2-(Substituted phenyl)amino analogs of 1-methoxyspirobrassinol methyl ether: Synthesis and anticancer activity

New analogs of indole phytoalexin 1-methoxyspirobrassinol methyl ether have been designed by replacement of its 2-methoxy group with 2-(substituted phenyl)amino group. Synthesized by spirocyclization methodology, trans- and cis-diastereoisomers of target compounds were isolated and evaluated as pote...

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Veröffentlicht in:Bioorganic & medicinal chemistry 2009-05, Vol.17 (10), p.3698-3712
Hauptverfasser: Kutschy, Peter, Salayová, Aneta, Čurillová, Zuzana, Kožár, Tibor, Mezencev, Roman, Mojžiš, Ján, Pilátová, Martina, Balentová, Eva, Pazdera, Pavel, Sabol, Marián, Zburová, Michaela
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Sprache:eng
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Zusammenfassung:New analogs of indole phytoalexin 1-methoxyspirobrassinol methyl ether have been designed by replacement of its 2-methoxy group with 2-(substituted phenyl)amino group. Synthesized by spirocyclization methodology, trans- and cis-diastereoisomers of target compounds were isolated and evaluated as potential anticancer and antimicrobial agents. Their molecular geometries were refined by ab initio minimizations. Pharmacophore modeling and QSAR studies were performed in order to correlate their molecular structure and biological activity.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2009.03.064