Synthesis, ligand-receptor modeling studies and pharmacological evaluation of novel 4-modified-2-aryl-1,2,4-triazolo[4,3-a]quinoxalin-1-one derivatives as potent and selective human A3 adenosine receptor antagonists

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 11, 2008, Pages 6086-6102

  Colotta, Vittoria ^a   Catarzi, Daniela ^a   Varano, Flavia ^a   Lenzi, Ombretta ^a   Filacchioni, Guido ^a   Martini, Claudia ^b   Trincavelli, Letizia ^b   Ciampi, Osele ^b   Traini, Chiara ^c   Pugliese, Anna Maria ^c   Pedata, Felicita ^c   Morizzo, Erika ^d   Moro, Stefano ^d  

^a Laboratorio di Progettazione   (Italy)

^b Dipartmento di Biologia   (Italy)

^c UNIVERSITY OF FLORENCE   (Italy)

^d UNIVERSITY OF PADOVA   (Italy)

Author keywords

Adenosine receptor antagonists; G protein coupled receptors; Ligand receptor modeling studies; Neuroprotective agents; Triazolo 4,3 a quinoxalin 1 ones; Tricyclic heteroaromatic systems

Indexed keywords

4 BISMETHANESULFONYLAMINO 2 PHENYL 1,2,4 TRIAZOLO[4,3 A]QUINOXALIN 1 ONE; ADENOSINE A1 RECEPTOR; ADENOSINE A2 RECEPTOR; ADENOSINE A3 RECEPTOR ANTAGONIST; CYCLIC AMP; GLUCOSE; QUINOXALINE DERIVATIVE;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BRAIN ISCHEMIA; DEPOLARIZATION; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; HIPPOCAMPUS; IC 50; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION; SYNAPTIC TRANSMISSION;

ANIMALS; BINDING, COMPETITIVE; BRAIN ISCHEMIA; CATTLE; CELL MEMBRANE; CEREBRAL CORTEX; DISEASE MODELS, ANIMAL; HUMANS; HYDROGEN BONDING; LIGANDS; MODELS, MOLECULAR; PROTEIN BINDING; QUINOXALINES; RATS; RECEPTOR, ADENOSINE A3; RHODOPSIN; STRUCTURAL HOMOLOGY, PROTEIN; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES; XANTHINES;

RATTUS;

EID: 44449163019     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.04.039     Document Type: Article

References (72)

1. Fredholm B.B., IJzerman A.P., Jacobson K.A., Klotz K.N., and Linden J. Pharmacol. Rev. 53 (2001) 527
2. Jacobson, K. A.; Knutsen, L. J. S. In Purinergic and Pyrimidinergic Signalling; Abbracchio, M. P., Williams, M., Eds.; Handbook of Experimental Pharmacology: Berlin, 2001; Vol. 151/1, p 129.
3. Abbracchio M.P., Brambilla R., Kim H.O., von Lubitz D.K.J.E., Jacobson K.A., and Cattabeni F. Mol. Pharmacol. 48 (1995) 1083
4. Ali H., Choi O.H., Fraundorfer P.F., Yamada K., Gonzaga H.M.S., and Beaven M.A. J. Pharmacol. Exp. Ther. 276 (1996) 837
5. Shneyvays V., Leshem D., Zinman T., Mamedova L.K., Jacobson K.A., and Shainberg A. Am. J. Physiol. Heart Circ. Physiol. 288 (2005) H2792
6. Linden J. Trends Pharmacol. Sci. 15 (1994) 298
7. Liang B.T., and Jacobson K.A. Proc. Natl. Acad. Sci. U.S.A. 95 (1998) 6995
8. Young H.W., Molina J.G., Dimina D., Zhong H., Jacobson M., Chan L.N., Chan L.-N.L., Chan T.-S., Lee J.J., and Blackburn M.R. J. Immunol. 173 (2004) 1380
9. Merighi S., Mirandola P., Varani K., Gessi S., Leung E., Baraldi P.G., Tabrizi M.A., and Borea P.A. Pharmacol. Ther. 100 (2003) 31
10. Jacobson K.A., and Gao Z.-G. Nat. Rev. Drug Disc. 5 (2006) 247
11. Lee H.T., Ota-Setlik A., Xu H., D'Agati V.D., Jacobson M.A., and Emala C.W. Am. J. Physiol. Renal Physiol. 284 (2003) 267
12. Brambilla R., Cattabeni F., Ceruti S., Barbieri D., Franceschi C., Kim Y.-C., Jacobson K.A., Klotz K.-N., Lohse M.J., and Abbracchio M.P. Naunyn-Schmiedeberg's Arch. Pharmacol. 361 (2000) 225
13. Pugliese A.M., Coppi E., Spalluto G., Corradetti R., and Pedata F. Br. J. Pharmacol. 147 (2006) 524
14. Merighi S., Benini A., Mirandola P., Gessi S., Varani K., Leung E., Maclennan S., and Borea P.A. Biochem. Pharmacol. 72 (2006) 19
15. Colotta V., Catarzi D., Varano F., Cecchi L., Filacchioni G., Martini C., Trincavelli L., and Lucacchini A. J. Med. Chem. 43 (2000) 3118
16. Colotta V., Catarzi D., Varano F., Cecchi L., Filacchioni G., Martini C., Trincavelli L., and Lucacchini A. J. Med. Chem. 43 (2000) 1158
17. Colotta V., Catarzi D., Varano F., Filacchioni G., Martini C., Trincavelli L., and Lucacchini A. Bioorg. Med. Chem. 11 (2003) 3541
18. Colotta V., Catarzi D., Varano F., Filacchioni G., Martini C., Trincavelli L., and Lucacchini A. Bioorg. Med. Chem. 11 (2003) 5509
19. Colotta V., Catarzi D., Varano F., Calabri F.R., Lenzi O., Filacchioni G., Trincavelli L., Martini C., Deflorian F., and Moro S. J. Med. Chem. 47 (2004) 3580
20. Catarzi D., Colotta V., Varano F., Calabri F.R., Lenzi O., Filacchioni G., Trincavelli L., Martini C., Tralli A., Montopoli C., and Moro S. Bioorg. Med. Chem. 13 (2005) 705
21. Catarzi D., Colotta V., Varano F., Lenzi O., Filacchioni G., Trincavelli L., Martini C., Montopoli C., and Moro S. J. Med. Chem. 48 (2005) 7932
22. Lenzi O., Colotta V., Catarzi D., Varano F., Filacchioni G., Martini C., Trincavelli L., Ciampi O., Marighetti F., Morizzo E., and Moro S. J. Med. Chem. 49 (2006) 3916
23. Colotta V., Catarzi D., Varano F., Capelli F., Lenzi O., Filacchioni G., Martini C., Trincavelli L., Ciampi O., Pugliese A.M., Pedata F., Schiesaro A., Morizzo E., and Moro S. J. Med. Chem. 50 (2007) 40
24. Chang L.C.W., Brussee J., and IJzerman A.P. Chem. Biodivers. 1 (2004) 1591
25. Ukena D., Jacobson K.A., Padgett W.L., Ayala C., Shamim M.T., Kirk K.L., Olsson R.O., and Daly J.W. FEBS Lett. 209 (1986) 122
26. Muller C. Exp. Opin. Ther. Patents 7 (1997) 419
27. Moro S., Deflorian F., Spalluto G., Pastorin G., Cacciari B., Kim S.-K., and Jacobson K.A. Chem. Commun. (Camb.) 24 (2003) 2949
28. Moro S., Spalluto G., and Jacobson K.A. Trends Pharmacol. Sci. 26 (2005) 44
29. Moro S., Deflorian F., Bacilieri M., and Spalluto G. Curr. Med. Chem. 13 (2006) 639
30. Moro S., Bacilieri M., Deflorian F., and Spalluto G. New J. Chem. 30 (2006) 301
31. Moro S., Deflorian F., Bacilieri M., and Spalluto G. Curr. Pharm. Des. 12 (2006) 2175
32. Tafi A., Bernardini C., Botta M., Corelli F., Andreini M., Martinelli A., Ortore G., Baraldi P.G., Fruttarolo F., Borea P.A., and Tuccinardi T. J. Med. Chem. 49 (2006) 4085
33. Kim S.K., Gao Z.G., Jeong L.S., and Jacobson K.A. J. Mol. Graphics Modell. 25 (2006) 562
34. Jiang Q., Lee B.X., Glashofer M., van Rhee A.M., and Jacobson K.A. J. Med. Chem. 40 (1997) 2588
35. Jiang Q., Van Rhee A.M., Kim J., Yehle S., Wess J., et al. Mol. Pharmacol. 50 (1996) 512
36. Latini S., and Pedata F. J. Neurochem. 79 (2001) 463
37. Pugliese A.M., Coppi E., Volpini R., Cristalli G., Corradetti R., Jeong L.S., Jacobson K.A., and Pedata F. Biochem. Pharmacol. 74 (2007) 768
38. Obeidat A.S., and Andrew R.D. Eur. J. Neurosci. 10 (1998) 3451
39. Somjen G.G. Physiol. Rev. 81 (2001) 1065
40. Latini S., Bordoni F., Pedata F., and Corradetti R. Br. J. Pharmacol. 127 (1999) 729
41. Pearson T., Damian K., Lynas R.E., and Frenguelli B.G. J. Neurochem. 97 (2006) 1357
42. Jeong L.S., Choe S.A., Gunaga P., Kim H.O., Lee H.W., Lee S.K., Tosh D., Patel A., Palaniappan K.K., Gao Z.G., Jacobson K.A., and Moon H.R. J. Med. Chem. 50 (2007) 3159
43. Li A.-H., Moro S., Melman N., Ji X.-d., and Jacobson K.A. J. Med. Chem. 41 (1998) 3186
44. Kim Y.-C., Ji X.-d., and Jacobson K.A. J. Med. Chem. 39 (1996) 4142
45. Maconi A., Pastorin G., da Ros T., Spalluto G., Gao Z.-G., Jacobson K.A., Baraldi P.G., Cacciari B., Varani K., Moro S., and Borea P.A. J. Med. Chem. 45 (2002) 3579
46. Ji X.D., Gallo-Rodrighuez C., and Jacobson K.A. Biochem. Biophys. Res. Commun. 203 (1994) 570
47. von Lubitz D.K. Eu. J. Pharmacol. 263 (1999) 59
48. Tanaka E., Yamamoto S., Kudo Y., Mihara S., and Higashi H. J. Neurophysiol. 78 (1997) 891
49. Yamamoto S., Tanaka E., Shoji Y., Kudo Y., Inokuchi H., and Higashi H. J. Neurophysiol. 78 (1997) 903
50. Nieber, K.; Hentschel, S. In Proceedings of the 8th International Symposium on Adenosine and Adenine Nucleotides, Ferrara, Italy, May 24-28, 2006.
51. Macek T.A., Schaffhauser H., and Conn P.J. J. Neurosci. 18 (1998) 6138
52. Yli-Kauhaluoma J.T., Ashkey J.A., Lo C.-H., Tuker L., Wolfe M.M., and Janda K.D. J. Am. Chem. Soc. 117 (1995) 7041
53. Yu D.-W., Gatley S.J., Wolf A.P., MacGregor R.R., Dewey S.L., Fowler J.S., and Schlyer D.J. J. Med. Chem. 35 (1992) 2178
54. Schnetteler R.A., Dage R.C., and Palopoli F.P. J. Med. Chem. 29 (1986) 860
55. OpenMosix: http://www.openMosix.org, 2004.
56. MOE (The Molecular Operating Environment) Version 2006.08, software available from Chemical Computing Group Inc., 1010 Sherbrooke Street West, Suite 910, Montreal, Canada H3A 2R7. http://www.chemcomp.com.
57. MOPAC 7, J.J.P. Stewart, Fujitsu Limited, Tokyo, Japan, 1993.
58. Palczewski K., Kumasaka T., Hori T., Behnke C.A., Motoshima H., et al. Science 289 (2000) 739
59. Cornell W.D.C.P., Bayly C.I., Gould I.R., Merz K.M., Ferguson D.M., Spellmeyer D.C., Fox T., Caldwell J.W., and Kollman P.A. J. Am. Chem. Soc. 117 (1995) 5179
60. Levitt M. J. Mol. Biol. 226 (1992) 507
61. Baxter C.A., Murray C.W., Clark D.E., Westhead D.R., and Eldridge M.D. Funct. Genet. 33 (1998) 367
62. Halgren T. J. Comput. Chem. 17 (1996) 490
63. Manetti F., Schenone S., Bondavalli F., Brullo C., Bruno O., Ranise A., Mosti L., Menozzi G., Fossa P., Trincavelli M.L., Martini C., Martinelli A., Tintori C., and Botta M. J. Med. Chem. 48 (2005) 7172
64. Colotta V., Catarzi D., Varano F., Melani F., Filacchioni G., Cecchi L., Trincavelli L., Martini C., and Lucacchini A. Farmaco 53 (1998) 189
65. Novellino E., Cosimelli B., Ehlardo M., Greco G., Iadanza M., Lavecchia A., Rimoli M.G., Sala A., Da Settimo A., Primofiore G., Da Settimo F., Taliani S., La Motta C., Klotz K.-N., Tuscano D., Trincavelli M.L., and Martini C. J. Med. Chem. 48 (2005) 8253
66. Klotz K.-N., Vogt H., and Tawfik-Schlieper H. Naunyn-Schmiedeberg's Arch Pharmacol. 343 (1991) 196
67. Mazzoni M.R., Buffoni R.S., Giusti L., and Lucacchini A. J. Recept. Signal Transduct. Res. 15 (1995) 905
68. Nordstedt C., and Fredholm B. Anal. Biochem. 189 (1990) 231
69. Cheng Y.C., and Prusoff W.H. Biochem. Pharmacol. 22 (1973) 3099
70. Pugliese A.M., Latini S., Corradetti R., and Pedata F. Br. J. Pharmacol. 140 (2003) 305
71. Anderson W.W., and Collingridge G.L. J. Neurosci. Methods 108 (2001) 7
72. Pedata F., Latini S., Pugliese A.M., and Pepeu G. J. Neurochem. 61 (1993) 284