Aryl Bis-Sulfonamide Inhibitors of IspF from Arabidopsis thaliana and Plasmodium falciparum

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Author(s) Thelemann, Jonas, Illarionov, Boris, Barylyuk, Konstantin, Geist, Julie, Kirchmair, Johannes, Schneider, Petra, Anthore, Lucile, Root, Katharina, Trapp, Nils, Bacher, Adelbert, Witschel, Matthias, Zenobi, Renato, Fischer, Markus, Schneider, Gisbert, Diederich, François
Publication Type Journal Items, Publication Status: Published
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Title Aryl Bis-Sulfonamide Inhibitors of IspF from Arabidopsis thaliana and Plasmodium falciparum
Author(s) Thelemann, Jonas
Illarionov, Boris
Barylyuk, Konstantin
Geist, Julie
Kirchmair, Johannes
Schneider, Petra
Anthore, Lucile
Root, Katharina
Trapp, Nils
Bacher, Adelbert
Witschel, Matthias
Zenobi, Renato
Fischer, Markus
Schneider, Gisbert
Diederich, François
Journal or Series Title ChemMedChem
Volume Number 10
Issue Number 12
Start Page 2090
End Page 2098
ISSN 1860-7179
Publisher Wiley
Publication Place Weinheim
Publication Date 2015-12
Keyword(s) Bis-sulfonamides
Isoprenoid biosynthesis
Non-mevalonate pathway
P. falciparum
Abstract 2-Methylerythritol 2,4-cyclodiphosphate synthase (IspF) is an essential enzyme for the biosynthesis of isoprenoid precursors in plants and many human pathogens. The protein is an attractive target for the development of anti-infectives and herbicides. Using a photometric assay, a screen of 40 000 compounds on IspF from Arabidopsis thaliana afforded symmetrical aryl bis-sulfonamides that inhibit IspF from A. thaliana (AtIspF) and Plasmodium falciparum (PfIspF) with IC50 values in the micromolar range. The ortho-bis-sulfonamide structural motif is essential for inhibitory activity. The best derivatives obtained by parallel synthesis showed IC50 values of 1.4 μm against PfIspF and 240 nm against AtIspF. Substantial herbicidal activity was observed at a dose of 2 kg ha-1. Molecular modeling studies served as the basis for an in silico search targeted at the discovery of novel, non-symmetrical sulfonamide IspF inhibitors. The designed compounds were found to exhibit inhibitory activities in the double-digit micromolar IC50 range.
DOI 10.1002/cmdc.201500382
Additional Notes Published online 5 October 2015
Document Type Article
Publication Status Published
Language English
Assigned Organisational Unit(s) 02024
Organisational Unit(s)
NEBIS System Number 005075273
Source Database ID SCOPUS-84949745572
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  author = "Thelemann, Jonas and Illarionov, Boris and Barylyuk, Konstantin and Geist, Julie and Kirchmair, Johannes and Schneider, Petra and Anthore, Lucile and Root, Katharina and Trapp, Nils and Bacher, Adelbert and Witschel, Matthias and Zenobi, Renato and Fischer, Markus and Schneider, Gisbert and Diederich, Fran{\c{c}}ois",
  title = "{A}ryl {B}is-{S}ulfonamide {I}nhibitors of {I}sp{F} from {A}rabidopsis thaliana and {P}lasmodium falciparum",
  journal = "ChemMedChem",
  year = 2015,
  volume = "10",
  number = "12",
  pages = "2090--2098",
  month = dec,

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