Novel potent and highly selective human A3 adenosine receptor antagonists belonging to the 4-amido-2-arylpyrazolo[3,4-c]quinoline series: Molecular docking analysis and pharmacological studies

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 1, 2009, Pages 401-410

  Colotta, Vittoria ^a   Capelli, Francesca ^a   Lenzi, Ombretta ^a   Catarzi, Daniela ^a   Varano, Flavia ^a   Poli, Daniela ^a   Vincenzi, Fabrizio ^b   Varani, Katia ^b   Borea, Pier Andrea ^b   Dal Ben, Diego ^c   Volpini, Rosaria ^c   Cristalli, Gloria ^c   Filacchioni, Guido ^a  

^a Laboratorio di Progettazione   (Italy)

^b UNIVERSITY OF FERRARA   (Italy)

^c UNIVERSITY OF CAMERINO   (Italy)

Author keywords

Adenosine receptor antagonists; G protein coupled receptors; Ligand receptor modeling studies; Pyrazoloquinolines; Tricyclic heteroaromatic systems

Indexed keywords

ADENOSINE A3 RECEPTOR ANTAGONIST; PYRAZOLOQUINOLINE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MOLECULAR DOCKING; NONHUMAN; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

AMIDES; COMPUTER SIMULATION; HUMANS; MODELS, MOLECULAR; PROTEIN BINDING; QUINOLINES; RECEPTOR, ADENOSINE A3; RHODOPSIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 57649224232     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.10.018     Document Type: Article

References (47)

1. Jacobson K.A., and Knutsen L.J.S. In: Abbracchio M.P., and Williams M. (Eds). Handbook of Experimental Pharmacology: Purinergic and Pyrimidinergic Signalling I Vol. 151 (2001), Springer, Berlin 129
2. Fredholm B.B., Ijzerman A.P., Jacobson K.A., Klotz K.N., and Linden J. Pharmacol. Rev. 53 (2001) 527
3. Abbracchio M.P., Brambilla R., Ceruti S., Kim H.O., von Lubitz D.K., Jacobson K.A., and Cattabeni F. Mol. Pharmacol. 48 (1995) 1038
4. Ali H., Choi O.H., Fraundorfer P.F., Yamada K., Gonzaga H.M., 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. Schulte G., and Fredholm B.B. Cell Signal. 15 (2003) 813
7. 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
8. Merighi S., Mirandola P., Varani K., Gessi S., Leung E., Baraldi P.G., Tabrizi M.A., and Borea P.A. Pharmacol. Ther. 100 (2003) 48
9. Merighi S., Benini A., Mirandola P., Gessi S., Varani K., Leung E., Maclennan S., and Borea P.A. Biochem. Pharmacol. 72 (2006) 19
10. 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) F267
11. Yang H., Avila M.Y., Peterson-Yantorno K., Coca-Prados M., Stone R.A., Jacobson K.A., and Civan M.M. Curr. Eye Res. 30 (2005) 747
12. Pugliese A.M., Coppi E., Spalluto G., Corradetti R., and Pedata F. Br. J. Pharmacol. 147 (2006) 524
13. 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
14. 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) 4061
15. Colotta V., Catarzi D., Varano F., Cecchi L., Filacchioni G., Martini C., Trincavelli L., and Lucacchini A.J. Med. Chem. 43 (2000) 1158
16. Colotta V., Catarzi D., Varano F., Cecchi L., Filacchioni G., Martini C., Trincavelli L., and Lucacchini A.J. Med. Chem. 43 (2000) 3118
17. Colotta V., Catarzi D., Varano F., Calabri F.R., Lenzi O., Filacchioni G., Martini C., Trincavelli L., Deflorian F., and Moro S.J. Med. Chem. 47 (2004) 3580
18. Catarzi D., Colotta V., Varano F., Lenzi O., Filacchioni G., Trincavelli L., Martini C., Montopoli C., and Moro S. Med. Chem. 48 (2005) 7932
19. Lenzi O., Colotta V., Catarzi D., Varano F., Filacchioni G., Martini C., Trincavelli L., Ciampi O., Varani K., Marighetti F., Morizzo E., and Moro S.J. Med. Chem. 49 (2006) 3916
20. Morizzo E., Capelli F., Lenzi O., Catarzi D., Varano F., Filacchioni G., Vincenzi F., Varani K., Borea P.A., Colotta V., and Moro S.J. Med. Chem. 50 (2007) 6596
21. Casnati G., and Ricca A. Gazz. Chim. Ital. 93 (1963) 355
22. Robert J.M.H., Robert-Piessard S., Courant J., Le Baut G., Robert B., Lang F., Petit J.Y., Grimaud N., and Welin L. Eur. J. Med. Chem. 30 (1995) 915
23. Dunn G.E., Lawler E.A., and Yamashita A.B. Can. J. Chem. 55 (1977) 2478
24. Tagawa Y., Yamashita K., Higuchi Y., and Goto Y. Heterocycles 60 (2003) 953
25. Moro S., Spalluto G., and Jacobson K.A. Trends Pharmacol. Sci. 26 (2005) 44
26. Molecular Operating Environment (MOE 2007.09); C.C.G., Inc., 1255 University St., Suite 1600, Montreal, Quebec, Canada H3B 3X3.
27. 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
28. Moro S., Braiuca P., Deflorian F., Ferrari C., Pastorin G., Cacciari B., Baraldi P.G., Varani K., Borea P.A., and Spalluto G.J. Med. Chem. 48 (2005) 152
29. Stewart J.J. J. Comput. Aided Mol. Des. 4 (1990) 1
30. Okada T., Fujiyoshi Y., Silow M., Navarro J., Landau E.M., and Shichida Y. Proc. Natl. Acad. Sci. U.S.A. 99 (2002) 5982
31. Cornell W.D., Cieplak 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. Am. Chem. Soc. 117 (1995) 5179
32. Halgren T.A.J. Comput. Chem. 17 (1996) 490
33. Halgren T.A.J. Comput. Chem. 17 (1996) 520
34. Halgren T.A.J. Comput. Chem. 17 (1996) 553
35. Halgren T.A.J. Comput. Chem. 17 (1996) 587
36. Halgren T.A., and Nachbar R.J. Comput. Chem. 17 (1996) 616
37. Halgren T.A.J. Comput. Chem. 20 (1999) 720
38. Halgren T.A.J. Comput. Chem. 20 (1999) 730
39. Hou T.J., Xia K., Zhang W., and Xu X.J.J. Chem. Inf. Comput. Sci. 44 (2004) 266
40. Lipinski C.A., Lombardo F., Dominy B.W., and Feeney P.J. Adv. Drug Deliv. Rev. 23 (1997) 3
41. Borea P.A., Dalpiaz A., Varani K., Gessi S., and Gilli G. Life Sci. 59 (1996) 1373
42. Varani K., Rigamonti D., Sipione S., Camurri A., Borea P.A., Cattabeni F., Abbracchio M.P., and Cattaneo E. FASEB J. 15 (2001) 1245
43. Varani K., Cacciari B., Baraldi P.G., Dionisotti S., Ongini E., and Borea P.A. Life Sci. 63 (1998) 81
44. Varani K., Gessi S., Merighi S., Vincenzi F., Cattabriga E., Benini A., Klotz K.N., Baraldi P.G., Tabrizi M.A., Lennan S.M., Leung E., and Borea P.A. Biochem. Pharmacol. 70 (2005) 1601
45. Bradford M.M. Anal. Biochem. 72 (1976) 248
46. Cheng Y., and Prusoff W.H. Biochem. Pharmacol. 22 (1973) 3099
47. Munson P.J., and Rodbard D. Anal. Biochem. 107 (1980) 220