A green synthetic approach toward the synthesis of structurally diverse spirooxindole derivative libraries under catalyst-free conditions

Nazia Kausar; Abdulla Al Masum; Md Maidul Islam; Asish R Das

doi:10.1007/s11030-017-9728-9

A green synthetic approach toward the synthesis of structurally diverse spirooxindole derivative libraries under catalyst-free conditions

Mol Divers. 2017 May;21(2):325-337. doi: 10.1007/s11030-017-9728-9. Epub 2017 Feb 11.

Authors

Nazia Kausar¹, Abdulla Al Masum², Md Maidul Islam², Asish R Das³

Affiliations

¹ Department of Chemistry, University of Calcutta, Kolkata, 700009, India.
² Department of Chemistry, Aliah University, Action Area IIA/27, New Town, Kolkata, 700156, India.
³ Department of Chemistry, University of Calcutta, Kolkata, 700009, India. ardchem@caluniv.ac.in.

PMID: 28190223
DOI: 10.1007/s11030-017-9728-9

Abstract

A catalyst-free green methodology for the synthesis of pharmacologically important spirooxindole derivatives has been developed by a three-component domino reaction between isatin, various amino compounds, and 1,3-dicarbonyl or 3-phenylisoxazolone compounds in ethyl L-lactate medium at room temperature. This new efficient synthetic method facilitated the formation of a wide range of biologically significant spirooxindole derivatives (including 17 new spirooxindoles) under very mild conditions. The cytotoxic activity of one of the isoxazole-fused spirooxindoles was evaluated in MDA-MB 468 breast cancer cell line. It was found that cell survivability decreases with increasing concentration of the selected compound in MDA-MB 468 breast cancer cells.

Keywords: Catalyst-free; Cytotoxic; Ethyl lactate; Green synthesis; Isoxazole; MCRs; Spirooxindole; Structure–activity relationship.

MeSH terms

Chemistry Techniques, Synthetic
Green Chemistry Technology
Indoles / chemical synthesis*
Indoles / chemistry*
Spiro Compounds / chemistry*
Temperature

Substances

Indoles
Spiro Compounds