Synthesis and biological activity of 1.ALPHA.-fluoro-25-hydroxyvitamin D3.
- 1 January 1984
- journal article
- research article
- Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN
- Vol. 32 (9) , 3525-3531
- https://doi.org/10.1248/cpb.32.3525
Abstract
Trans-Diaxial opening with potassium hydrogen difluoride of the 1.beta.,2.beta.-epoxy-3.beta.-ol derived from cholenic acid gave the 1.alpha.-fluoro-2.beta.,3.beta.-diol derivative. Construction of the 25-hydroxy cholesterol side chain and deoxygenation of the 2.beta.-hydroxy group afforded 1.alpha.-fluoro-3.beta.,25-dihydroxycholest-5-ene, which was transformed into 1.alpha.-fluoro-25-hydroxyvitamin D3. A single dose of 1.3 .mu.g of 1.alpha.-fluoro-25-hydroxyvitamin D3 produced neither an intestinal Ca transport response nor a bone Ca mobilization response in vitamin D-deficient rats. In the same rats, 50 ng of 25-hydroxyvitamin D3 produced a marked response. 1.alpha.-Fluoro-25-hydroxyvitamin D3 was 30 times more active than 25-hydroxyvitamin D3 in binding to the chick intestinal receptor for 1.alpha.,25-dihydroxyvitamin D3. Addition of 1.alpha.-fluoro-25-hydroxyvitamin D3 to human promylocytic leukemia cells resulted in strong phagocytic activity.This publication has 0 references indexed in Scilit: