Exploration of [2 + 2 + 2] cyclotrimerisation methodology to prepare tetrahydroisoquinoline-based compounds with potential aldo–keto reductase 1C3 target affinity† †Electronic supplementary information (ESI) available: Synthetic protocols, [2 + 2 + 2] cyclotrimerisation optimisation and binding mode of 14a in AKR1C2 protocols. See DOI: 10.1039/c9md00201d

• Published in: MedChemComm Vol. 10; no. 8; pp. 1476 - 1480
• Main Authors: Santos, Ana R. N., Sheldrake, Helen M., Ibrahim, Ali I. M., Danta, Chhanda Charan, Bonanni, Davide, Daga, Martina, Oliaro-Bosso, Simonetta, Boschi, Donatella, Lolli, Marco L., Pors, Klaus
• Format: Journal Article
• Language: English
• Published: Royal Society of Chemistry 27.06.2019
• Subjects: Chemistry
• ISSN: 2040-2503; 2040-2511
• DOI: 10.1039/c9md00201d

Tetrahydroisoquinoline (THIQ) is a key structural component in many biologically active molecules including natural products and synthetic pharmaceuticals. 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.