Synthetic studies of vitamin D analogs. XXIV. Synthesis of active vitamin D3 analogs substituted at the 2 beta-position and their preventive effects on bone mineral loss in ovariectomized rats.

Abstract

Analogs related to 1 alpha,25-dihydroxy-2 beta-(3-hydroxypropoxy)vitamin D3 (ED-71) (4), oxa-type and carba-type analogs of vitamin D3 bearing substituents at the 2 beta-position of 1 alpha,25-dihydroxyvitamin D3 (1), were synthesized from the alpha-epoxides (6 and 13). Three analogs, ED-71 (4) and two carba-type analogs (16 and 26), showed potent preventive effects on bone mineral loss in pre-osteoporosis model rats. ED-71 (4) was concluded to be an optimized analog and a promising candidate for the treatment of osteoporosis.

• Authors: Y Ono, H Watanabe, A Shiraishi, S Takeda, Y Higuchi, K Sato, N Tsugawa, T Okano, T Kobayashi, N Kubodera
• Journal: Chemical & pharmaceutical bulletin (Chem Pharm Bull (Tokyo)) Vol. 45 Issue 10 Pg. 1626-30 (Oct 1997) ISSN: 0009-2363 [Print] Japan
• PMID: 9353890 (Publication Type: Journal Article)

Chemical References

• Receptors, Calcitriol
• Vitamin D
• Cholecalciferol
• Calcitriol
• eldecalcitol

Topics

• Absorptiometry, Photon
• Animals
• Bone Density (drug effects)
• Calcitriol (analogs & derivatives, chemistry, pharmacology)
• Cholecalciferol (analogs & derivatives, pharmacology)
• Disease Models, Animal
• Drug Design
• Female
• Humans
• Osteoporosis, Postmenopausal (prevention & control)
• Ovariectomy
• Rats
• Rats, Wistar
• Receptors, Calcitriol (drug effects, metabolism)
• Vitamin D (analogs & derivatives)