Enantioselective synthesis of tetrahydrocarbazoles via trienamine catalysis and their anxiolytic-like activity.

Enantioselective synthesis of tetrahydrocarbazoles via trienamine catalysis and their anxiolytic-like activity.
Bioorg Med Chem Lett. 2020 Feb 27;:127063
Authors: Pawar TJ, Maqueda-Cabrera EE, Alonso-Castro AJ, Olivares-Romero JL, Cruz Cruz D, Villegas Gómez C
Abstract
The first study about the anxiolytic activity of two chiral tetrahydrocarbazoles is presented. This new chiral compounds were prepared through an organocatalytic strategy via trienamine activation. The in situ ortho-quinodimethane species, formed by the condensation of the N-protected 2-methylindole acrylaldehyde with a sterically hindred diarylsilylprolinol ether derivative as catalyst, easily participate in a Diels-Alder reaction with the ethyl cyanophenyl acrylate as dienophile, in good yields and excellent stereoselectivity. These compounds showed activity against anxiety and mood disorders that can possibly contribute in the discovery of new drugs. In addition, the use of N-protected 2-methylindole acrylaldehyde will set a new base for the synthesis of medically and pharmacologically important tetrahydrocarbazoles via trienamine catalysis.
PMID: 32139323 [PubMed - as supplied by publisher]

Source: Bioorganic and Medicinal Chemistry Letters - February 26, 2020 Category: Chemistry Authors: Pawar TJ, Maqueda-Cabrera EE, Alonso-Castro AJ, Olivares-Romero JL, Cruz Cruz D, Villegas Gómez C Tags: Bioorg Med Chem Lett Source Type: research