Synthesis of novel 1α,25-dihydroxy-19-norvitamin D3 with an amide conjugate

Yoshitomo Suhara; Keiichiro Ono; Akihiro Yoshida; Toshie Fujishima; Nozomi Saito; Shinobu Honzawa; Seishi Kishimoto; Takayuki Sugiura; Keizo Waku; Hiroaki Takayama; Atsushi Kittaka

doi:10.3987/com-03-s(p)34

Synthesis of novel 1α,25-dihydroxy-19-norvitamin D₃ with an amide conjugate

Yoshitomo Suhara, Keiichiro Ono, Akihiro Yoshida, Toshie Fujishima, Nozomi Saito, Shinobu Honzawa, Seishi Kishimoto, Takayuki Sugiura, Keizo Waku, Hiroaki Takayama, Atsushi Kittaka

研究成果: Article › 査読

4 被引用数 (Scopus)

抄録

The diene system of 1α,25-dihydroxy-19-norvitamin D₃ was replaced by a stable amide bond. A 3-hydroxypropoxy group, which was effective on enhancing binding affinity of 1α,25-dihydroxyvitamin D₃ for vitamin D receptor (VDR), was introduced to the C2-position of the amide type analogue of 1α,25-dihydroxy-19-norvitamin D₃. The amide analogue was found to be not suitable for binding to the ligand binding domain of the bovine thymus VDR, and additional modification at the C2-position did not improve the affinity. Potency in induction of HL-60 cell differentiation was evaluated for the novel amide analogues (3a-c).

本文言語	English
ページ（範囲）	423-436
ページ数	14
ジャーナル	Heterocycles
巻	62
DOI	https://doi.org/10.3987/com-03-s(p)34
出版ステータス	Published - 2004 1月 1
外部発表	はい

ASJC Scopus subject areas

分析化学
薬理学
有機化学

文献へのアクセス

10.3987/com-03-s(p)34

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引用スタイル

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abstract = "The diene system of 1α,25-dihydroxy-19-norvitamin D3 was replaced by a stable amide bond. A 3-hydroxypropoxy group, which was effective on enhancing binding affinity of 1α,25-dihydroxyvitamin D3 for vitamin D receptor (VDR), was introduced to the C2-position of the amide type analogue of 1α,25-dihydroxy-19-norvitamin D3. The amide analogue was found to be not suitable for binding to the ligand binding domain of the bovine thymus VDR, and additional modification at the C2-position did not improve the affinity. Potency in induction of HL-60 cell differentiation was evaluated for the novel amide analogues (3a-c).",

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AU - Fujishima, Toshie

AU - Saito, Nozomi

AU - Honzawa, Shinobu

AU - Kishimoto, Seishi

AU - Sugiura, Takayuki

AU - Waku, Keizo

AU - Takayama, Hiroaki

AU - Kittaka, Atsushi

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