Synthesis, biological evaluation, X-ray molecular structure and molecular docking studies of RGD mimetics containing 6-amino-2,3-dihydroisoindolin-1-one fragment as ligands of integrin αiIbβ3

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 15, 2013, Pages 4646-4661

  Krysko, Andrei A ^a   Samoylenko, Georgiy V ^a   Polishchuk, Pavel G ^a,b   Fonari, Marina S ^c   Kravtsov, Victor Ch ^c   Andronati, Sergei A ^a   Kabanova, Tatyana A ^a   Lipkowski, Janusz ^d   Khristova, Tetiana M ^a,b   Kuz'Min, Victor E ^a   Kabanov, Vladimir M ^a   Krysko, Olga L ^a   Varnek, Alexandre A ^b  

^a A V BOGATSKY PHYSICO CHEMICAL INSTITUTE   (Ukraine)

^b UNIVERSITÉ DE STRASBOURG   (France)

^c INSTITUTE OF APPLIED PHYSICS   (Moldova)

^d INSTITUTE OF PHYSICAL CHEMISTRY   (Poland)

Author keywords

IIb 3; Fibrinogen receptor antagonists; Phthalimidine; Platelet aggregation; RGD mimetics

Indexed keywords

3 [1 OXO 6 (2 PIPERIDINIUM 4 YL ACETYLAMINO) 1,3 DIHYDROISOINDOL 2 YL]BUTYRIC ACID TRIFLUOROACETATE; 3 [1 OXO 6 (2 PIPERIDINIUM 4 YL ACETYLAMINO) 1,3 DIHYDROISOINDOL 2 YL]PROPIONIC ACID TRIFLUOROACETATE; 3 [1 OXO 6 (3 PIPERAZINIUM 1 YL BENZOYLAMINO) 1,3 DIHYDROISOINDOL 2 YL]PROPIONIC ACID TRIFLUOROACETATE; 3 [1 OXO 6 (3 PIPERAZINIUM 4 YL BENZOYLAMINO) 1,3 DIHYDROISOINDOL 2 YL]BUTYRIC ACID CHLORIDE; 3 [1 OXO 6 (4 PIPERAZINIUM 1 YL BENZOYLAMINO) 1,3 DIHYDROISOINDOL 2 YL]PROPIONIC ACID TRIFLUOROACETATE; 3 [1 OXO 6 (4 PIPERAZINIUM 4 YL BENZOYLAMINO) 1,3 DIHYDROISOINDOL 2 YL]BUTYRIC ACID CHLORIDE; 3 [1 OXO 6 (4 PIPERIDINIUM 4 YL BENZOYLAMINO) 1,3 DIHYDROISOINDOL 2 YL]BUTYRIC ACID CHLORIDE; 3 [1 OXO 6 (4 PIPERIDINIUM 4 YL BENZOYLAMINO) 1,3 DIHYDROISOINDOL 2 YL]PROPIONIC ACID TRIFLUOROACETATE; 3 [1 OXO 6 (4 PIPERIDINIUM 4 YL BUTYRYLAMINO) 1,3 DIHYDROISOINDOL 2 YL]BUTYRIC ACID CHLORIDE; 3 [1 OXO 6 (4 PIPERIDINIUM 4 YL BUTYRYLAMINO) 1,3 DIHYDROISOINDOL 2 YL]PROPIONIC ACID TRIFLUOROACETATE; 3 [1 OXO 6 [(1,2,3,4 TETRAHYDROISOQUINOLINIUM 7 CARBONYL)AMINO] 1,3 DIHYDROISOINDOL 2 YL]BUTYRIC ACID CHLORIDE; 3 [1 OXO 6 [(1,2,3,4 TETRAHYDROISOQUINOLINIUM 7 CARBONYL)AMINO] 1,3 DIHYDROISOINDOL 2 YL]PROPIONIC ACID CHLORIDE; 4 [1 OXO 6 (2 PIPERIDINIUM 4 YL ACETYLAMINO) 1,3 DIHYDROISOINDOL 2 YL]BUTYRIC ACID TRIFLUOROACETATE; 4 [1 OXO 6 (4 PIPERIDINIUM 4 YL BENZOYLAMINO) 1,3 DIHYDROISOINDOL 2 YL]BUTYRIC ACID TRIFLUOROACETATE; 4 [1 OXO 6 (4 PIPERIDINIUM 4 YL BUTYRYLAMINO) 1,3 DIHYDROISOINDOL 2 YL]BUTYRIC ACID TRIFLUOROACETATE; 4 [1 OXO 6 [(1,2,3,4 TETRAHYDROISOQUINOLINIUM 7 CARBONYL)AMINO] 1,3 DIHYDROISOINDOL 2 YL]BUTYRIC ACID CHLORIDE; [1 OXO 6 (2 PIPERIDINIUM 4 YL ACETYLAMINO) 1,3 DIHYDROISOINDOL 2 YL]ACETIC ACID TRIFLUOROACETATE; [1 OXO 6 (4 PIPERAZINIUM 1 YL BENZOYLAMINO) 1,3-DIHYDROISOINDOL 2 YL]ACETIC ACID TRIFLUOROACETATE; [1 OXO 6 (4 PIPERIDINIUM 4 YL BENZOYLAMINO) 1,3 DIHYDROISOINDOL 2 YL]ACETIC ACID TRIFLUOROACETATE; [1 OXO 6 (4 PIPERIDINIUM 4 YL BUTYRYLAMINO) 1,3 DIHYDROISOINDOL 2 YL]ACETIC ACID TRIFLUOROACETATE; [1 OXO 6 [(1,2,3,4 TETRAHYDROISOQUINOLINIUM 7 CARBONYL)AMINO] 1,3 DIHYDROISOINDOL 2 YL]ACETIC ACID CHLORIDE; AMINO 2,3 DIHYDROISOINDOLIN 1 ONE DERIVATIVE; ARGINYLGLYCYLASPARTIC ACID; FIBRINOGEN; FIBRINOGEN RECEPTOR ANTAGONIST; INDOLE DERIVATIVE; INTEGRIN; INTEGRIN ALPHA2B BETA3; TIROFIBAN; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MOLECULAR DOCKING; STRUCTURE ACTIVITY RELATION; THROMBOCYTE AGGREGATION INHIBITION;

EID: 84879690592     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.05.019     Document Type: Article

References (24)

1. A. Tello-Montoliu, E. Jover, J. Rivera, M. Valdés, D.J. Angiolillo, and F. Marín Curr. Med. Chem. 19 2012 406
2. X. Wang, R.T. Dorsam, A. Lauver, H. Wang, F.A. Barbera, S. Gibbs, D. Varon, N. Savion, S.M. Friedman, and G.Z. Feuerstein J. Pharmacol. Exp. Ther. 303 2002 1114
3. N. Clappers, M.A. Brouwer, and F.W. Verheugt Heart 93 2007 258
4. K. Freson, C. Thys, C. Wittevrongel, and C. Van Geet Mini Rev. Med. Chem. 6 2006 719
5. J. Krakat, S. Mousa, R. Root, and S.S. Mousa Drugs Future 34 2009 27
6. P.B. Berger J. Am. Coll. Cardiol. 56 2010 476
7. J. Zhu, W.-S. Choi, J.G. McCoy, A. Negri, J. Zhu, S. Naini, J. Li, M. Shen, W. Huang, D. Bougie, M. Rasmussen, R. Aster, C.J. Thomas, M. Filizola, T.A. Springer, and B.S. Coller Sci. Transl. Med. 4 2012 125ra32
8. S.A. Andronati, T.L. Karaseva, and A.A. Krysko Curr. Med. Chem. 11 2004 1183
9. A. Perdih, and M.S. Dolenc Curr. Med. Chem. 17 2010 2371
10. A.A. Krysko, G.V. Samoylenko, P.G. Polishchuk, S.A. Andronati, T.A. Kabanova, T.M. Khristova, V.E. Kuz'min, V.M. Kabanov, O.L. Krysko, A.A. Varnek, and R.Y. Grygorash Bioorg. Med. Chem. Lett. 21 2011 5971
11. M. Bera, G.T. Musie, and D.R. Powell Inorg. Chem. Commun. 11 2008 293
12. D. Wilczyńska, P. Kosson, M. Kwasiborska, A. Ejchart, and A. Olma J. Pept. Sci. 15 2009 777
13. S.I. Klein, B.F. Molino, M. Czekaj, C.J. Gardner, V. Chu, K. Brown, R.D. Sabatino, J.S. Bostwick, C. Kasiewski, R. Bentley, V. Windisch, M. Perrone, C.T. Dunwiddie, and R.J. Leadley J. Med. Chem. 41 1998 2492
14. Frank, H.; Guenter, L.; Volkhard, A.; Helmut, P.; Thomas, M.; Johannes, W.; Brian, G. Eur. Patent 0,604,800, 1993.
15. Duggan, M. E.; Egbertson, M. S.; Hartman, G. D.; Young, S. D.; Ihle, N. C. U.S. Patent 5,854,245, 1998.
16. O.L. Malovichko, A.A. Krysko, T.A. Kabanova, S.A. Andronati, V.I. Grishkovets, V.V. Kachala, and D.A. Panov Med. Chem. 5 2009 158
17. G.V.R. Born Nature 194 1962 927
18. R. Hantgan Biochim. Biophys. Acta. 927 1987 55
19. Z. Xia, T. Wong, Q. Liu, A. Kasirer-Friede, E. Brown, and M.M. Frojmnvic Br. J. Haematol. 93 1996 204
20. FlexX, 2.1.2; BioSolveIT GmbH: Sankt Augustin, Germany.
21. (a) http://dx.doi.org/10.2210/pdb2vdm/pdb.
22. T. Xiao, J. Takagi, B.S. Coller, J.-H. Wang, and T.A. Springer Nature 432 2004 59
23. G.M. Sheldrick Acta Cryst. A64 2008 112
24. C.F. Macrae, I.J. Bruno, J.A. Chisholm, P.R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, R. Taylor, J. van de Streek, and P.A. Wood J. Appl. Cryst. 41 2008 466