Journal
BIOORGANIC & MEDICINAL CHEMISTRY
Volume 18, Issue 1, Pages 142-150Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2009.11.010
Keywords
Antiparasitic; Benzenesulfonyl; Tetrahydroquinolines; Stereoelectronic properties
Funding
- SECyT-UNC (Argentina)
- CONICET
Ask authors/readers for more resources
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.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available