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

Fumihiro Kawagoe; Toru Sugiyama; Motonari Uesugi; Atsushi Kittaka

doi:10.1016/j.jsbmb.2017.07.008

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

Fumihiro Kawagoe, Toru Sugiyama, Motonari Uesugi, Atsushi Kittaka

Faculty of Pharmaceutical Sciences

Research output: Contribution to journal › Review article › peer-review

16 Scopus citations

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 D ₃ ), 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.

Original language	English
Pages (from-to)	250-254
Number of pages	5
Journal	Journal of Steroid Biochemistry and Molecular Biology
Volume	177
DOIs	https://doi.org/10.1016/j.jsbmb.2017.07.008
State	Published - Mar 2018

Keywords

CD-ring
Falecalcitriol
Hexafluoroacetone (HFA)
Hexafluoroisopropanol unit
Ruppert-Prakash reagent (CF TMS)
Synthesis

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10.1016/j.jsbmb.2017.07.008

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title = "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 D 3 ), 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.",

keywords = "CD-ring, Falecalcitriol, Hexafluoroacetone (HFA), Hexafluoroisopropanol unit, Ruppert-Prakash reagent (CF TMS), Synthesis",

author = "Fumihiro Kawagoe and Toru Sugiyama and Motonari Uesugi and Atsushi Kittaka",

note = "Publisher Copyright: {\textcopyright} 2017 Elsevier Ltd",

year = "2018",

month = mar,

doi = "10.1016/j.jsbmb.2017.07.008",

language = "英語",

volume = "177",

pages = "250--254",

journal = "Journal of Steroid Biochemistry and Molecular Biology",

issn = "0960-0760",

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TY - JOUR

T1 - Recent developments for introducing a hexafluoroisopropanol unit into the Vitamin D side chain

AU - Kawagoe, Fumihiro

AU - Sugiyama, Toru

AU - Uesugi, Motonari

AU - Kittaka, Atsushi

PY - 2018/3

Y1 - 2018/3

N2 - 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 D 3 ), 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.

AB - 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 D 3 ), 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.

KW - CD-ring

KW - Falecalcitriol

KW - Hexafluoroacetone (HFA)

KW - Hexafluoroisopropanol unit

KW - Ruppert-Prakash reagent (CF TMS)

KW - Synthesis

UR - http://www.scopus.com/inward/record.url?scp=85026314556&partnerID=8YFLogxK

U2 - 10.1016/j.jsbmb.2017.07.008

DO - 10.1016/j.jsbmb.2017.07.008

M3 - 総説

C2 - 28716761

AN - SCOPUS:85026314556

SN - 0960-0760

VL - 177

SP - 250

EP - 254

JO - Journal of Steroid Biochemistry and Molecular Biology

JF - Journal of Steroid Biochemistry and Molecular Biology

ER -

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

Abstract

Keywords

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