Synthesis and biological activity of heterocycle-fused derivatives of pentacylic triterpenes as glycogen phosphorylase inhibitors
10.3321/j.issn:1000-5048.2009.06.003
- VernacularTitle:杂环并五环三萜化合物的合成及糖原磷酸化酶抑制活性
- Author:
Xiaoan WEN
;
Yingxia ZHANG
;
Jun LIU
;
Luyong ZHANG
;
Peizhou NI
;
Hongbin SUN
- Publication Type:Journal Article
- Keywords:
pentacyclic triterpene;
structural modification;
heterocyclic compounds;
glycogen phosphorylase inhibitors
- From:
Journal of China Pharmaceutical University
2009;40(6):491-496
- CountryChina
- Language:Chinese
-
Abstract:
Aim: To search for novel modulators of glycogen metabolism through structural modifications of natural pentacyclic triterpenes. Methods: A series of N-heterocyclic derivatives were synthesized by fusing indole, qui-noxaline and pyrazine rings with A-ring of oleanolic and ursolic acids. The compounds were biologically evaluated for their inhibitory activity against rabbit muscle glycogen phosphorylase. Results and Conclusion: Twelve heter-ocyclic triterpene derivatives were synthesized and their structures were confirmed by IR, ~1H NMR, ~(13)C NMR and MS. Except for compound 12, all of the compounds exhibited glycogen phosphorylase inhibitory activity with IC_(50) values in the range of 14-252 μmol/L Among this series of compounds, compound 15 showed the best potency with IC_(50), of 14 μmol/L
