Synthesis of 15alpha-fluoro-24,25-dihydrolanosterol as a potential inhibitor and/or mechanistic probe for lanosterol 14alpha-demethylase.
As a potential inhibitor and/or mechanistic probe for lanosterol 14alpha-demethylase, 15alpha-fluoro-24,25-dihydrolanosterol was prepared by fluorination of 15alpha-hydroxy-24,25-dihydrolanost-7-en-3beta-yl benzoate with diethylaminosulfur trifluoride, followed by hydrogen chloride-catalyzed isomerization of the delta7 to delta8 and reductive cleavage of the benzoate.
Morisaki
M
M
Kyoritsu College of Pharmacy, Tokyo, Japan.
Igata
T
T
Yamamoto
S
S
D065607:Cytochrome P-450 Enzyme Inhibitors; D003577:Cytochrome P-450 Enzyme System / Q000737:chemistry; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015335:Molecular Probes; D015394:Molecular Structure; D010088:Oxidoreductases / Q000037:antagonists & inhibitors* / Q000737:chemistry; D058886:Sterol 14-Demethylase
D065607:Cytochrome P-450 Enzyme Inhibitors; D004791:Enzyme Inhibitors; D015335:Molecular Probes; D003577:Cytochrome P-450 Enzyme System; D010088:Oxidoreductases; D058886:Sterol 14-Demethylase