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Article: Chemical library and structure-activity relationships of 11-demethyl-12-oxo calanolide A analogues as anti-HIV-1 agents

TitleChemical library and structure-activity relationships of 11-demethyl-12-oxo calanolide A analogues as anti-HIV-1 agents
Authors
Issue Date2008
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/jmc
Citation
Journal Of Medicinal Chemistry, 2008, v. 51 n. 5, p. 1432-1446 How to Cite?
Abstract(+)-Calanolide A (1) as a natural product was previously found as an inhibitor of HIV-1 reverse transcriptase. In our further investigation of its template, racemic 11-demethyl-12-oxo calanolide A (15), which had two fewer chiral carbon centers at the C-11 and C-12 positions than (+)-calanolide A, had a comparably inhibitory activity and better therapeutic index (EC 50 = 0.11 μM, TI = 818) against HIV-1 in vitro. A library based on its structural core was then designed and synthesized with introduction of nine diversity points in this article. The evaluations of anti-HIV-1 activity in vitro concluded their structure-activity relationships (SARs). A novel compound (10-bromomethyl-11-demethyl-12-oxo calanolide A, 123) was identified to have much higher inhibitory potency and therapeutic index (EC 50 = 2.85 nM, TI > 10,526) than those of the class compound against HIV-1. This finding provided a very important clue that modifications of the C ring at the C-10 position may be conducted to obtain drug candidates with better activity against HIV-1. © 2008 American Chemical Society.
Persistent Identifierhttp://hdl.handle.net/10722/157517
ISSN
2015 Impact Factor: 5.589
2015 SCImago Journal Rankings: 2.529
ISI Accession Number ID
References

 

DC FieldValueLanguage
dc.contributor.authorMa, Ten_US
dc.contributor.authorLiu, Len_US
dc.contributor.authorXue, Hen_US
dc.contributor.authorLi, Len_US
dc.contributor.authorHan, Cen_US
dc.contributor.authorWang, Len_US
dc.contributor.authorChen, Zen_US
dc.contributor.authorLiu, Gen_US
dc.date.accessioned2012-08-08T08:50:49Z-
dc.date.available2012-08-08T08:50:49Z-
dc.date.issued2008en_US
dc.identifier.citationJournal Of Medicinal Chemistry, 2008, v. 51 n. 5, p. 1432-1446en_US
dc.identifier.issn0022-2623en_US
dc.identifier.urihttp://hdl.handle.net/10722/157517-
dc.description.abstract(+)-Calanolide A (1) as a natural product was previously found as an inhibitor of HIV-1 reverse transcriptase. In our further investigation of its template, racemic 11-demethyl-12-oxo calanolide A (15), which had two fewer chiral carbon centers at the C-11 and C-12 positions than (+)-calanolide A, had a comparably inhibitory activity and better therapeutic index (EC 50 = 0.11 μM, TI = 818) against HIV-1 in vitro. A library based on its structural core was then designed and synthesized with introduction of nine diversity points in this article. The evaluations of anti-HIV-1 activity in vitro concluded their structure-activity relationships (SARs). A novel compound (10-bromomethyl-11-demethyl-12-oxo calanolide A, 123) was identified to have much higher inhibitory potency and therapeutic index (EC 50 = 2.85 nM, TI > 10,526) than those of the class compound against HIV-1. This finding provided a very important clue that modifications of the C ring at the C-10 position may be conducted to obtain drug candidates with better activity against HIV-1. © 2008 American Chemical Society.en_US
dc.languageengen_US
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/jmcen_US
dc.relation.ispartofJournal of Medicinal Chemistryen_US
dc.subject.meshAnti-Hiv Agents - Chemical Synthesis - Chemistry - Pharmacologyen_US
dc.subject.meshCell Lineen_US
dc.subject.meshChromones - Chemical Synthesis - Chemistry - Pharmacologyen_US
dc.subject.meshCombinatorial Chemistry Techniquesen_US
dc.subject.meshCoumarins - Chemical Synthesis - Chemistry - Pharmacologyen_US
dc.subject.meshHiv-1 - Drug Effectsen_US
dc.subject.meshHumansen_US
dc.subject.meshPyranocoumarins - Chemical Synthesis - Chemistry - Pharmacologyen_US
dc.subject.meshStereoisomerismen_US
dc.subject.meshStructure-Activity Relationshipen_US
dc.titleChemical library and structure-activity relationships of 11-demethyl-12-oxo calanolide A analogues as anti-HIV-1 agentsen_US
dc.typeArticleen_US
dc.identifier.emailChen, Z:zchenai@hkucc.hku.hken_US
dc.identifier.authorityChen, Z=rp00243en_US
dc.description.naturelink_to_subscribed_fulltexten_US
dc.identifier.doi10.1021/jm701405pen_US
dc.identifier.pmid18284187-
dc.identifier.scopuseid_2-s2.0-41749084640en_US
dc.identifier.hkuros147661-
dc.relation.referenceshttp://www.scopus.com/mlt/select.url?eid=2-s2.0-41749084640&selection=ref&src=s&origin=recordpageen_US
dc.identifier.volume51en_US
dc.identifier.issue5en_US
dc.identifier.spage1432en_US
dc.identifier.epage1446en_US
dc.identifier.eissn1520-4804-
dc.identifier.isiWOS:000253784900036-
dc.publisher.placeUnited Statesen_US
dc.identifier.scopusauthoridMa, T=35763830600en_US
dc.identifier.scopusauthoridLiu, L=36068379000en_US
dc.identifier.scopusauthoridXue, H=35084707100en_US
dc.identifier.scopusauthoridLi, L=36064664900en_US
dc.identifier.scopusauthoridHan, C=17345759200en_US
dc.identifier.scopusauthoridWang, L=15836048000en_US
dc.identifier.scopusauthoridChen, Z=35271180800en_US
dc.identifier.scopusauthoridLiu, G=8833437700en_US

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