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

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

4 Citations (Scopus)

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).

Original language	English
Pages (from-to)	423-436
Number of pages	14
Journal	Heterocycles
Volume	62
DOIs	https://doi.org/10.3987/com-03-s(p)34
Publication status	Published - 2004 Jan 1
Externally published	Yes

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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

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).",

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

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doi = "10.3987/com-03-s(p)34",

language = "English",

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journal = "Heterocycles",

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publisher = "Japan Institute of Heterocyclic Chemistry",

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TY - JOUR

T1 - Synthesis of novel 1α,25-dihydroxy-19-norvitamin D3 with an amide conjugate

AU - Suhara, Yoshitomo

AU - Ono, Keiichiro

AU - Yoshida, Akihiro

AU - Fujishima, Toshie

AU - Saito, Nozomi

AU - Honzawa, Shinobu

AU - Kishimoto, Seishi

AU - Sugiura, Takayuki

AU - Waku, Keizo

AU - Takayama, Hiroaki

AU - Kittaka, Atsushi

PY - 2004/1/1

Y1 - 2004/1/1

N2 - 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).

AB - 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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JO - Heterocycles

JF - Heterocycles

ER -

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

Abstract

ASJC Scopus subject areas

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