Synthesis and pharmacological evaluation of new pyridazin-based thioderivatives as formyl peptide receptor (FPR) agonists

Drug Development Research

Volumn 74, Issue 4, 2013, Pages 259-271

  Crocetti, Letizia ^a   Vergelli, Claudia ^a   Cilibrizzi, Agostino ^a   Graziano, Alessia ^a   Khlebnikov, Andrei I ^b   Kirpotina, Liliya N ^c   Schepetkin, Igor A ^c   Quinn, Mark T ^c   Giovannoni, Maria Paola ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

^b ALTAI STATE TECHNICAL UNIVERSITY   (Russian Federation)

^c MONTANA STATE UNIVERSITY   (United States)

Author keywords

Ca2+ mobilization; chemotaxis; formyl peptide receptors; neutrophil; pyridazin 3(2H) one; pyridazine

Indexed keywords

2 [3 METHYL 5 [4 (METHYLTHIO)BENZYL] 6 OXOPYRIDAZIN 1(6H) YL]ACETIC ACID; 2 [5 (3 METHOXYBENZYL) 3 METHYL 6 OXOPYRIDAZIN 1(6H) YL] N [4 (METHYLTHIO)PHENYL]ACETAMIDE; 4 (4 METHOXYBENZYL) 6 METHYLPYRIDAZINE 3(2H) THIONE; 4 (4 METHOXYPHENOXY) 6 PHENYLPYRIDAZIN 3 AMINE; 6 METHYL 4 [4 (METHYLTHIO)BENZYL]PYRIDAZIN 3(2H) ONE; ETHYL 2 [3 METHYL 5 [4 (METHYLTHIO)BENZYL] 6 OXOPYRIDAZIN 1(6H) YL]ACETATE; FORMYLPEPTIDE RECEPTOR; N (4 BROMOPHENYL) 2 [3 METHYL 5 [4 (METHYLTHIO)BENZYL] 6 OXO PYRIDAZIN 1(6H) YL]ACETAMIDE; N (4 BROMOPHENYL) 2 [5 (3 METHOXYBENZYL) 3 METHYL 6 OXO PYRIDAZIN 1(6H) YL]ETHANETHIOAMIDE; N (4 IODOPHENYL) 2 [3 METHYL 5 [4 (METHYLTHIO)BENZYL] 6 OXO PYRIDAZIN 1(6H) YL]ACETAMIDE; PYRIDAZINE DERIVATIVE; UNCLASSIFIED DRUG;

AGONIST; ARTICLE; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MOLECULAR DOCKING; MOLECULAR MODEL; NEUTROPHIL CHEMOTAXIS;

EID: 84879020368     PISSN: 02724391     EISSN: 10982299     Source Type: Journal    
DOI: 10.1002/ddr.21076     Document Type: Article

References (43)

1. Baraldi PG, Preti D, Tabrizi MA, Fruttarolo F, Saponaro G, Baraldi S, Romagnoli R, Moorman AR, Gessi S, Varani K, et al. 2007. 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: 2514-2527. (Pubitemid 46367714)
2. Bokoch GM, Gilman AG,. 1984. Inhibition of receptor-mediated release of arachidonic acid by pertussis toxin. Cell 39: 301-308. (Pubitemid 15191213)
3. Bokoch GM, Katada T, Northup JK, Ui M, Gilman AG,. 1984. Purification and properties of the inhibitory guanine nucleotide-binding regulatory component of adenylate cyclase. J Biol Chem 259: 3560-3567. (Pubitemid 14170085)
4. Chiang GCH, Olsson T,. 2004. Polymer-supported copper complex for C-N and C-O cross-coupling reactions with aryl boronic acids. Org Lett 6: 3079-3082. (Pubitemid 39233124)
5. Christophe T, Karlsson A, Rabiet MJ, Boulay F, Dahlgren C,. 2002. Phagocyte activation by Trp-Lys-Tyr-Met-Val-Met, acting through FPRL1/LXA4R, is not affected by lipoxin A4. Scand J Immunol 56: 470-476. (Pubitemid 35373683)
6. Cilibrizzi A, Quinn MT, Kirpotina LN, Schepetkin IA, Holderness J, Ye RD, Rabiet MJ, Biancalani C, Cesari N, Graziano A, et al. 2009. 6-Methyl-2,4-disubstituted pyridazin-3(2H)-ones: a novel class of small-molecule agonists for formyl peptide receptors. J Med Chem 52: 5044-5057.
7. Cilibrizzi A, Schepetkin IA, Bartolucci G, Crocetti L, Dal Piaz V, Giovannoni MP, Graziano A, Kirpotina LN, Quinn MT, Vergelli C,. 2012. 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: 3781-3792.
8. Cui Y, Le Y, Yazawa H, Gong W, Wang JM,. 2002. Potential role of the formyl peptide receptor-like 1 (FPRL1) in inflammatory aspects of Alzheimer's disease. J Leukoc Biol 72: 628-635. (Pubitemid 36277832)
9. De Paulis A, Montuori N, Prevete N, Fiorentino I, Rossi FW, Visconte V, Rossi G, Marone G, Ragno P,. 2004. 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: 5739-5748. (Pubitemid 39392163)
10. Didsbury JR, Uhing RJ, Tomhave E, Gerard C, Gerard N, Snyderman R,. 1992. Functional high efficiency expression of cloned leukocyte chemoattractant receptor cDNAs. FEBS Lett 297: 275-279.
11. Dufton N, Perretti M,. 2010. Therapeutic anti-inflammatory potential of formyl-peptide receptor agonists. Pharmacol Ther 127: 175-188.
12. Edwards BS, Bologa C, Young SM, Balakin KV, Prossnitz ER, Savchuck NP, Sklar LA, Oprea TI,. 2005. Integration of virtual screening with high-throughput flow cytometry to identify novel small molecule formylpeptide receptor antagonists. Mol Pharmacol 68: 1301-1310. (Pubitemid 41539986)
13. Fujita H, Kato T, Watanabe N, Takahashi T, Kitagawa S,. 2011. Stimulation of human formyl peptide receptors by calpain inhibitors: homology modeling of receptors and ligand docking simulation. Arch Biochem Biophys 516: 121-127.
14. i-proteins mediate formyl peptide receptor signal transduction in human leukemia (HL-60) cells. J Biol Chem 264: 21470-21473. (Pubitemid 20028703)
15. Gilroy DW, Lawrence T, Perretti P, Rossi AG,. 2004. Inflammatory resolution: new opportunities for drug discovery. Nat Rev Drug Discov 3: 401-416. (Pubitemid 38618123)
16. Güngör T, Chen Y, Golla R, Ma Z, Corte JR, Northrop JP, Bin B, Dickson JK, Stouch T, Zhou R, et al. 2006. Synthesis and characterization of 3-arylquinazolinone and 3-arylquinazolinethione derivatives as selective estrogen receptor beta modulators. J Med Chem 49: 2440-2455.
17. Jesberger M, Davis TP, Barner L,. 2003. Applications of Lawesson's reagent in organic and organometallic syntheses. Synthesis 13: 1929-1958. (Pubitemid 37179946)
18. Kelley LA, Sternberg MJ,. 2009. Protein structure prediction on the Web: a case study using the Phyre server. Nat Protoc 4: 363-371.
19. Khlebnikov AI, Schepetkin IA, Kirpotina LN, Brive L, Dahlgren C, Jutila MA, Quinn MT,. 2012. Molecular docking of 2-(benzimidazol-2-ylthio)-N- phenylacetamide-derived small-molecule agonists of human formyl peptide receptor 1. J Mol Model 18: 2831-2843.
20. Kilby JM, Hopkins S, Venetta TM, Di Massimo B, Cloud GA, Lee JY, Alldredge L, Hunter E, Lambertm D, Bolognesi D, et al. 1998. Potent suppression of HIV-1 replication in humans by T-20, a peptide inhibitor of gp41-mediated virus entry. Nat Med 4: 1302-1307. (Pubitemid 28512112)
21. Le Y, Murphy PM, Wang JM,. 2002. Formyl-peptide receptors revisited. Trends Immunol 23: 541-548. (Pubitemid 35223553)
22. Meng Q, Hesse M,. 1990. N-N Bond cleavage: a route to macrocyclic dilactams. Synlett 3: 148-150.
23. Migeotte I, Communi D, Parmentier M,. 2006. Formyl peptide receptors: a promiscuous subfamily of G protein-coupled receptors controlling immune responses. Cytok Growth Factor Rev 17: 501-519. (Pubitemid 44793122)
24. Mills JS, Miettinen HM, Jesaitis AJ,. 1999. The N-formyl peptide receptor: structure, signaling and disease. In:, Serhan CN, Ward PA, editors. Molecular biology of inflammation. Totowa, NJ: Humana Press, p 215-245.
25. Mills JS, Miettinen HM, Cummings D, Jesaitis AJ,. 2000. 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: 39012-39017. (Pubitemid 32058913)
26. Movitz C, Brive L, Hellstrand K, Rabiet MJ, Dahlgren C,. 2010. 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: 14338-14345.
27. Pieretti S, Di Giannuario A, De Felice M, Perretti M, Cirino G,. 2004. Stimulus-dependent specificity for annexin 1 inhibition of the inflammatory nociceptive response: the involvement of the receptor for formylated peptides. Pain 109: 52-63. (Pubitemid 38479770)
28. Prossnitz ER, Ye RD,. 1997. The N-formyl peptide receptor: a model for the study of chemoattractant receptor structure and function. Pharmacol Ther 74: 73-102. (Pubitemid 27337355)
29. Prossnitz ER, Quehenberger O, Cochrane CG, Ye RD,. 1991. Transmembrane signalling by the N-formyl peptide receptor in stably transfected fibroblasts. Biochem Biophys Res Commun 179: 471-476.
30. Quach TD, Batey RA,. 2003. Gand- and base-free copper (II)-catalyzed C-N bond formation: cross-coupling reactions of organoboron compounds with aliphatic amines and anilines. Org Lett 5: 4397-4400. (Pubitemid 37490637)
31. Quehenberger O, Prossnitz ER, Cavanagh SL, Cochrane CG, Ye RD,. 1993. 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: 18167-18175. (Pubitemid 23260338)
32. Schepetkin IA, Kirpotina LN, Khlebnikov AI, Quinn MT,. 2007. High-throughput screening for small-molecule activators of neutrophils: identification of novel N-formyl peptide receptor agonists. Mol Pharmacol 71: 1061-1074. (Pubitemid 46457010)
33. Schepetkin IA, Kirpotina LN, Khlebnikov AI, Leopoldo M, Lucente E, Lacivita E, De Giorgio P, Quinn MT,. 2013. 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: 404-416.
34. Schiffmann E, Showell HV, Corcoran BA, Ward PA, Smith E, Becker EL,. 1975. The isolation and partial characterization of neutrophil chemotactic factors from Escherichia coli. J Immunol 114: 1831-1837.
35. Serhan CN, Brain SD, Buckley CD, Gilroy DW, Haslett C, O'Neill LA, Perretti M, Rossi AG, Wallace JL,. 2007. Resolution of inflammation: state of the art, definitions and terms. FASEB J 21: 325-332. (Pubitemid 46213480)
36. Simon MI, Strathmann MP, Gautam N,. 1991. Diversity of G proteins in signal transduction. Science 252: 802-808. (Pubitemid 121000516)
37. Sircar I,. 1983. Synthesis of 4-amino-6-phenyl-3(2H)-pyridazinones: a general procedure. J Heterocycl Chem 20: 1473-1476. (Pubitemid 14184913)
38. Tsuruky T, Takahata K, Yoshikawa M,. 2007. Mechanism of protective effect of intraperitoneally administered agonists for formyl peptide receptors against chemotherapy induced alopecia. Biosci Biothecnol Biochem 71: 1198-1202. (Pubitemid 47164248)
39. Wood PA, Pidcock E, Allen FH,. 2008. Interaction geometries and energies of hydrogen bonds to C=O and C=S acceptors: a comparative study. Acta Crystallogr B 64: 491-496.
40. Wrobel J, Millen J, Sredy J, Dietrich A, Kelly JM, Gorham BJ, Sestanj K,. 1989. Orally active aldose reductase inhibitors derived from bioisosteric substitutions on tolrestat. J Med Chem 32: 2493-2500. (Pubitemid 19269979)
41. Ye RD, Boulay F, Wang JM, Dahlgren C, Gerard C, Parmentier M, Serhan CN, Murphy PM,. 2009. International Union of Basic and Clinical Pharmacology. LXXIII. Nomenclature for the formyl peptide receptor (FPR) family. Pharmacol Rev 61: 119-161.
42. Zhang L, Falla TJ,. 2009. Host defense peptides for use as potential therapeutics. Curr Opin Invest Drugs 10: 164-171.
43. Zhou H, Zhou X, Kouadir M, Zhang Z, Yin X, Yang L, Zhao D,. 2009. Induction of macrophage migration by neurotoxic prion protein fragment. J Neurosci Methods 181: 1-5.