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Efficient synthesis and biological evaluation of epiceanothic acid and related compounds
- Source :
-
Bioorganic & Medicinal Chemistry Letters . Jan2011, Vol. 21 Issue 1, p338-341. 4p. - Publication Year :
- 2011
-
Abstract
- Abstract: Epiceanothic acid (1) is a naturally occurring, but very rare pentacyclic triterpene with a unique pentacyclic triterpene (PT) structure. An efficient synthesis of 1 starting from betulin (3) has been accomplished in 12-steps with a total yield of 10% in our study. Compound 1 and selected synthetic intermediates were further evaluated as anti-HIV-1 agents, inhibitors of glycogen phosphorylase (GP), and cytotoxic agents. Compound 1 exhibited moderate HIV-1 inhibition. Most importantly, compound 5, with an opened A-ring, showed significant GP inhibitory activity with an IC50 of 0.21μM, suggesting a potential for development as an anti-diabetic agent. On the other hand, compound 12, with a closed A-ring, showed potent cytotoxicity against A549 and MCF-7 human tumor cell lines, with IC50 values of 0.89 and 0.33μM, respectively. These results suggest that the A-ring of PTs is an important pharmacophore that could be modified to involve different biological activities. [Copyright &y& Elsevier]
Details
- Language :
- English
- ISSN :
- 0960894X
- Volume :
- 21
- Issue :
- 1
- Database :
- Academic Search Index
- Journal :
- Bioorganic & Medicinal Chemistry Letters
- Publication Type :
- Academic Journal
- Accession number :
- 56497252
- Full Text :
- https://doi.org/10.1016/j.bmcl.2010.11.004