ACAT inhibitors derived from hetero-Diels-Alder cycloadducts of thioaldehydes

Bioorganic and Medicinal Chemistry

Volumn 4, Issue 9, 1996, Pages 1493-1513

  Wilde, Richard G ^a   Billheimer, Jeffrey T ^a   Germain, Sandie J ^a   Hausner, Elizabeth A ^a   Meunier, Paul C ^a   Munzer, Deborah A ^a   Stoltenborg, Janet K ^a   Gillies, Peter J ^a   Burcham, Deborah L ^a   Huang, Shiew Mai ^a   Klaczkiewicz, John D ^a   Ko, Soo S ^a   Wexler, Ruth R ^a  

^a DUPONT COMPANY   (United States)

Author keywords

Acyl CoA:cholesterol; Acyltransferase; Atherosclerosis; Cycloaddition; thioaldehyde

Indexed keywords

CHOLESTEROL ACYLTRANSFERASE INHIBITOR; THIOPYRAN DERIVATIVE;

ADRENAL GLAND; ANIMAL EXPERIMENT; ARTICLE; BIOAVAILABILITY; CONTROLLED STUDY; DRUG BLOOD LEVEL; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TOXICITY; ENZYME INHIBITION; HUMAN; HUMAN CELL; HUMAN TISSUE; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; LIPID METABOLISM; LIVER; MACROPHAGE; MALE; MASS SPECTROMETRY; NORMAL HUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORAL DRUG ADMINISTRATION; RABBIT; RAT; STEREOCHEMISTRY;

EID: 16044368449     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/0968-0896(96)00143-5     Document Type: Article

References (48)

1. (a) Suckling, K. E.; Stange, E. F. J. Lipid Res. 1985. 26. 647
2. (b) Billheimer, J. T.; Gillies, P. J. Advances in Cholesterol Research; Esfahem, M.; Swaney, J. B., Eds.; Telford, New Jersey: 1990; pp 1-45.
3. Meittinen, T. A.; Kesaniem, Y, A, Am. J. Clin. Nutr. 1989. 49. 629.
4. (a) Huff, M. W.; Telford, D. E.; Barrett, P. H. R.; Billheimer, J. T.; Gillies, P. J. Arterioscler. Thromb. 1994, 14, 1498
5. (b) Carr, T. P.; Rudel, L. L, Arteriosclerosis 1990, 10, 823a.
6. Gillies, P. J.; Robinson, C. S., Rathgeb, K. A. Arterioscler. 1990, 83, 177.
7. Bocan, T. M. A.; BakMueller, S.; Uhlendorf, P. D.; Newton, R. S.; Krause, B. R. Artenoscler. Thromb. 1991. 11, 1830.
8. (a) Heider, J. G. Pharmacological Control of Hyperlipidaemia; J. R. Prous Science: Barcelona, 1986; pp 423-438
9. (b) Sliskovic, D. R.; White, A. D. Trends Pharm. Sci. 1991. 12, 194
10. (c) Billheimer, J, T.; Wilde, R. G. Curr. Drugs 1991, B5.
11. Presented in part at the 210th American Chemical Society meeting, Chicago 1995; Abstr. MEDI-066.
12. McCarthy, P. A.; Hamanaka, E. S.; Marzetta, C. A.; Bamberger, M. J.; Gaynor, B. J.; Chang, G.; Kelly, S. E.; Inskeep, P. B.; Mayne, J. T.; Beyer, T. A.; Walker, F. J.; Goldberg, D. I.; Savoy, Y. E.; Davis, K. M.; Diaz, C. L.; Freeman, A. M.; Johnson, D. A.; LaCour, T. G.; Long, C. A.; Maloney, M. E.; Martingano, R. J.; Pettini, J. L.; Sand, T. M.; Wint, L. T. J. Med. Chem. 1994, 37, 1252.
13. Ashlon, M. J.; Bridge, A. W.; Bush, R. C.; Dron, D. I.; Harris, N. V.; Jones, G. D.; Lythgoe, D. J.; Riddell, D.; Smith, C. Bioorg. Med. Chem. Lett. 1992, 2, 375.
14. Ashton, M. J.; Bridge, A. W.; Bush, R. C.; Dron, D. I.; Joamou, D. R.; Riddell, D.; Roberts, S.; Stevenson, G. V. W.; Warne, P. J. 9th International Symposium on Atherosclerosis. Rosemont IL, 1991, Abstr. 92.
15. (a) Higley, C. A.; Wilde, R. G.; Maduskuie, T. P.; Johnson, A. L.; Pennev, P.; Billheimer, J. T.; Robinson, C. S.; Gillies, P. J.; Wexler, R. R. J. Med Chem. 1994, 37, 3511
16. (b) Hainer, J. W.; Terry, J. G.; Connell, J. M.; Zyruk, H.; Jenkins, R. M.; Shand, D. L.; Gillies, P. J.; Livak, K. J.; Hunt, T. L.; Crouse, J. R. Clin. Pharmacol. Ther. 1994, 56, 65.
17. For a review, see: Boger, D. L.; Weinreb, S. M. Hetero Diels-Alder Methodology in Organic Synthesis: Academic: San Diego, 1987.
18. Older reviews: (a) Campaigne, F., Chem. Rev. 1946, 39, 1; (b) Wagner, A. Methoden der Organischen Chemie; Muller, E., Ed.: Houben-Weyl: Berlin, 1944; Vol. IX, pp 699-778.
19. Older reviews: (a) Campaigne, F., Chem. Rev. 1946, 39, 1; (b) Wagner, A. Methoden der Organischen Chemie; Muller, E., Ed.: Houben-Weyl: Berlin, 1944; Vol. IX, pp 699-778.
20. Vedejs, E.; Perry, D. A.; Wilde, R. G. J. Am. Chem, Soc. 1986, 108, 2985.
21. Recent reviews: (a) Vedejs, E. Perspectives in the Organic Chemistry of Sulfur; Elsevier: Amsterdam, 1987; pp 75-99 (b) Metzner, P. Synthesis 1992, 1185 (c) McGregor, W. M.; Sherrington, D. C. Chem. Soc. Rev. 1993, 22, 199.
22. Recent reviews: (a) Vedejs, E. Perspectives in the Organic Chemistry of Sulfur; Elsevier: Amsterdam, 1987; pp 75-99 (b) Metzner, P. Synthesis 1992, 1185 (c) McGregor, W. M.; Sherrington, D. C. Chem. Soc. Rev. 1993, 22, 199.
23. Recent reviews: (a) Vedejs, E. Perspectives in the Organic Chemistry of Sulfur; Elsevier: Amsterdam, 1987; pp 75-99 (b) Metzner, P. Synthesis 1992, 1185 (c) McGregor, W. M.; Sherrington, D. C. Chem. Soc. Rev. 1993, 22, 199.
24. Vedejs, E.; Perry, D. A.; Honk, K. N.; Rondan, N. G. J. Am. Chem. Soc. 1983, 105, 6999.
25. Vedejs, E.; Stults, J. S.; Wilde, R. G. J. Am. Chem. Soc. 1988, 110, 5452.
26. Araki, S.; Ohmura, M.; Butsugan, Y. Synthesis 1985, 963.
27. Zweifel, G.; Miller, R. L. J. Am. Chem. Soc. 1970, 92, 6678.
28. Brown, H. C.; Gupta, S. K. J Am. Chem. Soc. 1972, 94, 4370.
29. Larock, R. C.; Gupta, S. K.; Brown, H. C. J. Am. Chem. Soc. 1972, 94, 4371.
30. Larock, R. C.; Riefling, B.J. Org, Chem. 1978, 43, 1468.
31. Hogeveen, H.; Smit, P. J. Rec. Trav. Chim. Pays Bas 1966, 85, 489.
32. (a) Vedejs, F.; Eberlein, T. H.; Varie, D. L. J. Am. Chem. Soc. 1982, 104, 1445
33. (b) Vedejs, E.; Eberlein, T. H.; Mazur, D. J.; McClure, C. K.; Perry, D, A.; Ruggeri, R.; Schwartz, E.; Stults, J. S.; Varie, D. L.; Wilde, R. G.; Wittenberger, S. J. Org. Chem. 1986, 51, 1556.
34. Caserio, M. C.; Lauer, W.; Novinson, T. J. Am. Chem. Soc. 1970, 92, 6082.
35. Padwa, A.; Pashayan, D.J. Org. Chem. 1971, 36, 3550.
36. Wagner, P, J.; Lindstrom, M. J. J. Am. Chem, Soc. 1987, 109, 3057.
37. (a) Bladon, C. M.; Ferguson, I. F. G.; Kirby, G. W.; Lochead, A. W.; McDougall, D. C. J. Chem. Soc., Chem. Commun. 1983, 423
38. (b) Bladon, C. M.; Ferguson, I. E. G.; Kirby, G. W.; Lochead, A. W.; McDougall, D. C. J. Chem. Soc., Perkin Trans. I 1985, 1541.
39. Bonjouklian, R.; Ruden, R. A. J. Org. Chem. 1977, 42, 4095.
40. Maduskuie, T. P., Jr; Wilde, R. G.; Billheimer, J. T.; Cromley, D. A.; Germain, S.; Gillies, P. J.; Higley, C. A.; Johnson, A. L.; Pennev, P.; Shimshick, E. J.; Wcxlcr, R. R. J. Med. Chem. 1995, 38, 1067.
41. Trivedi, B. K.; Purchase, T. S.; Holmes, A.; Augelli-Szafran, C. E.; Essenburg. A. D.; Hamelehle, K. L.; Stanfield, R. L.; Bousley, R. F.; Krause, B. R. J. Med. Chem. 1994, 37, 1652.
42. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
43. Billheimer, J. T.; Tavani, D.; Nes, W. R. Anal. Biochem. 1981, 111, 331.
44. Bierer, D. F.; Kabalka, G. W. Org. Prep. Proc. Int. 1988, 20, 63.
45. Wang, C. S. J. Heterocyel. Chem. 1970, 389.
46. Albert, A.; Brown D. J.; Wood, H. S. C. J. Chem. Soc. 1954, 3832.
47. McCarthy, P. A.; Walker, F. J.; Truong, T.; Hamanaka, E. S.; Chang, G. European Patent Application no. 418,071 A2.
48. Thiele, J. Liebigs Ann. Chem. 1892, 271, 127.