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J Org Chem. 2019 Jun 7;84(11):7123-7137. doi: 10.1021/acs.joc.9b00808. Epub 2019 May 22.

Synthesis of Spiro[indole-3,5'-isoxazoles] with Anticancer Activity via a Formal [4 + 1]-Spirocyclization of Nitroalkenes to Indoles.

Author information

1
Department of Chemistry , North Caucasus Federal University , 1a Pushkin Street , Stavropol 355009 , Russian Federation.
2
Department of Chemistry and Biochemistry , Texas State University , San Marcos , Texas 78666 , United States.
3
Department of Chemistry , University of Kansas , 1567 Irving Hill Road , Lawrence , Kansas 66045 , United States.

Abstract

An acid-assisted [4 + 1]-cycloaddition of indoles with nitrostyrenes affords 4' H-spiro[indole-3,5'-isoxazoles] in a diastereomerically pure form. Several of these spirocyclic molecules exhibit promising anticancer activity by reducing viability and inducing differentiation of neuroblastoma cells.

PMID:
31070030
DOI:
10.1021/acs.joc.9b00808

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