Synthesis and structure-activity relationship studies on a novel series of naphthylidinoylureas as inhibitors of acyl-CoA:cholesterol O-acyltransferase (ACAT)

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 5, 2004, Pages 1309-1311

  Ohnuma, Satoshi ^a   Muraoka, Masami ^a   Ioriya, Katsuhisa ^a   Ohashi, Naohito ^a  

^a DAINIPPON SUMITOMO PHARMA CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHOLESTEROL; CHOLESTEROL ACYLTRANSFERASE INHIBITOR; SM 32504; UNCLASSIFIED DRUG; UREA DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; ATHEROGENIC DIET; CHOLESTEROL BLOOD LEVEL; CHOLESTEROL DIET; CONTROLLED STUDY; DRUG INHIBITION; DRUG POTENCY; DRUG SYNTHESIS; IC 50; NONHUMAN; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

EID: 1242293871     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2003.12.045     Document Type: Article

References (35)

1. Suckling K.E., Stange E.F. J. Lipid Res. 26:1985;647.
2. Field F.J., Salome R.G. Biochim. Biophys. Acta. 712:1982;557.
3. Heider J.G., Pickens C.E., Kelly L.A. J. Lipid Res. 24:1983;1127.
4. Drevon C.A., Engelhorn S.C., Steinberg D. J. Lipid Res. 21:1980;1065.
5. Khan B., Wilcox H.G., Heimberg M. Biochem. J. 258:1989;807.
6. Cianflone K.M., Yasruel Z., Rodriguez M.A., Sniderman A.D. J. Lipid Res. 31:1990;2045.
7. Sliskovic D.R., White A.D. Trends Pharmacol. Sci. 12:1991;194.
8. Rodriguez A., User D.C. Atherosclerosis. 161:2002;45.
9. Hirakawa Y., Shimokawa H. Folia Pharamacaol. Jpn. 118:2001;389.
10. Matsuda K. Med. Res. Rev. 14:1994;271.
11. McCarthy P.A. Med. Res. Rev. 13:1993;139.
12. For examples of fatty acid anilides, see: Roth B.D., Stanfield R.L. J. Med. Chem. 35:1992;1609.
13. McCathy P.A. J. Med. Chem. 37:1994;1252.
14. Kataoka K., Yamaguchi H. J. Med. Chem. 38:1995;3174.
15. Matsuyama N. Bioorg. Med. Chem. Lett. 9:1999;2039.
16. Krause B.R. J. Lipid Res. 34:1993;279.
17. Murakami S. Cell. Mol. Biol. 42:1996;865.
18. Kataoka K., Yamaguchi H. J. Med. Chem. 39:1996;1262.
19. For examples of phenylureas, see: Meguro K., Tawada H. J. Med. Chem. 37:1994;2079.
20. Tawada H., Meguro K. Chem. Pharm. Bull. 43:1995;616.
21. Higley C.A., Wexler R.R. J. Med. Chem. 37:1994;3511.
22. J. Lipid Res. 30:1989;681.
23. Sekiya T., Umezu K. Chem. Pharm. Bull. 42:1994;586.
24. O'Brien P.M., Stanfield R.L. J. Med. Chem. 37:1994;1810.
25. Trivedi B.K., Krause B.R. J. Med. Chem. 37:1994;1652.
26. Kimura T., Yamatsu I. J. Med. Chem. 36:1993;1641.
27. Tanaka A., Tanaka H. Bioorg. Med. Chem. 6:1998;15.
28. Estel L., Linard F., Marsais F., Godard A., Queguiner G. J. Heterocyclic Chem. 26:1989;105.
29. Bell S.C., Sulkowsky T.S., Gochman C., Childness S.J. J. Org. Chem. 27:1962;562.
30. Ninomiya K., Shioiri T., Yamada S. Tetrahedron. 30:1974;2151.
31. Heider J.G., Pickens C.E., Kelly L.A. J. Lipid Res. 22:1983;271.
32. Miyazaki A., Horiuchi S. Biochim. Biophys. Acta. 1126:1992;73.
33. Yamashita S. Eur. J. Pharm. Sci. 10:2000;195. The apparent permeability coefficient, Papp value for 2-methoxy isomer 3p was 15(nm/s) compared to 29(nm/s) for 3m.
34. +).
35. Ioriya K., Noguchi T., Muraoka M., Fujita K., Shimizu H., Ohashi N. Pharmacology. 65:2002;18.