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dc.contributor.author Qian, K
dc.contributor.author Kuo, RY
dc.contributor.author Chen, CH
dc.contributor.author Huang, L
dc.contributor.author Morris-Natschke, SL
dc.contributor.author Lee, KH
dc.coverage.spatial United States
dc.date.accessioned 2011-06-21T17:26:38Z
dc.date.issued 2010-04-22
dc.identifier http://www.ncbi.nlm.nih.gov/pubmed/20329730
dc.identifier.citation J Med Chem, 2010, 53 (8), pp. 3133 - 3141
dc.identifier.uri http://hdl.handle.net/10161/4063
dc.description.abstract In our continuing study of triterpene derivatives as potent anti-HIV agents, different C-3 conformationally restricted betulinic acid (BA, 1) derivatives were designed and synthesized in order to explore the conformational space of the C-3 pharmacophore. 3-O-Monomethylsuccinyl-betulinic acid (MSB) analogues were also designed to better understand the contribution of the C-3' dimethyl group of bevirimat (2), the first-in-class HIV maturation inhibitor, which is currently in phase IIb clinical trials. In addition, another triterpene skeleton, moronic acid (MA, 3), was also employed to study the influence of the backbone and the C-3 modification toward the anti-HIV activity of this compound class. This study enabled us to better understand the structure-activity relationships (SAR) of triterpene-derived anti-HIV agents and led to the design and synthesis of compound 12 (EC(50): 0.0006 microM), which displayed slightly better activity than 2 as a HIV-1 maturation inhibitor.
dc.format.extent 3133 - 3141
dc.language ENG
dc.language.iso en_US en_US
dc.relation.ispartof J Med Chem
dc.relation.isversionof 10.1021/jm901782m
dc.subject Anti-HIV Agents
dc.subject Cell Line
dc.subject Drug Design
dc.subject HIV-1
dc.subject Mutation
dc.subject Oleanolic Acid
dc.subject Stereoisomerism
dc.subject Structure-Activity Relationship
dc.subject Triterpenes
dc.subject Virion
dc.subject Virus Replication
dc.title Anti-AIDS agents 81. Design, synthesis, and structure-activity relationship study of betulinic acid and moronic acid derivatives as potent HIV maturation inhibitors.
dc.title.alternative en_US
dc.type Journal Article
dc.description.version Version of Record en_US
duke.date.pubdate 2010-4-22 en_US
duke.description.endpage 3141 en_US
duke.description.issue 8 en_US
duke.description.startpage 3133 en_US
duke.description.volume 53 en_US
dc.relation.journal Journal of medicinal chemistry en_US
pubs.author-url http://www.ncbi.nlm.nih.gov/pubmed/20329730
pubs.issue 8
pubs.organisational-group /Duke
pubs.organisational-group /Duke/School of Medicine
pubs.organisational-group /Duke/School of Medicine/Clinical Science Departments
pubs.organisational-group /Duke/School of Medicine/Clinical Science Departments/Surgery
pubs.organisational-group /Duke/School of Medicine/Clinical Science Departments/Surgery/Surgery, Surgical Sciences
pubs.organisational-group /Duke/School of Medicine/Institutes and Centers
pubs.organisational-group /Duke/School of Medicine/Institutes and Centers/Duke Cancer Institute
pubs.publication-status Published
pubs.volume 53
dc.identifier.eissn 1520-4804

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