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Stereospecific Synthesis of Chiral 2,3‐Dihydro‐1,4‐benzodithiine and Methyl‐2,3‐dihydro‐1,4‐benzodithiine Derivatives and their Toxic Effects on Trypanosoma brucei
Author(s) -
Ali Shah Syed Tasadaque,
Merkel Patrick,
Ragge Hubert,
Duszenko Michael,
Rademann Jörg,
Voelter Wolfgang
Publication year - 2005
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.200400375
Subject(s) - trypanosoma brucei , stereospecificity , chemistry , stereochemistry , organic chemistry , biochemistry , catalysis , gene
Abstract Preparation of chiral 2,3‐dihydro‐1,4‐benzodithiine and methyl‐2,3‐dihydro‐1,4‐benzodithiine derivatives with known absolute configurations from the easily accessible chiral synthons benzyl 4‐ O ‐trifloxy‐2,3‐anhydro‐β‐ L ‐ribopyranoside and benzyl 4‐ O ‐trifloxy‐2,3‐anhydro‐α‐ D ‐ribopyranoside is described. These compounds showed significant in vitro toxicity of the bloodstream form of Trypanosoma brucei with an IC 50 of 11 μ M . The parasites' energy metabolism and consumption of oxygen were found to be affected during incubation.