Synthesis, computer modeling and biological evaluation of novel protein kinase C agonists based on a 7-membered lactam moiety

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 2, 1999, Pages 173-178

  Endo, Yasuyuki ^a   Shimazu, Masako ^a   Fukasawa, Hiroshi ^a   Driedger, Paul E ^b   Kimura, Kaname ^c   Tomioka, Nobuo ^c   Itai, Akiko ^c   Shudo, Koichi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b Procyon Pharmaceuticals Inc   (United States)

^c Inst of Medicinal Molecular Design   (Japan)

Author keywords

Agonist; Molecular Modeling; Receptors

Indexed keywords

4 HYDROXYMETHYL 5A METHYL 1,3,4,5,5ABETA,6,7,8,9,9AALPHA DECAHYDRO 2H BENZ[D]AZEPIN 2 ONE; LACTAM DERIVATIVE; PHORBOL DIBUTYRATE; PROTEIN KINASE C; PROTEIN KINASE C ACTIVATOR; TRITIUM; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BINDING SITE; HYDROGEN BOND; MOLECULAR MODEL; SIGNAL TRANSDUCTION; SYNTHESIS; TUMOR CELL;

TRITIUM;

EID: 0033579855     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00724-0     Document Type: Article

References (27)

1. Nishizuka Y. Nature 1984; 308: 693-697.
2. Macfarlane DE, Manzel L. J. Biol. Chem. 1994; 269: 4327-4330.
3. Protein Kinase C. Current Concepts and Future Perspectives; Lester DS, Epand RM, Eds., Ellis Horwood: New York, 1992.
4. Castagna M, Takai Y, Kaibuchi K, Sano K, Kikkawa U, Nishizuka Y. J. Biol. Chem. 1982; 257: 7847-7851.
5. Ashendel CL, Staller JM, Boutwell RK. Cancer Res. 1983; 43: 4333-4337.
6. Fujiki H, Mori M.; Nakayasu M, Terada M, Sugimura T, Moore RE. Proc. Natl. Acad. Sci. U.S.A. 1981; 78: 3872-3876.
7. Kawai T, Ichinose T, Endo Y, Shudo K, Itai A. J. Med. Chem. 1992; 25: 2248-2253; Kawai T, Ichinose T, Takeda M, Tomioka N, Endo Y, Yamaguchi K, Shudo K, Itai A. J. Org. Chem. 1992; 57: 6150-6155.
8. Kawai T, Ichinose T, Endo Y, Shudo K, Itai A. J. Med. Chem. 1992; 25: 2248-2253; Kawai T, Ichinose T, Takeda M, Tomioka N, Endo Y, Yamaguchi K, Shudo K, Itai A. J. Org. Chem. 1992; 57: 6150-6155.
9. Endo Y, Shudo K, Itai A, Hasegawa M, Sakai S. Tetrahedron, 1986; 42: 5905-5924.
10. Ohno M, Endo Y, Hirano M, Itai A, Shudo K. Tetrahedron Lett. 1993; 34: 8119-8122; Endo Y, Ohno M, Hirano M, Takeda M, Itai A, Shudo K. Biomed. Chem. Lett. 1994; 4: 491-494.
11. Ohno M, Endo Y, Hirano M, Itai A, Shudo K. Tetrahedron Lett. 1993; 34: 8119-8122; Endo Y, Ohno M, Hirano M, Takeda M, Itai A, Shudo K. Biomed. Chem. Lett. 1994; 4: 491-494.
12. Endo Y, Ohno M, Hirano M, Itai A, Shudo K. J. Am. Chem. Soc. 1996; 118: 1841-1855.
13. Itai A, Matsuo A, Mizutani MY, Tomioka N, Endo Y, Shudo K. Chem. Pharm. Bull., 1997; 45: 573-575.
14. Endo Y, Takehana S, Ohno M, Driedger PE, Stabel S, Mizutani MY, Tomioka N, Itai A, Shudo K. J. Med. Chem. 1998; 41: 1476-1496.
15. Zhang G, Kazanietz MG, Blumberg PM, Hurley JH. Cell 1995; 81: 917-924.
16. Endo Y, Ohno M, Takehana S, Driedger PE, Stabel S, Shudo K. Chem. Pharm. Bull. 1997; 45: 424-426.
17. Endo Y, Hirano M, Driedger PE, Stabel S, Shudo K. Biomed. Chem. Lett. 1997; 3: 2997-3000.
18. Endo Y, Sato Y, Shudo K. Tetrahedron, 1987; 43: 2241-2247; Irie K, Hayashi H, Arai M, Koshimizu K. Agric. Biol. Chem. 1986, 50, 2679-2680; Irie K, Hagiwara N, Tokuda H, Koshimizu K. Carcinogenesis 1987; 8: 547-552.
19. Endo Y, Sato Y, Shudo K. Tetrahedron, 1987; 43: 2241-2247; Irie K, Hayashi H, Arai M, Koshimizu K. Agric. Biol. Chem. 1986, 50, 2679-2680; Irie K, Hagiwara N, Tokuda H, Koshimizu K. Carcinogenesis 1987; 8: 547-552.
20. Endo Y, Sato Y, Shudo K. Tetrahedron, 1987; 43: 2241-2247; Irie K, Hayashi H, Arai M, Koshimizu K. Agric. Biol. Chem. 1986, 50, 2679-2680; Irie K, Hagiwara N, Tokuda H, Koshimizu K. Carcinogenesis 1987; 8: 547-552.
21. Endo Y, Yamaguchi M, Hirano M, Shudo K. Chem. Pharm. Bull. 1996; 44: 1138-1140.
22. Thomson JT, Jackson WS, Haarburger D, Klabunovsky El, Pavlov VA. Aust. J. Chem., 1987; 40: 1083-1106.
23. Oka K, Hara S. J. Am Chem. Soc. 1977; 99:3859-3860
24. Fujiki H, Mori M, Nakayasu M, Terada M, Sugimura T. Biochem. Biophys. Res. Commun. 1979; 90: 976-983; Huberman E, Callaham MF. Proc. Natl. Acad. Sci. U.S.A. 1979; 76: 1293-297; Fujiki H, Suganuma M, Hakii H, Nakayasu M, Endo Y, Shudo K, Irie K, Koshimizu K, Sugimura T. Proc. Japan. Acad. Ser. B. 1985; 61: 45-47.
25. Fujiki H, Mori M, Nakayasu M, Terada M, Sugimura T. Biochem. Biophys. Res. Commun. 1979; 90: 976-983; Huberman E, Callaham MF. Proc. Natl. Acad. Sci. U.S.A. 1979; 76: 1293-1297; Fujiki H, Suganuma M, Hakii H, Nakayasu M, Endo Y, Shudo K, Irie K, Koshimizu K, Sugimura T. Proc. Japan. Acad. Ser. B. 1985; 61: 45-47.
26. Fujiki H, Mori M, Nakayasu M, Terada M, Sugimura T. Biochem. Biophys. Res. Commun. 1979; 90: 976-983; Huberman E, Callaham MF. Proc. Natl. Acad. Sci. U.S.A. 1979; 76: 1293-1297; Fujiki H, Suganuma M, Hakii H, Nakayasu M, Endo Y, Shudo K, Irie K, Koshimizu K, Sugimura T. Proc. Japan. Acad. Ser. B. 1985; 61: 45-47.
27. Driedger PE, Stabel S, Frith D, Horgan TJ. Receptors and Channels 1994; 2: 99-106.