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

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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

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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    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, 62, 423-436.