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Synthesis of dammarane-type triterpene derivatives and their ability to inhibit HIV and HCV proteases
- Source :
-
Bioorganic & Medicinal Chemistry . Apr2009, Vol. 17 Issue 8, p3003-3010. 8p. - Publication Year :
- 2009
-
Abstract
- Abstract: We synthesized dammarane-type triterpene derivatives and evaluated their ability to inhibit HIV-1 and HCV proteases to understand their structure–activity relationships. All of the mono- and di-succinyl derivatives (5a–5f) were powerful inhibitors of HIV-1 protease (IC50 <10μM). However, only di-succinyl (5e) and 2,3-seco-2,3-dioic acid (3b) derivatives similarly inhibited HCV protease (IC50 <10μM). A-nor dammarane-type triterpenes (4a and 4b, IC50 10.0 and 29.9μM, respectively) inhibited HIV-1 protease moderately or strongly, but were inactive against HCV protease. All compounds that powerfully inhibited HIV-1 or HCV protease did not appreciably inhibit the general human proteases, renin and trypsin (IC50 >1000μM). These findings indicated that the mono-succinyl dammarane type derivatives (5a–5d) selectively inhibited HIV-1 protease and that the di-succinyl (5e, 5f) as well as 2,3-seco-2,3-dioic acid (3b) derivatives preferably inhibited both viral proteases. [Copyright &y& Elsevier]
Details
- Language :
- English
- ISSN :
- 09680896
- Volume :
- 17
- Issue :
- 8
- Database :
- Academic Search Index
- Journal :
- Bioorganic & Medicinal Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 37573177
- Full Text :
- https://doi.org/10.1016/j.bmc.2009.03.019