Synthesis and biological activity of a 1 alpha,25-dihydroxyvitamin D2 analog bearing an amide group in the side-chain.
Synthesis of a 1 alpha,25-dihydroxyvitamin D2 analog (3), in which the double bond in the side-chain is replaced by an amide group, is described. Condensation of a carboxylic acid (8) with an amine (6) gave an amide (9), which in turn led to 3 via several steps. The analog (3) could not bind to the chick cytosol vitamin D receptor, which indicated the importance of the hydrophobic interaction of the C(22)-C(23) double bond in 1 alpha,25-dihydroxyvitamin D2 (2) with the vitamin D receptor.
Konno
K
K
Faculty of Pharmaceutical Sciences, Teikyo University, Japan.
Ojima
K
K
Hayashi
T
T
Tanabe
M
M
Takayama
H
H
D004872:Ergocalciferols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018167:Receptors, Calcitriol / Q000737:chemistry / Q000187:drug effects
D004872:Ergocalciferols; D018167:Receptors, Calcitriol; C003564:1,25-dihydroxyergocalciferol