Abstract
The design and synthesis of new 1α,25-dihydroxy-19-norvitamin D3 analogues 3a-c, which have an amide bond in the molecule instead of the diene, are described. The A-ring moiety was constructed by a (3S,5S)-3,5-dihydroxypiperidine derivative (9, 11, or 13) prepared from D-mannose, and a CD-ring carboxylic acid 16 was synthesized from Grundmann's ketone. Coupling those parts gave desired 3a-c in good yield. This strategy can be applied in combinatorial chemistry; therefore, those compounds would be applicable as useful tools in the development of new drugs.
| Original language | English |
|---|---|
| Pages (from-to) | 3533-3536 |
| Number of pages | 4 |
| Journal | Bioorganic and Medicinal Chemistry Letters |
| Volume | 12 |
| Issue number | 24 |
| DOIs | |
| Publication status | Published - 2002 Dec |
| Externally published | Yes |
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ASJC Scopus subject areas
- Biochemistry
- Molecular Biology
- Organic Chemistry
- Drug Discovery
- Pharmaceutical Science
Cite this
Design and efficient synthesis of new stable 1α,25-dihydroxy-19-norvitamin D3 analogues containing amide bond. / Suhara, Yoshitomo; Kittaka, Atsushi; Ono, Keiichiro; Kurihara, Masaaki; Fujishima, Toshie; Yoshida, Akihiro; Takayama, Hiroaki.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 12, No. 24, 12.2002, p. 3533-3536.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Design and efficient synthesis of new stable 1α,25-dihydroxy-19-norvitamin D3 analogues containing amide bond
AU - Suhara, Yoshitomo
AU - Kittaka, Atsushi
AU - Ono, Keiichiro
AU - Kurihara, Masaaki
AU - Fujishima, Toshie
AU - Yoshida, Akihiro
AU - Takayama, Hiroaki
PY - 2002/12
Y1 - 2002/12
N2 - The design and synthesis of new 1α,25-dihydroxy-19-norvitamin D3 analogues 3a-c, which have an amide bond in the molecule instead of the diene, are described. The A-ring moiety was constructed by a (3S,5S)-3,5-dihydroxypiperidine derivative (9, 11, or 13) prepared from D-mannose, and a CD-ring carboxylic acid 16 was synthesized from Grundmann's ketone. Coupling those parts gave desired 3a-c in good yield. This strategy can be applied in combinatorial chemistry; therefore, those compounds would be applicable as useful tools in the development of new drugs.
AB - The design and synthesis of new 1α,25-dihydroxy-19-norvitamin D3 analogues 3a-c, which have an amide bond in the molecule instead of the diene, are described. The A-ring moiety was constructed by a (3S,5S)-3,5-dihydroxypiperidine derivative (9, 11, or 13) prepared from D-mannose, and a CD-ring carboxylic acid 16 was synthesized from Grundmann's ketone. Coupling those parts gave desired 3a-c in good yield. This strategy can be applied in combinatorial chemistry; therefore, those compounds would be applicable as useful tools in the development of new drugs.
UR - http://www.scopus.com/inward/record.url?scp=0036889635&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0036889635&partnerID=8YFLogxK
U2 - 10.1016/S0960-894X(02)00800-4
DO - 10.1016/S0960-894X(02)00800-4
M3 - Article
VL - 12
SP - 3533
EP - 3536
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
SN - 0960-894X
IS - 24
ER -