Arocalciferols: synthesis and biological evaluation of aromatic side-chain analogues of 1 alpha,25-dihydroxyvitamin D3(1a).
Aromatic side-chain analogues (arocalciferols 6-9) of the steroid hormone 1 alpha,25-dihydroxyvitamin D3 (1) were synthesized and biologically evaluated. The analogues were prepared by coupling the vitamin D A-ring enyne 14 with the appropriate enol triflate of a modified CD steroid fragment of the type 22. The resulting dienyne 23 was then transformed in three steps to the vitamin D analogues 6-9. Biological evaluation of these analogues have provided information concerning side-chain topographical effects on in vivo and in vitro activity.
Figadère
B
B
Department of Chemistry, University of California, Riverside 92521.
Norman
A W
AW
Henry
H L
HL
Koeffler
H P
HP
Zhou
J Y
JY
Okamura
W H
WH
D000818:Animals; D001667:Binding, Competitive; D002117:Calcitriol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D002454:Cell Differentiation / Q000187:drug effects; D002455:Cell Division / Q000187:drug effects; D055598:Chemical Phenomena; D002621:Chemistry; D002645:Chickens; D006801:Humans; D007413:Intestinal Mucosa / Q000378:metabolism; D015473:Leukemia, Promyelocytic, Acute; D008968:Molecular Conformation; D015394:Molecular Structure; D018167:Receptors, Calcitriol; D011987:Receptors, Steroid / Q000378:metabolism; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured; D014809:Vitamin D-Binding Protein / Q000378:metabolism
D018167:Receptors, Calcitriol; D011987:Receptors, Steroid; D014809:Vitamin D-Binding Protein; D002117:Calcitriol