Ferrocenyl derivatives of the anthelmintic praziquantel : design, synthesis and biological evaluation

Patra, M. and Ingram, K. and Pierroz, V. and Ferrari, S. and Spingler, B. and Keiser, J. and Gasser, G.. (2012) Ferrocenyl derivatives of the anthelmintic praziquantel : design, synthesis and biological evaluation. Journal of medicinal chemistry, 55 (20). pp. 8790-8798.

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Official URL: http://edoc.unibas.ch/dok/A6094175

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The design, synthesis and biological evaluation of eighteen ferrocenyl derivatives (4A-12A and 4B-12B) of the most-well known drug against schistosomiasis, namely praziquantel (PZQ), are reported. These compounds which have been all isolated as racemates were unambiguously characterized by 1H and 13C NMR spectroscopy, mass spectrometry and elemental analysis as well as by X-ray crystallography for 4A, 5A and 7A. Cytotoxicity studies revealed that the complexes were moderately toxic towards a cervical cancer cell line (HeLa) and, importantly, significantly less active towards a noncancerous cell line (MRC-5). The in vitro anthelmintic activity of the eighteen ferrocenyl PZQ derivatives was tested against Schistosoma mansoni and values in the micromolar range (26-68 microM) were determined for the four most active compounds. It was also demonstrated using two compounds of the series as models (8A and 8B) that the complexes were stable when incubated for 24 h at 37 degrees C in human plasma
Faculties and Departments:09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH) > Department of Medical Parasitology and Infection Biology (MPI) > Helminth Drug Development (Keiser)
UniBasel Contributors:Keiser, Jennifer
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:American Chemical Society
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:20 Oct 2017 11:58
Deposited On:19 Jul 2013 07:40

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