Synthesis and biological evaluation of 4,5-dihydro-1H-pyrazole derivatives as potential nNOS/iNOS selective inhibitors. Part 2: Influence of diverse substituents in both the phenyl moiety and the acyl group

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 14, 2013, Pages 4132-4142

  Carrión, M Dora ^a   Chayah, Mariem ^a   Entrena, Antonio ^a   López, Ana ^b   Gallo, Miguel A ^a   Acuña Castroviejo, Darío ^b   Camacho, M Encarnación ^a  

^a UNIVERSITY OF GRANADA   (Spain)

^b UNIVERSITY OF GRANADA   (Spain)

Author keywords

4,5 Dihydro 1H pyrazoles; Inducible nitric oxide synthase (iNOS); Inhibition; Neuronal nitric oxide synthase (nNOS)

Indexed keywords

3 (2 AMINO 4,5 DICHLOROPHENYL) 1 BENZOYL 4,5 DIHYDRO 1H PYRAZOLE; 3 (2 AMINO 4,5 DICHLOROPHENYL) 1 CYCLOPROPYLCARBONYL 4,5 DIHYDRO 1H PYRAZOLE; 3 (2 AMINO 4,5 DICHLOROPHENYL) 1 PHENYLACETYL 4,5 DIHYDRO 1H PYRAZOLE; 3 (2 AMINO 4,5 DICHLOROPHENYL) 1 PHENYLPROPANOYL 4,5 DIHYDRO 1H PYRAZOLE; 3 (2 AMINO 4,5 DIMETHOXYPHENYL) 1 BENZONYL 4,5 DIHYDRO 1H PYRAZOLE; 3 (2 AMINO 4,5 DIMETHOXYPHENYL) 1 CYCLOPROPYLCARBONYL 4,5 DIHYDRO 1H PYRAZOLE; 3 (2 AMINO 4,5 DIMETHOXYPHENYL) 1 PHENYLACETYL 4,5 DIHYDRO 1H PYRAZOLE; 3 (2 AMINO 4,5 DIMETHOXYPHENYL) 1 PHENYLPROPANOYL 4,5 DIHYDRO 1H PYRAZOLE; 3 (2 AMINO 5 CHLOROPHENYL) 1 PHENYLACETYL 4,5 DIHYDRO 1H PYRAZOLE; 3 (2 AMINO 5 CHLOROPHENYL) 1 PHENYLPROPANOYL 4,5 DIHYDRO 1H PYRAZOLE; 3 (2 AMINO 5 METHOXYPHENYL) 1 PHENYLACETYL 4,5 DIHYDRO 1H PYRAZOLE; 3 (2 AMINO 5 METHOXYPHENYL) 1 PHENYLPROPANOYL 4,5 DIHYDRO 1H PYRAZOLE; 3 (2 AMINOPHENYL) 1 PHENYLACETYL 4,5 DIHYDRO 1H PYRAZOLE; 3 (2 AMINOPHENYL) 1 PHENYLPROPANOYL 4,5 DIHYDRO 1H PYRAZOLE; 3 (6 AMINO 2,3,4 TRIMETHOXYPHENYL) 1 BENZOYL 4,5 DIHYDRO 1H PYRAZOLE; 3 (6 AMINO 2,3,4 TRIMETHOXYPHENYL) 1 CYCLOPROPYLCARBONYL 4,5 DIHYDRO 1H PYRAZOLE; 3 (6 AMINO 2,3,4 TRIMETHOXYPHENYL) 1 PHENYLACETYL 4,5 DIHYDRO 1H PYRAZOLE; 3 (6 AMINO 2,3,4 TRIMETHOXYPHENYL) 1 PHENYLPROPANOYL 4,5 DIHYDRO 1H PYRAZOLE; ARGININE; BENZENE DERIVATIVE; CYCLOPROPANE DERIVATIVE; GLUTAMIC ACID; INDUCIBLE NITRIC OXIDE SYNTHASE; NEURONAL NITRIC OXIDE SYNTHASE; PHENYL GROUP; PYRAZOLE DERIVATIVE; SERINE; UNCLASSIFIED DRUG;

ARTICLE; CONCENTRATION (PARAMETERS); DRUG DETERMINATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HYDROGEN BOND; IN VITRO STUDY; MOLECULAR DOCKING; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

ACYLATION; ANIMALS; BINDING SITES; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME ACTIVATION; ENZYME INHIBITORS; HUMANS; INHIBITORY CONCENTRATION 50; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NITRIC OXIDE SYNTHASE TYPE I; NITRIC OXIDE SYNTHASE TYPE II; PYRAZOLES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84879031451     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.05.016     Document Type: Article

References (34)

1. A.K. Mustafa, M.M. Gadalla, and S.H. Sydner Sci. Signalling 2 2009 1
2. W.K. Alderton, C.E. Cooper, and R.G. Knowles Biochem. J. 357 2001 593
3. G.M. Rosen, P. Tsai, and S. Pou Chem. Rev. 102 2002 1191
4. D.J. Stuehr, J. Santolini, Z.Q. Wang, C.C. Wei, and S. Adak J. Biol. Chem. 279 2004 36167
5. C. Hierholzer, B. Harbrecht, J.M. Menezes, J. Kane, J. MacMicking, C.F. Nathan, A.B. Peitzman, T.R. Billiar, and D.J. Tweardy J. Exp. Med. 187 1998 1
6. P. Ghafourifar, and E. Cadenas Trends Pharmacol. Sci. 26 2005 190
7. G. Escames, J. León, M. Macías, H. Khadly, and D. Acuña-Castroviejo FASEB J. 17 2003 932
8. G. Escames, L.C. López, F. Ortiz, A. López, J.A. García, E. Ros, and D. Acuña-Castroviejo FEBS J. 274 2007 2135
9. E.P. Erdal, E.A. Litzinger, J. Seo, y. Zhu, H. Li, and R.B. Silverman Curr. Top. Med. Chem. 5 2005 603
10. P. Vallance, and J. Leiper Nat. Rev. Drug Disc. 1 2002 939
11. J. Ramnauth, J. Speed, S.P. Maddaford, P. Dove, S.C. Annedi, P. Renton, S. Rakhit, J. Andrews, S. Silverman, G. Mladenova, S. Zinghini, S. Nair, C. Catalano, D.K.H. Lee, M. De Felice, and F. Porreca J. Med. Chem. 54 2011 5562
12. V. Calabrese, C. Mancuso, M. Calvani, E. Rizzarelli, A.D. Butterfield, and A.M.G. Stella Nat. Rev. Neurosci. 8 2007 766
13. D.M. Wilcock, M.R. Lewis, W.E. Van Nostrand, J. Davis, M.L. Previti, N. Gharkholonarehe, M.P. Vitek, and C.A. Colton J. Neurosci. 28 2008 1537
14. D. Levy, and D.W. Zochodne Pain Pract. 4 2004 11
15. J. Wu, L. Fang, Q. Lin, and W.D. Willis Pain 94 2001 47
16. T. Dehmer, J. Lindenau, S. Haid, J. Dichgan, and J.B. Schulz J. Neurochem. 74 2000 2213
17. V. Tapias, G. Escames, L.C. López, A. López, E. Camacho, M.D. Carrión, E. Entrena, M.A. Gallo, A. Espinosa, and D. Acuña-Castroviejo J. Neurochem. 87 2009 3002
18. M.E. Camacho, J. León, M.D. Carrión, A. Entrena, G. Escames, H. Khaldy, D. Acuña-Castroviejo, M.A. Gallo, and A. Espinosa J. Med. Chem. 45 2002 263
19. A. Entrena, M.E. Camacho, M.D. Carrión, L.C. López-Cara, G. Velasco, J. León, G. Escames, D. Acuña-Castroviejo, V. Tapias, M.A. Gallo, A. Vivó, and A. Espinosa J. Med. Chem. 48 2005 8174
20. M.E. Camacho, J. León, A. Entrena, G. Velasco, M.D. Carrión, G. Escames, A. Vivó, D. Acuña-Castroviejo, M.A. Gallo, and A. Espinosa J. Med. Chem. 47 2004 5641
21. M.D. Carrión, M.E. Camacho, J. León, G. Escames, V. Tapias, D. Acuña-Castroviejo, M.A. Gallo, and A. Espinosa Tetrahedron 60 2004 4051
22. M.D. Carrión, L.C. López-Cara, M.E. Camacho, A. Espinosa, M.A. Gallo, V. Tapias, G. Escames, D. Acuña-Castroviejo, and A. Entrena Eur. J. Med. Chem. 43 2008 2579
23. L.C. López-Cara, M.E. Camacho, M.D. Carrión, V. Tapias, M.A. Gallo, G. Escames, D. Acuña-Castroviejo, A. Espinosa, and A. Entrena Eur. J. Med. Chem. 44 2009 2655
24. L.C. López-Cara, M.D. Carrión, A. Entrena, M.A. Gallo, A. Espinosa, A. López, G. Escames, A. Acuña-Castroviejo, and M.E. Camacho Eur. J. Med. Chem. 50 2012 129
25. A. Zhu, B. Lippa, and L.B. Townsend J. Org. Chem. 64 1999 4159
26. B. Shen, D. Löffler, G. Reischl, H. Machulla, and K. Zeller J. Fluorine Chem. 130 2009 216
27. J. Ottl, D. Gabriel, and G. Marriott Bioconjugate Chem. 9 1998 143
28. F.D. Bellamy, and K. Ou Tetrahedron Lett. 25 1984 839
29. R. Fedorov, E. Hartmann, D.K. Ghosh, and I. Schlichting J. Biol. Chem. 278 2003 45818
30. Schrödinger Suite 2012 Update 2.
31. Schrödinger Suite 2012 Protein Preparation Wizard; Epik version 2.3, Schrödinger, LLC, New York, NY, 2012; Impact version 5.8, Schrödinger, LLC, New York, NY, 2012; Prime version 3.1, Schrödinger, LLC, New York, NY, 2012.
32. LigPrep, version 2.5, Schrödinger, LLC, New York, NY, 2012.
33. Figures were built using the PyMOL Molecular Graphics System, Version 1.4, Schrödinger. LLC.
34. D.S. Bredt, and S.H. Snyder Proc. Natl. Acad. Sci. U.S.A. 87 1990 682