Please use this identifier to cite or link to this item: http://hdl.handle.net/20.500.12779/5189
DC FieldValueLanguage
dc.contributor.authorM., Biavaen_us
dc.contributor.authorG. C., Porrettaen_us
dc.contributor.authorG., Poceen_us
dc.contributor.authorS., Supinoen_us
dc.contributor.authorD., Deiddaen_us
dc.contributor.authorR., Pompeien_us
dc.contributor.authorP., Molicottien_us
dc.contributor.authorManetti, Fabrizioen_us
dc.contributor.authorBotta, Maurizioen_us
dc.date.accessioned2021-03-30T15:49:46Z-
dc.date.available2021-03-30T15:49:46Z-
dc.date.issued2006-
dc.identifier.issn0022-2623en_US
dc.identifier.urihttp://hdl.handle.net/20.500.12779/5189-
dc.description38600en_US
dc.description.abstractOn the basis of suggestions derived either from a pharmacophoric model for antitubercular agents or from a structure-activity relationship analysis of many pyrroles previously described by us, we report here the design and synthesis of new analogues of 1,5-(4-chlorophenyl)-2-methyl-3-(4-methylpiperazin-1-yl)methyl-1H-pyrrole (BM212). Various substituents with different substitution patterns were added to both positions 1 and 5 of the pyrrole nucleus to evaluate their influence on the activity toward Mycobacterium tuberculosis (MTB) and atypical mycobacteria. Biological data showed that, although some nontuberculosis mycobacterial strains were found to be sensitive, MIC values were higher than those found toward MTB. The best compound (1-(4-fluorophenyl)-2-methyl-3-(thiomorpholin-4-yl)methyl-5-(4-methylphenyl)-1H-pyrrole, 5) possessed a MIC of 0.4 microg/mL (better than BM212 and streptomycin) and a very high protection index (160), better than BM212, isoniazid, and streptomycin (6, 128, and 128, respectively). Finally, molecular modeling studies were performed to rationalize the activity of the new compounds in terms of both superposition onto a pharmacophoric model for antitubercular compounds and their hydrophobic character.en_US
dc.language.isoenen_US
dc.relationNoneen_US
dc.relation.ispartofJOURNAL OF MEDICINAL CHEMISTRYen_US
dc.titleAntimycobacterial Agents. Novel Diarylpyrrole Derivatives of BM212 Endowed with High Activity toward Mycobacterium tuberculosis and Low Cytotoxicityen_US
dc.typeArticleen_US
dc.identifier.doi10.1021/jm0602662en_US
dc.identifier.pmid16884306en_US
dc.identifier.scopus2-s2.0-33746924405en_US
dc.identifier.isiWOS:000239459800018en_US
dc.relation.volume49en_US
dc.description.firstpage4946en_US
dc.description.lastpage4952en_US
dc.description.thirdmissionNot applicableen_US
item.cerifentitytypePublications-
item.grantfulltextnone-
item.languageiso639-1en-
item.openairecristypehttp://purl.org/coar/resource_type/c_18cf-
item.openairetypeArticle-
item.fulltextNo Fulltext-
crisitem.author.orcid0000-0002-9598-2339-
crisitem.author.orcid0000-0003-0456-6995-
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