title: 2-(substituted phenyl)amino analogs of 1-methoxyspirobrassinol methyl ether: synthesis and anticancer activity.
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.
authors.affiliation: 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
authors.forename: Peter
authors.initials: P
authors.lastname: Kutschy
authors.forename: Aneta
authors.initials: A
authors.lastname: Salayová
authors.forename: Zuzana
authors.initials: Z
authors.lastname: Curillová
authors.forename: Tibor
authors.initials: T
authors.lastname: Kozár
authors.forename: Roman
authors.initials: R
authors.lastname: Mezencev
authors.forename: Ján
authors.initials: J
authors.lastname: Mojzis
authors.forename: Martina
authors.initials: M
authors.lastname: Pilátová
authors.forename: Eva
authors.initials: E
authors.lastname: Balentová
authors.forename: Pavel
authors.initials: P
authors.lastname: Pazdera
authors.forename: Marián
authors.initials: M
authors.lastname: Sabol
authors.forename: Michaela
authors.initials: M
authors.lastname: Zburová
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity*; D008956:Models, Chemical; D021281:Quantitative Structure-Activity Relationship; D012717:Sesquiterpenes; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis / Q000737:chemistry; D000094162:Phytoalexins
chemical_list: D000970:Antineoplastic Agents; D007211:Indoles; D012717:Sesquiterpenes; D013729:Terpenes; D000094162:Phytoalexins