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

Peter Kutschy; Aneta Salayová; Zuzana Curillová; Tibor Kozár; Roman Mezencev; Ján Mojzis; Martina Pilátová; Eva Balentová; Pavel Pazdera; Marián Sabol; Michaela Zburová

doi:10.1016/j.bmc.2009.03.064

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

Bioorg Med Chem. 2009 May 15;17(10):3698-712. doi: 10.1016/j.bmc.2009.03.064. Epub 2009 Apr 11.

Authors

Peter Kutschy¹, Aneta Salayová, Zuzana Curillová, Tibor Kozár, Roman Mezencev, Ján Mojzis, Martina Pilátová, Eva Balentová, Pavel Pazdera, Marián Sabol, Michaela Zburová

Affiliation

¹ Department of Organic Chemistry, Institute of Chemical Sciences, Faculty of Science, P.J. Safárik University, Moyzesova 11, 040 01 Kosice, Slovak Republic. peter.kutschy@upjs.sk

PMID: 19394829
DOI: 10.1016/j.bmc.2009.03.064

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / chemistry
Antineoplastic Agents / toxicity*
Cell Line, Tumor
Drug Screening Assays, Antitumor
Humans
Indoles / chemical synthesis*
Indoles / chemistry
Indoles / toxicity*
Models, Chemical
Phytoalexins
Quantitative Structure-Activity Relationship
Sesquiterpenes
Stereoisomerism
Terpenes / chemical synthesis
Terpenes / chemistry

Substances

Antineoplastic Agents
Indoles
Sesquiterpenes
Terpenes
Phytoalexins