Structure-activity analysis of fluorinated 1-N-arylamino-1-arylmethane-phosphonic acid esters as inhibitors of the NADH:ubiquinone oxidoreductase (complex I) | Journal of Computer-Aided Molecular Design Skip to main content
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Structure-activity analysis of fluorinated 1-N-arylamino-1-arylmethane-phosphonic acid esters as inhibitors of the NADH:ubiquinone oxidoreductase (complex I)

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Summary

The structural and electronic properties of fluorinated 1-N-arylamino-1-arylmethanephosphonic acid esters were studied and related to the inhibitory effects on NADH:ubiquinone oxidoreductase (complex I). Electrostatic potential surfaces, dipole moments and molecular geometries were analysed. Based on the conformational analysis and the electronic parameters, a simple model for the active site of the fluorinated 1-N-arylamino-1-arylmethanephosphonic acid esters was developed, explaining the inhibitory power. The strongest inhibition effects were found for the 1-(N-4-trifluoromethoxyphenyl)-amino-1-phenylmethanephosphonic acid diethyl ester 1bab.

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Authors and Affiliations

  1. Institut für Anorganische Chemie und Strukturchemie I, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, D-40225, Düsseldorf, Germany

    H. Dronia, U. Gruß & G. Hägele

  2. Institut für Biochemie, Heinrich-Heine-Universität Düsseldorf, Universitätsstrasse 1, D-40225, Düsseldorf, Germany

    T. Friedrich & H. Weiss

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  1. H. Dronia
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  2. U. Gruß
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  3. G. Hägele
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  4. T. Friedrich
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  5. H. Weiss
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Dronia, H., Gruß, U., Hägele, G. et al. Structure-activity analysis of fluorinated 1-N-arylamino-1-arylmethane-phosphonic acid esters as inhibitors of the NADH:ubiquinone oxidoreductase (complex I). J Computer-Aided Mol Des 10, 100–106 (1996). https://doi.org/10.1007/BF00402818

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  • DOI: https://doi.org/10.1007/BF00402818

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