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Volumn 10, Issue 13, 2010, Pages 1339-1350

Discovery of 3,4-diaminocyclobut-3-ene-1,2-dione-based CXCR2 receptor antagonists for the treatment of inflammatory disorders

Author keywords

2 dione; 3,4 diaminocyclobut 3 ene 1; CXCR2; SCH 527123

Indexed keywords

3,4 DIAMINOCYCLOBUT 3 ENE 1,2 DIONE DERIVATIVE; AZ 8309; CHEMOKINE RECEPTOR ANTAGONIST; CHEMOKINE RECEPTOR CCR2; REPARIXIN; SB 332235; SB 656933; SCH 527123; UNCLASSIFIED DRUG;

EID: 77955609137     PISSN: 15680266     EISSN: None     Source Type: Journal    
DOI: 10.2174/156802610791561246     Document Type: Article
Times cited : (9)

References (74)
  • 1
    • 0036136424 scopus 로고    scopus 로고
    • Leukocyte adhesion and deficiency syndromes: Adhesion and tethering defects involving beta 2 integrins and selectin ligands
    • Bunting, M.; Harris, E.S.; Mclntyre, T.M.; Prescott, S.M.; Zimmerman, G.A. Leukocyte adhesion and deficiency syndromes: Adhesion and tethering defects involving beta 2 integrins and selectin ligands. Curr. Opin. Hematol., 2002, 9(1), 30-35.
    • (2002) Curr. Opin. Hematol , vol.9 , Issue.1 , pp. 30-35
    • Bunting, M.1    Harris, E.S.2    McLntyre, T.M.3    Prescott, S.M.4    Zimmerman, G.A.5
  • 2
    • 0031040539 scopus 로고    scopus 로고
    • Chemokines: Leucocyte recruitment and activation cytokines
    • Adams, D.H.; Lioyd, A.R. Chemokines: Leucocyte recruitment and activation cytokines. Lancet, 1997, 349(9055), 490-496.
    • (1997) Lancet , vol.349 , Issue.9055 , pp. 490-496
    • Adams, D.H.1    Lioyd, A.R.2
  • 3
    • 0033083950 scopus 로고    scopus 로고
    • Opportunities for novel therapeutic agents acting on chemokine receptors. Drug Discov
    • Saunders, J.; Tarby, C.M. Opportunities for novel therapeutic agents acting on chemokine receptors. Drug Discov. Today, 1999, 4(2), 80-92.
    • (1999) Today , vol.4 , Issue.2 , pp. 80-92
    • Saunders, J.1    Tarby, C.M.2
  • 4
    • 0029684314 scopus 로고    scopus 로고
    • Immunology: Chemokines take center stage in inflammatory ills
    • Gura, T. Immunology: Chemokines take center stage in inflammatory ills. Science, 1996, 272(5264), 954-960.
    • (1996) Science , vol.272 , Issue.5264 , pp. 954-960
    • Gura, T.1
  • 5
    • 0033081379 scopus 로고    scopus 로고
    • Structure of a CXC chemokine-receptor fragment in complex with interleukin-8
    • Skelton, N.J.; Quan, C.; Reilly, D.; Lowman, H. Structure of a CXC chemokine-receptor fragment in complex with interleukin-8. Structure, 1999, 7(2), 157-168.
    • (1999) Structure , vol.7 , Issue.2 , pp. 157-168
    • Skelton, N.J.1    Quan, C.2    Reilly, D.3    Lowman, H.4
  • 6
    • 0034849509 scopus 로고    scopus 로고
    • Chemokine receptors
    • Horuk, R. Chemokine receptors. Cytokine Growth Factor Rev., 2001, 72(4), 313-335.
    • (2001) Cytokine Growth Factor Rev , vol.72 , Issue.4 , pp. 313-335
    • Horuk, R.1
  • 8
    • 0026095795 scopus 로고
    • Structure and functional expression of a human interleukin-8 receptor
    • Holmes, W.E.; Lee, J.; Kuang, W.J.; Rice, G.C.; Wood, W.I. Structure and functional expression of a human interleukin-8 receptor. Science, 1991, 253(5025), 1278-1280.
    • (1991) Science , vol.253 , Issue.5025 , pp. 1278-1280
    • Holmes, W.E.1    Lee, J.2    Kuang, W.J.3    Rice, G.C.4    Wood, W.I.5
  • 9
    • 0026018108 scopus 로고
    • Cloning of complementary DNA encoding a functional human interleukin-8 receptor
    • Murphy, P.M.; Tiffany, H.L. Cloning of complementary DNA encoding a functional human interleukin-8 receptor. Science, 1991, 253(5025), 1280-1282.
    • (1991) Science , vol.253 , Issue.5025 , pp. 1280-1282
    • Murphy, P.M.1    Tiffany, H.L.2
  • 10
    • 0025888267 scopus 로고
    • Structure and neutrophil activating properties of a novel inflammatory peptide (ENA-78) with homology to interleu-kin-8
    • Walz, A.; Burgener, R.; Carr, B.; Baggiolini, M.; Kunkel, S.L.; Strieter, R.M. Structure and neutrophil activating properties of a novel inflammatory peptide (ENA-78) with homology to interleu-kin-8. J. Exp. Med., 1991, 774(6), 1355-1362.
    • (1991) J. Exp. Med , vol.774 , Issue.6 , pp. 1355-1362
    • Walz, A.1    Burgener, R.2    Carr, B.3    Baggiolini, M.4    Kunkel, S.L.5    Strieter, R.M.6
  • 12
    • 0037377567 scopus 로고    scopus 로고
    • Pathophysiological roles of interleukin-8/CXCL8 in pulmonary diseases
    • Mukaida, N. Pathophysiological roles of interleukin-8/CXCL8 in pulmonary diseases. Am. J. Physiol., 2003, 284(4,Pt.1), L566-L577.
    • (2003) Am. J. Physiol , vol.284 , Issue.4 Pt.1
    • Mukaida, N.1
  • 13
    • 0028052968 scopus 로고
    • Interleukin-8 and related chemotactic cytokines CXC and CC chemokines
    • Baggiolini, M.; Dewald, B.; Moser, B. Interleukin-8 and related chemotactic cytokines CXC and CC chemokines. Adv. Immunol., 1994, 55, 97-179.
    • (1994) Adv. Immunol , vol.55 , pp. 97-179
    • Baggiolini, M.1    Dewald, B.2    Moser, B.3
  • 14
    • 0032509889 scopus 로고    scopus 로고
    • Chemokines - Chemotactic cytokines that mediate inflammation
    • Luster, A.D. Chemokines - Chemotactic cytokines that mediate inflammation. N. Engl. J. Med., 1998, 338(7), 436-445.
    • (1998) N. Engl. J. Med , vol.338 , Issue.7 , pp. 436-445
    • Luster, A.D.1
  • 16
    • 0030071687 scopus 로고    scopus 로고
    • Differences in interleukin-8 and tumor necrosis factor-a in induced sputum from patients with chronic obstructive pulmonary disease or asthma
    • Keatings, V.M.; Collins, R.D.; Scott, D.M.; Barnes, P. Differences in interleukin-8 and tumor necrosis factor-a in induced sputum from patients with chronic obstructive pulmonary disease or asthma. Am. J. Respir. Crit. Care Med., 1996, 153(2), 530-534.
    • (1996) Am. J. Respir. Crit. Care Med , vol.153 , Issue.2 , pp. 530-534
    • Keatings, V.M.1    Collins, R.D.2    Scott, D.M.3    Barnes, P.4
  • 17
    • 0035376543 scopus 로고    scopus 로고
    • Interleukin-8 receptor antagonists in pulmonary diseases
    • Hay, D.W.; Sarau, H.M. Interleukin-8 receptor antagonists in pulmonary diseases. Curr. Opin. Pharmacol., 2001, 1(3), 242-247.
    • (2001) Curr. Opin. Pharmacol , vol.1 , Issue.3 , pp. 242-247
    • Hay, D.W.1    Sarau, H.M.2
  • 18
    • 33748580720 scopus 로고    scopus 로고
    • Chemokine receptors as therapeutic targets in chronic obstructive pulmonary diseas
    • Donnelly, L.E.; Barnes, P.J. Chemokine receptors as therapeutic targets in chronic obstructive pulmonary disease. Trends in Pharmacol. Sci., 2006, 27(10), 546-553.
    • (2006) Trends In Pharmacol. Sci , vol.27 , Issue.10 , pp. 546-553
    • Donnell, L.E.1    Barnes, P.2
  • 19
    • 0028067339 scopus 로고
    • Neutrophil and B cell expansion in mice that lack the murine IL-8 receptor homolog
    • Cacalano, G.; Lee, J.; Kikly, K.; Ryan, A.M.; Pitts-Meek, S.; Hult-gren, B.; Wood, I.; Moore, W. Neutrophil and B cell expansion in mice that lack the murine IL-8 receptor homolog. Science, 1994, 265(5172), 682-684.
    • (1994) Science , vol.265 , Issue.5172 , pp. 682-684
    • Cacalano, G.1    Lee, J.2    Kikly, K.3    Ryan, A.M.4    Pitts-Meek, S.5    Hult-Gren, B.6    Wood, I.7    Moore, W.8
  • 22
    • 0035207793 scopus 로고    scopus 로고
    • Small molecule interleukin-8 modulators
    • Li, J.J. Small molecule interleukin-8 modulators. Expert Opin. Ther. Patents, 2001, 11(12), 1905-1910.
    • (2001) Expert Opin. Ther. Patents , vol.11 , Issue.12 , pp. 1905-1910
    • Li, J.J.1
  • 23
    • 0141789715 scopus 로고    scopus 로고
    • Unraveling the chemistry of chemokine receptor ligands
    • Gao, A.; Metz, W.A. Unraveling the chemistry of chemokine receptor ligands. Chem. Rev., 2003, 103(9), 3733-3752.
    • (2003) Chem. Rev , vol.103 , Issue.9 , pp. 3733-3752
    • Gao, A.1    Metz, W.A.2
  • 24
    • 33746582271 scopus 로고    scopus 로고
    • Small molecule antagonists of the CXCR2 and CXCR1 chemokine receptors as therapeutic agents for the treatment of inflammatory diseases
    • Busch-Peterson, J. Small molecule antagonists of the CXCR2 and CXCR1 chemokine receptors as therapeutic agents for the treatment of inflammatory diseases. Curr. Top. Med. Chem., 2006, 6(13), 1354-1362.
    • (2006) Curr. Top. Med. Chem , vol.6 , Issue.13 , pp. 1354-1362
    • Busch-Peterson, J.1
  • 25
    • 33748142935 scopus 로고    scopus 로고
    • ELR+ CXC chemokines and their receptors (CXC chemokine receptor 1 and CXC chemokine receptor 2) as therapeutic targets
    • Bizzarri, C.; Beccari, A.R.; Bertini, R.; Cavicchia, M.R.; Giorgini, S.; Allegretti, M. ELR+ CXC chemokines and their receptors (CXC chemokine receptor 1 and CXC chemokine receptor 2) as therapeutic targets. Pharmacol. Ther., 2006, 112, 139-149.
    • (2006) Pharmacol. Ther , vol.112 , pp. 139-149
    • Bizzarri, C.1    Beccari, A.R.2    Bertini, R.3    Cavicchia, M.R.4    Giorgini, S.5    Allegretti, M.6
  • 26
    • 46849120181 scopus 로고    scopus 로고
    • Phenol-containing antagonists of the CXCR2 receptor
    • Busch-Petersen, J.; Wang, Y. Phenol-containing antagonists of the CXCR2 receptor. Expert Opin. Ther. Patents, 2008, 18(6), 629-637.
    • (2008) Expert Opin. Ther. Patents , vol.18 , Issue.6 , pp. 629-637
    • Busch-Petersen, J.1    Wang, Y.2
  • 27
    • 33751072679 scopus 로고    scopus 로고
    • Interleukin-8: Novel roles in human airway smooth muscle cell contraction and migration
    • Govindaraju, V.; Michoud, M.-C.; Al-Chalabi, M.; Ferraro, P.; Powell, W. S.; Martin, J.G. Interleukin-8: novel roles in human airway smooth muscle cell contraction and migration. Am. J. Phys., 2006, 291(5,Pt.1), C957-C965.
    • (2006) Am. J. Phys , vol.291 , Issue.5 Pt.1
    • Govindaraju, V.1    Michoud, M.-C.2    Al-Chalabi, M.3    Ferraro, P.4    Powell, W.S.5    Martin, J.G.6
  • 28
    • 34247645138 scopus 로고    scopus 로고
    • CXCR2 -the receptor to hit?
    • Reutershan, J. CXCR2 -the receptor to hit? Drug News Perspect., 2006, 19(10), 615-623.
    • (2006) Drug News Perspect , vol.19 , Issue.10 , pp. 615-623
    • Reutershan, J.1
  • 29
    • 33744821605 scopus 로고    scopus 로고
    • Chemokine receptors in chronic obstructive pulmonary disease (COPD)
    • Panina, P.; Mariani, M.; D'Ambrosio, D. Chemokine receptors in chronic obstructive pulmonary disease (COPD). Curr. Drug Targets, 2006, 7(6), 669-674.
    • (2006) Curr. Drug Targets , vol.7 , Issue.6 , pp. 669-674
    • Panina, P.1    Mariani, M.2    D'ambrosio, D.3
  • 30
    • 34247500507 scopus 로고    scopus 로고
    • New molecular targets for the treatment of neutrophilic diseases
    • Barnes, P.J. New molecular targets for the treatment of neutrophilic diseases. J. Allergy Clin. Immunol., 2007, 119(5), 1055-1062.
    • (2007) J. Allergy Clin. Immunol , vol.119 , Issue.5 , pp. 1055-1062
    • Barnes, P.J.1
  • 31
    • 77955612605 scopus 로고    scopus 로고
    • IL-8 receptor antagonist: Basic research and clinical utility
    • Moser, B., Letts, G.L., Neote, K., Eds., Birkhaeuser Verlag: Basel, Switzerland
    • White, J.R.; Sarau, H.M. IL-8 receptor antagonist: basic research and clinical utility. In: Chemokine Biology-Basic Research and Clinical Application; Moser, B., Letts, G.L., Neote, K., Eds.; Birkhaeuser Verlag: Basel, Switzerland, 2007, vol. 2, pp. 89-102.
    • (2007) Chemokine Biology-Basic Research and Clinical Application , vol.2 , pp. 89-102
    • White, J.R.1    Sarau, H.M.2
  • 34
    • 15144339410 scopus 로고    scopus 로고
    • Design and synthesis of [2-(8,9-Dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)-ethyl]phosphonic acid (EAA-090), a potent N-methyl-D-aspartate antagonist, via the use of 3-cyclobutene-1,2-dione as an achiral a-amino acid bioisostere
    • Kinney, W.A.; Abou-Gharbia, M.; Garrison, D.T.; Schmid, J.; Kowal, D.M.; Bramlett, D.R.; Miller, T.L.; Tasse, R.P.; Zaleska, M.M.; Moyer, J.A. Design and synthesis of [2-(8,9-Dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)-ethyl]phosphonic acid (EAA-090), a potent N-methyl-D-aspartate antagonist, via the use of 3-cyclobutene-1,2-dione as an achiral a-amino acid bioisostere. J. Med. Chem., 1998, 41(2), 236-246.
    • (1998) J. Med. Chem , vol.41 , Issue.2 , pp. 236-246
    • Kinney, W.A.1    Abou-Gharbia, M.2    Garrison, D.T.3    Schmid, J.4    Kowal, D.M.5    Bramlett, D.R.6    Miller, T.L.7    Tasse, R.P.8    Zaleska, M.M.9    Moyer, J.A.10
  • 40
    • 40849126299 scopus 로고    scopus 로고
    • Synthesis and structure-activity relationships or new disubstituted phenyl-containing 3,4-diamino-3-cyclobutene-1,2-diones as CXCR2 receptor antagonists
    • Lai, G.; Merritt, J.R.; He, Z.; Feng, D.; Chao, J.; Czarniecki, M.F.; Rokosz, L.L.; Stauffer, T.M.; Rindgen, D.; Taveras, A.G. Synthesis and structure-activity relationships or new disubstituted phenyl-containing 3,4-diamino-3-cyclobutene-1,2-diones as CXCR2 receptor antagonists. Bioorg. Med. Chem. Lett., 2008, 18, 1864-1868.
    • (2008) Bioorg. Med. Chem. Lett , vol.18 , pp. 1864-1868
    • Lai, G.1    Merritt, J.R.2    He, Z.3    Feng, D.4    Chao, J.5    Czarniecki, M.F.6    Rokosz, L.L.7    Stauffer, T.M.8    Rindgen, D.9    Taveras, A.G.10
  • 41
    • 60449110305 scopus 로고    scopus 로고
    • Fluoroalkyl a side chain containing 3,4-diamino-cyclobutenediones as potent and orally bioavailable CXCR2-CXCR1 dual antagonists
    • Biju, P.; Taveras, A.G.; Dwyer, M.P.; Yu, Y.; Chao, J.; Hipkin, R.W.; Fan, X.; Rindgen, D.; Fine, J.; Lundell, D. Fluoroalkyl a side chain containing 3,4-diamino-cyclobutenediones as potent and orally bioavailable CXCR2-CXCR1 dual antagonists. Bioorg. Med. Chem. Lett., 2009, 19, 1431-1433.
    • (2009) Bioorg. Med. Chem. Lett , vol.19 , pp. 1431-1433
    • Biju, P.1    Taveras, A.G.2    Dwyer, M.P.3    Yu, Y.4    Chao, J.5    Hipkin, R.W.6    Fan, X.7    Rindgen, D.8    Fine, J.9    Lundell, D.10
  • 43
    • 67650084297 scopus 로고    scopus 로고
    • Synthesis of functionalized hy-droxyl-thiophene motifs as amido- and sulfonamide-phenol bioisosteres
    • Chao, J.; Taveras, A.G.; Aki, C.J. Synthesis of functionalized hy-droxyl-thiophene motifs as amido- and sulfonamide-phenol bioisosteres. Tetrahedron Lett., 2009, 50, 5005-5008.
    • (2009) Tetrahedron Lett , vol.50 , pp. 5005-5008
    • Chao, J.1    Taveras, A.G.2    Aki, C.J.3
  • 50
    • 77955645117 scopus 로고    scopus 로고
    • Preparation of arylamino het-erocyclylmethyl cyclobutenediones as antiinflammatories
    • Press, N.J.; Watson, S.J.; Porter, D. Preparation of arylamino het-erocyclylmethyl cyclobutenediones as antiinflammatories. WO 148790A1, 2008.
    • (2008) WO 148790A1
    • Press, N.J.1    Watson, S.J.2    Porter, D.3
  • 55
    • 58149232586 scopus 로고    scopus 로고
    • The Interleukin-8 pathway in cancer
    • Waugh, D.J.J.; Wilson, C. The Interleukin-8 pathway in cancer. Clin. Cancer Res., 2008, 14(21), 6735-6741.
    • (2008) Clin. Cancer Res , vol.14 , Issue.21 , pp. 6735-6741
    • Waugh, D.J.J.1    Wilson, C.2
  • 56
    • 65249183876 scopus 로고    scopus 로고
    • Small-molecule antagonists for CXCR2 and CXCR1 inhibit human melanoma growth by decreasing tumor cell proliferation, survival, and angiogenesis
    • Singh, S.; Sadanandam, A.; Nannura, K.C.; Varney, M.L.; Mayer-Ezell, R.; Bond, R.; Singh, R.K. Small-molecule antagonists for CXCR2 and CXCR1 inhibit human melanoma growth by decreasing tumor cell proliferation, survival, and angiogenesis. Clin. Cancer Res., 2009, 15(7), 2380-2386.
    • (2009) Clin. Cancer Res , vol.15 , Issue.7 , pp. 2380-2386
    • Singh, S.1    Sadanandam, A.2    Nannura, K.C.3    Varney, M.L.4    Mayer-Ezell, R.5    Bond, R.6    Singh, R.K.7
  • 59
    • 77955593857 scopus 로고    scopus 로고
    • Study to Evaluate the Safety and Dose-Range of SCH 527123 in Subjects With Moderate to Severe Chronic Obstructive Pulmonary Disease (COPD), NCT00441701, Study P04592AM1, Accessed September 2009
    • Study to Evaluate the Safety and Dose-Range of SCH 527123 in Subjects With Moderate to Severe Chronic Obstructive Pulmonary Disease (COPD). (NCT00441701, Study P04592AM1). http://www.clinicaltrials.gov/, [Accessed September 2009].
  • 60
    • 77955592602 scopus 로고    scopus 로고
    • Neutrophilic Asthma Study with SCH 527123 (NCT00632502, Study P05365AM2), Accessed September 2009
    • Neutrophilic Asthma Study with SCH 527123 (NCT00632502, Study P05365AM2). http://www.clinicaltrials.gov/, [Accessed September 2009].
  • 61
    • 77955607801 scopus 로고    scopus 로고
    • Efficacy and Safety of SCH 527123 in Subjects with Allergen-Induced Asthma (NCT00688467, Study P05363), Accessed September 2009
    • Efficacy and Safety of SCH 527123 in Subjects with Allergen-Induced Asthma (NCT00688467, Study P05363). http://www.clinicaltrials.gov/, [Accessed September 2009].
  • 62
    • 77955647106 scopus 로고    scopus 로고
    • A study to assess the clinical effects of SCH 527123 in psoriasis (NCT00684593, study P04481), accessed: September 2009
    • A study to assess the clinical effects of SCH 527123 in psoriasis (NCT00684593, study P04481). http://www.clinicaltrials.gov/ [accessed: September 2009].
  • 68
    • 65349133069 scopus 로고    scopus 로고
    • 6-Amino-4-oxo-1,3-diphenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonyl derivatives as a new class of potent inhibitors of Interleukin-8-induced neutrophil chemotaxis
    • Cesarini, S.; Spallarossa, A.; Ranise, A.; Bruno, O.; Arduino, N.; Bertolotto, M.; Dallegri, F.; Tognolini, M.; Gobbetti, T.; Barocelli, E. 6-Amino-4-oxo-1,3-diphenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonyl derivatives as a new class of potent inhibitors of Interleukin-8-induced neutrophil chemotaxis. Bioorg. Med. Chem., 2009, 17, 3580-3587.
    • (2009) Bioorg. Med. Chem , vol.17 , pp. 3580-3587
    • Cesarini, S.1    Spallarossa, A.2    Ranise, A.3    Bruno, O.4    Arduino, N.5    Bertolotto, M.6    Dallegri, F.7    Tognolini, M.8    Gobbetti, T.9    Barocelli, E.10


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