Further studies on 2-arylacetamide pyridazin-3(2H)-ones: Design, synthesis and evaluation of 4,6-disubstituted analogs as formyl peptide receptors (FPRs) agonists

European Journal of Medicinal Chemistry

Volumn 64, Issue , 2013, Pages 512-528

  Giovannoni, Maria Paola ^a   Schepetkin, Igor A ^b   Cilibrizzi, Agostino ^a   Crocetti, Letizia ^a   Khlebnikov, Andrei I ^c   Dahlgren, Claes ^d   Graziano, Alessia ^a   Dal Piaz, Vittorio ^a   Kirpotina, Liliya N ^b   Zerbinati, Serena ^a   Vergelli, Claudia ^a   Quinn, Mark T ^b  

^a UNIVERSITY OF FLORENCE   (Italy)

^b MONTANA STATE UNIVERSITY   (United States)

^c ALTAI STATE TECHNICAL UNIVERSITY   (Russian Federation)

^d UNIVERSITY OF GOTHENBURG   (Sweden)

Author keywords

Dual agonist; Formyl peptide receptor; Human neutrophils; Molecular docking; Pyridazin 3(2H) one

Indexed keywords

2 ARYLACETAMIDE PYRIDAZIN 3(2H) ONE; ANTIINFLAMMATORY AGENT; FORMYL PEPTIDE RECEPTOR AGONIST; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; CALCIUM CELL LEVEL; CALCIUM TRANSPORT; CHEMOTAXIS; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MOLECULAR DOCKING;

ACETAMIDES; ANTINEOPLASTIC AGENTS; CELL PROLIFERATION; CELL SURVIVAL; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HL-60 CELLS; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NEUTROPHILS; PYRIDAZINES; RECEPTORS, FORMYL PEPTIDE; STRUCTURE-ACTIVITY RELATIONSHIP; TUMOR CELLS, CULTURED;

EID: 84877838713     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.03.066     Document Type: Article

References (57)

1. Y. Le, P.M. Murphy, and J.M. Wang Formyl-peptide receptors revisited Trends Immunol. 23 2002 541 548 (Pubitemid 35223553)
2. I. Migeotte, D. Communi, and M. Parmentier Formyl peptide receptors: a promiscuous subfamily of G protein-coupled receptors controlling immune responses Cytok. Growth Factor Rev. 17 2006 501 519 (Pubitemid 44793122)
3. R.D. Ye, F. Boulay, J.M. Wang, C. Dahlgren, C. Gerard, M. Parmentier, C.N. Serhan, and P.M. Murphy International Union of Basic and Clinical Pharmacology. LXXIII. Nomenclature for the formyl peptide receptor (FPR) family Pharmacol. Rev. 61 2009 119 161
4. O. Quehenberger, E.R. Prossnitz, S.L. Cavanagh, C.G. Cochrane, and R.D. Ye Multiple domains of the N-formyl peptide receptor are required for high-affinity ligand binding. Construction and analysis of chimeric N-formyl peptide receptors J. Biol. Chem. 268 1993 18167 18175 (Pubitemid 23260338)
5. I. Migeotte, E. Riboldi, J.D. Franssen, F. Grégoire, C. Loison, V. Wittamer, M. Detheux, P. Robberecht, S. Costagliola, G. Vassart, S. Sozzani, M. Parmentier, and D. Communi Identification and characterization of an endogenous chemotactic ligand specific for FPRL2 J. Exp. Med. 201 2005 83 93 (Pubitemid 40130086)
6. N. Dufton, and M. Perretti Therapeutic anti-inflammatory potential of formyl-peptide receptor agonists Pharmacol. Ther. 127 2010 175 188
7. F.N.E. Gavins Are formyl peptide receptors novel targets for therapeutic intervention in ischaemia-reperfusion injury? Trends Pharmacol. Sci. 31 2010 266 276
8. Y. Cui, Y. Le, H. Yazawa, W. Gong, and J.M. Wang Potential role of the formyl peptide receptor-like 1 (FPRL1) in inflammatory aspects of Alzheimer's disease J. Leukoc. Biol. 72 2002 628 635 (Pubitemid 36277832)
9. F. Cattaneo, G. Guerra, and R. Ammendola Expression and signaling of formyl-peptide receptors in the brain Neurochem. Res. 35 2010 2018 2026
10. J.M. Kilby, S. Hopkins, T.M. Venetta, B. Di Massimo, G.A. Cloud, J.Y. Lee, L. Alldredge, E. Hunter, D. Lambertm, D. Bolognesi, T. Matthews, M.R. Johnson, M.A. Nowak, G.M. Shaw, and M.S. Saag Potent suppression of HIV-1 replication in humans by T-20, a peptide inhibitor of gp41-mediated virus entry Nat. Med. 4 1998 1302 1307 (Pubitemid 28512112)
11. A. De Paulis, N. Montuori, N. Prevete, I. Fiorentino, F.W. Rossi, V. Visconte, G. Rossi, G. Marone, and P. Ragno Urokinase induces basophil chemotaxis through a urokinase receptor epitope that is an endogenous ligand for formyl peptide receptor-like 1 and -like 2 J. Immunol. 173 2004 5739 5748 (Pubitemid 39392163)
12. B.S. Edwards, C. Bologa, S.M. Young, K.V. Balakin, E.R. Prossnitz, N.P. Savchuck, L.A. Sklar, and T.I. Oprea Integration of virtual screening with high-throughput flow cytometry to identify novel small molecule formylpeptide receptor antagonists Mol. Pharmacol. 68 2005 1301 1310 (Pubitemid 41539986)
13. S. Pieretti, A. Di Giannuario, M. De Felice, M. Perretti, and G. Cirino Stimulus-dependent specificity for annexin 1 inhibition of the inflammatory nociceptive response: the involvement of the receptor for formylated peptides Pain 109 2004 52 63 (Pubitemid 38479770)
14. C.N. Serhan, S.D. Brain, C.D. Buckley, D.W. Gilroy, C. Haslett, L.A. O'Neill, M. Perretti, A.G. Rossi, and J.L. Wallace Resolution of inflammation: state of the art, definitions and terms FASEB J. 21 2007 325 332 (Pubitemid 46213480)
15. L. Zhang, and T.J. Falla Host defense peptides for use as potential therapeutics Curr. Opin. Invest. Drugs 10 2009 164 171
16. A. Cilibrizzi, M.T. Quinn, L.N. Kirpotina, I.A. Schepetkin, J. Holderness, R.D. Ye, M.J. Rabiet, C. Biancalani, N. Cesari, A. Graziano, C. Vergelli, S. Pieretti, V. Dal Piaz, and M.P. Giovannoni 6-Methyl-2,4- disubstituted pyridazin-3(2H)-ones: a novel class of small-molecule agonists for formyl peptide receptors J. Med. Chem. 52 2009 5044 5057
17. H. Forsman, C. Kalderén, A. Nordin, E. Nordling, A.J. Jensen, and C. Dahlgren Stable formyl peptide receptor agonists that activate the neutrophil NADPH-oxidase identified through screening of a compound library Biochem. Pharmacol. 81 2011 402 411
18. M. Frohn, H. Xu, X. Zou, C. Chang, M. McElvain, M.H. Plant, M. Wong, P. Tagari, R. Hungate, and R.W. Bürli New 'chemical probes' to examine the role of the hFPRL1 (or ALXR) receptor in inflammation Bioorg. Med. Chem. Lett. 17 2007 6633 6637 (Pubitemid 350026311)
19. A. Cilibrizzi, I.A. Schepetkin, G. Bartolucci, L. Crocetti, V. Dal Piaz, M.P. Giovannoni, A. Graziano, L.N. Kirpotina, M.T. Quinn, and C. Vergelli Synthesis, enantioresolution, and activity profile of chiral 6-methyl-2,4-disubstituted pyridazin-3(2H)-ones as potent N-formyl peptide receptor agonists Bioorg. Med. Chem. 20 2012 3781 3792
20. Y. Sogawa, T. Ohyama, H. Maeda, and K. Hirahara Formyl peptide receptor 1 and 2 dual agonist inhibits human neutrophil chemotaxis by the induction of chemoattractant receptor cross-desensitization J. Pharmacol. Sci. 115 2011 63 68
21. R.S. Reddy, K. Saravanan, and P. Kumar An efficient approach to γ-alkylidene γ-butyrolactones: application to the syntheses of pyridazinones and diazocinones Tetrahedron 54 1998 6553 6564 (Pubitemid 28231264)
22. J. Druey Pyridazine in der Arzneimittelsynthese Angew. Chem. 70 1958 5 13
23. M. Barberis, and L. Pérez-Prieto Enantioselective synthesis of sabina ketone Tetrahedron Lett. 44 2003 6683 6685 (Pubitemid 36945114)
24. H. Shinkai, H. Ozeki, T. Motomura, T. Ohta, N. Furukawa, and I. Uchida 4-(trans-4-Methylcyclohexyl)-4-oxobutyric acid (JTT-608). A new class of antidiabetic agent J. Med. Chem. 41 1998 5420 5428 (Pubitemid 29031326)
25. S. Singh, M. Verma, and K.N. Singh Superoxide ion induced oxidation of γ-lactones to γ-ketocarboxylic acids in aprotic medium Synth. Commun. 34 2004 4471 4475 (Pubitemid 40070225)
26. C. Grundmann Über sulfanilamido-pyridazine (heterocyclische sulfonamide, I. Mitteil) Chem. Ber. 81 1948 1 11
27. N. Gouault, J.F. Cupif, S. Picard, A. Lecat, and M. David Synthesis of diverse 4,5-dihydro-3(2H)-pyridazinones on Wang resin J. Pharm. Pharmacol. 53 2001 981 985 (Pubitemid 32640281)
28. P.S. Banerjee, P.K. Sharma, and R.K. Nema Synthesis and anticonvulsant activity of pyridazinone derivatives Int. J. Chem. Tech. Res. 1 2009 522 525
29. G. Steiner, J. Gries, and D. Lenke Synthesis and antihypertensive activity of new 6-heteroaryl-3-hydrazinopyridazine derivatives J. Med. Chem. 24 1981 59 63 (Pubitemid 11189903)
30. G. Kaupp, and J. Schmeyers Solid-state reactivity of the hydrazine-hydroquinone complex J. Phys. Org. Chem. 13 2000 388 394
31. W. Hu, H. Ralay Ranaivo, S.M. Roy, H.A. Behanna, L.K. Wing, L. Munoz, L. Guo, L.J. Van Eldik, and D.M. Watterson Development of a novel therapeutic suppressor of brain proinflammatory cytokine up-regulation that attenuates synaptic dysfunction and behavioral deficits Bioorg. Med. Chem. Lett. 17 2007 414 418 (Pubitemid 46084908)
32. E.A. Steck, R.P. Brundage, and L.T. Fletcher Pyridazine derivatives. I. Some amebacidal 3-pyridazones J. Am. Chem. Soc. 75 1953 1117 1119
33. E.R. Castleman, and F.Y. Wiselogle Studies in the pyridazine series. The absorption spectrum of pyridazine J. Am. Chem. Soc. 67 1945 60 62
34. A.M. Kaddah, and A.M. Khalil Reactions of 3-pyridazinones with aldehydes and Grignard reagents Indian J. Chem. 15B 1977 1025 1028
35. M.F. Ismail, A.A. El Khamry, N.A. Shams, and O.M. El Sawy Base-catalyzed condensation of aromatic aldehydes with 4,5-dihydro-6-methylpyridazin-3(2H)-one Indian J. Chem. 19B 1980 203 205
36. P. Powell, and M.H. Sosabowski Preparation and reactions of some 2-thienyl- and 3-thienylpyridazinones and -pyridazines J. Chem. Res. (S) 8 1995 306 307
37. N.G. Kandile, and E.A. Ahmed Synthesis of some new pyridazinones Acta Chim. Hung. 127 1990 829 835
38. P.G. Baraldi, D. Preti, M.A. Tabrizi, F. Fruttarolo, G. Saponaro, S. Baraldi, R. Romagnoli, A.R. Moorman, S. Gessi, K. Varani, and P.A. Borea N6-[(Hetero)aryl/(cyclo)alkyl-carbamoyl-methoxy-phenyl]-(2-chloro) -5′-N-ethylcarbox-amido-adenosines: the first example of adenosine-related structures with potent agonist activity at the human A2B adenosine receptor Bioorg. Med. Chem. 15 2007 2514 2527 (Pubitemid 46367714)
39. W.G. Overend, and L.F. Wiggins The conversion of sucrose into pyridazine derivatives. Part I. 3-sulfanilamido-6-methylpyridazine J. Chem. Soc. 1947 239 244
40. L. Costantino, G. Rastelli, M.C. Gamberoni, M.P. Giovannoni, V. Dal Piaz, P. Vinello, and D. Barlocco Isoxazolo-[3,4-d]-pyridazin-7-(6H)-one as a potential substrate for new aldose reductase inhibitors J. Med. Chem. 42 1999 1894 1900 (Pubitemid 29269622)
41. W.J. Coates, and A. McKillop Preparation of 4-amino-3(2H)-pyridazinones by direct amination of 3(2H)-pyridazinones with hydrazine Heterocycles 29 1989 1077 1090
42. C. Biancalani, M.P. Giovannoni, S. Pieretti, N. Cesari, A. Graziano, C. Vergelli, A. Cilibrizzi, A. Di Gianuario, M. Colucci, G. Mangano, B. Garrone, L. Polenzani, and V. Dal Piaz Further studies on arylpiperazinyl alkyl pyridazinones: discovery of an exceptionally potent, orally active, antinociceptive agent in thermally induced pain J. Med. Chem. 52 2009 7397 7409
43. H. Lerche, D. Koenig, and T. Severin Reactions with nitroenamines. XII. Reaction of esters and lactones with nitroenamines Chem. Ber. 107 1974 1509 1517
44. 4 Scand. J. Immunol. 56 2002 470 476 (Pubitemid 35373683)
45. H. Forsman, E. Andréasson, J. Karlsson, F. Boulay, M.J. Rabiet, and C. Dahlgren Structural characterization and inhibitory profile of formyl peptide receptor 2 selective peptides descending from a PIP2-binding domain of gelsolin J. Immunol. 189 2012 629 637
46. C. Movitz, L. Brive, K. Hellstrand, M.J. Rabiet, and C. Dahlgren The annexin I sequence gln(9)-ala(10)-trp(11)-phe(12) is a core structure for interaction with the formyl peptide receptor 1 J. Biol. Chem. 285 2010 14338 14345
47. A.I. Khlebnikov, I.A. Schepetkin, L.N. Kirpotina, L. Brive, C. Dahlgren, M.A. Jutila, and M.T. Quinn Molecular docking of 2-(benzimidazol-2-ylthio)-N- phenylacetamide-derived small-molecule agonists of human formyl peptide receptor 1 J. Mol. Model. 18 2012 2831 2843
48. F. Deflorian, and K.A. Jacobson Comparison of three GPCR structural templates for modeling of the P2Y12 nucleotide receptor J. Comput. Aided Mol. Des. 25 4 2011 329 338
49. I.A. Schepetkin, L.N. Kirpotina, A.I. Khlebnikov, M. Leopoldo, E. Lucente, E. Lacivita, P. De Giorgio, and M.T. Quinn 3-(1H-Indol-3-yl)-2-[3-(4- nitrophenyl)ureido]propanamide enantiomers with human formyl-peptide receptor agonist activity: molecular modeling of chiral recognition by FPR2 Biochem. Pharmacol. 85 3 2013 404 416
50. J.S. Mills, H.M. Miettinen, D. Cummings, and A.J. Jesaitis Characterization of the binding site on the formyl peptide receptor using three receptor mutants and analogs of Met-Leu-Phe and Met-Met-Trp-Leu-Leu J. Biol. Chem. 275 2000 39012 39017 (Pubitemid 32058913)
51. H. Fujita, T. Kato, N. Watanabe, T. Takahashi, and S. Kitagawa Stimulation of human formyl peptide receptors by calpain inhibitors: homology modeling of receptors and ligand docking simulation Arch. Biochem. Biophys. 516 2011 121 127
52. 4 receptor Blood 95 2000 1810 1818 (Pubitemid 30120847)
53. I.A. Schepetkin, L.N. Kirpotina, A.I. Khlebnikov, and M.T. Quinn High throughput screening for small-molecule activators of neutrophils: identification of novel N-formyl peptide receptor agonists Mol. Pharmacol. 71 2007 1061 1074 (Pubitemid 46457010)
54. C. Ferrari, A. Macchiarulo, G. Costantino, and R. Pellicciari Pharmacophore model for bile acids recognition by the FPR receptor J. Comput. Aided Mol. Des. 20 2006 295 303
55. H.M. Miettinen, J.S. Mills, J.M. Gripentrog, E.A. Dratz, B.L. Granger, and A.J. Jesaitis The ligand binding site of the formyl peptide receptor maps in the transmembrane region J. Immunol. 159 1997 4045 4054 (Pubitemid 127469662)
56. L.A. Kelley, and M.J. Sternberg Protein structure prediction on the Web: a case study using the Phyre server Nat. Protoc. 4 2009 363 371
57. I.A. Schepetkin, L.N. Kirpotina, A.I. Khlebnikov, M.A. Jutila, and M.T. Quinn Gastrin-releasing peptide/neuromedin B receptor antagonists PD176252, PD168368, and related analogs are potent agonists of human formyl-peptide receptors Mol. Pharmacol. 79 2011 77 90