Synthesis and antimalarial activity of chain substituted pivaloyloxymethyl ester analogues of Fosmidomycin and FR900098

Thomas Kurz; Katrin Schlüter; Uwe Kaula; Bärbel Bergmann; Rolf D Walter; Detlef Geffken

doi:10.1016/j.bmc.2006.04.018

Synthesis and antimalarial activity of chain substituted pivaloyloxymethyl ester analogues of Fosmidomycin and FR900098

Bioorg Med Chem. 2006 Aug 1;14(15):5121-35. doi: 10.1016/j.bmc.2006.04.018. Epub 2006 May 5.

Authors

Thomas Kurz¹, Katrin Schlüter, Uwe Kaula, Bärbel Bergmann, Rolf D Walter, Detlef Geffken

Affiliation

¹ Institute of Pharmacy, University of Hamburg, Bundesstrasse 45, D-20146 Hamburg, Germany. kurz@chemie.uni-hamburg.de

PMID: 16679022
DOI: 10.1016/j.bmc.2006.04.018

Abstract

Fosmidomycin is a promising antimalarial drug candidate with a unique chemical structure and a novel mode of action. Chain substituted pivaloyloxymethyl ester derivatives of Fosmidomycin and its acetyl analogue FR900098 have been synthesized and their in vitro antimalarial activity versus the Chloroquine sensitive strain 3D7 of Plasmodium falciparum has been determined.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Animals
Antimalarials / chemical synthesis*
Antimalarials / chemistry
Antimalarials / pharmacology*
Dose-Response Relationship, Drug
Fosfomycin / analogs & derivatives*
Fosfomycin / chemistry
Fosfomycin / pharmacology
Molecular Structure
Parasitic Sensitivity Tests
Pentanoic Acids / chemical synthesis*
Pentanoic Acids / pharmacology*
Plasmodium falciparum / classification
Plasmodium falciparum / drug effects
Plasmodium falciparum / growth & development
Prodrugs / chemical synthesis
Prodrugs / chemistry
Prodrugs / pharmacology
Stereoisomerism
Structure-Activity Relationship

Substances

Antimalarials
Pentanoic Acids
Prodrugs
Fosfomycin
fosmidomycin
3-(N-acetyl-N-hydroxy)aminopropylphosphonic acid