Issue 23, 2002

Synthesis and antimalarial activity in vitro of new ruthenocene–chloroquine analogues

Abstract

The syntheses of the new compounds (7-chloroquinolin-4-yl)(2-dimethylaminomethylruthenocen-1-ylmethyl)amine 3 and N-(7-chloroquinolin-4-yl)-N′-(2-dimethylaminomethylruthenocen-1-ylmethyl)ethane-1,2-diamine 5 are reported. The reactions are compared to those previously reported for the preparation of the ferrocene analogues. The key step in the reaction is the regioselective synthesis of 2-dimethylaminomethylruthenocene carboxaldehyde 10 by deprotonation of dimethylaminomethylruthenocene with t-BuLi in diethyl ether, followed by the addition of DMF. In addition, 1′-dimethylaminomethylruthenocene carboxaldehyde 11 was also prepared leading to the unexpected synthesis of the 1,1′-isomers (7-chloroquinolin-4-yl)(1′-dimethylaminomethylruthenocen-1-ylmethyl)amine 17 and N-(7-chloroquinolin-4-yl)-N′-(1′-dimethylaminomethylruthenocen-1-ylmethyl)ethane-1,2-diamine 18. X-Ray crystal and molecular structures for compounds 3 and 17·H2O are reported. The 4-aminoquinoline complexes show high efficacy against the chloroquine sensitive and resistant strains of the Plasmodium falciparum parasite in vitro; these results are compared with those obtained for the analogous ferrocene compounds.

Graphical abstract: Synthesis and antimalarial activity in vitro of new ruthenocene–chloroquine analogues

Supplementary files

Article information

Article type
Paper
Submitted
05 Jun 2002
Accepted
19 Sep 2002
First published
07 Nov 2002

J. Chem. Soc., Dalton Trans., 2002, 4426-4433

Synthesis and antimalarial activity in vitro of new ruthenocene–chloroquine analogues

P. Beagley, M. A. L. Blackie, K. Chibale, C. Clarkson, J. R. Moss and P. J. Smith, J. Chem. Soc., Dalton Trans., 2002, 4426 DOI: 10.1039/B205432A

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