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Synthesis, stereoelectronic characterization and antiparasitic activity of new 1-benzenesulfonyl-2-methyl-1,2,3,4-tetrahydroquinolines

Pagliero, R. J. and Lusvarghi, S. and Pierini, A. B. and Brun, R. and Mazzieri, M. R.. (2010) Synthesis, stereoelectronic characterization and antiparasitic activity of new 1-benzenesulfonyl-2-methyl-1,2,3,4-tetrahydroquinolines. Bioorganic & Medicinal Chemistry, 18 (1). pp. 142-150.

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Official URL: http://edoc.unibas.ch/dok/A5843034

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Abstract

The synthesis and full 3D structural characterization of nine new 1-benzenesulfonyl-2-methyl-1,2,3,4-tetrahydroquinoline derivatives are reported. These belong to a library whose rationale for the design was the previous knowledge of the biological relevant properties of both structural moieties. From protozoan antiparasitic screening, compounds 3 demonstrated interesting activity against Trypanozoma cruzi with low cytotoxicity. Besides, most compounds were moderately active against Plasmodium falciparum. Of these, 3 and 9 can be considered as lead scaffolds for further optimization. The substituent on BS did not influence the 3D structure properties and the H-1 NMR spectra revealed the existence of an intramolecular weak hydrogen bond, C-H center dot center dot center dot O=S. Molecular modeling and X-ray crystallography also confirmed this finding, which is relevant to compound conformational preference. (C) 2009 Elsevier Ltd. All rights reserved
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
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
Identification Number:
Last Modified:13 Sep 2018 14:40
Deposited On:08 Jun 2012 06:47

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