Derivatives of 1,2,3,4-tetrahydroisoquinoline-7-carboxylic acid as novel fibrinogen receptor antagonists

Medicinal Chemistry

Volumn 5, Issue 2, 2009, Pages 158-164

  Malovichko, Olga L ^a   Krysko, Andrei A ^a   Kabanova, Tatyana A ^a   Andronati, Sergei A ^a   Grishkovets, Vladimir I ^b   Kachala, Vadim V ^c   Panov, Denis A ^b  

^a A V BOGATSKY PHYSICO CHEMICAL INSTITUTE   (Ukraine)

^b V I VERNADSKY CRIMEAN FEDERAL UNIVERSITY   (Russian Federation)

^c N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

IIb 3; 1,2,3,4 tetrahydroisoquinoline; Fibrinogen receptor antagonists; Platelet aggregation; RGD mimetics

Indexed keywords

1,2,3,4 TETRAHYDROISOQUINOLINE 7 CARBOXYLIC ACID DERIVATIVE; ALPHAIIB BETA3 INTEGRIN; FIBRINOGEN RECEPTOR ANTAGONIST; FLUORESCEIN ISOTHIOCYANATE; INTEGRIN; THROMBOCYTE RECEPTOR; UNCLASSIFIED DRUG; ARGINYL-GLYCYL-ASPARTIC ACID; ARGINYLGLYCYLASPARTIC ACID; FIBRINOGEN; FIBRINOGEN RECEPTOR; OLIGOPEPTIDE; TETRAHYDROISOQUINOLINE DERIVATIVE;

ARTICLE; DRUG EFFECT; DRUG IDENTIFICATION; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; PRIORITY JOURNAL; RECEPTOR BINDING; THROMBOCYTE AGGREGATION INHIBITION; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN BINDING; SYNTHESIS; THROMBOCYTE; THROMBOCYTE AGGREGATION; THROMBOCYTE RICH PLASMA;

BLOOD PLATELETS; FIBRINOGEN; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OLIGOPEPTIDES; PLATELET AGGREGATION; PLATELET GLYCOPROTEIN GPIIB-IIIA COMPLEX; PLATELET-RICH PLASMA; PROTEIN BINDING; RECEPTORS, FIBRINOGEN; TETRAHYDROISOQUINOLINES;

EID: 65349155140     PISSN: 15734064     EISSN: None     Source Type: Journal    
DOI: 10.2174/157340609787582909     Document Type: Article

References (17)

1. Lawson, E.C.; Hoekstra, W.J.; Addo, M.F.; Andrade-Gordon, P.; Damiano, B.P.; Kauffman, J.A.; Mitchell, J.A.; Maryanoff, B.E. 1,2,4-Triazolo[3,4-a]pyridine as a novel, constrained template for fibrinogen receptor (GP IIb/IIIa) antagonists. Bioorg. Med. Chem. Lett., 2001, 11, 2619-22.
2. Phillips, D.R.; Charo, I.F.; Parise, L.V.; Fitzgerald, L.A. The platelet membrane glycoprotein IIb-IIIa complex. Blood, 1988, 71, 831-43.
3. Zablocki, J.A.; Rao, S.N.; Baron, D.A.; Flynn, D.L.; Nicholson, N.S.; Feigen, L.P. Fibrinogen Receptor Antagonists. Curr. Pharm. Des., 1995, 1, 533-58.
4. Scarborough, R.M. Eptifibatide. Drugs Future, 1998, 23, 585-90.
5. Cook, J.J.; Bednar, B.; Lynch, J.J.; Gould, R.J.; Egbertson, M.S.; Halczenko, W.; Duggan, M.E.; Hartman, G.D.; Lo, M.; Murphy, G.M.; Deckelbaum, L.I.; Sax, F.L.; Barr, E. Tirofiban (Aggrastat®). Cardiovasc. Drug Rev., 1999, 17, 199-224.
6. Therous, P.; Kouz, S.; Roy, L.; Knudtson, M.L.; Diodati, J.G.; Marquis, J.; Nasmith, J.; Fung, A. Y.; Boudreault, J.; Delage, F.; Dupuis, R.; Kells, C.; Bokslag, M.; Steiner, B.; Rapold, H.J. Platelet membrane receptor glycoprotein IIb/IIIa antagonism in unstable angina. The Canadian Lamifiban Study. Circulation, 1996, 94, 899-905.
7. Faulds, D.; Sorkin, E.M. Abciximab (c7E3 Fab). A review of its pharmacology and therapeutic potential in ischaemic heart disease. Drugs, 1994, 48, 583-98.
8. Andronati, S.A.; Karaseva, T.L.; Krysko, A.A. Peptidomimetics - antagonists of the fibrinogen receptors: molecular design, structures, properties and therapeutic applications. Curr. Med. Chem., 2004, 11, 1183-211.
9. Krysko, A.A.; Chugunov, B.M., Malovichko, O.L.; Andronati, S.A.; Kabanova, T.A.; Karaseva, T.L.; Kiriyak, A.V. Novel fibrinogen receptor antagonists. RGDF mimetics, derivatives of 4-(isoindoline-5-yl)amino-4-oxobutyric acid. Bioorg. Med. Chem. Lett., 2004, 14, 5533-5.
10. Andronati, S.A.; Krysko, A.A.; Chugunov, B.M., Kabanova, T.A.; Artemenko, A.G. 4-(Isoindolin-5-yl)amino- 4-oxobutyryl-β-alkoxyphenyl- β-alanines, new RGDF mimetics. Synthesis, affinity to fibrinogen receptors, antiaggregatory properties, and their correlation with the hydrophobicity. Russ. J. Org. Chem., 2006, 42, 1174-82.
11. Krysko, A.A.; Malovichko, O.L.; Andronati, S.A.; Kabanova, T.A.; Karaseva, T.L.; Petrus, A.S. Novel fibrinogen receptor antagonists - RGDF mimetics, 4-(1,2,3,4-tetrahydro-isoquinoline- 7-yl)amino-4-oxo- butyric acid derivatives. Med. Chem., 2006, 2, 295-8.
12. Malovichko, O.L.; Petrus, A.S.; Krysko, A.A.; Kabanova, T.A.; Andronati, S.A.; Karaseva, T.L.; Kiriyak, A.V. Derivatives of 7-amino-1,2,3,4-tetrahydroisoquinoline and isophthalic acids as novel fibrinogen receptor antagonists. Bioorg. Med. Chem. Lett., 2006, 16, 5294-7.
13. Anderluh, M.; Cesar, J.; Štefanič, P.; Kikelj, D.; Janeš, D.; Murn, J.; Nadrah, K.; Tominc, M.; Addicks, E.; Giannis, A.; Stegnar, M.; Dolenc, M.S. Design and synthesis of novel platelet fibrinogen receptor antagonists with 2H-1,4-benzoxazine-3(4H)-one scaffold. A systematic study. Eur. J. Med. Chem., 2005, 40, 25-49.
14. Andronati, S.A.; Krysko, A.A.; Kabanov, V.M.; Karaseva, T.L.; Kabanova, T.A. Synthesis and properties of peptidomimetics - platelet aggregation inhibitors. Acta Poloniae Pharm. Drug Res., 2000, 57 (Suppl.), 15-21.
15. Born, G.V.R. Aggregation of blood platelets by adenosine diphosphate and its reversal. Nature, 1962, 194, 927-9.
16. Xia, Z.; Wong, T.; Liu, Q.; Kasirer-Friede, A.; Brown, E.; Frojmnvic, M.M. Optimally functional flourescein isothiocyanate labelled fibrinogen for quantitative studies of binding to activated platelets and platelet aggregation. Br. J. Haematol., 1996, 93, 204-14.
17. Hantgan, R. An investigation of fibrin-platelet adhesive interactions by microfluorimetry. Biochim. Biophys. Acta, 1987, 927, 55-64.