Design and synthesis of new (E)-cinnamic N-acylhydrazones as potent antitrypanosomal agents

Carvalho, S. A. and Feitosa, L. O. and Soares, M. and Costa, T. E. and Henriques, M. G. and Salomao, K. and de Castro, S. L. and Kaiser, M. and Brun, R. and Wardell, J. L. and Wardell, S. M. and Trossini, G. H. and Andricopulo, A. D. and da Silva, E. F. and Fraga, C. A.. (2012) Design and synthesis of new (E)-cinnamic N-acylhydrazones as potent antitrypanosomal agents. European journal of medicinal chemistry, 54. pp. 512-521.

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Official URL: http://edoc.unibas.ch/dok/A6094118

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We report herein the synthesis and trypanocidal profile of new (E)-cinnamic N-acylhydrazones (NAHs) designed by exploiting molecular hybridization between the potent cruzain inhibitors (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(4-bromophenyl)prop-2-en-1-one and (E)-3-hydroxy-N'-((2-hydroxynaphthalen-1-yl)methylene)-7-methoxy-2-naphthohydrazi de. These derivatives were evaluated against both amastigote and trypomastigote forms of Trypanosoma cruzi and lead us to identify two compounds that were approximately two times more active than the reference drug, benznidazole, and with good cytotoxic index. Although designed as cruzain inhibitors, the weak potency displayed by the best cinnamyl NAH derivatives indicated that another mechanism of action was likely responsible for their trypanocide action
Faculties and Departments:09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH) > Department of Medical Parasitology and Infection Biology (MPI) > Parasite Chemotherapy (Mäser)
UniBasel Contributors:Brun, Reto and Kaiser, Marcel
Item Type:Article, refereed
Article Subtype:Research Article
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:05 Dec 2017 10:08
Deposited On:19 Jul 2013 07:38

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