Structure-activity analysis of fluorinated 1-N-arylamino-1-arylmethanephosphonic acid esters as inhibitors of the NADH:ubiquinone oxidoreductase (complex I)

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 o...

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Bibliographic Details
Published in:Journal of computer-aided molecular design 1996-04, Vol.10 (2), p.100-106
Main Authors: Dronia, H, Gruss, U, Hägele, G, Friedrich, T, Weiss, H
Format: Article
Language:English
Subjects:
Animals
Binding Sites
Cattle
Computer Simulation
Electrochemistry
Enzyme Inhibitors - chemistry
Enzyme Inhibitors - pharmacology
Mitochondria, Heart - enzymology
Mitochondria, Heart - metabolism
Models, Molecular
Molecular Conformation
Molecular Structure
NAD(P)H Dehydrogenase (Quinone) - antagonists & inhibitors
NAD(P)H Dehydrogenase (Quinone) - chemistry
Organophosphorus Compounds - chemistry
Organophosphorus Compounds - pharmacology
Oxygen Consumption
Protein Conformation
Software
Structure-Activity Relationship
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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.
ISSN:0920-654X
DOI:10.1007/BF00402818