title: 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.
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-beta-L-ribopyranoside and benzyl 4-O-trifloxy-2,3-anhydro-alpha-D-ribopyranoside is described. These compounds showed significant in vitro toxicity of the bloodstream form of Trypanosoma brucei with an IC50 of 11 microM. The parasites' energy metabolism and consumption of oxygen were found to be affected during incubation.
authors.affiliation: Physiologisch-chemisches Institut der Universität Tübingen, Hoppe-Seyler Strasse 4, 72076 Tübingen, Germany.
authors.forename: Syed Tasadaque
authors.initials: ST
authors.lastname: Ali Shah
authors.forename: Patrick
authors.initials: P
authors.lastname: Merkel
authors.forename: Hubert
authors.initials: H
authors.lastname: Ragge
authors.forename: Michael
authors.initials: M
authors.lastname: Duszenko
authors.forename: Jörg
authors.initials: J
authors.lastname: Rademann
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Voelter
mesh_terms: D000818:Animals; D004305:Dose-Response Relationship, Drug; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis* / Q000737:chemistry / Q000633:toxicity; D021261:Parasitic Sensitivity Tests; D013237:Stereoisomerism; D014344:Trypanocidal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D014346:Trypanosoma brucei brucei / Q000187:drug effects*
chemical_list: D006575:Heterocyclic Compounds, 3-Ring; D014344:Trypanocidal Agents; C504686:methyl-2,3-dihydro-1,4-benzodithiine