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Research Article

Studies on the antiplatelet and antithrombotic profile of anti-inflammatory coumarin derivatives

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Pages 925-933 | Received 16 Oct 2014, Accepted 16 Nov 2014, Published online: 25 Mar 2015

References

  • Sattari M, Lowenthal DT. Novel oral anticoagulants in development: Dabigatran, Rivaroxaban, and Apixaban. Am J Ther 2011;18:332–8
  • Alvarez R, Taylor A, Fazzari JJ, Jacobs JR. Regulation of cyclic AMP metabolism in human platelets. Sequential activation of adenylate cyclase and cyclic AMP phosphodiesterase by prostaglandins. Mol Pharmacol 1981;20:302–9
  • Tani T, Sakurai K, Kimura Y, et al. Pharmacological manipulation of tissue cyclic AMP by inhibitors. Effects of phosphodiesterase inhibitors on the functions of platelets and vascular endothelial cells. Adv Second Messenger Phosphoprotein Res 1992;25:215–27
  • Angiolillo DJ. The evolution of antiplatelet therapy in the treatment of acute coronary syndromes: from aspirin to the present day. Drugs 2012;72:2087–116
  • Wijeyeratne YD, Heptinstall S. Anti-platelet therapy: ADP receptor antagonists. Br J Clin Pharmacol 2011;72:647–57
  • Schneider DJ. Anti-platelet therapy: glycoprotein IIb-IIIa antagonists. Br J Clin Pharmacol 2011;72:672–82
  • Rondina MT, Weyrich AS. Targeting phosphodiesterases in anti-platelet therapy. Handb Exp Pharmacol 2012;210:225–38
  • Egan D, O'Kennedy R, Moran E, et al. The pharmacology, metabolism, analysis, and applications of coumarin and coumarin-related compounds. Drug Metab Rev 1990;22:503–29
  • Kimura Y, Tani T, Kanbe T, Watanabe K. Effect of cilostazol on platelet aggregation and experimental thrombosis. Arzneimittelforschung 1985;35:1144–9
  • Murray RDH, Mendez I, Brawn SA. The natural coumarins. New York: Wiley; 1982
  • Catto M, Pisani L, Leonetti F, et al. Design, synthesis and biological evaluation of coumarin alkylamines as potent and selective dual binding site inhibitors of acetylcholinesterase. Bioorg Med Chem 2013;21:146–52
  • Fylaktakidou KC, Hadjipavlou-Litina DJ, Litinas KE, Nicolaides DN. Natural and synthetic coumarin derivatives with anti-inflammatory/antioxidant activities. Curr Pharm Des 2004;10:3813–33
  • Wilkinson P. New oral anticoagulants: an alternative to warfarin. Br J Hosp Med (Lond) 2012;7:498–501
  • Deitelzweig S, Jaff MR. Medical management of venous thromboembolic disease. Tech Vasc Interv Radiol 2004;7:63–7
  • Pochet L, Doucet C, Schynts M, et al. Esters and amides of 6-(chloromethyl)-2-oxo-2H-1-benzopyran-3-carboxylic acid as inhibitors of alpha-chymotrypsin: significance of the “aromatic” nature of the novel ester-type coumarin for strong inhibitory activity. J Med Chem 1996;39:2579–85
  • Pochet L, Doucet C, Dive G, et al. Coumarinic derivatives as mechanism-based inhibitors of alpha-chymotrypsin and human leukocyte elastase. Bioorg Med Chem 2000;8:1489–501
  • Wouters J, Huygens M, Pochet L, et al. Structural approach of the mechanism of inhibition of alpha-chymotrypsin by coumarins. Bioorg Med Chem Lett 2002;12:1109–12
  • Frédérick R, Robert S, Charlier C, et al. 3,6-Disubstituted coumarins as mechanism-based inhibitors of thrombin and factor Xa. J Med Chem 2005;48:7592–603
  • Bruno O, Brullo C, Schenone S, et al. Synthesis, antiplatelet and antithrombotic activities of new 2-substituted benzopyrano[4,3-d]pyrimidin-4-cycloamines and 4-amino/cycloamino-benzopyrano[4,3-d]pyrimidin-5-ones. Bioorg Med Chem 2006;14:121–30
  • Bruno O, Brullo C, Schenone S, et al. Synthesis and pharmacological evaluation of 5H-[1]benzopyrano[4,3-d]pyrimidines effective as antiplatelet/analgesic agents. Bioorg Med Chem 2004;12:553–61
  • Roma G, Cinone N, Di Braccio M, et al. Synthesis, antiplatelet activity and comparative molecular field analysis of substituted 2-amino-4H-pyrido[1,2-a]pyrimidin-4-ones, their congeners and isosteric analogues. Bioorg Med Chem 2000;8:751–68
  • Kontogiorgis CA, Hadjipavlou-Litina DJ. Synthesis and antiinflammatory activity of coumarin derivatives. J Med Chem 2005;48:6400–8
  • Kontogiorgis CA, Hadjipavlou-Litina DJ. Synthesis and biological evaluation of novel coumarin derivatives with a 7-azomethine linkage. Bioorg Med Chem Lett 2004;14:611–14
  • Kontogiorgis CA, Savvoglou K, Hadjipavlou-Litina DJ. Antiinflammatory and antioxidant evaluation of novel coumarin derivatives. J Enzyme Inhib Med Chem 2006;21:21–9
  • Kontogiorgis CA, Hadjipavlou Litina D. Nitric oxide release from coumarin-7-azomethine derivatives in the presence of thiol. Arzneimittelforschung 2007;57:143–6
  • Born GV. Aggregation of blood platelets by adenosine diphosphate and its reversal. Nature 1962;194:927–9
  • Bellavite P, Andrioli G, Guzzo P, et al. A colorimetric method for the measurement of platelet adhesion in microtiter plates. Anal Biochem 1994;216:444–50
  • Davidson I, Henry JB. Clinical diagnosis of laboratory methods. 15th ed. Philadelphia: WB Sanders Company;1974:438–9
  • Apodaca R, Dvorak CA, Xiao W, et al. A new class of diamine-based human histamine H3 receptor antagonists: 4-(aminoalkoxy)benzylamines. J Med Chem 2003;46:3938–44
  • Denizot F, Lang R. Rapid colorimetric assay for cell growth and survival. Modifications to the tetrazolium dye procedure giving improved sensitivity and reliability. J Immunol Methods 1986;89:271–7
  • Nicolotti O, Carotti A. QSAR and QSPR studies of a highly structured physicochemical domain. J Chem Inf Model 2006;46:264–76
  • Nicolotti O, Benfenati E, Carotti A, et al. REACH and in silico methods: an attractive opportunity for medicinal chemists. Drug Disc Today 2014;19:1757–68
  • Gissi A, Gadaleta D, Floris M, et al. An alternative QSAR-based approach for predicting the bioconcentration factor for regulatory purposes. Altex 2014;31:23–36
  • C-QSAR, version 4 31. Claremont (CA): Biobyte Corp.; 2003. Available from: www.biobyte.com [last accessed Nov 2013]
  • Hansch C, Leo AJ. Exploring QSAR fundamentals and applications in chemistry and biology. In: Heller SR, ed. ACS Professional Reference Book. Washington DC: American Chemical Society. 1995:279–80
  • Cramer RD, Patterson DE, Bunce JD. Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J Am Chem Soc 1988;110:5959–67
  • SPARTAN SGI, version 5.1.3 OpenGL. Irvine (CA): Wavefunction, Inc
  • Dewar MJS, Zoebisch EG, Healy EF, Stewart JJP. Development and use of quantum mechanical molecular models. 76.AM1: a new general purpose quantum mechanical molecular model. J Am Chem Soc 1985;107:3902–9
  • Halggren TA. Merck molecular force field I. Basis, form, scope, parameterization and performance of MMFF94. J Comput Chem 1996;17:490–519
  • Stewart JJP. Optimization of parameters for semi-empirical methods I-Method. J Comp Chem 1989;10:209–20
  • Scapin G, Patel SB, Chung C, et al. Crystal structure of human phosphodiesterase 3B: atomic basis for substrate and inhibitor specificity. Biochemistry 2004;43:6091–100
  • http://www.pdb.org
  • USCF CHIMERA. University of California, San Francisco, CA, USA; 1994. Available from: http://www.cgl.ucsf.edu/chimera [last accessed 10 Feb 2010]
  • Lindorff Larsen K, Piana S, et al. Improved side-chain torsion potentials for the Amber ff99SB protein force field. Proteins 2010;78:1950–8
  • Wang J, Wolf RM, Caldwell JW, et al. Development and testing of a general amber force field. J Comput Chem 2004;25:1157–74
  • OpenBabel, version 2.2.3, Open Source Chemistry Toolbox. OELib Cheminformatics Company, USA; 2006. Available from: http://sourceforge.net/projects/openbabel [last accessed 10 Feb 2010]
  • Autodock Vina v. 1.1.1., The Scripps Research Institute, San Diego, CA, USA; 2010. Copyright© 1989–2010
  • Jin J, Kunapuli SP. Coactivation of two different G protein-coupled receptors is essential for ADP-induced platelet aggregation. Proc Natl Acad Sci USA 1998;95:8070–4
  • Nurtjahja-Tjendraputra E, Ammit AJ, Roufogalis BD, et al. Effective anti-platelet and COX-1 enzyme inhibitors from pungent constituents of ginger. Thromb Res 2003;111:259–65
  • Eisert WG. Near-field amplification of antithrombotic effects of dipyridamole through vessel wall cells. Neurology 2001;57:S20–3
  • Nicolotti O, Giangreco I, Miscioscia TF, Carotti A. Improving quantitative structure-activity relationships through multiobjective optimization. J Chem Inf Model 2009;49:2290–302

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