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 journalArticle

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 languageEnglish
Pages (from-to)423-436
Number of pages14
JournalHeterocycles
Volume62
Publication statusPublished - 2004 Jan 1
Externally publishedYes

Fingerprint

Amides
Calcitriol Receptors
Thymus
Calcitriol
Ligands
1,25-dihydroxy-19-norvitamin D3

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Suhara, Y., Ono, K., Yoshida, A., Fujishima, T., Saito, N., Honzawa, S., ... Kittaka, A. (2004). Synthesis of novel 1α,25-dihydroxy-19-norvitamin D3 with an amide conjugate. Heterocycles, 62, 423-436.

Synthesis of novel 1α,25-dihydroxy-19-norvitamin D3 with an amide conjugate. / Suhara, Yoshitomo; Ono, Keiichiro; Yoshida, Akihiro; Fujishima, Toshie; Saito, Nozomi; Honzawa, Shinobu; Kishimoto, Seishi; Sugiura, Takayuki; Waku, Keizo; Takayama, Hiroaki; Kittaka, Atsushi.

In: Heterocycles, Vol. 62, 01.01.2004, p. 423-436.

Research output: Contribution to journalArticle

Suhara, Y, Ono, K, Yoshida, A, Fujishima, T, Saito, N, Honzawa, S, Kishimoto, S, Sugiura, T, Waku, K, Takayama, H & Kittaka, A 2004, 'Synthesis of novel 1α,25-dihydroxy-19-norvitamin D3 with an amide conjugate', Heterocycles, vol. 62, pp. 423-436.
Suhara Y, Ono K, Yoshida A, Fujishima T, Saito N, Honzawa S et al. Synthesis of novel 1α,25-dihydroxy-19-norvitamin D3 with an amide conjugate. Heterocycles. 2004 Jan 1;62:423-436.
Suhara, Yoshitomo ; Ono, Keiichiro ; Yoshida, Akihiro ; Fujishima, Toshie ; Saito, Nozomi ; Honzawa, Shinobu ; Kishimoto, Seishi ; Sugiura, Takayuki ; Waku, Keizo ; Takayama, Hiroaki ; Kittaka, Atsushi. / Synthesis of novel 1α,25-dihydroxy-19-norvitamin D3 with an amide conjugate. In: Heterocycles. 2004 ; Vol. 62. pp. 423-436.
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