Design and synthesis of novel 1,25-dihydroxyvitamin D3 analogues having a spiro-oxetane fused at the C2 position in the A-ring
| Autor: | Toshie Fujishima, Takato Nozaki, Tsutomu Suenaga |
|---|---|
| Rok vydání: | 2013 |
| Předmět: |
Stereochemistry
medicine.medical_treatment Clinical Biochemistry Pharmaceutical Science Oxetane Ring (chemistry) Biochemistry Calcitriol receptor Pentaerythritol Steroid chemistry.chemical_compound Structure-Activity Relationship Ethers Cyclic Drug Discovery medicine Vitamin D and neurology Moiety Animals Spiro Compounds Vitamin D Molecular Biology Enyne Chemistry Organic Chemistry Drug Design Molecular Medicine Receptors Calcitriol Cattle Protein Binding |
| Zdroj: | Bioorganicmedicinal chemistry. 21(17) |
| ISSN: | 1464-3391 |
| Popis: | Four structurally novel stereoisomeric analogues of 1,25-dihydroxyvitamin D3 (3a-d) bearing a spiro-oxetane fused at the C2 position of the A-ring have been designed and synthesised in a convergent manner. The requisite A-ring enyne precursors (13a,b) for the vitamin D analogues (3a,b) and (3c,d), respectively, were synthesised from pentaerythritol according to an eleven-step procedure. Preliminary biological evaluation of the analogues using the bovine thymus vitamin D receptor (VDR) suggested that the incorporation of the spiro-oxetane moiety instead of a gem-dimethyl group at the C2 position had a beneficial effect on the VDR affinity. |
| Databáze: | OpenAIRE |
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