Synthesis and biological activity of 2-methyl-20-epi analogues of 1 alpha,25-dihydroxyvitamin D3.
Synthesis and biological evaluation of all eight possible A-ring diastereomers of 2-methyl-20-epi-1,25-dihydroxyvitamin D3 are described. Among the analogues synthesized. 2 alpha-methyl-20-epi-1 alpha,25-dihydroxyvitamin D3 exhibited exceptionally high potency. The double modification of 2-methyl substitution and 20-epimerization yielded analogues with unique activity profiles.
Fujishima
T
T
Faculty of Pharmaceutical Sciences, Teikyo University, Kanagawa, Japan.
Liu
Z
Z
Miura
D
D
Chokki
M
M
Ishizuka
S
S
Konno
K
K
Takayama
H
H
D000818:Animals; D002117:Calcitriol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002118:Calcium / Q000378:metabolism; D002417:Cattle; D002454:Cell Differentiation / Q000187:drug effects; D018922:HL-60 Cells; D006801:Humans; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D018167:Receptors, Calcitriol / Q000378:metabolism; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013950:Thymus Gland / Q000378:metabolism
D018167:Receptors, Calcitriol; D002117:Calcitriol; D002118:Calcium