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

• Authors: KUTSCHY Peter; SALAYOVA Aneta; CURILLOVA Zuzana; KOZAR Tibor; MEZENCEV Roman; MOJZIS Jan; PILATOVA Martina; BALENTOVA Eva; PAZDERA Pavel; SABOL Marian; ZBUROVA Michaela
• Year of publication: 2009
• Type: Article in Periodical
• Magazine / Source: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
• MU Faculty or unit: Faculty of Science
• Web: https://www.sciencedirect.com/science/article/pii/S0968089609003125
• Doi: http://dx.doi.org/10.1016/j.bmc.2009.03.064
• Keywords: Phytoalexins; Spiroindolines; Anticancer activity; QSAR
• Description: 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.