZHAO
;
Jingxiang YANG
;
Zhenhua JING
;
Xianxi GUO
- Keywords:
Schiff base of gossypol with 1;
3;
4;
6-tetra-O-acetyl-β-D-glucosamine;
Synthesis;
Spectroscopic analysis;
PM6 semi-classical calculation;
Anti-HIV-1
- From:
China Pharmacist
2017;20(5):787-790
- CountryChina
- Language:Chinese
-
Abstract:
Objective: To confirm the structure and preferential conformation of the Schiff base of gossypol with 1, 3, 4, 6-tetra-O-acetyl-β-D-glucosamine and explore its anti-HIV-1 activity.Methods: The Schiff base of gossypol with 11, 3, 4, 6-tetra-O-acetyl-β-D-glucosamine was synthesized and identified by FT-IR, NMR spectroscopy and the PM6 semi-classical calculation.The inhibitory activity of the novel compound against the laboratory-adapted HIV-1IIIB strain was examined using the HIV-1IIIB/TZM-bl indicator cell culture system.Results: The 1H and 13C-NMR signals of the new Schiff base were assigned.The PM6 semi-classical calculation indicated that enamine-enamine tautomeric form of the new Schiff base was more stable,which was stabilized by the intramolecular hydrogen bonds.The anti-HIV-1 test showed that the compound could block the entry of HIV-1IIIB into the target cells.Conclusion: The Schiff base of gossypol with 1, 3, 4, 6-tetra-O-acetyl-β-D-glucosamine exhibits enamine-enamine tautomeric form in solution, which shows potential anti-HIV-1 activity.
