Syntheses and biological evaluation of novel 2α-substituted 1α,25-dihydroxyvitamin D3 analogues

Yoshitomo Suhara; Ken Ichi Nihei; Hirokazu Tanigawa; Toshie Fujishima; Katsuhiro Konno; Kimie Nakagawa; Toshio Okano; Hiroaki Takayama

doi:10.1016/S0960-894X(00)00189-X

Syntheses and biological evaluation of novel 2α-substituted 1α,25-dihydroxyvitamin D₃ analogues

Yoshitomo Suhara, Ken Ichi Nihei, Hirokazu Tanigawa, Toshie Fujishima, Katsuhiro Konno, Kimie Nakagawa, Toshio Okano, Hiroaki Takayama

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

66 Citations (Scopus)

Abstract

Novel 2α-substituted 1α,25-dihydroxyvitamin D₃ analogues were efficiently synthesized and their biological activities were evaluated. 2α-Methyl-1α25-dihydroxyvitamin D₃ (2), whose unique biological activities were previously reported, was modified to 2α-alkyl (ethyl and propyl) and 2α-hydroxyalkyl (hydroxymethyl, hydroxyethyl, and hydroxypropyl) analogues 3-7 by elongation of the alkyl chain and/or introduction of a terminal hydroxyl group. 2α-Hydroxypropyl-1α,25-dihydroxyvitamin D₃ (7) exhibited an exceptionally potent calcium-regulating effect and a unique activity profile. (C) 2000 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	1129-1132
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	10
Issue number	10
DOIs	https://doi.org/10.1016/S0960-894X(00)00189-X
Publication status	Published - 2000 May 15
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/S0960-894X(00)00189-X

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title = "Syntheses and biological evaluation of novel 2α-substituted 1α,25-dihydroxyvitamin D3 analogues",

abstract = "Novel 2α-substituted 1α,25-dihydroxyvitamin D3 analogues were efficiently synthesized and their biological activities were evaluated. 2α-Methyl-1α25-dihydroxyvitamin D3 (2), whose unique biological activities were previously reported, was modified to 2α-alkyl (ethyl and propyl) and 2α-hydroxyalkyl (hydroxymethyl, hydroxyethyl, and hydroxypropyl) analogues 3-7 by elongation of the alkyl chain and/or introduction of a terminal hydroxyl group. 2α-Hydroxypropyl-1α,25-dihydroxyvitamin D3 (7) exhibited an exceptionally potent calcium-regulating effect and a unique activity profile. (C) 2000 Elsevier Science Ltd. All rights reserved.",

author = "Yoshitomo Suhara and Nihei, {Ken Ichi} and Hirokazu Tanigawa and Toshie Fujishima and Katsuhiro Konno and Kimie Nakagawa and Toshio Okano and Hiroaki Takayama",

note = "Funding Information: This work was supported in part by a Grant-in-Aid from the Ministry of Education, Science and Culture of Japan.",

year = "2000",

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doi = "10.1016/S0960-894X(00)00189-X",

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T1 - Syntheses and biological evaluation of novel 2α-substituted 1α,25-dihydroxyvitamin D3 analogues

AU - Suhara, Yoshitomo

AU - Nihei, Ken Ichi

AU - Tanigawa, Hirokazu

AU - Fujishima, Toshie

AU - Konno, Katsuhiro

AU - Nakagawa, Kimie

AU - Okano, Toshio

AU - Takayama, Hiroaki

N1 - Funding Information: This work was supported in part by a Grant-in-Aid from the Ministry of Education, Science and Culture of Japan.

PY - 2000/5/15

Y1 - 2000/5/15

N2 - Novel 2α-substituted 1α,25-dihydroxyvitamin D3 analogues were efficiently synthesized and their biological activities were evaluated. 2α-Methyl-1α25-dihydroxyvitamin D3 (2), whose unique biological activities were previously reported, was modified to 2α-alkyl (ethyl and propyl) and 2α-hydroxyalkyl (hydroxymethyl, hydroxyethyl, and hydroxypropyl) analogues 3-7 by elongation of the alkyl chain and/or introduction of a terminal hydroxyl group. 2α-Hydroxypropyl-1α,25-dihydroxyvitamin D3 (7) exhibited an exceptionally potent calcium-regulating effect and a unique activity profile. (C) 2000 Elsevier Science Ltd. All rights reserved.

AB - Novel 2α-substituted 1α,25-dihydroxyvitamin D3 analogues were efficiently synthesized and their biological activities were evaluated. 2α-Methyl-1α25-dihydroxyvitamin D3 (2), whose unique biological activities were previously reported, was modified to 2α-alkyl (ethyl and propyl) and 2α-hydroxyalkyl (hydroxymethyl, hydroxyethyl, and hydroxypropyl) analogues 3-7 by elongation of the alkyl chain and/or introduction of a terminal hydroxyl group. 2α-Hydroxypropyl-1α,25-dihydroxyvitamin D3 (7) exhibited an exceptionally potent calcium-regulating effect and a unique activity profile. (C) 2000 Elsevier Science Ltd. All rights reserved.

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Syntheses and biological evaluation of novel 2α-substituted 1α,25-dihydroxyvitamin D₃ analogues

Abstract

ASJC Scopus subject areas

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