Synthetic studies of vitamin D analogs. XXII. Synthesis and antiproliferation activity of putative metabolites of 1α,25-dihydroxy-22-oxavitamin D3

Chemical and Pharmaceutical Bulletin

Volumn 44, Issue 12, 1996, Pages 2280-2286

  Watanabe, Hiroyoshi ^a   Hatakeyama, Susumi ^b,d   Tazumi, Kazuki ^b   Takano, Seiichi ^b   Masuda, Sonoko ^c   Okano, Toshio ^c   Kobayashi, Tadashi ^c   Kubodera, Noboru ^a  

^a CHUGAI PHARMACEUTICAL CO LTD   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

^c KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

^d NAGASAKI UNIVERSITY   (Japan)

Author keywords

1 ,25 dihydroxy 22 oxavitamin D3; 1 ,25 dihydroxyvitamin D3; Antiproliferation activity; Metabolite; OCT; Vitamin D3 analog

Indexed keywords

22 OXACALCITRIOL; 24 HYDROXY 22 OXACALCITRIOL; 24 OXO 22 OXACALCITRIOL; 26 HYDROXY 22 OXACALCITRIOL; CALCITRIOL DERIVATIVE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER INHIBITION; CELL PROLIFERATION; DRUG CONFORMATION; DRUG POTENCY; DRUG SYNTHESIS; GROWTH INHIBITION; HUMAN; HUMAN CELL; PROMYELOCYTIC LEUKEMIA; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; CALCITRIOL; CATTLE; CELL DIVISION; HUMANS; RECEPTORS, CALCITRIOL;

EID: 0030473697     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.44.2280     Document Type: Article

References (25)

1. Part XXI: Kawase A., Hirata M., Endo K., Kubodera N., BioMed. Chem. Lett., 5, 279-282 (1995).
2. A part of this work has appeared as a preliminary communication. Kubodera N., Watanabe H., Hatakeyama S., Tazumi K., Takano S., BioMed. Chem. Lett., 4, 753-756 (1994).
3. Murayama E., Miyamoto K., Kubodera N., Mori T., Matsunaga I., Chem. Pharm. Bull., 34, 4410-4413 (1986).
4. Kubodera N., Watanabe H., Kawanishi T., Matsumoto M., Chem. Pharm. Bull., 40, 1494-1499 (1992).
5. Abe J., Morikawa M., Miyamoto K., Kaiho S., Fukushima M., Miyaura C., Abe E., Suda T., Nishii Y., FEBS Lett., 226, 58-62 (1987).
6. Brown A. J., Ritter C. R., Finch J. L., Morrissey J., Martin K. J., Murayama E., Nishii Y., Slatopolsky E., J. Clin. Invest., 84, 728-732 (1989).
7. Morimoto S., Imanaka S., Koh E., Shiraishi T., Nabata T., Kitano S., Miyashita Y., Nishii Y., Ogihara T., Biochem. Int., 19, 1143-1149 (1989).
8. Takasaki Y., Suda T., Yamada S., Takayama H., Nishii Y., Biochemistry, 20, 1681-1686 (1981).
9. Yamada S., Ohmori M., Takayama, H., Takasaki Y., Suda T., J. Biol. Chem., 258, 457-463 (1983).
10. Mayer E., Reddy G. S., Chandraratna R. A. S., Okamura W. H., Kruse J. R., Popjak G., Bishop J. E., Norman A. W., Biochemistry, 22, 1798-1805 (1983).
11. Ikekawa N., Fujimoto Y., Yuki Gosei Kagaku Kyokai Shi, 46, 455-466 (1988).
12. Ikekawa N., Med. Chem. Rev., 7, 333-366 (1987).
13. Takayama H., Ohmori M., Yamada S., Tetrahedron Lett., 21, 5027-5028 (1980).
14. Yamada S., Ohmori M., Takayama H., Suda T., Takasaki Y., Chem. Pharm. Bull., 29, 1187-1188 (1981).
15. Yamada S., Ohmori M., Takayama H., Nishii Y., J. Biol. Chem., 257, 3732-3738 (1982).
16. Dumont R., Pfander H., Helv. Chim. Acta, 66, 814-823 (1983) and references cited therein.
17. Payne G. B., J. Org. Chem., 27, 3819-3822 (1962).
18. Kubodera N., Miyamoto K., Watanabe H., Kato M., Sasahara K., Ochi K., J. Org. Chem., 57, 5019-5020 (1992).
19. Katsuki T., Sharpless K. B., J. Am. Chem. Soc., 102, 5974-5976 (1980).
20. Koizumi N., Ishiguro M., Yasuda M., Ikekawa N., J. Chem. Soc., Perkin Trans. 1, 1983, 1401-1410.
21. Kubodera N., Watanabe H., Miyamoto K., Matsumoto M., Matsuoka S., Kawanishi T., Chem. Pharm. Bull., 41, 1659-1663 (1993).
22. Murayama E., Miyamoto K., Ochi K., Kubodera N., BioMed. Chem. Lett., 2, 1289-1292 (1992).
23. Miyaura C., Abe E., Kuribayashi H., Tanaka H., Kanno K., Nishii Y., Suda T., Biochem. Biophys. Res. Commun., 102, 937-943 (1981).
24. Brown A. J., Berkoben M., Ritter C., Kubodera N., Nishii Y., Slatopolsky E., Biochem. Biophys. Res. Commun., 189, 759-764 (1992).
25. Masuda S., Byford V., Kremer R., Makin H. L. J., Kubodera N., Nishii Y., Okazaki A., Okano T., Kobayashi T., Jones G., J. Biol. Chem., 271, 8700-8708 (1996).