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Issue 15, 2003
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Synthesis and antiplasmodial activity in vitro of new ferrocenechloroquine analogues

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Abstract

The synthesis of the new compounds (7-chloroquinolin-4-yl)-N′-(1′-dimethylaminomethylferrocen-1-ylmethyl)-amine (4a) and N-(7-chloroquinolin-4-yl)-N′-(1′-dimethylaminomethylferrocen-1-ylmethyl)-ethane-1,2-diamine (6a) is reported. The key step in the synthesis is the cleavage of a ferrocene–Sn bond with n-BuLi to give a lithiumferrocenide species (10), which is then treated with an electrophile. Thus, 1′-dimethylaminomethyl-1-tri-n-butylstannyl-ferrocene (11) and subsequently 1′-dimethylaminomethylferrocene-1-carbaldehyde (7a) were synthesised from 1,1′-bis(tri-n-butylstannyl)ferrocene, employing [CH2[double bond, length as m-dash]NMe2]I and DMF to introduce the amine and then the aldehyde functionalities. In addition, the compound 1′-dimethylaminomethyl-1-lithiumferrocenide was isolated and the 1H and 13C NMR data are reported. X-Ray crystal and molecular structures are reported for compound 4a and the related compound N-(7-chloroquinolin-4-yl)-N′-(2-dimethylaminomethylferrocen-1-ylmethyl)-ethane-1,2-diamine (5a). The antiplasmodial activity in vitro against chloroquine sensitive and resistant strains of Plasmodium falciparum is reported and compared to a series of ferrocene, ruthenocene and phenylene analogues.

Graphical abstract: Synthesis and antiplasmodial activity in vitro of new ferrocene–chloroquine analogues

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Publication details

The article was received on 24 Mar 2003, accepted on 06 Jun 2003 and first published on 04 Jul 2003


Article type: Paper
DOI: 10.1039/B303335J
Citation: Dalton Trans., 2003,0, 3046-3051
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    Synthesis and antiplasmodial activity in vitro of new ferrocenechloroquine analogues

    P. Beagley, M. A. L. Blackie, K. Chibale, C. Clarkson, R. Meijboom, J. R. Moss, P. J. Smith and H. Su, Dalton Trans., 2003, 0, 3046
    DOI: 10.1039/B303335J

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