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 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.
Kutschy
Peter
P
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
Salayová
Aneta
A
Curillová
Zuzana
Z
Kozár
Tibor
T
Mezencev
Roman
R
Mojzis
Ján
J
Pilátová
Martina
M
Balentová
Eva
E
Pazdera
Pavel
P
Sabol
Marián
M
Zburová
Michaela
M
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
D000970:Antineoplastic Agents; D007211:Indoles; D012717:Sesquiterpenes; D013729:Terpenes; D000094162:Phytoalexins