Design, synthesis and anticancer activity of trifluoromethylphenylamino substituted spiroindoles

[Display omitted] •Biologically active 2´-aminoanalogs and 2,2´-diaminoanalogs containing 4-trifluoromethylphenylamino group have been prepared.•The target aminoanalogs were prepared by spirocyclization protocol utilizing thioureas as starting compounds.•Prepared fluorinated aminoanalogs demonstrated notable antiproliferative activity against various cell lines. Organofluorines are a group of fluorinated substances with broad application as pharmaceuticals, agrochemicals and polymers. We designed and synthesized a series of new biologically active trifluoromethyl containing indole derivatives. Target 2´-aminoanalogs and 2,2´-diaminoanalogs of 1-methoxyspirobrassinol methyl ether bearing (4-trifluoromethylphenylamino) or 3,5-bis(trifluoromethyl)phenylamino moiety were prepared by spirocyclization methodology. The newly synthesized indole analogs display higher potency of antiproliferative effect against eight human leukemia and solid tumor cell lines than their parental natural phytoalexin. The most potent antiproliferative agents were 2,2´-diaminoanalogs possessing two 3,5-bis(trifluoromethyl)phenylamino groups, which displayed higher potency than cisplatin against screened cancer cell lines, but at the same time lower cytotoxicity than cisplatin on non-malignant murine fibroblasts NIH 3T3.