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

Abstract

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

Photoredox- and piezo-catalysed access to complex trifluoromethylated polycyclic structures from ynamides

“…We are confident that the piezocatalysis methodology is a viable access route to highly functionalized polycyclic derivatives and prompt further discovery of new bioactive compounds. Yields were determined by 19 Chem., 2006, 71, 8028-8036.…”

“…16 Schizozygane indoline showed good antimicrobial activity against fungi and bacteria, 17 while Tylophora alkaloids were found to have good hypoxia-inducible factor-1 (HIF-1) and HIV inhibitory activity. 18 A tetrahydroisoquinoline derivative has been used to target AKR1C3, 19 displaying good inhibitory properties for the treatment of pancreatic cancer.…”

Overview of AKR1C3: Inhibitor Achievements and Disease Insights

“…Recently, a series of tetrahydroisoquinoline compounds were synthesized with potential AKR1C3 affinity through the [2 + 2 + 2] ring trimerization method. 115 Compared with BBR, the selectivity of compound 14 toward AKR1C2 was improved. Docking analysis results showed that 14 extends into the SP1 and SP3 pockets of AKR1C3 and forms hydrogen bonding interactions in the oxyanion site.…”

“…Recently, a series of tetrahydroisoquinoline compounds were synthesized with potential AKR1C3 affinity through the [2 + 2 + 2] ring trimerization method . Compared with BBR, the selectivity of compound 14 toward AKR1C2 was improved.…”