QSAR of adenosine receptor antagonists: Exploring physicochemical requirements for binding of pyrazolo[4,3-e]-1,2,4-triazolo[1,5-c]pyrimidine derivatives with human adenosine A 3 receptor subtype

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 2, 2011, Pages 818-823

  Pran Kishore, D ^a   Balakumar, C ^a   Raghuram Rao, A ^a   Roy, Partha Pratim ^b   Roy, Kunal ^b  

^a PANJAB UNIVERSITY   (India)

^b JADAVPUR UNIVERSITY   (India)

Author keywords

Adenosine A 3 receptor; G PLS; GFA; Pyrazolotriazolopyrimidines; QSAR

Indexed keywords

ADENOSINE A3 RECEPTOR; ADENOSINE RECEPTOR BLOCKING AGENT; PYRAZOLO[4,3 E] 1,2,4 TRIAZOLO[1,5 C]PYRIMIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CARBAMOYLATION; DRUG RECEPTOR BINDING; MOLECULAR MODEL; PHYSICAL CHEMISTRY; QUANTITATIVE STRUCTURE ACTIVITY RELATION; THERMODYNAMICS;

ADENOSINE A3 RECEPTOR ANTAGONISTS; HUMANS; MODELS, MOLECULAR; PROTEIN BINDING; PYRIMIDINES; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RECEPTOR, ADENOSINE A3; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES;

HUMAN ECHOVIRUS 1;

EID: 78651226072     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.11.094     Document Type: Article

References (81)

1. B.B. Fredholm, A.P. Ijzerman, K.A. Jacobson, K.N. Klotz, and J. Linden Pharmacol. Rev. 53 2001 527
2. K.A. Jacobson, and Z.G. Gao Nat. Rev. Drug Disc. 5 2006 247
3. S. Moro, Z.G. Gao, K.A. Jacobson, and G. Spalluto Med. Res. Rev. 26 2006 131
4. C.E. Muller, and T. Scior Pharm. Acta Helv. 68 1993 77
5. C.E. Muller Curr. Med. Chem. 7 2000 1269
6. S.E. Keeling, F.D. Albinson, B.E. Ayres, P.R. Butchers, C.L. Chambers, P.C. Cherry, F. Ellis, G.B. Ewan, M. Gregson, J. Knight, K. Mills, P. Ravenscroft, L.H. Reynolds, S. Sanjar, and M.J. Sheehan Bioorg. Med. Chem. Lett. 10 2000 403
7. C.E. Muller Drugs Future 25 2000 1043
8. C.E. Muller, M. Thorand, R. Qurishi, M. Diekmann, K.A. Jacobson, W.L. Padgett, and J.W. Daly J. Med. Chem. 45 2002 3440
9. C.E. Muller Mini-Rev. Med. Chem. 1 2001 433
10. W. Meyerhof, R.M. Brechlin, and D. Richter FEBS Lett. 284 1991 155
11. F.G. Sajjadi, and G.S. Firestein Biochim. Biophys. Acta 1179 1993 105
12. C.A. Salvatore, M.A. Jacobson, H.E. Taylor, J. Linden, and R.G. Johnson Proc. Natl. Acad. Sci. U.S.A. 90 1993 10365
13. J. Linden, H.E. Taylor, A.S. Robeva, A.L. Tucker, J. Stehle, S.A. Rivkees, J.S. Fink, and S.M. Reppert Mol. Pharmacol. 44 1993 524
14. Z.H. Zhao, S. Ravid, and K. Ravid Genomics 30 1995 118
15. R.J. Hill, J.J. Oleynek, C.F. Hoth, M.A. Kiron, W.F. Weng, R.T. Wester, W.R. Tracey, D.R. Knight, R. Buchholz, and S.P. Kennedy J. Pharmacol. Exp. Ther. 280 1997 122
16. J. Linden Trends Pharmacol. Sci. 15 1994 298
17. K.A. Jacobson Trends Pharmacol. Sci. 19 1998 184
18. P.G. Baraldi, B. Cacciari, S. Moro, R. Romagnoli, J. Xiao-duo, K.A. Jacobson, S. Gessi, P.A. Borea, and G. Spalluto J. Med. Chem. 44 2001 2735
19. C.E. Muller Curr. Top. Med. Chem. 3 2003 445
20. M.P. Abbracchio, R. Brambilla, H.O. Kim, K.A. Jacobson, and F. Cattabeni Mol. Pharmacol. 48 1995 1083
21. M. Parsons, L. Young, J.E. Lee, K.A. Jacobson, and B.T. Liang FASEB J. 14 2000 1423
22. H. Ali, O.H. Choi, P.F. Fraundorfer, K. Yamada, H.M.S. Gonzaga, and M.A. Beaven J. Pharmacol. Exp. Ther. 276 1996 837
23. V. Shneyvays, D. Leshem, T. Zinman, L.K. Mamedova, K.A. Jacobson, and A. Shainberg Am. J. Physiol. Heart Circ. Physiol. 288 2005 2792
24. M. Englert, U. Quitterer, and K.N. Klotz Biochem. Pharmacol. 64 2002 61
25. G. Schulte, and B.B. Fredholm Cell. Signalling 15 2003 813
26. R. Brambilla, F. Cattabeni, S. Ceruti, D. Barbieri, C. Franceschi, Y.-C. Kim, K.A. Jacobson, K.N. Klotz, M.J. Lohse, and M.P. Abbracchio Arch. Pharmacol. 361 2000 225
27. S. Gessi, S. Merighi, K. Varani, E. Leung, S. Mac Lennan, and P.A. Borea Pharmacol. Ther. 117 2008 123
28. S. Merighi, P. Mirandola, K. Varani, S. Gessi, E. Leung, P.G. Baraldi, M. Tabrizi, and P.A. Borea Pharmacol. Ther. 100 2003 31
29. L. Madi, A. Ochaion, R.L. Wolfson, S.B. Yehuda, A. Erlanger, G. Ohana, A. Harish, O. Merimski, F. Barer, and P. Fishman Clin. Cancer Res. 10 2004 4472
30. S. Merighi, A. Benini, P. Mirandola, S. Gessi, K. Varani, E. Leung, S. Maclennan, and P.A. Borea Biochem. Pharmacol. 72 2006 19
31. B.T. Liang, and K.A. Jacobson Proc. Natl. Acad. Sci. U.S.A. 95 1998 6995
32. H.W. Young, J.G. Molina, D. Dimina, H. Zhong, M. Jacobson, L.N. Chan, T.S. Chan, J.J. Lee, and M.R. Blackburn J. Immunol. 173 2004 1380
33. T. Okamura, Y. Kurogi, K. Hashimoto, S. Sato, H. Nishikawa, K. Kiryu, and Y. Nagao Bioorg. Med. Chem. Lett. 14 2004 3775
34. R. Brambilla, F. Cattabeni, S. Ceruti, D. Barbieri, C. Franceschi, Y.-C. Kim, K.A. Jacobson, K.-N. Klotz, M.J. Lohse, and M.P. Abbracchio Arch. Pharmacol. 361 2000 225
35. A.M. Pugliese, E. Coppi, G. Spalluto, R. Corradetti, and F. Pedata Br. J. Pharmacol. 147 2006 524
36. S. Gessi, E. Cattabriga, A. Avitabile, R. Gafa, G. Lanza, L. Cavazzini, N. Bianchi, R. Gambari, C. Feo, A. Liboni, S. Gullini, E. Leung, S.M. Lennan, and P.A. Borea Clin. Cancer Res. 10 2004 5895
37. H.T. Lee, A.O. Setlik, H. Xu, V.D. Agati, M.A. Jacobson, and C.W. Emala Am. J. Physiol. Renal Physiol. 284 2003 267
38. C.N. Wilson Br. J. Pharmacol. 155 2008 475
39. T. Okamura, Y. Kurogi, H. Nishikawa, K. Hashimoto, H. Fujiwara, and Y. Nagao J. Med. Chem. 45 2002 3703
40. V. Colotta, D. Catarzi, F. Varano, L. Cecchi, G. Filacchioni, C. Martini, L. Trincavelli, and Lucacchini J. Med. Chem. 43 2000 1158
41. V. Colotta, D. Catarzi, F. Varano, F.R. Calabri, O. Lenzi, G. Filacchioni, C. Martini, L. Trincavelli, F. Deflorian, and S. Moro J. Med. Chem. 47 2004 3580
42. K.Y. Jung, S.K. Kim, S.K. Gao, Z.G. Gross, A.S. Melman, K.A. Jacobson, and Y.C. Kim Bioorg. Med. Chem. 12 2004 613
43. N.J. Press, T.H. Keller, P. Tranter, D. Beer, K. Jones, A. Faessler, R. Heng, C. Lewis, T. Howe, P. Gedeck, L. Mazzoni, and J.R. Fozard Curr. Top. Med. Chem. 4 2004 863
44. E.M. Priego, V.D. Kuenzel, A.P. Ijzerman, M.J. Camarasa, and M.P. Perez J. Med. Chem. 45 2002 3337
45. V. Colotta, D. Catarzi, F. Varano, F. Capelli, O. Lenzi, G. Filacchioni, C. Martini, L. Trincavelli, O. Ciampi, A.M. Pugliese, F. Pedata, A. Schiesaro, E. Morizzo, and S. Moro J. Med. Chem. 50 2007 4061
46. P.G. Baraldi, M.A. Tabrizi, D. Preti, A. Bovero, F. Fruttarolo, R. Romagnoli, N.A. Zaid, A.R. Moorman, K. Varani, and P.A. Borea J. Med. Chem. 48 2005 5001
47. M. Raghu Prasad, A.R. Rao, P.S. Rao, K.S. Rajan, S. Meena, and K. Madhavi Eur. J. Med. Chem. 43 2008 614
48. S. Moro, B. Paolo, D. Francesca, F. Cristina, G. Pastorin, B. Cacciari, P.G. Baraldi, K. Varani, P.A. Borea, and G. Spalluto J. Med. Chem. 48 2005 152
49. Z.G. Gao, B.V. Joshi, A.M. Klutz, S.K. Kim, H.W. Lee, H.O. Kim, L.S. Jeong, and K.A. Jacobson Bioorg. Med. Chem. Lett. 16 2006 596
50. L.S. Jeong, S. Choe, P. Gunaga, H.O. Kim, H.W. Lee, S.K. Lee, D.K. Tosh, A. Patel, K.K. Palaniappan, Z.G. Gao, K.A. Jacobson, and H.R. Moon J. Med. Chem. 50 2007 3159
51. L.S. Jeong, H.W. Lee, H.O. Kim, D.K. Tosh, S. Pal, W.J. Choi, Z.G. Gao, A.R. Patel, W. Williams, K.A. Jacobson, and H.D. Kim Bioorg. Med. Chem. Lett. 18 2008 1612
52. A. Drabczyn, B. Schumacher, C.E. Müller, J.K. Wojciechowska, B. Michalak, E.P. Kala, and K.K. Kononowicz Eur. J. Med. Chem. 38 2003 397
53. K.N. Klotz Naunyn-Schmiedebergs Arch. Pharmacol. 362 2000 382
54. S. Grover, and Bakshi Pharm. Sci. Technol. Today 3 2000 28
55. M.P. González, H.G. Diaz, R.R. Molina, M.A. Cabrera, and A.R. Ramos J. Chem. Inf. Comput. Sci. 43 2003 1192
56. S. Moro, A.M. van Rhee, L.H. Sanders, and K.A. Jacobson J. Med. Chem. 41 1998 46
57. K. Roy Indian J. Chem. 42B 2003 1485
58. P. Bhattacharya, and K. Roy Bioorg. Med. Chem. Lett. 15 2005 3737
59. K. Roy QSAR Comb. Sci. 22 2003 614
60. K. Roy, J.T. Leonard, and C. Sengupta Bioorg. Med. Chem. Lett. 14 2004 3705
61. A.H. Li, S. Moro, N. Forsyth, N. Melman, X.D. Ji, and K.A. Jacobson J. Med. Chem. 42 1999 706
62. P. Bhattacharya, J.T. Leonard, and K. Roy Bioorg. Med. Chem. 13 2005 1159
63. A. Borghini, D. Pietra, P. Domenichelli, and A.M. Bianucci Bioorg. Med. Chem. 13 2005 5330
64. Cerius2 Version 4.10 is a product of Accelrys Inc., San Diego, CA.
65. P.P. Roy, J.T. Leonard, and K. Roy Chemom. Intell. Lab. Syst. 90 2008 31
66. K. Roy Expert Opin. Drug Discov. 2 2007 1567
67. B. Everitt, S. Landau, and M. Leese Cluster Analysis 2001 Arnold London
68. H. Kubinyi, F. Hamprecht, and A.T. Mietzner J. Med. Chem. 41 1998 2553
69. G.R. Marshall H. Kubinyi, 3D QSAR in Drug Design - Theory, Methods and Applications 1994 ESCOM Leiden 117
70. P.P. Roy, and K. Roy QSAR Comb. Sci. 27 2008 302
71. P.P. Roy, S. Paul, I. Mitra, and K. Roy Molecules 14 2009 1660
72. I. Mitra, A. Saha, and K. Roy Mol. Simul 36 2010 1067
73. A.J. Hopfinger, and J.S. Tokarsi P.S. Charifson, Practical Applications of Computer-aided Drug Design 1997 Marcel Dekker New York 105
74. D. Rogers, and A.J. Hopfinger J. Chem. Inf. Comput. Sci. 34 1994 854
75. A.K. Ghose, and G.M. Crippen J. Comput. Chem. 7 1986 565
76. A. Hirashima, T. Eiraku, E. Kuwano, and M. Eto Internet Electron. J. Mol. Des. 2 2003 511
77. S. Wold H.E. van de Waterbeemd, Chemometric Methods in Molecular Design 1995 VCH Weinheim, Germany 195
78. Y. Fan, L.M. Shi, K.W. Kohn, Y. Pommier, and J.N. Weinstein J. Med. Chem. 44 2001 3254
79. MINITAB is statistical software of Minitab Inc., USA.
80. O. Lenzi, V. Vittoria Colotta, D. Catarzi, F. Varano, D. Poli, G. Filacchioni, K. Varani, F. Vincenzi, P.A. Borea, S. Paoletta, E. Morizzo, and S. Moro J. Med. Chem. 52 2009 7640
81. D. Lednicer The Organic Chemistry of Drug Synthesis Vol. 6 1999 Wiley Interscience New York