Synthesis and in vitro anti-protozoal activity of a series of benzotropolone derivatives incorporating endocyclic hydrazines


Ren, HY; Grady, S; Banghart, M; Moulthrop, JS; Kendrick, H; Yardley, V; Croft, SL; Moyna, G; (2003) Synthesis and in vitro anti-protozoal activity of a series of benzotropolone derivatives incorporating endocyclic hydrazines. European journal of medicinal chemistry, 38 (11-12). p. 949. ISSN 0223-5234 DOI: https://doi.org/10.1016/s0223-5234(03)00180-6

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Abstract

The preparation and evaluation as potential anti-protozoal agents of molecules bearing an endocyclic hydrazine moiety is presented. The synthetic route to this new series of compounds is straightforward, involving a hetero Diels-Alder reaction between different benzotropolone esters and diethyl azodicarboxylate (DEAD). While they show limited or no in vitro activity against Leishmania donovani, Plasmodium falciparum and Trypanosoma brucei rhodesiense, several of the compounds have activities against Trypanosoma cruzi in the 15.8-41.0 muM range. These activities are comparable to that, of benznidazole (IC50 6.0 muM), the main chemotherapy employed in the treatment of T cruzi infections. In addition; all but one of the new bicyclic hydrazine esters are virtually non-toxic, one of the most important drawbacks of currently available trypanocidal drugs. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

Item Type: Article
Keywords: benzotropolone derivatives, endocyclic hydrazines, hetero, Diels-Alder reaction, anti-protozoal activity, Diels-alder reactions, trypanosoma-cruzi, sensitivity, chemistry, invitro, design, drugs
Faculty and Department: Faculty of Infectious and Tropical Diseases > Dept of Immunology and Infection
Research Centre: Leishmaniasis Group
PubMed ID: 14642327
Web of Science ID: 188000400005
URI: http://researchonline.lshtm.ac.uk/id/eprint/15021

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