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†

Ana R. N. Santos,^a Helen M. Sheldrake,

^a Ali I. M. Ibrahim,‡^a Chhanda Charan Danta,^a Davide Bonanni,

^b Martina Daga,^b Simonetta Oliaro-Bosso,^b Donatella Boschi,

^b Marco L. Lolli

^b and Klaus Pors

*^a

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* Corresponding authors

^a Institute of Cancer Therapeutics, Faculty of Life Sciences, University of Bradford, West Yorkshire, UK
E-mail: k.pors1@bradford.ac.uk

^b 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.

MedChemComm

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

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

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