Novel A-ring analogs of the hormone 1alpha,25-dihydroxyvitamin D3: synthesis and preliminary biological evaluation.
Prepared from a commercial prostaglandin building block, novel vitamin D3 analogs with a contracted five-membered A-ring were designed and synthesized to mimic the A-ring diol structure of the natural hormone 1alpha,25-dihydroxyvitamin D3. Prepared from commercial 1,4-cyclohexanedione, a structurally simplified analog was designed and synthesized in which a suitably oriented primary allylic hydroxyl group at the C-2 position might be a surrogate for the biologically important 1alpha-OH in the natural hormone.
Posner
Gary H
GH
Department of Chemistry, The Johns Hopkins University, Baltimore, MD 21218, USA. ghp@jhu.edu
Lee
S H Tony
SH
Kim
Hyung Jin
HJ
Peleg
Sara
S
Dolan
Patrick
P
Kensler
Thomas W
TW
D000818:Animals; D019556:COS Cells; D049109:Cell Proliferation / Q000187:drug effects; D002478:Cells, Cultured; D002522:Chlorocebus aethiops; D006801:Humans; D015603:Keratinocytes / Q000187:drug effects; D013329:Structure-Activity Relationship; D014807:Vitamin D / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
C116441:2-methyl-1,25-dihydroxyvitamin D3; D014807:Vitamin D