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Synthetic Strategy and Biological Activity of A-ring Stereoisomers of 1,25- Dihydroxyvitamin D3 and C2-Modified Analogues

[ Vol. 14 , Issue. 21 ]

Author(s):

Toshie Fujishima, Tsutomu Suenaga and Takato Nozaki   Pages 2446 - 2453 ( 8 )

Abstract:


The hormonally active form of vitamin D3, 1α,25-dihydroxyvitamin D3 (1a), has a wide variety of biological activities and its major molecular target is considered to be the vitamin D receptor (VDR). The A-ring stereoisomers of 1a as well as its C2-modified analogues, which have different stereochemistry at the C1 and/or C3 hydroxy groups, are of interest since recent metabolic studies have shown that catabolism could occur through A-ring modification. In this review, a practical and versatile synthesis of the A-ring enyne precursors by the convergent method of Trost and coworkers, which is needed to construct all possible A-ring stereoisomers of 1,25-dihydroxyvitamin D3 (1a-d), and the C2-modified analogues (4a-d, 5a-d, 6a-d and 7a-d) is described. A strategy for the synthesis and evaluation of all possible A-ring stereoisomers of 1a and their A-ring modified analogues is important, and this will stimulate synthesis and biological studies into vitamin D.

Keywords:

Analogue, Chemical synthesis, Hormone, Nuclear receptor, Steroid, Vitamin.

Affiliation:

Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, Shido, Sanuki, Kagawa 769-2193, Japan.

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