Reductive Cleavage of 4' H-Spiro[indole-3,5'-isoxazoles] En Route to 2-(1 H-Indol-3-yl)acetamides with Anticancer Activities

Alexander V Aksenov; Nikita K Kirilov; Nikolai A Arutiunov; Dmitrii A Aksenov; Iliya K Kuzminov; Nicolai A Aksenov; Danielle N Turner; Snezna Rogelj; Alexander Kornienko; Michael Rubin

doi:10.1021/acs.joc.2c01627

Reductive Cleavage of 4' H-Spiro[indole-3,5'-isoxazoles] En Route to 2-(1 H-Indol-3-yl)acetamides with Anticancer Activities

J Org Chem. 2022 Nov 4;87(21):13955-13964. doi: 10.1021/acs.joc.2c01627. Epub 2022 Oct 19.

Affiliations

¹ Department of Chemistry, North Caucasus Federal University, 1a Pushkin Street, Stavropol 355009, Russian Federation.
² Departments of Biology, New Mexico Institute of Mining and Technology, Socorro, New Mexico 87801, United States.
³ Department of Chemistry and Biochemistry, Texas State University, San Marcos, Texas 78666, United States.
⁴ Department of Chemistry, University of Kansas, 1567 Irving Hill Road, Lawrence, Kansas 66045, United States.

PMID: 36260110
DOI: 10.1021/acs.joc.2c01627

Abstract

Unusual cascade transformation involving ring opening and 1,2-alkyl shift was observed upon the reduction of 4'H-spiro[indole-3,5'-isoxazoles] or 2-(3-oxoindolin-2-yl)acetonitriles with sodium borohydride. This reaction allowed for expeditious and highly efficient preparation of 2-(1H-Indol-3-yl)acetamides with antiproliferative properties.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetamides* / pharmacology
Indoles / pharmacology
Isoxazoles*
Structure-Activity Relationship

Substances

Isoxazoles
Acetamides
Indoles