Synthesis and evaluation of A-ring diastereomers of 1α,25-dihydroxy-22-oxavitamin D3 (OCT)

Susumi Hatakeyama; Toshio Okano; Junji Maeyama; Tomoyuki Esumi; Hiroko Hiyamizu; Yoshiharu Iwabuchi; Kimie Nakagawa; Keiichi Ozono; Akira Kawase; Noboru Kubodera

doi:10.1016/S0968-0896(00)00259-5

Synthesis and evaluation of A-ring diastereomers of 1α,25-dihydroxy-22-oxavitamin D₃ (OCT)

Susumi Hatakeyama, Toshio Okano, Junji Maeyama, Tomoyuki Esumi, Hiroko Hiyamizu, Yoshiharu Iwabuchi, Kimie Nakagawa, Keiichi Ozono, Akira Kawase, Noboru Kubodera

Research output: Contribution to journal › Article › peer-review

13 Citations (Scopus)

Abstract

A-ring diastereomers of 1α,25-dihydroxy-22-oxavitamin D₃ (OCT) (2), 3-epi-1α,25-dihydroxy-22-oxavitamin D₃ (3-epiOCT) (3) and 1,3-diepi-1α,25-dihydroxy-22-oxavitamin D₃ (1,3-diepiOCT) (4) were synthesized by the convergent method. In vitro binding affinity for rat vitamin D binding protein and calf-thymus vitamin D receptor, differentiation-inducing activity on HL-60 cells, and transcriptional activity of 3-epiOCT (3) and 1,3-diepiOCT (4) were evaluated in comparison with OCT (2), 1-epi-1α,25-dihydroxy-22-oxavitamin D₃ (1-epiOCT) (5) and 1α,25-dihydroxyvitamin D₃ (1).

Original language	English
Pages (from-to)	403-415
Number of pages	13
Journal	Bioorganic and Medicinal Chemistry
Volume	9
Issue number	2
DOIs	https://doi.org/10.1016/S0968-0896(00)00259-5
Publication status	Published - 2001
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/S0968-0896(00)00259-5

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Synthesis and evaluation of A-ring diastereomers of 1α,25-dihydroxy-22-oxavitamin D₃ (OCT). / Hatakeyama, Susumi; Okano, Toshio; Maeyama, Junji; Esumi, Tomoyuki; Hiyamizu, Hiroko; Iwabuchi, Yoshiharu; Nakagawa, Kimie; Ozono, Keiichi; Kawase, Akira; Kubodera, Noboru.

In: Bioorganic and Medicinal Chemistry, Vol. 9, No. 2, 2001, p. 403-415.

Research output: Contribution to journal › Article › peer-review

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title = "Synthesis and evaluation of A-ring diastereomers of 1α,25-dihydroxy-22-oxavitamin D3 (OCT)",

abstract = "A-ring diastereomers of 1α,25-dihydroxy-22-oxavitamin D3 (OCT) (2), 3-epi-1α,25-dihydroxy-22-oxavitamin D3 (3-epiOCT) (3) and 1,3-diepi-1α,25-dihydroxy-22-oxavitamin D3 (1,3-diepiOCT) (4) were synthesized by the convergent method. In vitro binding affinity for rat vitamin D binding protein and calf-thymus vitamin D receptor, differentiation-inducing activity on HL-60 cells, and transcriptional activity of 3-epiOCT (3) and 1,3-diepiOCT (4) were evaluated in comparison with OCT (2), 1-epi-1α,25-dihydroxy-22-oxavitamin D3 (1-epiOCT) (5) and 1α,25-dihydroxyvitamin D3 (1).",

author = "Susumi Hatakeyama and Toshio Okano and Junji Maeyama and Tomoyuki Esumi and Hiroko Hiyamizu and Yoshiharu Iwabuchi and Kimie Nakagawa and Keiichi Ozono and Akira Kawase and Noboru Kubodera",

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doi = "10.1016/S0968-0896(00)00259-5",

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AU - Hatakeyama, Susumi

AU - Okano, Toshio

AU - Maeyama, Junji

AU - Esumi, Tomoyuki

AU - Hiyamizu, Hiroko

AU - Iwabuchi, Yoshiharu

AU - Nakagawa, Kimie

AU - Ozono, Keiichi

AU - Kawase, Akira

AU - Kubodera, Noboru

PY - 2001

Y1 - 2001

N2 - A-ring diastereomers of 1α,25-dihydroxy-22-oxavitamin D3 (OCT) (2), 3-epi-1α,25-dihydroxy-22-oxavitamin D3 (3-epiOCT) (3) and 1,3-diepi-1α,25-dihydroxy-22-oxavitamin D3 (1,3-diepiOCT) (4) were synthesized by the convergent method. In vitro binding affinity for rat vitamin D binding protein and calf-thymus vitamin D receptor, differentiation-inducing activity on HL-60 cells, and transcriptional activity of 3-epiOCT (3) and 1,3-diepiOCT (4) were evaluated in comparison with OCT (2), 1-epi-1α,25-dihydroxy-22-oxavitamin D3 (1-epiOCT) (5) and 1α,25-dihydroxyvitamin D3 (1).

AB - A-ring diastereomers of 1α,25-dihydroxy-22-oxavitamin D3 (OCT) (2), 3-epi-1α,25-dihydroxy-22-oxavitamin D3 (3-epiOCT) (3) and 1,3-diepi-1α,25-dihydroxy-22-oxavitamin D3 (1,3-diepiOCT) (4) were synthesized by the convergent method. In vitro binding affinity for rat vitamin D binding protein and calf-thymus vitamin D receptor, differentiation-inducing activity on HL-60 cells, and transcriptional activity of 3-epiOCT (3) and 1,3-diepiOCT (4) were evaluated in comparison with OCT (2), 1-epi-1α,25-dihydroxy-22-oxavitamin D3 (1-epiOCT) (5) and 1α,25-dihydroxyvitamin D3 (1).

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Synthesis and evaluation of A-ring diastereomers of 1α,25-dihydroxy-22-oxavitamin D₃ (OCT)

Abstract

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