A class of 3 S -2-aminoacyltetrahydro-β-carboline-3-carboxylic acids: Their facile synthesis, inhibition for platelet activation, and high in vivo anti-thrombotic potency

Journal of Medicinal Chemistry

Volumn 53, Issue 8, 2010, Pages 3106-3116

  Liu, Jiawang ^a   Jiang, Xueyun ^a   Zhao, Ming ^a   Zhang, Xiaoyi ^a   Zheng, Meiqing ^a   Peng, Li ^a   Peng, Shiqi ^a  

^a CAPITAL MEDICAL UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2 ISOLEUCYL 1,2,3,4 TETRAHYDRO BETA CARBOLINE 3 CARBOXYLIC ACID; 2 METHIONINYL 1,2,3,4 TETRAHYDRO BETA CARBOLINE 3 CARBOXYLIC ACID; ACETYLSALICYLIC ACID; ADENOSINE DIPHOSPHATE; AMINE; ANTICOAGULANT AGENT; CARBOLINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG; 1,2,3,4-TETRAHYDRO-BETA-CARBOLINE-3-CARBOXYLIC ACID; 3 TRYPTOLINECARBOXYLIC ACID; AMINO ACID; ANTITHROMBOCYTIC AGENT; FIBRINOLYTIC AGENT;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CHEMICAL MODIFICATION; CONTROLLED STUDY; DOSE RESPONSE; DRUG CONFORMATION; DRUG DOSE COMPARISON; DRUG POTENCY; DRUG SYNTHESIS; IC 50; IN VITRO STUDY; IN VIVO STUDY; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION; THROMBOCYTE ACTIVATION; THROMBOSIS; ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DRUG EFFECT; MALE; STEREOISOMERISM; SWINE; SYNTHESIS; WISTAR RAT;

AMINO ACIDS; ANIMALS; CARBOLINES; FIBRINOLYTIC AGENTS; MALE; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PLATELET ACTIVATION; PLATELET AGGREGATION INHIBITORS; RATS; RATS, WISTAR; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SWINE;

EID: 77951143986     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm901816j     Document Type: Article

References (37)

1. Chaireti, R.; Jennersjö, C.; Lindahl, T. L. Thrombin generation and D-dimer concentrations in a patient cohort investigated for venous thromboembolism. Relations to venous thrombosis, factor V Leiden and prothrombin G20210A. The LIST study Thromb. Res. 2009, 124, 178-184
2. Arias-Salgado, E. G.; Larrucea, S.; Butta, N.; Fernández, D.; García-Muñoz, S.; Parrilla, R.; Ayuso, M. S. Variations in platelet protein associated with arterial thrombosis Thromb. Res. 2008, 122, 640-647
3. Surin, W. R.; Barthwal, M. K.; Dikshit, M. Platelet collagen receptors, signaling and antagonism: emerging approaches for the prevention of intravascular thrombosis Thromb. Res. 2008, 122, 786-803
4. Gibbins, J. M. Tweaking the gain on platelet regulation: the tachykinin connection Atherosclerosis 2009, 206, 1-7
5. Skinner, M. P. Thrombosis and thrombolysis: platelet membrane glycoproteins Heart Lung 2007, 16, 176-179
6. Tonin, L. T. D.; Barbosa, V. A.; Bocca, C. C.; Ramos, R. F.; Nakamura, C. V.; da Costa, W. F.; Basso, E. A.; Nakamura, T. U.; Sarragiotto, M. H. Comparative study of the trypanocidal activity of the methyl 1-nitrophenyl-1,2,3,4-9 H -tetrahydro-β-carboline-3-carboxylate derivatives and benznidazole using theoretical calculations and cyclic voltammetry Eur. J. Med. Chem. 2009, 44, 1745-1750
7. Valdeza, R. H.; Tonin, L. T. D.; Ueda-Nakamura, T.; Filho, B. P. D.; Morgado-Diazd, J. A.; Sarragiotto, M. H.; Nakamura, C. V. Biological activity of 1,2,3,4-tetrahydro-β-carboline-3-carboxamides against Trypanosoma cruzi Acta Trop. 2009, 110, 7-14
8. Trujillo, J. I.; Meyers, M. J.; Anderson, D. R.; Hegde, S.; Mahoney, M. W.; Vernier, W. F.; Buchler, I. P.; Wu, K. K.; Yang, S.; Hartmann, S. J.; Reitz, D. B. Novel tetrahydro-β-carboline-1-carboxylic acids as inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2) Bioorg. Med. Chem. Lett. 2007, 17, 4657-4663
9. Jenkins, P. R.; Wilson, J.; Emmerson, D.; Garcia, M. D.; Smith, M. R.; Gray, S. J.; Britton, R. G.; Mahale, S.; Chaudhuri, B. Design, synthesis and biological evaluation of new tryptamine and tetrahydro-β-carboline-based selective inhibitors of CDK4 Bioorg. Med. Chem. 2008, 16, 7728-7739
10. Song, Y.; Wang, J.; Teng, S. F.; Kesuma, D.; Deng, Y.; Duan, J.; Wang, J. H.; Qi, R. Z.; Sima, M. M. β-Carbolines as specific inhibitors of cyclin-dependent kinases Bioorg. Med. Chem. Lett. 2002, 12, 1129-1132
11. Gupta, L.; Srivastava, K.; Singh, S.; Puri, S. K.; Chauhan, P. M. S. Synthesis of 2-[3-(7-chloro-quinolin-4-ylamino)- alkyl]-1-(substituted phenyl)-2,3,4,9-tetrahydro-1 H -β-carbolines as a new class of antimalarial agents Bioorg. Med. Chem. Lett. 2008, 18, 3306-3309
12. Takasu, K.; Shimogama, T.; Saiin, C.; Kim, H.-S.; Wataya, Y.; Ihara, M. π-Delocalized β-carbolinium cations as potential antimalarials Bioorg. Med. Chem. Lett. 2004, 14, 1689-1692
13. Cao, R.; Peng, W.; Chen, H.; Hou, X.; Guan, H.; Chen, Q.; Ma, Y.; Xu, A. Synthesis and in vitro cytotoxic evaluation of 1,3-bisubstituted and 1,3,9-trisubstituted β-carboline derivatives Eur. J. Med. Chem. 2005, 40, 249-257
14. Formagio, A. S. N.; Tonin, L. T. D.; Foglio, M. A.; Madjarof, C.; de Carvalho, J. E.; da Costa, W. F.; Cardoso, F. P.; Sarragiotto, M. H. Synthesis and antitumoral activity of novel 3-(2-substituted-1,3,4-oxadiazol-5-yl) and 3-(5-substituted-1,2,4-triazol-3-yl)-β-carboline derivatives Bioorg. Med. Chem. 2008, 16, 9660-9667
15. Cao, R.; Chen, Q.; Hou, X.; Chen, H.; Guan, H.; Ma, Y.; Peng, W.; Xu, A. Synthesis, acute toxicities, and antitumor effects of novel 9-substituted β-carboline derivatives Bioorg. Med. Chem. 2004, 12, 4613-4623
16. Cao, R.; Chen, H.; Peng, W.; Ma, Y.; Hou, X.; Guan, H.; Liu, X.; Xu, A. Design, synthesis and in vitro and in vivo antitumor activities of novel β-carboline derivatives Eur. J. Med. Chem. 2005, 4, 991-1001
17. Baruah, B.; Dasu, K.; Vaitilingam, B.; Mamnoor, P.; Venkata, P. P.; Rajagopal, S.; Yeleswarapu, K. R. Synthesis and cytotoxic activity of novel quinazolino-β-carboline- 5-one derivatives Bioorg. Med. Chem. 2004, 12, 1991-1994
18. Solyis, R. P.; Mcgee, V. L.; Smith, M. R. Cardiovascular effects of the β-carboline FG 7142 in borderline hypertensive rats Physiol. Behav. 1998, 63, 407-412
19. Hamann, J.; Wernicke, C.; Lehmann, J.; Reichmann, H.; Rommelspacher, H.; Gille, G. 9-Methyl-β-carboline up-regulates the appearance of differentiated dopaminergic neurones in primary mesencephalic culture Neurochem. Int. 2008, 52, 688-700
20. Herraiz, T.; Chaparro, C. Human monoamine oxidase is inhibited by tobacco smoke: β-carboline alkaloids act as potent and reversible inhibitors Biochem. Biophys. Res. Commun. 2005, 326, 378-386
21. Moura, D. J.; Rorig, C.; Vieira, D. L.; Henriques, J. A. P.; Roesler, R.; Saffi, J.; Boeira, J. M. Effects of β-carboline alkaloids on the object recognition task in mice Life Sci. 2006, 79, 2099-2104
22. Formagio, A. S. N.; Santos, P. R.; Zanoli, K.; Ueda-Nakamura, T.; Tonin, L. T. D.; Nakamura, C. V.; Sarragiotto, M. H. Synthesis and antiviral activity of β-carboline derivatives bearing a substituted carbohydrazide at C-3 against poliovirus and herpes simplex virus (HSV-1) Eur. J. Med. Chem. 2009, 44, 4695-4701
23. Husbands, S. M.; Glennon, R. A.; Gorgerat, S.; Gough, R.; Tyacke, R.; Crosby, J.; Nutt, D. J.; Lewis, J. W.; Hudson, A. L. β-Carboline binding to imidazoline receptors Drug Alcohol Depend. 2001, 64, 203-208
24. Glennon, R. A.; Grella, B.; Tyacke, R. J.; Lau, A.; Westaway, J.; Hudson, A. L. Binding of β-carbolines at imidazoline I2 receptors: a structure-affinity investigation Bioorg. Med. Chem. Lett. 2004, 14, 999-1002 (Pubitemid 38167629)
25. Sunder-Plassmann, N.; Sarli, V.; Gartner, M.; Utz, M.; Seiler, J.; Huemmer, S.; Mayer, T. U.; Surrey, T.; Giannis, A. Synthesis and biological evaluation of new tetrahydro-β-carbolines as inhibitors of the mitotic kinesin Eg5 Bioorg. Med. Chem. 2005, 13, 6094-6111 (Pubitemid 41400131)
26. Tu, L. C.; Chen, C.-S.; Hsiao, I.-C.; Chern, J.-W.; Lin, C.-H.; Shen, Y.-C.; Yeh, S. F. The β-carboline analog manahox causes mitotic aberration by interacting with DNA Chem. Biol. 2005, 12, 1317-1324
27. Csányi, D.; Hajós, G.; Riedl, Z.; Timári, G.; Bajor, Z.; Cochard, F.; Sapi, J.; Laronze, J.-Y. Synthesis of two new heteroaromatic β-carboline- fused pentacycles. Observation of a new intercalating agent Bioorg. Med. Chem. Lett. 2000, 10, 1767-1769
28. Fabio, R. D.; Micheli, F.; Alvaro, G.; Cavanni, P.; Donati, D.; Gagliardi, T.; Fontana, G.; Giovannini, R.; Maffeis, M.; Mingardi, A.; Tranquillini, M. E.; Vitulli, G. From pyrroles to 1-oxo-2,3,4,9-tetrahydro-1 H -β-carbolines: a new class of orally bioavailable mGluR1 antagonists Bioorg. Med. Chem. Lett. 2007, 17, 2254-2259
29. Kumar, A.; Katiyar, S. B.; Gupta, S.; Chauhan, P. M. S. Syntheses of new substituted triazino tetrahydroisoquinolines and β-carbolines as novel antileishmanial agents Eur. J. Med. Chem. 2006, 41, 106-113
30. Santos, L. S.; Theoduloz, C.; Pilli, R. A.; Rodriguez, J. Antiproliferative activity of arborescidine alkaloids and derivatives Eur. J. Med. Chem. 2009, 44, 3810-3815
31. Bahekar, R. H.; Jain, M. R.; Jadav, P. A.; Goel, A.; Patel, D. N.; Prajapati, V. M.; Gupta, A. A.; Modi, H.; Patel, P. R. Synthesis of 3,8,9-trisubstituted-1,7,9-triazafluorene-6-carboxylic acid derivatives as a new class of insulin secretagogues Bioorg. Med. Chem. 2007, 15, 5950-5964
32. Grella, B.; Teitler, M.; Smith, C.; Herrick-Davis, K.; Glennon, R. A. Binding of β-carbolines at 5-HT2 serotonin receptors Bioorg. Med. Chem. Lett. 2003, 13, 4421-4425 (Pubitemid 37490830)
33. Seefeld, M. A.; Miller, W. H.; Newlander, K. A.; Burgess, W. J.; Payne, D. J.; Rittenhouse, S. F.; Moore, T. D.; DeWolf, W. E., Jr.; Keller, P. M.; Qiu, X.; Janson, C. A.; Vaidya, K.; Fosberry, A. P.; Smyth, M. G.; Jaworski, D. D.; Slater-Radosti, C.; Huffman, W. F. Inhibitors of bacterial enoyl acyl carrier protein reductase (FabI): 2,9-disubstituted 1,2,3,4-tetrahydropyrido[3,4- b ]indoles as potential antibacterial agents Bioorg. Med. Chem. Lett. 2001, 11, 2241-2244 (Pubitemid 32781674)
34. Schott, Y.; Decker, M.; Rommelspacherb, H.; Lehmanna, J. 6-Hydroxy- and 6-methoxy-b-carbolines as acetyl- and butyryl- cholinesterase inhibitors Bioorg. Med. Chem. Lett. 2006, 16, 5840-5843
35. Dorey, G.; Dubois, L.; de Carvalho, L.P.; Potier, P.; Dodd, R. H. Synthetic routes to 4-amino-3-carboxy-β-carboline derivatives: Incidental formation of novel furo[3,4- c ]-β-carbolin-2-on displaying high affinities for the benzodiazepine receptor J. Med. Chem. 1995, 38, 189-198
36. Im, J.-H.; Jin, Y.-R.; Lee, J.-J.; Yu, J.-Y.; Han, X.-H.; Im, S.-H.; Hong, J. T.; Yoo, H.-S.; Pyo, M.-Y.; Yun, Y.-P. Antiplatelet activity of β-carboline alkaloids from Perganum harmala: A possible mechanism through inhibiting PLCγ2 phosphorylation Vasc. Pharmacol. 2009, 50, 147-152
37. Zhao, M.; Bi, L.; Bi, W.; Wang, C.; Yang, Z.; Ju, J.; Peng, S. Synthesis of new class dipeptide analogues with improved permeability and antithrombotic activity Bioorg. Med. Chem. 2006, 14, 4761-4774