Imidazo[1,2-a]pyridin-3-amines as potential HIV-1 non-nucleoside reverse transcriptase inhibitors

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dc.contributor.authorBode M.L.
dc.contributor.authorGravestock D.
dc.contributor.authorMoleele S.S.
dc.contributor.authorVan Der Westhuyzen C.W.
dc.contributor.authorPelly S.C.
dc.contributor.authorSteenkamp P.A.
dc.contributor.authorHoppe H.C.
dc.contributor.authorKhan T.
dc.contributor.authorNkabinde L.A.
dc.date.accessioned2011-10-13T16:58:53Z
dc.date.available2011-10-13T16:58:53Z
dc.date.issued2011
dc.description.abstractDuring random screening of a small in-house library of compounds, certain substituted imidazo[1,2-a]pyridines were found to be weak allosteric inhibitors of HIV-1 reverse transcriptase (RT). A library of these compounds was prepared using the Groebke reaction and a subset of compounds prepared from 2-chlorobenzaldehyde, cyclohexyl isocyanide and a 6-substituted 2-aminopyridine showed good inhibitory activity in enzymatic (RT) and HIV anti-infectivity MAGI whole cell assays. The compound showing the best anti-HIV-1 IIIB whole cell activity (MAGI IC50 = 0.18 μM, IC90 = 1.06 μM), along with a good selectivity index (>800), was 2-(2-chlorophenyl)-3- (cyclohexylamino)imidazo[1,2-a]pyridine-5-carbonitrile 38. © 2011 Elsevier Ltd. All rights reserved.
dc.description.versionArticle
dc.identifier.citationBioorganic and Medicinal Chemistry
dc.identifier.citation19
dc.identifier.citation14
dc.identifier.citationhttp://www.scopus.com/inward/record.url?eid=2-s2.0-79960004985&partnerID=40&md5=e71ae92d4cdeee251cfe3f87290495f1
dc.identifier.issn9680896
dc.identifier.other10.1016/j.bmc.2011.05.062
dc.identifier.urihttp://hdl.handle.net/10019.1/16894
dc.subjectAntiretroviral
dc.subjectGroebke reaction
dc.subjectHIV
dc.subjectImidazo[1,2-a]pyridine
dc.subjectNNRTI
dc.subjectReverse transcriptase
dc.subject2 (2 bromophenyl) n cyclohexylimidazo[1,2 a]pyridin 3 amine
dc.subject2 (2 chlorophenyl) 3 (cyclohexylamino)imidazo[1,2 a]pyridine 5 carbonitrile
dc.subject2 (2 chlorophenyl) n cyclohexylimidazo[1,2 a]pyridin 3 amine
dc.subject2 (3 bromophenyl) n cyclohexylimidazo[1,2 a]pyridin 3 amine
dc.subject2 (3 chlorophenyl) n cyclohexylimidazo[1,2 a]pyridin 3 amine
dc.subject2 (4 bromophenyl) n cyclohexylimidazo[1,2 a]pyridin 3 amine
dc.subject2 (4 chlorophenyl) n cyclohexylimidazo[1,2 a]pyridin 3 amine
dc.subject2 aminopyridine derivative
dc.subject2 chlorobenzaldehyde
dc.subject2 sec butyl n cyclohexylimidazo[1,2 a]pyridin 3 amine
dc.subjectcyclohexyl isocyanide
dc.subjectetravirine
dc.subjectimidazo[1,2 a]pyridine amine derivative
dc.subjectisopropyl n (pentan 2 yl)imidazo[1,2 a]pyridin 3 amine
dc.subjectisopropyl n pentylimidazo[1,2 a]pyridin 3 amine
dc.subjectn butyl 2 isopropylimidazo[1,2 a]pyridin 3 amine
dc.subjectn cyclohexyl 2 (2 fluorophenyl)imidazo[1,2 a]pyridin 3 amine
dc.subjectn cyclohexyl 2 (4 fluorophenyl)imidazo[1,2 a]pyridin 3 amine
dc.subjectn cyclohexyl 2 [2 (trifluorophenyl)phenyl]imidazo[1,2 a]pyridin 3 amine
dc.subjectn cyclohexyl 2 [4 (trifluorophenyl)phenyl]imidazo[1,2 a]pyridin 3 amine
dc.subjectn cyclohexyl 2 cyclopropylimidazo[1,2 a]pyridin 3 amine
dc.subjectn cyclohexyl 2 isopropylimidazo[1,2 a]pyridin 3 amine
dc.subjectn cyclohexyl 2 octylimidazo[1,2 a]pyridin 3 amine
dc.subjectn cyclohexyl 2 phenylimidazo[1,2 a]pyridin 3 amine
dc.subjectn cyclopentyl 2 isopropylimidazo[1,2 a]pyridin 3 amine
dc.subjectnonnucleoside reverse transcriptase inhibitor
dc.subjectreagent
dc.subjectrilpivirine
dc.subjectRNA directed DNA polymerase
dc.subjectunclassified drug
dc.subjectunindexed drug
dc.subjectantiviral activity
dc.subjectarticle
dc.subjectcontrolled study
dc.subjectdrug selectivity
dc.subjectdrug structure
dc.subjectdrug synthesis
dc.subjectdrug targeting
dc.subjectenzyme inhibition
dc.subjectIC 50
dc.subjectmolecular model
dc.subjectsolvent effect
dc.subjectHuman immunodeficiency virus 1
dc.titleImidazo[1,2-a]pyridin-3-amines as potential HIV-1 non-nucleoside reverse transcriptase inhibitors
dc.typeArticle
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