Studies on 5-lipoxygenase inhibitors. II. Discovery, optical resolution and enantioselective synthesis of FR110302, a highly potent non-redox type 5- lipoxygenase inhibitor

Chemical and Pharmaceutical Bulletin

Volumn 46, Issue 10, 1998, Pages 1556-1565

  Yatabe, Takumi ^a   Kayakiri, Hiroshi ^a   Kawai, Yoshio ^a   Oku, Teruo ^a   Tanaka, Hirokazu ^a  

^a ASTELLAS PHARMA INC   (Japan)

Author keywords

(+) 2,2 dibutyl 5 (2 quinolylmethoxy) 1,2,3,4 tetrahydro 1 naphthol; 5 lipoxygenase inhibitor; FR110302; Neutrophil migration; Rat air pouch model; Rat polymorphonuclear leukocyte

Indexed keywords

2,2 DIBUTYL 1,2,3,4 TETRAHYDRO 5 (2 QUINOLYLMETHOXY) 1 NAPHTHOL; ARACHIDONATE 5 LIPOXYGENASE; KETONE; LEUKOTRIENE; LIPOXYGENASE INHIBITOR;

ARTICLE; CELL MIGRATION; DRUG INHIBITION; DRUG SYNTHESIS; ENANTIOMER; ENZYME ACTIVITY; ENZYME CONFORMATION; RACEMIC MIXTURE;

EID: 0031772324     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.46.1556     Document Type: Article

References (22)

1. Brooks C. D. W, Summers J. B., J. Med. Chem., 39, 2629-2654 (1996).
2. Yatabe T., Kawai Y., Oku T., Tanaka H., Chem. Pharm. Bull., 46, 966-972 (1998).
3. Smith III A. B., Lupo Jr. A. T., Ohba M., Chen K., J. Am. Chem. Soc., 111, 6648-6656 (1989).
4. Itsuno S., Nakano M., Miyazaki K., Masuda H., Ito K., Hirao A., Nakahama S., J. Chem. Soc., Perkin Trans. 1, 1985, 2039-2044.
5. Itsuno S., Ito K., Hirao A., Nakahama S., J. Chem. Soc., Chem. Commun., 1983, 469-470.
6. Sato T., Goto Y., Fujisawa T., Tetrahedron Lett., 23, 4111-4112 (1982).
7. Benoiton L., Can. J. Chem., 40, 570-572 (1962).
8. Vanderhoek J. Y., Bryant R. W., Bailey J. M., J, Biol. Chem., 255, 5996-5998 (1980).
9. Vanderhoek J. Y., Bryant R. W., Bailey J. M., J, Biol. Chem., 255, 10064-10066 (1980); idem, Biochem. Pharmacol., 31, 3463-3467 (1982).
10. Vanderhoek J. Y., Bryant R. W., Bailey J. M., J, Biol. Chem., 255, 10064-10066 (1980); idem, Biochem. Pharmacol., 31, 3463-3467 (1982).
11. Sok D. E., Han C. Q., Shieh W. R., Zhou B. N., Sih C. J., Biochem. Biophys. Res. Commun., 104, 1363-1370 (1982).
12. Sok D. E., Han C. Q., Shieh W. R., Zhou B. N., Sih C. J., Biochem. Biophys. Res. Commun., 107, 101-108 (1982).
13. a) Musser J. H., Chakraborty U. R., Sciortino S., Gordon R. J., Khandwala A., Neiss E. S., Pruss T. P., Van Inwegen R., Weinryb I., Coutts S. M., J. Med. Chem., 30, 96-104 (1987);
14. b) Huang F., Drugs of the Future, 16, 1121-1127 (1991).
15. McMillan R. M., Walker E. R. H., TiPS, 13, 323-330 (1992).
16. Proudman K. E., Moores S. M., McMillan R. M., Br. J. Pharmacol., 102, 364P (1991).
17. Asano M., Inamura N., Nakahara K., Nagayoshi A., Isono T., Hamada K., Oku T., Notsu Y., Kohsaka M. Ono, T., Agents and Actions, 36, 215-221 (1992).
18. Hagihara H., Nomoto A., Mutoh S., Yamaguchi I., Ono T., Atherosclerosis, 91, 107-116 (1991).
19. a) Genzer D. J., Conrad A. G., Ger. Patent, 2219116 (1972) [Chem. Abstr., 78, 43137c (1973)];
20. a) Genzer D. J., Conrad A. G., Ger. Patent, 2219116 (1972) [Chem. Abstr., 78, 43137c (1973)];
21. b) Owton W. M., J. Chem. Soc., Perkin Trans. 1, 1994, 2131-2135;
22. c) Sanchez I. H., Mendoza M. T., Aguilar M. A., Martell E, A., Gonzalez M. E., Lemini C., Chem. Lett., 1980, 1501-1502 .