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Synthesis and antitrypanosomal evaluation of derivatives of N-benzyl-1,2-dihydroquinolin-6-ols : effect of core substitutions and salt formation

Reid, C. S. and Patrick, D. A. and He, S. and Fotie, J. and Premalatha, K. and Tidwell, R. R. and Wang, M. Z. and Liu, Q. and Gershkovich, P. and Wasan, K. M. and Wenzler, T. and Brun, R. and Werbovetz, K. A.. (2011) Synthesis and antitrypanosomal evaluation of derivatives of N-benzyl-1,2-dihydroquinolin-6-ols : effect of core substitutions and salt formation. 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 (1). pp. 513-523.

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Official URL: http://edoc.unibas.ch/dok/A6002360

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Abstract

Analogs of the trypanocidal lead compound 1-benzyl-1,2-dihydro-2,2,4-trimethylquinolin-6-yl acetate were prepared to extend the structure-activity relationship in this series of molecules, improve the in vivo antitrypanosomal activity of the lead, and determine whether ester prodrugs are needed to overcome the instability of the dihydroquinolin-6-ols. Two of the most active compounds identified in this study were 1-benzyl-1,2-dihydro-2,2,4-trimethylquinolin-6-ol hydrochloride and 1-(2-methoxy)benzyl-1,2-dihydro-2,2,4-trimethylquinolin-6-ol hydrochloride. These stable solids possessed low nanomolar IC(50) values against Trypanosoma brucei rhodesiense STIB900 in vitro and provided cures in an early treatment acute mouse model of African trypanosomiasis when given ip at 50mg/kg/day for four consecutive days
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 14:43
Deposited On:08 Nov 2012 16:20

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