Chalcone-based derivatives as new scaffolds for hA3 adenosine receptor antagonists

Journal of Pharmacy and Pharmacology

Volumn 65, Issue 5, 2013, Pages 697-703

  Vazquez Rodriguez, Saleta ^a   Matos, Maria João ^a,b   Santana, Lourdes ^a   Uriarte, Eugenio ^a   Borges, Fernanda ^b   Kachler, Sonja ^c   Klotz, Karl Norbert ^c  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b UNIVERSITY OF PORTO   (Portugal)

^c UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

adenosine receptor; chalcone; coumarin chalcone hybrids; structure activity relationship

Indexed keywords

3 [3 (THIOPHEN 3 YL)ACRYLOYL]COUMARIN; 4 HYDROXY 3 [3 (THIOPHEN 3 YL)ACRYLOYL]COUMARIN; 7 HYDROXY 8 [3 (4 METHOXYPHENYL)ACRYLOYL]COUMARIN; 7 HYDROXY 8 [3 (THIOPHEN 3 YL)ACRYLOYL]COUMARIN; ADENOSINE A1 RECEPTOR; ADENOSINE A2A RECEPTOR; ADENOSINE A2B RECEPTOR; ADENOSINE A3 RECEPTOR; ADENYLATE CYCLASE; CHALCONE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; IC 50; NONHUMAN;

ANIMALS; BINDING, COMPETITIVE; CHALCONE; CHO CELLS; COUMARINS; CRICETINAE; CRICETULUS; HUMANS; LIGANDS; PURINERGIC P1 RECEPTOR ANTAGONISTS; RADIOLIGAND ASSAY; RECEPTOR, ADENOSINE A1; RECEPTOR, ADENOSINE A2A; RECEPTOR, ADENOSINE A2B; RECEPTOR, ADENOSINE A3; STRUCTURE-ACTIVITY RELATIONSHIP; THIOPHENES;

EID: 84876471857     PISSN: 00223573     EISSN: 20427158     Source Type: Journal    
DOI: 10.1111/jphp.12028     Document Type: Article

References (42)

1. Poulsen SA, Quinn RJ,. Adenosine receptors: new opportunities for future drugs. Bioorg Med Chem 1998; 6: 619-641.
2. Fredholm BB, et al. International union of pharmacology. XXV. Nomenclature and classification of adenosine receptors. J Pharmacol Rev 2001; 53: 527-552.
3. Fredholm BB, et al. Structure and function of adenosine receptors and their genes. Arch Pharmacol 2000; 362: 364-374.
4. Klotz K-N,. Adenosine receptors and their ligands. Naunyn Schmiedebergs Arch Pharmacol 2000; 362: 382-391.
5. Baraldi PG, et al. A3 adenosine receptor ligands: history and perspectives. Med Res Rev 2000; 20: 103-128.
6. Baraldi PG,. Recent improvements in the development of A2B adenosine receptor agonists. Purinergic Signal 2009; 5: 3-19.
7. Jacobson KA, et al. Preparation of N6-benzyladenosine-5'-uronamides, modified xanthine ribosides, and related compounds as adenosine A3 receptor agonists. WO 9502604 A1 19950126. Patent 1995.
8. Feoktistov I, et al. Adenosine A2B receptors as therapeutic targets. Drug Dev Res 1998; 45: 198-206.
9. Jacobson KA,. Adenosine A3 receptors: novel ligands and paradoxical effects. Trends Pharmacol Sci 1998; 19: 184-195.
10. Gessi S, et al. Elevated expression of A3 adenosine receptors in human colorectal cancer is reflected in peripheral blood cells. Clin Cancer Res 2004; 10: 5895-5901.
11. Jacobson KA, Gao ZG,. Adenosine receptors as therapeutic targets. Nat Rev Drug Discov 2006; 49: 247-264.
12. Kim Y, et al. Novel 2- and 4-substituted 1H-imidazo[4,5-c]quinolin-4- amine derivatives as allosteric modulators of the A3 adenosine receptor. J Med Chem 2009; 52: 2098-2108.
13. Sitkovsky MV, et al. Physiological control of immune response and inflammatory tissue damage by hypoxia-inducible factors and adenosine A2A receptors. Annu Rev Immunol 2004; 22: 657-682.
14. Lappas CM, et al. Adenosine A2A agonists in development for the treatment of inflammation. Expert Opin Investig Drugs 2005; 14: 797-806.
15. Shah R, Frishman WH,. Adenosine1 receptor antagonism: a new therapeutic approach for the treatment of decompensated heart failure. Cardiol Rev 2009; 17: 125-131.
16. Shook BC, et al. Design and characterization of optimized adenosine A2A/A1 receptor antagonists for the treatment of Parkinson's disease. J Med Chem 2012; 55: 1402-1417.
17. Stone TW, et al. Adenosine receptors and neurological disease: neuroprotection and neurodegeneration. Handb Exp Pharmacol 2009; 193: 535-597.
18. Baraldi PG, et al. Adenosine receptor antagonists: translating medicinal chemistry and pharmacology into clinical utility. Chem Rev 2008; 108: 238-263.
19. Moro S, et al. Progress in the pursuit of therapeutic adenosine receptor antagonists. Med Res Rev 2006; 26: 131-159.
20. Okajima F, et al. Genistein, an inhibitor of protein tyrosine kinase, is also a competitive antagonist for P1-purinergic (adenosine) receptor in FRTL-5 thyroid cells. Biochem Biophys Res Commun 1994; 203: 1488-1495.
21. Jacobson KA, et al. Interactions of flavones and other phytochemicals with adenosine receptors. Adv Exp Med Biol 2002; 505: 163-171.
22. Borges F, et al. Simple coumarins and analogues in medicinal chemistry: occurrence, synthesis and biological activity. Curr Med Chem 2005; 12: 887-916.
23. Go ML, et al. Chalcones: an update on cytotoxic and chemoprotective properties. Curr Med Chem 2005; 12: 483-495.
24. Nowakowska Z,. A review of anti-infective and anti-inflammatory chalcones. Eur J Med Chem 2007; 42: 125-137.
25. Bryskier A, Klich M,. Coumarin antibiotics: novobiocin, coumermycin, and clorobiocin. In: Bryskier A, ed. Antimicrob Agents Washington, DC, USA: American Society for Microbiology Press 2005: 816-825.
26. Viña D, et al. 3-Substituted coumarins as dual inhibitors of AChE and MAO for the treatment of Alzheimer's disease. Med Chem Comm 2012; 3: 213-218.
27. Matos MJ, et al. Synthesis and study of a SEries of 3-arylcoumarins as Potent and selective monoamine oxidase B inhibitors. J Med Chem 2011; 54: 7127-7137.
28. Matos MJ, et al. New halogenated phenylcoumarins as tyrosinase inhibitors. Bioorg Med Chem Lett 2011; 21: 3342-3345.
29. Sashidhara KV, et al. Synthesis and in vitro evaluation of novel coumarin-chalcone hybrids as potential anticancer agents. Bioorg Med Chem Lett 2010; 20: 7205-7211.
30. Vukovic N, et al. An efficient synthesis and antioxidant properties of novel imino and amino derivatives of 4-hydroxycoumarins. Arch Pharm Res 2010; 33: 5-15.
31. Vogel S, et al. Natural and non-narural prenylated chalcones: synthesis, cytotoxicity and anti-oxidative activity. Bioorg Med Chem 2008; 16: 4286-4293.
32. Chimenti F, et al. Chalcones: a valid scaffold for monoamine oxidases inhibitors. J Med Chem 2009; 52: 28218-22824.
33. Liu XH, et al. Synthesis and molecular docking study of novel coumarin derivatives containing 4,5-dihydropyrazole moiety as potential antitumor agents. Biorg Med Chem Lett 2010; 20: 5705-5708.
34. Sugino T, Tanaka K,. Solvent-free coumarin synthesis. Chem Lett 2001; 30: 110-111.
35. Hamdi N, et al. A rapid access to new coumarinyl chalcone and substituted chromeno[4,3-c]pyrazol-4(1H)-ones and their antibacterial and DPPH radical scavenging activities. Med Chem Res 2011; 20: 522-530.
36. Klotz KN, et al. Comparative pharmacology of human adenosine receptor subtypes-characterization of stably transfected receptors in CHO cells. Naunyn Schmiedebergs Arch Pharmacol 1998; 357: 1-9.
37. 3 receptor. Eur J Pharmacol 2007; 556: 14-18.
38. i) and the concentration of inhibitor which causes fifty per cent inhibition (I50) of an enzymic reaction. Biochem Pharmacol 1973; 22: 3099-3108.
39. De Lean A, et al. Validation and statistical analysis of a computer modeling method for quantitative analysis of radioligand binding data for mixtures of pharmacological receptor subtypes. Mol Pharmacol 1982; 21: 5-16.
40. M Cheminformatics, Bratislava, Slovak Republic. 2009. http://www.molinspiration.com/services/properties.html
41. Lipinski CA, et al. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 1997; 23: 3-25.
42. Ertl P, et al. Fast calculation of molecular polar surface area as a sum of fragment-based contributions and its application to the prediction of drug transport properties. J Med Chem 2000; 43: 3714-3717.