Synthesis and biological activity of 2-alkylated deoxyadenosine bisphosphate derivatives as P2Y1 receptor antagonists

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 7, 2004, Pages 1769-1779

  Mathieu, Romain ^a   Baurand, Anthony ^b   Schmitt, Martine ^a   Gachet, Christian ^b   Bourguignon, Jean Jacques ^a  

^a Laboratoire de Pharmacochimie   (France)

^b Etablissement Francais Sang Alsace   (France)

Author keywords

Nucleotides; P2Y1 receptor; Palladium catalyzed cross coupling reaction; Platelet aggregation

Indexed keywords

2 ETHYL N 6 METHYL 2' DEOXYADENOSINE 3',5' DIPHOSPHATE; 2 ETHYNYL N 6 METHYL 2' DEOXYADENOSINE 3',5' DIPHOSPHATE; 2 METHYLTHIOADENOSINE 5' DIPHOSPHATE; ADENOSINE DIPHOSPHATE; N 6 METHYL 2 (2 PHENYLETHYL) 2' DEOXYADENOSINE 3',5' DIPHOSPHATE; N 6 METHYL 2 (PROP 1 YNYL) 2' DEOXYADENOSINE 3',5' DIPHOSPHATE; N 6 METHYL 2 PROPYL 2' DEOXYADENOSINE 3',5' DIPHOSPHATE; PALLADIUM; PHOSPHORUS; PHOSPHORUS 33; PURINE P2Y1 RECEPTOR; PURINERGIC RECEPTOR BLOCKING AGENT; PYROPHOSPHORIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; BINDING AFFINITY; CALCIUM CELL LEVEL; CATALYSIS; CATALYST; CONTROLLED STUDY; CROSS COUPLING REACTION; DRUG ACTIVITY; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IODINATION; ISOTOPE LABELING; THROMBOCYTE AGGREGATION;

ADENOSINE DIPHOSPHATE; ADENYLATE CYCLASE; BINDING, COMPETITIVE; BLOOD PLATELETS; CALCIUM; DEOXYADENINE NUCLEOTIDES; HUMANS; MEMBRANE PROTEINS; MOLECULAR STRUCTURE; PALLADIUM; PLATELET AGGREGATION; RECEPTORS, PURINERGIC P2; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 1542404524     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2003.12.041     Document Type: Article

References (33)

1. Ralevic V., Burnstock G. Pharmacol. Rev. 50:1998;413.
2. von Kügelgen I., Wetter A. Naunyn-Schmiedeberg's Arch. Pharmacol. 362:2000;310.
3. Gachet C. Int. J. Hematol. 74:2001;375.
4. Storey R.F., Newby L.J., Heptinstall S. Platelets. 12:2001;443.
5. Hechler B., Eckly A., Ohlmann P., Cazenave J.-P., Gachet C. Br. J. Haematol. 103:1998;858.
6. Geiger J., Brich J., Hönig-Liedl P., Eigenthaler M., Schanzenbacher P., Herbert J.M., Walter U. Arterioscler., Thromb., Vasc. Biol. 19:1999;2007.
7. Humphries R.G., Tomlinson W., Ingall A.H., Cage P.A., Leff P. Br. J. Pharmacol. 113:1994;1057.
8. Fagura M.S., Dainty I.A., McKay G.D., Kirk I.P., Humphries R.G., Robertson M.J., Dougall I.G., Leff P. Br. J. Pharmacol. 124:1998;157.
9. Daniel J.L., Dangelmaier C., Jin J., Ashby B., Smith J.B., Kunapuli S.P. J. Biol. Chem. 273:1998;2024.
10. Hechler B., Léon C., Vial C., Vigne P., Frelin C., Cazenave J.-P., Gachet C. Blood. 92:1998;152.
11. Jin J., Kunapuli S.P. Proc. Natl. Acad. Sci. U.S.A. 95:1998;8070.
12. Léon C., Freund M., Ravanat C., Baurand A., Cazenave J.-P., Gachet C. Circulation. 103:2001;718.
13. Léon C., Hechler B., Freund M., Eckly A., Vial C., Ohlmann P., Dierich A., LeMeur M., Cazenave J.-P., Gachet C. J. Clin. Invest. 104:1999;1731.
14. Fabre J.E., Nguyen M.T., Latour A., Keifer J.A., Audoly L.P., Coffman T.M., Koller B.H. Nat. Med. 5:1999;1199.
15. Baurand A., Gachet C. Cardiovasc. Drug Rev. 21:2003;67.
16. Lenain N., Freund M., Léon C., Cazenave J.-P., Gachet C. J. Thromb. Haemost. 1:2003;1144.
17. Boyer J.L., Romero-Avila T., Schachter J.B., Harden T.K. Mol. Pharmacol. 50:1996;1323.
18. Camaioni E., Boyer J.L., Mohanram A., Harden T.K., Jacobson K.A. J. Med. Chem. 41:1998;183.
19. Boyer J.L., Mohanram A., Camaioni E., Jacobson K.A., Harden T.K. Br. J. Pharmacol. 124:1998;1.
20. Nandanan E., Camaioni E., Jang S.-Y., Kim Y.-C., Cristalli G., Herdewijn P., Secrist J.A., Tiwari K.N., Mohanram A., Harden T.K., Boyer J.L., Jacobson K.A. J. Med. Chem. 42:1999;1625.
21. Nandanan E., Jang S.-Y., Moro S., Kim H.O., Siddiqui M.A., Russ P., Marquez V.E., Busson R., Herdewijn P., Harden T.K., Boyer J.L., Jacobson K.A. J. Med. Chem. 43:2000;829.
22. Raboisson P., Baurand A., Cazenave J.-P., Gachet C., Retat M., Spiess B., Bourguignon J.-J. J. Med. Chem. 45:2002;962.
23. Nair V., Purdy D.F. Tetrahedron. 47:1991;365.
24. Golisade A., Van Calenbergh S., Link A. Tetrahedron. 56:2000;3167.
25. Kumamoto H., Tanaka H., Tsukioka R., Ishida Y., Nakamura A., Kimura S., Hayakawa H., Kato K., Miyasaka T. J. Org. Chem. 64:1999;7773.
26. Kato K., Hayakawa H., Tanaka H., Kumamoto H., Shindoh S., Shuto S., Miyasaka T. J. Org. Chem. 62:1997;6833.
27. Vacca J.P., deSolms S.J., Huff J.R. J. Am. Chem. Soc. 109:1987;3478.
28. Perich J.W., Johns R.B. Synthesis. 2:1988;142.
29. Baurand A., Raboisson P., Freund M., Léon C., Cazenave J.-P., Bourguignon J.-J., Gachet C. Eur. J. Pharmacol. 412:2001;213.
30. Humphries R.G. Haematologica. 85:2000;66. supplement.
31. Gachet C., Cattaneo M., Ohlmann P., Hechler B., Lecchi A., Chevalier J., Mannuccio Mannucci P., Cazenave J.-P. Br. J. Haematol. 91:1995;434.
32. Cazenave J.-P., Hemmendinger S., Beretz A., Sutter-Bay A., Launay J. Ann. Biol. Clin. 41:1983;167.
33. Baurand A., Eckly A., Bari N., Léon C., Hechler B., Cazenave J.-P., Gachet C. Thromb. Haemostasis. 84:2000;484.