Inhibitors of acyl-CoA:cholesterol O-acetyltransferase (ACAT). Part 1: Identification and structure-activity relationships of a novel series of substituted N-alkyl-N-biphenylmethyl-N'-arylureas

Bioorganic and Medicinal Chemistry

Volumn 6, Issue 1, 1998, Pages 15-30

  Tanaka, Akira ^a   Terasawa, Takeshi ^a   Hagihara, Hiroyuki ^a   Sakuma, Yuri ^a   Ishibe, Noriko ^a   Sawada, Masae ^a   Takasugi, Hisashi ^a   Tanaka, Hirokazu ^a  

^a ASTELLAS PHARMA INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BIPHENYLMETHYLUREA DERIVATIVE; CHOLESTEROL ACYLTRANSFERASE; CHOLESTEROL ACYLTRANSFERASE INHIBITOR; FR 179254; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CHOLESTEROL BLOOD LEVEL; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; ENZYME ACTIVITY; HYPERCHOLESTEROLEMIA; INTESTINE EPITHELIUM; MALE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RABBIT; RAT; STRUCTURE ACTIVITY RELATION;

ANILIDES; ANIMALS; BIOLOGICAL AVAILABILITY; BIPHENYL COMPOUNDS; CHOLESTEROL; CHOLESTEROL, DIETARY; ENZYME INHIBITORS; INTESTINAL MUCOSA; MALE; METHYLUREA COMPOUNDS; MICROSOMES; PHENYLUREA COMPOUNDS; PYRIDINES; RABBITS; RATS; RATS, SPRAGUE-DAWLEY; STEROL O-ACYLTRANSFERASE; STRUCTURE-ACTIVITY RELATIONSHIP;

ANIMALIA; ORYCTOLAGUS CUNICULUS;

EID: 0031976074     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(97)10009-8     Document Type: Article

References (55)

1. [1] (a) Martin MJ, Hulley SB, Browner WS, Kuller LH, Wentworth D. Lancet 1986;2:933.
2. (b) Badimon JJ, Fuster V, Chesebro JH, Badimon L. Circulation 1993;87 Suppl II:3.
3. [2] (a) The Lipid Research Clinics Program. J Am Med Assoc 1984;251:351 and 365.
4. (b) Brown G, Albers JJ, Fisher LD, Schaefer SM, Lin J-T, Kaplan C, Zhao X-Q, Bisson BD, Fitzpatrick VF, Dodge HT. N Engl J Med 1990;323:1289.
5. (c) Brown WV. Eur Heart J 1990;11 Suppl H:15.
6. [3] (a) Spector AA, Mathur SN, Kaduce TL. Prog Lipid Res. 1979;18:31.
7. (b) Suckling KE, Stange, EF. J Lipid Res 1985;26:647.
8. [4] (a) Krause BR, Anderson, M, Bisgaier, CL, Bocan T, Bousley R, DeHart P, Essenburg A, Hamelehle K, Homan R, Kieft K, McNally W, Stanfield R, Newton RS. J Lipid Res 1993;34:279.
9. (b) Largis EE, Wang CH, DeVries VG, Schaffer SA. J Lipid Res 1989;30:681.
10. (c) Carr TP, Rudel LL. Arteriosclerosis 1990;10:823a.
11. (d) Carr TP, Parks JS, Rudel LL. Arterioscler Thromb 1992;12:1274.
12. (e) Burrier RE, Deren S, McGregor DG, Hoos LM, Smith AA, Davis HR Jr. Biochem Pharmacol 1994;47:1545.
13. [5] (a) Brown MS, Goldstein JL. Ann Rev Biochem 1983;52:223.
14. (b) Gillies PJ, Robinson CS, Rathgeb KA. Atherosclerosis 1990;83:177.
15. [6] Sliskovic DR, White AD. Trends Pharmacol Sci 1991;12: 194.
16. [7] (a) Picard JA. Curr Opin Ther Patents 1993;3:151.
17. (b) Matsuda K. Med Res Rev 1994;14:271.
18. (c) Sliskovic DR, Trivedi BK. Curr Med Chem 1994;1:204.
19. [8] (a) Roth BD, Blankley CJ, Hoefle ML, Holmes A, Roark WH, Trivedi BK, Essenburg AD, Kieft KA, Krause BR, Stanfield RL. J Med Chem 1992;35:1609.
20. (b) Field FJ, Albright E, Mathur S. Lipids 1991;26:1.
21. [9] DeVries VG, Schaffer SA, Largis EE, Dutia MD, Wang C-H, Bloom JD, Katocs AS Jr. J Med Chem 1986;29: 1131.
22. [10] (a) Roark WH, Roth BD. Exp Opin Invest Drugs 1994;3:1143.
23. (b) Lee HT, Picard JA. Exp Opin Ther Patents 1995;5:397 and references cited therein.
24. [11] Roomi MW, MacDonald SF. Can J Chem 1970;48:139.
25. [12] (a) Sivasubramanian S, Ravichandran K. Indian J Chem 1991;30B:1148.
26. (b) Sindelar K, Kmonicek V, Hrubantova M, Polivka Z. Collect Czech Chem Commun 1992;57:194.
27. [13] Marck G, Villiger A, Buchecker R. Tetrahedron Lett 1994;35:3277.
28. [14] Link PAJ, van der Plas HC, Müller, F. J. Heterocyclic Chem 1985;22:873.
29. [15] Dhal PK. Macromol Rep 1992;A29 Suppl 1:39.
30. [16] (a) Laarhoven WH, Veldhuis RGM. Tetrahedron 1972;28: 1811.
31. (b) Hatanaka Y, Hiyama T. Tetrahedron Lett 1990; 31:2719.
32. [17] (a) Shieh W-C, Carlson JA. J Org Chem 1992;57:379.
33. (b) Koch K-H, Müllen K. Chem Ber 1991;124:2091.
34. (c) Siddiqui MA, Snieckus V. Tetrahedron Lett 1988;29:5463 and references cited therein.
35. [18] Chou P-T, Chang C-P, Clements JH, Meng-Shin K. J Fluoresc 1995;5:369.
36. [19] Michaelis A. Ann 1901;315:19.
37. [20] Yeager GW, Schissel DN. Synthesis 1991;63.
38. [21] Grovenstein E Jr, Wentworth G. J Am Chem Soc 1967;89:2348.
39. [22] McCarthy PA, Hamanaka ES, Marzetta CA, Bamberger MJ, Gaynor BJ, Chang G, Kelly SE, Inskeep PB, Mayne JT, Beyer TA, Walker FJ, Goldberg DI, Savoy YE, Davis KM, Diaz CL, Freeman AM, Johnson DA, LaCour TG, Long CA, Maloney ME, Martingano RJ, Pettini JL, Sand TM, Wint LT. J Med Chem 1994;37:1252.
40. [23] Heider JG, Pickens CE, Kelly LA. J Lipid Res 1983; 24:1127.
41. [24] Sakurna Y, Hagihara H, Ohne K, Nagayoshi A, Mutoh S, Ito Y, Notsu Y, Okuhara M. Jpn. J Pharmacol 1996;70:35.
42. [25] (a) Roark WH, Roth BD, Holmes A, Trivedi BK, Kieft KA, Essenburg AD, Krause BR, Stanfield RL. J Med Chem 1993;36:1662.
43. (b) Trivedi BK, Holmes A, Stoeber TL, Blankley CJ, Roark WH, Picard JA, Shaw MK, Essenburg AD, Stanfield RL, Krause BR. J Med Chem 1993;36:3300.
44. (c) Trivedi BK, Purchase TS, Holmes A, Augelli-Szafran CE, Essenburg AD, Hamelehle KL, Stanfield RL, Bousley RF, Krause BR. J. Med. Chem. 1994;37:1652.
45. (d) Trivedi BK, Holmes A, Purchase TS, Essenburg AD, Hamelehle KL, Krause BR, Shaw Hes MK, Stanfield RL. Bioorg Med Chem Lett 1995;5:2229.
46. (e) Sekiya T, Inoue S, Shirasaka T, Miyajima C, Okushima H, Suzuki K, Kawai M, Mitsuka M, Umezu K. Chem Pharm Bull 1994;42:586.
47. (f) White AD, Creswell MW, Chucholowski AW, Blankley CJ, Wilson MW, Bousley RF, Essenburg AD, Hamelehle KL, Krause BR, Stanfield RL, Dominick MA, Neub M. J Med Chem 1996;39:4382.
48. [26] (a) Veldhuis JD, Strauss III JF, Silavin SL, Kolp LA, Klase PA, Juchter D, Garmey J. Endocrinology 1985; 116:25.
49. (b) Sugiyama Y, Ishikawa E, Odaka H, Miki N, Tawada H, Ikeda H. Atherosclerosis 1995;113:71.
50. (c) Chiari A, Lovisolo PP, Radice A, Giorgini L, Fancelli D, Severino D, Ghiselli G. Pharmacol Res 1995;32:189.
51. (d) Bello AA, Bright C, Burton BJ, Bush RC, Casey JH, Dron DI, Facchini V, Joannou PP, Parrott DP, Riddell D, Roberts SA, Williams RJ. Biochem Pharmacol 1996;51: 413.
52. [27] Kataoka K-i, Shiota T, Takeyasu T, Minoshima T, Watanabe K, Tanaka H, Mochizuki T, Taneda K, Ota M, Tanabe H, Yamaguchi H. J Med Chem 1996;39:1262.
53. [28] Inskeep PB, Davis KM, Reed AE. J Pharm Sci 1995; 84:131.
54. [29] Marzetta CA, Savoy YE, Freeman AM, Long CA, Pettini JL, Hagar RE, Inskeep PB, Davis K, Stucchi AF, Nicolosi RJ, Hamanaka ES. J Lipid Res 1994;35:1829.
55. [30] O'Brien PM, Sliskovic DR, Anderson MK, Bousley RF, Krause BR, Stanfield RL. Bioorg Med Chem Lett 1995; 5:289.