6-Methyl-2,4-disubstituted pyridazin-3(2H)-ones: A novel class of small-molecule agonists for formyl peptide receptors

Journal of Medicinal Chemistry

Volumn 52, Issue 16, 2009, Pages 5044-5057

  Cilibrizzi, Agostino ^a   Quinn, Mark T ^b   Kirpotina, Liliya N ^b   Schepetkin, Igor A ^b   Holderness, Jeff ^b   Ye, Richard D ^c   Rabiet, Marie Josephe ^d   Biancalani, Claudio ^a   Cesari, Nicoletta ^a   Graziano, Alessia ^a   Vergelli, Claudia ^a   Pieretti, Stefano ^e   Dal Piaz, Vittorio ^a   Giovannoni, Maria Paola ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

^b MONTANA STATE UNIVERSITY   (United States)

^c UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^d CEA GRENOBLE   (France)

^e Department of Therapeutic Research and Medicine Evaluation ^*  (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1 (4 BROMOPHENYL) 3 (6 METHYL 3 OXO 2 PHENYL 2,3 DIHYDROPYRIDAZIN 4 YL)UREA; 1 (4 BUTOXYPHENYL) 3 (6 METHYL 3 OXO 2 PHENYL 2,3 DIHYDROPYRIDAZIN 4 YL)UREA; 1 (4 CHLOROPHENYL) 3 (6 METHYL 3 OXO 2 PHENYL 2,3 DIHYDROPYRIDAZIN 4 YL)UREA; 1 (4 IODOPHENYL) 3 (6 METHYL 3 OXO 2 PHENYL 2,3 DIHYDROPYRIDAZIN 4 YL)UREA; 2 [5 (3 METHOXYBENZYL) 3 METHYL 6 OXO 6H PYRIDAZIN 1 YL] N (4 METHOXYPHENYL)ACETAMIDE; 2 [5 (3 METHOXYBENZYL) 3 METHYL 6 OXO 6H PYRIDAZIN 1 YL] N 4 TOLYLACETAMIDE; 2 [5 (3 METHOXYBENZYL) 3 METHYL 6 OXO 6H PYRIDAZIN 1 YL] N PHENYLACETAMIDE; 4 (3 METHOXYBENZYL) 6 METHYLPYRIDAZIN 3(2H) ONE; 4 (4 BUTOXYPHENYLAMINO) 6 METHYL 2 PHENYLPYRIDAZIN 3(2H) ONE; 4 BUTOXY N (6 METHYL 3 OXO 2 PHENYL 2,3 DIHYDROPYRIDAZIN 4 YL)BENZAMIDE; [5 (3 METHOXYBENZYL) 3 METHYL 6 OXO 6H PYRIDAZIN 1 YL]ACETIC ACID; [5 (3 METHOXYBENZYL) 3 METHYL 6 OXO 6H PYRIDAZIN 1 YL]ACETIC ACID ETHYL ESTER; [5 (4 METHOXYBENZYL) 3 METHYL 6 OXO 6H PYRIDAZIN 1 YL]ACETIC ACID; FORMYLPEPTIDE RECEPTOR; FORMYLPEPTIDE RECEPTOR 1; FORMYLPEPTIDE RECEPTOR 1 STIMULATING AGENT; FORMYLPEPTIDE RECEPTOR LIKE 1; FORMYLPEPTIDE RECEPTOR LIKE 1 STIMULATING AGENT; FORMYLPEPTIDE RECEPTOR LIKE 2; N (2 BROMOPHENYL) 2 [5 (3 METHOXYBENZYL) 3 METHYL 6 OXO 6H PYRIDAZIN 1 YL]ACETAMIDE; N (3 BROMOPHENYL) 2 [5 (3 METHOXYBENZYL) 3 METHYL 6 OXO 6H PYRIDAZIN 1 YL]ACETAMIDE; N (4 BROMOPHENYL) 2 [5 (3 METHOXYBENZYL) 3 METHYL 6 OXO 6H PYRIDAZIN 1 YL]ACETAMIDE; N (4 BUTOXYPHENYL) 2 [5 (3 METHOXYBENZYL) 3 METHYL 6 OXO 6H PYRIDAZIN 1 YL]ACETAMIDE; N (4 CHLOROPHENYL) 2 [5 (3 METHOXYBENZYL) 3 METHYL 6 OXO 6H PYRIDAZIN 1 YL]ACETAMIDE; N (4 FLUOROPHENYL) 2 [5 (3 METHOXYBENZYL) 3 METHYL 6 OXO 6H PYRIDAZIN 1 YL]ACETAMIDE; N (4 IODOPHENYL) 2 [5 (3 METHOXYBENZYL) 3 METHYL 6 OXO 6H PYRIDAZIN 1 YL]ACETAMIDE; N (4 TERT BUTYLPHENYL) 2 [5 (3 METHOXYBENZYL) 3 METHYL 6 OXO 6H PYRIDAZIN 1 YL]ACETAMIDE; PYRIDAZIN 3(2H) ONE DERIVATIVE; PYRIDAZINONE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CALCIUM MOBILIZATION; CALCIUM TRANSPORT; CELL STRAIN HL 60; CONCENTRATION RESPONSE; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; DRUG DESIGN; DRUG IDENTIFICATION; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SELECTIVITY; DRUG SPECIFICITY; DRUG SYNTHESIS; GENETIC TRANSFECTION; HUMAN; HUMAN CELL; NEUTROPHIL CHEMOTAXIS; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION;

CALCIUM; CHEMOTAXIS, LEUKOCYTE; HL-60 CELLS; HUMANS; NEUTROPHILS; PYRIDAZINES; RECEPTORS, FORMYL PEPTIDE; RECEPTORS, LIPOXIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 69049103120     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900592h     Document Type: Article

References (27)

1. Lee, H. Y.; Bae, Y. S. The Anti-infective Peptide, Innate Defense-Regulator Peptide, Stimulates Neutrophil Chemotaxis Via a Formyl Peptide Receptor. Biochem. Biophys. Res. Commun. 2008, 369, 573-578.
2. Gouin, J. P.; Hantsoo, L.; Kiekolt-Glaser, J. K. Immune Disregulation and Chronic Stress Among Older Adults: A Review. Neuroimmunomodulation 2008, 15, 251-259.
3. Jones, R. N. Resistance Patterns Among Nosocomial Phatogens: Trends Over the Past Few Years. Chest 2001, 119, 397S-4045S.
4. Zhang, L.; Falla, T. J. Host Defense Peptides for Use as Potential Therapeutics. Curr. Opin. Invest. Drugs 2009, 10, 164-171.
5. Selvatici, R.; Falzarano, S.; Mollica, A.; Spisani, S. Signal Transduction Pathways Triggered by Selective Formylpeptide Analogues in Human Neutrophils. Eur. J. Pharmacol. 2006, 534, 1-11.
6. Migeotte, I.; Communi, D.; Parmentier, M. Formylpeptide Receptors: A Promiscuous Subfamily of G Protein-Coupled Receptors Controlling Immune Responses. Cytokine Growth Factor Rev. 2006, 17, 501-519.
7. Schiffmann, E.; Showell, H. V.; Corcoran, B. A.; Ward, P. A.; Smith, E.; Becker, E. L. The Isolation and Partial Characterization of Neutrophil Chemotatic Factors from Escherichia coli.. J. Immunol. 1975, 114, 1831-1837.
8. Gao, J. L.; Lee, E. J.; Murphy, P. M. Impaired Antibacterial Host Defence in Mice Lacking the N-Formylpeptide Receptor. J. Exp. Med. 1999, 189, 657-662.
9. Le, Y.; Oppenheim, J. J.; Wang, J. M. Pleiotropic Roles of Formyl Peptide Receptors. Cytokine Growth Factor Rev. 2001, 12, 91-105.
10. Kilby, J. M.; Hopkins, S.; Venetta, T. M.; DiMassimo, B.; Cloud, G. A.; Lee, J. Y.; Alldredge, L.; Hunter, E.; Lambert, D.; Bolognesi, D.; Matthews, T.; Johnson, M. R.; Nowak, M. A.; Shaw, G. M.; Saag, M. S. Potent Suppression of HIV-1 Replication in Human by T-20 a Peptide Inhibitor of gp41-mediated Virus Entry. Nat. Med. 1998, 4, 1302-1307.
11. Le, Y.; Gong, W.; Tiffany, H. L.; Tumanov, A.; Nedospasov, S.; Shen, W.; Dunlop, N. M.; Gao, J. L.; Murphy, P. M.; Oppenheim, J. J.; Wang, J. M. Amyloid (beta)42 Activates a G-protein-coupled Chemoattractant Receptor, FPR-like-1. J.Neurosci. 2001, 21, RC123.
12. Le, Y.; Yazawa, H.; Gong, W.; Yu, Z.; Ferrans, V. J.; Murphy, M. P.; Wang, J. M. The Neurotoxic Prion Peptide Fragment PrP(106-126) is a Chemotactic Agonist for the G-Protein-Coupled Receptor Formyl Peptide Receptor-like 1. J. Immunol. 2001, 66, 1448-1451.
13. Chiang, N.; Serhan, C. N.; Dahlén, S. E.; Drazen, J. M.; Hay, D. W.; Rovati, G. E.; Shimizu, T.; Yokomizo, T.; Brink, C. The Lipoxin Receptor ALX: Potent Ligand-Specific and Stereoselective Actions in Vivo. Pharmacol Rev. 2006, 58, 463-487.
14. Perretti, M.; Chiang, N.; La, M.; Fierro, I. M.; Marullo, S.; Getting, S. J.; Solito, E.; Serhan, C. N. Endogenous Lipid- and Peptide-Derived Anti-inflammatory Pathways Generated with Glucocorticoid and Aspirin Treatment Activate the Lipoxin A4 Receptor. Nat. Med. 2002, 8, 1296-1302.
15. Edwards, B. S.; Bologa, C.; Young, S. M.; Balakin, V.; Prossnitz, E. R.; Savchuck, N. P.; Skalar, L. A.; Oprea, T. I. Integration of Virtual Screening with High-Throughput Flow Cytometry to Identify Novel Small Molecule Formyl Peptide Receptor Antagonists. Mol. Pharmacol. 2005, 68, 1301-1310.
16. Bae, Y. S.; Song, J. Y.; Kim, Y.; He, R.; Ye, R. D.; Kwak, J. Y.; Suh, P. G.; Ryu, S. H. Differential Activation of Formyl Peptide Receptor Signalling by Peptide Ligands. Mol. Pharmacol. 2003, 64, 841-847.
17. Le, Y.; Gong, W.; Li, B.; Dunlop, N. M.; Shen, W.; Su, S. B.; Ye, R. D.; Wang, J. M. Utilization of Two Seven-Transmembrane, G Protein-Coupled Receptors, Formyl Peptide Receptor-like 1 and Formyl Peptide Receptor, by the Synthetic Hexapeptide WKYMVm for Human Phagocyte Activation. J. Immunol. 1999, 163, 6777-6784.
18. Nanamori, M.; Cheng, X.; Mei, J.; Sang, H.; Xuan, Y.; Zhou, C.; Wang, M. W.; Ye, R. D. A novel nonpeptide ligand for formyl peptide receptor-like 1. Mol. Pharmacol. 2004, 66, 1213-1222.
19. Frohn, M.; Xu, H.; Zou, X.; Chang, C.; McElvaine, M.; Plant, M. H.; Wong, M.; Tagari, P.; Hungate, R.; Burli, R. W. New "Chemical Probes" to Examine the Role of the hFPRL1 (or ALXR) Receptor in Inflammation. Bioorg. Med. Chem. Lett. 2007, 17, 6633-6637.
20. Burli, R. W.; Xu, H.; Zou, X.; Muller, K.; Golden, J.; Frohn, M.; Adlam, M.; Plant, M. H.; Wong, M.; McElvain, M.; Regal, K.; Viswanadhan, V. N.; Tagari, P.; Hungate, R. Potent hFPRL1 (ALXR) Agonists as Potential Anti-inflammatory Agents. Bioorg. Med. Chem. Lett. 2006, 16, 3713-3718.
21. Overend, W. G.; Wiggins, L. F. Conversion of Sucrose into Pyridazine Derivatives. II. 4-Amino-2-phenyl-6-methyl-3-pyridazinone, 4-Amino-2-(p- nitrophenyl)-6-methyl-3-pyridazone, and Their Sulfalinamide Derivatives. J. Chem. Soc. 1947, 549-554.
22. Meng, Q.; Hesse, M. Nitrogen-Nitrogen Bond Cleavage: a Route to Macrocyclic Dilactams. Synlett 1990, 3, 148-150.
23. Ismail, M. F.; El Khamry, A. A.; Shams, N. A.; El Sawi, O. M. Base-Catalyzed Condensation of Aromatic Aldehydes with 4,5-Dihydrogen-6- methylpyridazin-3(2H)-one. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1980, 19, 203-206.
24. Ismail, M. F.; Shams, N. A.; El Sawi, O. M. Synthesis of 3-Mercaptopyridazine Derivatives. Synthesis 1980, 410-412.
25. Ismail, M. F.; Shams, N. A.; El Sawi, O. M. Some Reaction with 4-(Arylmethyl)-6-Methylpyridazin-3(2H)-ones. Egyptian J. Chem. 1982, 24, 223-226.
26. 4R, Is Not Affected by Lipoxin A4. J. Immunol. 2002, 56, 470-476.
27. Schepetkin, I. A.; Kirpotina, L. N.; Khlebnikov, A. I.; Quinn, M. T. High-throughput Screening for Small-Molecule Activators of Neutrophils: Indentification of Novel N-Formyl Peptide Receptor Aagonists. Mol. Pharmacol. 2007, 71, 1061-1074.