Preparation and biological activity of 24-epi-26,26,26,27,27,27-hexafluoro- 1 alpha,25-dihydroxyvitamin D2.
A new fluorinated analog of vitamin D2, 24-epi-26,26,26,27,27,27-hexafluoro- 1 alpha,25-dihydroxyvitamin D2, was efficiently synthesized starting from (R)-4-isopropyl-3-propionyl-2- oxazolidinone with high stereochemical control. In all four physiological test systems, the fluorinate vitamin D2 analog was found to be slightly less active than 1 alpha,25-dihydroxyvitamin D3.
Iseki
K
K
MEC Laboratory, Daikin Industries, Ltd., Ibaraki, Japan.
Oishi
S
S
Namba
H
H
Taguchi
T
T
Kobayashi
Y
Y
D000818:Animals; D001665:Binding Sites; D015519:Bone Density / Q000187:drug effects*; D002117:Calcitriol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism / Q000494:pharmacology; D002118:Calcium / Q000097:blood*; D002642:Chick Embryo; D003600:Cytosol / Q000187:drug effects / Q000378:metabolism; D005269:Femur / Q000187:drug effects / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D009929:Organ Size / Q000187:drug effects; D010080:Oxazoles / Q000737:chemistry; D023303:Oxazolidinones; D051381:Rats; D017208:Rats, Wistar; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism; D014808:Vitamin D Deficiency / Q000378:metabolism; D005466:Fluorocarbons
D002117:Calcitriol; D002118:Calcium; D010080:Oxazoles; D023303:Oxazolidinones; C098094:4-isopropyl-3-propionyl-2-oxazolidinone; C040488:26,26,26,27,27,27-hexafluoro-1,25-dihydroxyvitamin D3; D005466:Fluorocarbons