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Dicationic phenyl-2,2'-bichalcophenes and analogues as antiprotozoal agents

Ismail, M. A. and Bialy, S. A. and Brun, R. and Wenzler, T. and Nanjunda, R. and Wilson, W. D. and Boykin, D. W.. (2011) Dicationic phenyl-2,2'-bichalcophenes and analogues as antiprotozoal agents. Bioorganic & medicinal chemistry : a Tetrahedron publication for the rapid dissemenination of full original research papers and critical reviews on biomolecular chemistry, medicinal chemistry and related disciplines, 19 (2). pp. 978-984.

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Official URL: http://edoc.unibas.ch/dok/A6002168

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Abstract

A series of phenyl-2,2'-bichalcophene diamidines 1a-h were synthesized from the corresponding dinitriles either via a direct reaction with LiN(TMS)(2), followed by deprotection with ethanolic HCl or through the bis-O-acetoxyamidoxime followed by hydrogenation in acetic acid and EtOH over Pd-C. These diamidines show a wide range of DNA affinities as judged from their DeltaT(m) values which are remarkably sensitive to replacement of a furan unit with a thiophene one. These differences are explained in terms of the effect of subtle changes in geometry of the diamidines on binding efficacy. Five of the eight compounds were highly active (below 6nM IC(50)) in vitro against Trypanosoma brucei rhodesiense (T. b. r.) and four gave IC(50)values less than 7nM against Plasmodium falciparum (P. f.). Only one of the compounds was as effective as reference compounds in the T. b. r. mouse model for the acute phase of African trypanosomiasis
Faculties and Departments:09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH) > Department of Medical Parasitology and Infection Biology > Parasite Chemotherapy (Mäser)
UniBasel Contributors:Brun, Reto and Wenzler, Tanja
Item Type:Article, refereed
Article Subtype:Research Article
Bibsysno:Link to catalogue
Publisher:Pergamon
ISSN:0968-0896
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:13 Sep 2018 14:42
Deposited On:11 Oct 2012 15:30

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