Synthesis and structural analysis of the active enantiomer of famoxadone, a potent inhibitor of cytochrome bc(1)

Citation
Yj. Zheng et al., Synthesis and structural analysis of the active enantiomer of famoxadone, a potent inhibitor of cytochrome bc(1), BIOORG MED, 10(10), 2000, pp. 1059-1062
Citations number
21
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN journal
0960894X → ACNP
Volume
10
Issue
10
Year of publication
2000
Pages
1059 - 1062
Database
ISI
SICI code
0960-894X(20000515)10:10<1059:SASAOT>2.0.ZU;2-V
Abstract
Famoxadone is a newly commercialized fungicide and potent Q(o)-site inhibit or of cytochrome bet. The S-(-)-enantiomer of famoxadone (the active compon ent) 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 an d the oxygen atoms of the heterocycle. (C) 2000 Elsevier Science Ltd. All r ights reserved.