Issue 44, 2014

1-Aryl-1,2,3,4-tetrahydroisoquinolines as potential antimalarials: synthesis, in vitro antiplasmodial activity and in silico pharmacokinetics evaluation

Abstract

In the present study, twenty-one 1-aryl-6-hydroxy-1,2,3,4-tetrahydroisoquinoline (THIQ) analogues were synthesized by base-catalyzed Pictet–Spengler reaction, and tested in vitro against P. falciparum using the [3H]hypoxanthine incorporation assay. Two compounds were found to be inactive while seventeen compounds displayed moderate antiplasmodial activity and two compounds were found to be highly active (IC50 < 0.2 μg ml−1). The two highly active compounds, 1-(4-chlorophenyl)-6-hydroxyl-1,2,3,4-tetrahydroisoquinoline and 6-hydroxyspiro[1,2,3,4-tetrahydroisoquinoline-1:1′-cyclohexane], also displayed low cytotoxicity, against rat skeletal myoblast cells, with CC50 values of 257.6 and 174.2 μM respectively. These results justify further investigation of simple 1-aryl-1,2,3,4-tetrahydroisoquinolines as potential anti-malarial agents.

Graphical abstract: 1-Aryl-1,2,3,4-tetrahydroisoquinolines as potential antimalarials: synthesis, in vitro antiplasmodial activity and in silico pharmacokinetics evaluation

Supplementary files

Article information

Article type
Paper
Submitted
18 Nov 2013
Accepted
01 Apr 2014
First published
03 Apr 2014

RSC Adv., 2014,4, 22856-22865

Author version available

1-Aryl-1,2,3,4-tetrahydroisoquinolines as potential antimalarials: synthesis, in vitro antiplasmodial activity and in silico pharmacokinetics evaluation

J. N. Hanna, F. Ntie-Kang, M. Kaiser, R. Brun and S. M. N. Efange, RSC Adv., 2014, 4, 22856 DOI: 10.1039/C3RA46791K

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