Enantioselective synthesis of tetrahydrocarbazoles via trienamine catalysis and their anxiolytic-like activity. Issue 9 (1st May 2020)

• Record Type: Journal Article
• Authors: Pawar, Tushar Janardan; Maqueda-Cabrera, Edson E.; Alonso-Castro, Angel Josabad; Olivares-Romero, José Luis; Cruz Cruz, David; Villegas Gómez, Clarisa
• Is Part Of: Bioorganic & medicinal chemistry letters. Volume 30:Issue 9(2020)
• Publication Date: 2020-05-01
• Subjects: Tetrahydrocarbazoles -- Organocatalysis -- Trienamine catalysis -- Anxiolytic activity; Bioorganic chemistry -- Periodicals; Pharmaceutical chemistry -- Periodicals; 572
• DOI: 10.1016/j.bmcl.2020.127063
• Languages: English
• ISSNs: 0960-894X

Abstract

Graphical abstract: 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.