Exploration of [2 + 2 + 2] cyclotrimerisation methodology to prepare tetrahydroisoquinoline-based compounds with potential aldo-keto reductase 1C3 target affinity

Ana R N Santos; Helen M Sheldrake; Ali I M Ibrahim; Chhanda Charan Danta; Davide Bonanni; Martina Daga; Simonetta Oliaro-Bosso; Donatella Boschi; Marco L Lolli; Klaus Pors

doi:10.1039/c9md00201d

Exploration of [2 + 2 + 2] cyclotrimerisation methodology to prepare tetrahydroisoquinoline-based compounds with potential aldo-keto reductase 1C3 target affinity

Medchemcomm. 2019 Jun 27;10(8):1476-1480. doi: 10.1039/c9md00201d. eCollection 2019 Aug 1.

Affiliations

¹ Institute of Cancer Therapeutics , Faculty of Life Sciences , University of Bradford , West Yorkshire , BD7 1DP , UK . Email: k.pors1@bradford.ac.uk.
² Department of Science and Drug Technology , University of Torino , Via Pietro Giuria 9 , 10125 Torino , Italy.

Abstract

Tetrahydroisoquinoline (THIQ) is a key structural component in many biologically active molecules including natural products and synthetic pharmaceuticals. Here, we report on the use of transition-metal mediated [2 + 2 + 2] cyclotrimerisation of alkynes to generate tricyclic THIQs with potential to selectively inhibit AKR1C3.