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

Authors :
Aksenov AV
Aksenov DA
Arutiunov NA
Aksenov NA
Aleksandrova EV
Zhao Z
Du L
Kornienko A
Rubin M
Source :
The Journal of organic chemistry [J Org Chem] 2019 Jun 07; Vol. 84 (11), pp. 7123-7137. Date of Electronic Publication: 2019 May 22.
Publication Year :
2019

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.

Details

Language :
English
ISSN :
1520-6904
Volume :
84
Issue :
11
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
31070030
Full Text :
https://doi.org/10.1021/acs.joc.9b00808