Recent developments for introducing a hexafluoroisopropanol unit into the Vitamin D side chain.

Abstract

Among numerous studies on synthetic approaches to and the biological activities of vitamin D analogues, we herein focused on falecalcitriol, an analogue of calcitriol (1α,25-dihydroxyvitamin D3), in which a 26,26,26,27,27,27-hexafluoroisopropanol unit has been introduced into the side chain. Falecalcitriol was designed to escape from the metabolism of CYP24A1 and has been used as a drug to treat secondary hyperparathyroidism since 2001. Its metabolite, the 23-hydroxy form, retains biological activity and resistants to further metabolism. Recent developments in synthetic methodologies for introducing the hexafluoroisopropanol unit into the vitamin D CD-ring side chain were described herein.

• Authors: Fumihiro Kawagoe, Toru Sugiyama, Motonari Uesugi, Atsushi Kittaka
• Journal: The Journal of steroid biochemistry and molecular biology (J Steroid Biochem Mol Biol) Vol. 177 Pg. 250-254 (03 2018) ISSN: 1879-1220 [Electronic] England
• PMID: 28716761 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't, Review)
• Copyright: Copyright © 2017 Elsevier Ltd. All rights reserved.

Chemical References

• Fluorocarbons
• Propanols
• Acetone
• hexafluoroisopropanol
• hexafluoroacetone
• Calcitriol
• 26,26,26,27,27,27-hexafluoro-1,25-dihydroxyvitamin D3

Topics

• Acetone (analogs & derivatives, chemistry)
• Calcitriol (analogs & derivatives, chemistry)
• Fluorocarbons (chemistry)
• Propanols (chemistry)