Please use this identifier to cite or link to this item: https://doi.org/10.1016/j.bmc.2009.09.008
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dc.titleSynthesis and evaluation of functionalized isoindigos as antiproliferative agents
dc.contributor.authorWee, X.K.
dc.contributor.authorYeo, W.K.
dc.contributor.authorZhang, B.
dc.contributor.authorTan, V.B.C.
dc.contributor.authorLim, K.M.
dc.contributor.authorTay, T.E.
dc.contributor.authorGo, M.-L.
dc.date.accessioned2014-04-24T09:37:20Z
dc.date.available2014-04-24T09:37:20Z
dc.date.issued2009-11-01
dc.identifier.citationWee, X.K., Yeo, W.K., Zhang, B., Tan, V.B.C., Lim, K.M., Tay, T.E., Go, M.-L. (2009-11-01). Synthesis and evaluation of functionalized isoindigos as antiproliferative agents. Bioorganic and Medicinal Chemistry 17 (21) : 7562-7571. ScholarBank@NUS Repository. https://doi.org/10.1016/j.bmc.2009.09.008
dc.identifier.issn09680896
dc.identifier.urihttp://scholarbank.nus.edu.sg/handle/10635/51531
dc.description.abstractA series of functionalized isoindigos structurally related to meisoindigo (1-methylisoindigo), a therapeutic agent used for the treatment of a form of leukemia, were synthesized and evaluated for antiproliferative activities on a panel of human cancer cells. Two promising compounds (1 -phenpropylisoindigo and 1-(p-methoxy-phenethyl)-isoindigo) that were more potent than meisoindigo and comparable to 6bromoindirubin-3'-oxime on leukemic K562 and liver HuH7 cells were identified. Structure-activity relationships showed the importance of keeping one of the lactam NH in an unsubstituted state. Substitution of the other lactam NH with aryl or arylalkyl side chains retained or improved activity in most instances. An intact exocyclic double bond was also essential, possibly to maintain planarity and rigidity of the isoindigo scaffold. None of the compounds were found to inhibit CDK2 in an in vitro assay, in spite of reports linking the antiproliferative activities of meisoindigo and other isoindigos to CDK2 inhibition. Hence, these functionalized isoindigos disrupted cell growth and proliferation by other mechanistic pathways that did not involve CDK2 inhibition. © 2009 Elsevier Ltd. All rights reserved.
dc.description.urihttp://libproxy1.nus.edu.sg/login?url=http://dx.doi.org/10.1016/j.bmc.2009.09.008
dc.sourceScopus
dc.subjectAntiproliferative activity
dc.subjectCDK2 inhibition
dc.subjectIsoindigo
dc.subjectMolecular modeling
dc.subjectSAR
dc.typeArticle
dc.contributor.departmentMECHANICAL ENGINEERING
dc.contributor.departmentPHARMACY
dc.description.doi10.1016/j.bmc.2009.09.008
dc.description.sourcetitleBioorganic and Medicinal Chemistry
dc.description.volume17
dc.description.issue21
dc.description.page7562-7571
dc.description.codenBMECE
dc.identifier.isiut000270903100020
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