Syntheses and preventive effects of analogues related to 1α,25-dihydroxy-2β-(3-hydroxypropoxy)vitamin D3 (ED-71) on bone mineral loss in ovariectomized rats

Bioorganic and Medicinal Chemistry

Volumn 6, Issue 12, 1998, Pages 2517-2523

  Ono, Yoshiyuki ^a   Kawase, Akira ^a   Watanabe, Hiroyoshi ^a   Shiraishi, Ayako ^a   Takeda, Satoshi ^a   Higuchi, Yoshinobu ^a   Sato, Katsuhiko ^a   Yamauchi, Tsuyoshi ^a   Mikami, Tetsuhiro ^a   Kato, Masahiro ^a   Tsugawa, Naoko ^b   Okano, Toshio ^b   Kubodera, Noboru ^a  

^a CHUGAI PHARMACEUTICAL CO LTD   (Japan)

^b KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

26,27 DIMETHYL 2BETA (3 HYDROXYPROPOXY) 1ALPHA,3BETA,25 TRIHYDROXY 9,10 SECOCHOLESTA 5,7,10(19) TRIENE; 2BETA (3 HYDROXYPROPOXY)CALCITRIOL; CALCITRIOL DERIVATIVE; UNCLASSIFIED DRUG; VITAMIN D BINDING PROTEIN;

ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BONE MINERAL; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; FEMALE; IN VITRO STUDY; INFRARED RADIATION; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORAL DRUG ADMINISTRATION; OSTEOPOROSIS; OVARIECTOMY; RAT; REACTION ANALYSIS;

EID: 13044293395     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(98)80025-4     Document Type: Article

References (14)

1. This forms part 25 of 'Synthetic Studies of Vitamin D Analogues.' Part 24; Hatakeyama, S.; Ikeda, T.; Maeyama, J.; Esumi, T.; Iwabuchi, Y.; Irie, H.; Kawase, A.; Kubodera, N. Bioorg. Med. Chem. Lett. 1997, 7, 2871.
2. Bouillon, R.; Okamura, W. H.; Norman, A. W. Endocrine Rev. 1995, 16, 200.
3. Miyamoto, K.; Murayama, E.; Ochi, K.; Watanabe, H.; Kubodera, N. Chem. Pharm. Bull. 1993, 43, 1111.
4. Okano, T.; Tsugawa, N.; Masuda, S.; Takeuchi, A.; Kobayashi, T.; Takita, Y.; Nishii, Y. Biochem. Biophys. Res. Commun. 1989, 163, 1444.
5. Kobayashi, T.; Okano, T.; Tsugawa, N.; Murano, M.; Masuda, S.; Takeuchi, A.; Sato, K.; Nishii, Y. Bioorg. Med. Chem. Lett. 1993, 3, 1815.
6. Ono, Y.; Watanabe, H.; Shiraishi, A.; Takeda, S.; Higuchi, Y.; Sato, K.; Tsugawa, N.; Okano, T.; Kobayashi, T.; Kubodera, N. Chem. Pharm. Bull. 1997, 45, 1626.
7. Kubodera, N.; Watanabe, H.; Kawanishi, T.; Matsumoto, M. Chem. Pharm. Bull. 1992, 40, 1494.
8. cf. Ochi, K.; Matsunaga, I.; Shindo, M.; Kaneko, C. J. Chem. Soc. Perkin I, 1979, 161.
9. Ochi, K.; Matsunaga, I.; Nagano, H.; Fukushima, M.; Shindo, M.; Kaneko, C.; Ishikawa, M.; DeLuca, H. F. J. Chem. Soc. Perkin I, 1979, 165.
10. When the reaction is carried out without protection of the 3β-hydroxy part, the epoxidation takes place at the opposite side (β-side) predominantly due to the participation of the 3β-hydroxy substituent (see Ref. 9). In a protected situation such as in TBS ether, however, the epoxide is formed at the less congested α-side than the β-side.
11. Kubodera, N.; Miyamoto, K.; Watanabe, H.; Kato, M.; Sasahara, K.; Ochi, K. J. Org. Chem. 1992, 57, 5019.
12. Mikami, T.; Iwaoka, T.; Kato, M.; Watanabe, H.; Kubodera, N. Syn. Commun. 1997, 27, 2363.
13. Revelle, L. K.; Londowski, J. M.; Bollman K. S.; Corradino, R. A.; Kumar, R. J. Steroid Biochem. 1985, 22, 469.
14. Revelle, L. K.; Solan, V.; Londowski, J. M.; Bollman, K. S.; Kumar, R. Biochemistry 1984, 23, 1983.