Synthesis of new class dipeptide analogues with improved permeability and antithrombotic activity

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 14, 2006, Pages 4761-4774

  Zhao, Ming ^a,b   Bi, Lanrong ^a,b   Bi, Wei ^b,c   Wang, Chao ^a,b   Yang, Zhe ^a,b   Ju, Jingfang ^b,d   Peng, Shiqi ^a,b  

^a CAPITAL MEDICAL UNIVERSITY   (China)

^b PEKING UNIVERSITY   (China)

^c HEBEI MEDICAL UNIVERSITY   (China)

^d USA   (United States)

Author keywords

Antithrombotic activity; Dipeptide analogue; Membrane permeability

Indexed keywords

3 (S) 1,2,3,4 TETRAHYDRO BETA CARBOLINE 3 CARBOXYLIC ACID; ACETYLSALICYLIC ACID; AMINO ACID; DIPEPTIDE DERIVATIVE; TRYPTOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BIOLOGICAL ACTIVITY; CONTROLLED STUDY; DRUG DESIGN; DRUG EFFECT; DRUG PENETRATION; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; MALE; MEMBRANE PERMEABILITY; NONHUMAN; RAT; THROMBOCYTE AGGREGATION;

ANIMALS; ASPIRIN; BIOLOGICAL AVAILABILITY; CACO-2 CELLS; DIPEPTIDES; DRUG EVALUATION, PRECLINICAL; FIBRINOLYTIC AGENTS; HUMANS; MALE; PERMEABILITY; PLATELET AGGREGATION; RABBITS; RATS; RATS, WISTAR;

EID: 33646818277     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.03.026     Document Type: Article

References (40)

1. Fowkes F.J.I., Price J.F., and Fowkes F.G.R. Eur. J. Vasc. Endovasc. Surg. 25 (2003) 1-5
2. Collins B., and Hollidge C. Nat. Rev. Drug Discov. 2 (2003) 11-12
3. Gresele P., and Agnelli G. Trends Pharmacol. Sci. 23 (2002) 25-32
4. Golino P., Loffredo F., Riegler L., Renzullo E., and Cocchia R. Curr. Opin. Investig. Drugs 6 (2005) 298-306
5. Eriksson U.G., Bredberg U., Hoffmann K.-J., Thuresson A., Gabrielsson M., and Ericsson H. Drug Metab. Dispos. 31 (2003) 294-305
6. Raskob G.E. Haemostasis 23 (1993) 32-41
7. Lee K., Park C.W., Jung W.-H., Park H.D., Lee S.H., Chung K.H., Park S.K., Kwon O.H., Kang M., Park D.-H., Lee S.K., Kim E.E., Yoon S.K., and Kim A. J. Med. Chem. 46 (2003) 3612-3622
8. Quan M.L., Lam P.Y.S., Han Q., Pinto D.J.P., He M.Y., Li R., Ellis C.D., Clark C.G., Teleha C.A., Sun J.-H., Alexander R.S., Bai S., Luettgen J.M., Knabb R.M., Wong P.C., and Wexler R.R. J. Med. Chem. 48 (2005) 1729-1744
9. Tucker T.J., Lumma W.C., Lewis S.D., Gardell S.J., Lucas B.J., Baskin E.P., Woltmann R., Lynch J.J., Lyle E.A., Appleby S.D., Chen I.-W., Dancheck K.B., and Vacca J.P. J. Med. Chem. 40 (1997) 1565-1569
10. Tucker T.J., Brady S.F., Lumma W.C., Lewis S.D., Gardell S.J., Naylor-Olsen A.M., Yan Y., Sisko J.T., Stauffer K.J., Lucas B.J., Lynch J.J., Cook J.J., Stranieri M.T., Holahan M.A., Lyle E.A., Baskin E.P., Chen I.-W., Dancheck K.B., Krueger J.A., Cooper C.M., and Vacca J.P. J. Med. Chem. 41 (1998) 3210-3219
11. Lam P.Y.S., Clark C.G., Li R., Pinto D.J.P., Orwat M.J., Galemmo R.A., Fevig J.M., Teleha C.A., Alexander R.S., Smallwood A.M., Rossi K.A., Wright M.R., Bai S.A., He K., Luettgen J.M., Wong P.C., Knabb R.M., and Wexler R.R. J. Med. Chem. 46 (2003) 4405-4418
12. Lipka E., Crison J., and Amidon G.L. J. Control Release 39 (1996) 121-129
13. Yang C., Dantzig A.H., and Pidgeon C. Pharm. Res. 16 (1999) 1331-1343
14. Dantzig A.H., Duckworth D.C., and Tabas L.B. Biochim. Biophys. Acta 1191 (1994) 7-13
15. Dantzig A.H., and Bergin L. Biochem. Biophys. Res. Commun. 155 (1988) 1082-1087
16. Dantzig A.H., Tabas L.B., and Bergin L. Biochim. Biophys. Acta 1112 (1992) 167-173
17. Kramer W., Girbig F., Gutjahr U., Kleeman H.W., Leipe I., Urbach H., and Wagner A. Biochim. Biophys. Acta 1027 (1990) 25-30
18. Thwaites D.T., Cavet M., Hirst B.H., and Simmons N.L. Br. J. Pharmacol. 114 (1995) 981-986
19. Friedman D.I., and Amidon G.L. J. Pharm. Pharmacol. 78 (1989) 995-998
20. Tomita Y., Katsura T., Okano T., Inui K.I., and Hori R. J. Pharmacol. Exp. Ther. 252 (1990) 859-862
21. Addison J.M., Burston D., Dalrymple J.A., Matthews D.M., Payne J.W., Sleisenger M.H., and Wilkinson S. Clin. Sci. Mol. Med. 49 (1975) 313-322
22. Kramer W., Girbig F., Gutjahr U., and Kowalewski S. The Intestinal Oligopeptide Transporter: Molecular Characterization and Substrate Specificity. In: Taylor M.D., and Amidon G.L. (Eds). Peptide-based Drug Design (1995), American Chemical Society, Washington 149-180
23. Zhao M., Liu J., Wang C., Wang Li., Liu H., and Peng S. J. Med. Chem. 48 (2005) 4285-4292
24. Zhao M., Wang C., Liu J., Zhou K., and Peng S. Bioorg. Med. Chem. 12 (2004) 2275-2286
25. Zhao M., Wang C., Wu Y., Zhou K., and Peng S. Prep. Biochem. Biotech. 34 (2004) 57-76
26. Tang Z., Wang Y., Xiao Y., Zhao M., and Peng S. Thrombosis Res. 110 (2003) 127-133
27. Liu J., Zhao M., Wang C., and Peng S. Bioorg. Med. Chem. Lett. 13 (2003) 4065-4069
28. Zhao M., Wang C., Yang J., Liu J., Xu Y., Wu Y., and Peng S. Bioorg. Med. Chem. 11 (2003) 4913-4920
29. Zhao M., Lin Na., Wang C., and Peng S. Bioorg. Med. Chem. Lett. 13 (2003) 961-964
30. Wu Y., Zhao M., Wang C., and Peng S. Bioorg. Med. Chem. Lett. 12 (2002) 2331-2333
31. Lin N., Zhao M., Wang C., and Peng S. Bioorg. Med. Chem. Lett. 12 (2002) 585-587
32. Busnel O., Bi L., and Baudy-Floch. Tetrahedron Lett. 46 (2005) 7073-7075
33. Peng J., Qiao Y., and Yao X. Chinese J. Med. Chem. 5 (1995) 134
34. Artursson P., and Karlsson J. Biochem. Biophys. Res. Commun. 175 (1991) 880-885
35. Stewart B.H., and Chan O.H. J. Pharm. Sci. 87 (1998) 1471-1478
36. Yee S. Pharm. Res. 14 (1997) 763-766
37. Kaldas M.I., Walle U.K., and Walle T. J. Pharm. Pharmacol. 55 (2003) 307-312
38. Camenisch G., Alsenz J., Van de Waterbeemd H., and Folkers G. Eur. J. Pharm. Sci. 6 (1998) 313-319
39. Camenisch G., Folkers G., and Van de Waterbeemd H. Int. J. Pharm. 147 (1997) 61-70
40. Burton P.S., Goodwin J.T., Conradi R.A., Ho N.F.H., and Hilgers A.R. Adv. Drug Delivery Rev. 23 (1997) 143-156