Synthesis and structural analysis of the active enantiomer of famoxadone, a potent inhibitor of cytochrome bc1

Famoxadone is a newly commercialized fungicide and potent Qo-site inhibitor of cytochrome bc1. The S-(-)-enantiomer of famoxadone (the active component) was synthesized by two routes and was analyzed computationally and by X-ray crystallography. The molecule displays an extended conformation with fl...

Full description

Saved in:
Bibliographic Details
Published inBioorganic & medicinal chemistry letters Vol. 10; no. 10; p. 1059
Main Authors Zheng, Y J, Shapiro, R, Marshall, W J, Jordan, D B
Format Journal Article
LanguageEnglish
Published England 15.05.2000
Subjects
Crystallography, X-Ray
Electron Transport Complex III - antagonists & inhibitors
Enzyme Inhibitors - chemical synthesis
Enzyme Inhibitors - chemistry
Enzyme Inhibitors - pharmacology
Fungicides, Industrial - chemical synthesis
Fungicides, Industrial - chemistry
Fungicides, Industrial - pharmacology
Hydrogen Bonding
Methacrylates
Oxazoles - chemical synthesis
Oxazoles - chemistry
Oxazoles - pharmacology
Strobilurins
Online AccessGet full text

Cover

More Information
Summary:Famoxadone is a newly commercialized fungicide and potent Qo-site inhibitor of cytochrome bc1. The S-(-)-enantiomer of famoxadone (the active component) was synthesized by two routes and was analyzed computationally and by X-ray crystallography. The molecule displays an extended conformation with flexibility in the structure imparted by the two terminal phenyl groups. In the crystal lattice, intermolecular hydrogen bonds occur between the NH and the oxygen atoms of the heterocycle.
ISSN:0960-894X
DOI:10.1016/S0960-894X(00)00164-5