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dc.contributor.authorA. Gakh, Andrei
dc.contributor.authorV. Sosnov, Andrey
dc.contributor.authorKrasavin, Mikhail
dc.contributor.authorNguyen, Tam Luong
dc.contributor.authorHamel, Ernest
dc.date.accessioned2017-05-03T12:43:23Z
dc.date.available2017-05-03T12:43:23Z
dc.date.issued2013
dc.date.modified2014-03-30T22:11:54Z
dc.identifier.issn0960894X
dc.identifier.doi10.1016/j.bmcl.2013.01.007
dc.identifier.urihttp://hdl.handle.net/10072/57428
dc.description.abstractThe combination of experimental (inhibition of colchicine binding) and computational (COMPARE, docking studies) data unequivocally identified diaryl 5-amino-1,2,4-oxadiazoles as potent tubulin inhibitors. Good correlation was observed between tubulin binding and cytostatic properties for all tested compounds with the notable exception of the lead candidate, 3-(3-methoxyphenyl)-5-(4-methoxyphenyl)amino-1,2,4-oxadiazole (DCP 10500078). This compound was found to be substantially more active in our in vitro experiments than the monofluorinated title compound, 3-(2-fluorophenyl)-5-(4-methoxyphenyl)amino-1,2,4-oxadiazole (DCP 10500067/NSC 757486), which in turn demonstrated slightly better tubulin binding activity. Comparative SAR analysis of 25 diaryl 5-amino-1,2,4-oxadiazoles with other known tubulin inhibitors, such as combretastatin A-4 (CA-4) and colchicine, provides further insight into the specifics of their binding as well as a plausible mechanism of action.
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.languageEnglish
dc.language.isoeng
dc.publisherPergamon
dc.publisher.placeUnited Kingdom
dc.relation.ispartofstudentpublicationN
dc.relation.ispartofpagefrom1262
dc.relation.ispartofpageto1268
dc.relation.ispartofissue5
dc.relation.ispartofjournalBioorganic & Medicinal Chemistry Letters
dc.relation.ispartofvolume23
dc.rights.retentionY
dc.subject.fieldofresearchMedicinal and biomolecular chemistry
dc.subject.fieldofresearchOrganic chemistry
dc.subject.fieldofresearchMedical biochemistry - amino acids and metabolites
dc.subject.fieldofresearchMedical biochemistry - inorganic elements and compounds
dc.subject.fieldofresearchPharmacology and pharmaceutical sciences
dc.subject.fieldofresearchcode3404
dc.subject.fieldofresearchcode3405
dc.subject.fieldofresearchcode320501
dc.subject.fieldofresearchcode320503
dc.subject.fieldofresearchcode3214
dc.titleIdentification of diaryl 5-amino-1,2,4-oxadiazoles as tubulin inhibitors: The special case of 3-(2-fluorophenyl)-5-(4-methoxyphenyl)amino-1,2,4-oxadiazole
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.date.issued2013
gro.hasfulltextNo Full Text
gro.griffith.authorKrasavin, Mikhail


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