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Volumn 49, Issue , 2012, Pages 102-109

New inhibitors of dihydroorotate dehydrogenase (DHODH) based on the 4-hydroxy-1,2,5-oxadiazol-3-yl (hydroxyfurazanyl) scaffold

Author keywords

Brequinar; Dihydroorotate dehydrogenase inhibitors; Hydroxyfurazan; Leflunomide

Indexed keywords

4 BENZYLOXY 1,2,5 OXADIAZOLE 3 CARBONYL CHLORIDE; 4 BENZYLOXY N (BIPHENYL 4 YL) 1,2,5 OXADIAZOLE 3 CARBOXAMIDE; 4 BENZYLOXY N [(1 TRIFLUOROMETHYL)PHENYL 4 YL] 1,2,5 OXADIAZOLE 3 CARBOXAMIDE; 4 BENZYLOXY N [(2,3,5,6 TETRAFLUORO 3' TRIFLUOROMETHYL)BIPHENYL 4 YL] 1,2,5 OXADIAZOLE 3 CARBOXYAMIDE; 4 BENZYLOXY N [(2,3,5,6 TETRAFLUORO 4' TRIFLUOROMETHYL)BIPHENYL 4 YL] 1,2,5 OXADIAZOLE 3 CARBOXYAMIDE; 4 BENZYLOXY N [(2,3,5,6 TETRAFLUORO)BIPHENYL 4 YL] 1,2,5 OXADIAZOLE 3 CARBOXYAMIDE; 4 BENZYLOXY N [(3,5 DIFLUORO 3' TRIFLUOROMETHYL)BIPHENYL 4 YL] 1,2,5 OXADIAZOLE 3 CARBOXYAMIDE; 4 BENZYLOXY N [(3,5 DIFLUORO 4' TRIFLUOROMETHYL)BIPHENYL 4 YL] 1,2,5 OXADIAZOLE 3 CARBOXYAMIDE; 4 BENZYLOXY N [(3,5 DIFLUORO)BIPHENYL 4 YL] 1,2,5 OXADIAZOLE 3 CARBOXYAMIDE; 4 BENZYLOXY N [3' (TRIFLUOROMETHYL)BIPHENYL 4 YL] 1,2,5 OXADIAZOLE 3 CARBOXYAMIDE; 4 HYDROXY N (BIPHENYL 2 YL) 1,2,5 OXADIAZOLE 3 CARBOXYAMIDE; 4 HYDROXY N (BIPHENYL 4 YL) 1,2,5 OXADIAZOLE 3 CARBOXYAMIDE; 4 HYDROXY N [(1 TRIFLUOROMETHYL)PHENYL 4 YL] 1,2,5 OXADIAZOLE 3 CARBOXYAMIDE; 4 HYDROXY N [(2,3,5,6 (TETRAFLUORO)BIPHENYL 4 YL)] 1,2,5 OXADIAZOLE 3 CARBOXYAMIDE; 4 HYDROXY N [(2,3,5,6 TETRAFLUORO 3' TRIFLUOROMETHOXY)BIPHENYL 4 YL] 1,2,5 OXADIAZOLE 3 CARBOXYAMIDE; 4 HYDROXY N [(2,3,5,6 TETRAFLUORO 3' TRIFLUOROMETHYL)BIPHENYL 4 YL] 1,2,5 OXADIAZOLE 3 CARBOXYAMIDE; 4 HYDROXY N [(2,3,5,6 TETRAFLUORO 4' TRIFLUOROMETHYL)BIPHENYL 4 YL] 1,2,5 OXADIAZOLE 3 CARBOXYAMIDE; 4 HYDROXY N [(3,5 DIFLUORO 3' TRIFLUOROMETHYL)BIPHENYL 4 YL] 1,2,5 OXADIAZOLE 3 CARBOXYAMIDE; 4 HYDROXY N [(3,5 DIFLUORO 4' TRIFLUOROMETHYL)BIPHENYL 4 YL] 1,2,5 OXADIAZOLE 3 CARBOXYAMIDE; 4 HYDROXY N [(3,5 DIFLUORO)BIPHENYL 4 YL] 1,2,5 OXADIAZOLE 3 CARBOXYAMIDE; 4 HYDROXY N [3' (TRIFLUOROMETHYL)BIPHENYL 4 YL] 1,2,5 OXADIAZOLE 3 CARBOXYAMIDE; 4 HYDROXY N [4' (TRIFLUOROMETHYL)BIPHENYL 4 YL] 1,2,5 OXADIAZOLE 3 CARBOXYAMIDE; BIPHENYL DERIVATIVE; DIHYDROOROTATE DEHYDROGENASE; DIHYDROOROTATE DEHYDROGENASE INHIBITOR; FLUORINE; UNCLASSIFIED DRUG;

EID: 84857234672     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.12.038     Document Type: Article
Times cited : (29)

References (37)
  • 1
    • 0018823799 scopus 로고
    • Pyrimidine nucleotide biosynthesis in animals: Genes, enzymes, and regulation of UMP biosynthesis
    • M.E. Jones Pyrimidine nucleotide biosynthesis in animals: genes, enzymes, and regulation of UMP biosynthesis Ann. Rev. Biochem. 49 1980 253 279
    • (1980) Ann. Rev. Biochem. , vol.49 , pp. 253-279
    • Jones, M.E.1
  • 2
    • 0030032806 scopus 로고    scopus 로고
    • The immunosuppressive metabolite of leflunomide is a potent inhibitor of human dihydroorotate dehydrogenase
    • DOI 10.1021/bi952168g
    • J.P. Davis, G.A. Cain, W.J. Pitts, R.L. Magolda, and R.A. Copeland The immunosuppressive metabolite of leflunomide is a potent inhibitor of human dihydroorotate dehydrogenase Biochemistry 35 1996 1270 1273 (Pubitemid 26050790)
    • (1996) Biochemistry , vol.35 , Issue.4 , pp. 1270-1273
    • Davis, J.P.1    Cain, G.A.2    Pitts, W.J.3    Magolda, R.L.4    Copeland, R.A.5
  • 3
    • 0034122123 scopus 로고    scopus 로고
    • Leflunomide: An immunomodulatory drug for the treatment of rheumatoid arthritis and other autoimmune diseases
    • DOI 10.1016/S0162-3109(00)00191-0, PII S0162310900001910
    • M.L. Herrmann, R. Schleyerbach, and B.J. Kirschbaum Leflunomide: an immunomodulatory drug for the treatment of rheumatoid arthritis and other autoimmune diseases Immunopharmacology 47 2000 273 289 (Pubitemid 30394543)
    • (2000) Immunopharmacology , vol.47 , Issue.2-3 , pp. 273-289
    • Herrmann, M.L.1    Schleyerbach, R.2    Kirschbaum, B.J.3
  • 4
    • 2342627946 scopus 로고    scopus 로고
    • Leflunomide in the treatment of rheumatoid arthritis
    • DOI 10.1016/S0149-2918(04)90048-3
    • E.K. Li, L.-S. Tam, and B. Tomlinson Leflunomide in the treatment of rheumatoid arthritis Clin. Ther. 26 2004 447 459 (Pubitemid 38586447)
    • (2004) Clinical Therapeutics , vol.26 , Issue.4 , pp. 447-459
    • Li, E.K.1    Tam, L.-S.2    Tomlinson, B.3
  • 5
    • 0032524362 scopus 로고    scopus 로고
    • Side effects of brequinar and brequinar analogues, in combination with cyclosporine, in the rat
    • DOI 10.1016/S0300-483X(98)00026-2, PII S0300483X98000262
    • C. Pally, D. Smith, B. Jaffee, R. Magolda, H. Zehender, B. Dorobek, P. Donatsch, C. Papageorgiou, and H.J. Schuurman Side effects of brequinar and brequinar analogues, in combination with cyclosporine, in the rat Toxicology 127 1998 207 222 (Pubitemid 28341830)
    • (1998) Toxicology , vol.127 , Issue.1-3 , pp. 207-222
    • Pally, C.1    Smith, D.2    Jaffee, B.3    Magolda, R.4    Zehender, H.5    Dorobek, B.6    Donatsch, P.7    Papageorgiou, C.8    Schuurman, H.-J.9
  • 6
    • 0029635196 scopus 로고
    • ABC of rheumatology. Rheumatoid arthritis. 1. Clinical features and diagnosis
    • M. Akil, and R.S. Amos ABC of rheumatology. Rheumatoid arthritis. 1. Clinical features and diagnosis Br. Med. J. 310 1995 587 590
    • (1995) Br. Med. J. , vol.310 , pp. 587-590
    • Akil, M.1    Amos, R.S.2
  • 8
    • 8644280316 scopus 로고    scopus 로고
    • A search for endogenous mechanisms of anti-inflammation uncovers novel chemical mediators: Missing links to resolution
    • DOI 10.1007/s00418-004-0695-8
    • C.N. Serhan A search for endogenous mechanisms of anti-inflammation uncovers novel chemical mediators: missing links to resolution Histochem. Cell Biol. 122 2004 305 321 (Pubitemid 39506589)
    • (2004) Histochemistry and Cell Biology , vol.122 , Issue.4 , pp. 305-321
    • Serhan, C.N.1
  • 11
    • 34848863617 scopus 로고    scopus 로고
    • Non-steroidal anti-inflammatory drugs and myocardial infarctions: Comparative systematic review of evidence from observational studies and randomised controlled trials
    • DOI 10.1136/ard.2006.068650
    • P.A. Scott, G.H. Kingsley, C.M. Smith, E.H. Choy, and D.L. Scott Non-steroidal anti-inflammatory drugs and myocardial infarctions: comparative systematic review of evidence from observational studies and randomised controlled trials Ann. Rheum. Dis. 66 2007 1296 1304 (Pubitemid 47492471)
    • (2007) Annals of the Rheumatic Diseases , vol.66 , Issue.10 , pp. 1296-1304
    • Scott, P.A.1    Kingsley, G.H.2    Smith, C.M.3    Choy, E.H.4    Scott, D.L.5
  • 12
    • 0029641947 scopus 로고
    • ABC of rheumatology. Rheumatoid arthritis. 2. Treatment
    • M. Akil, and R.S. Amos ABC of rheumatology. Rheumatoid arthritis. 2. Treatment Br. Med. J. 310 1995 652 655
    • (1995) Br. Med. J. , vol.310 , pp. 652-655
    • Akil, M.1    Amos, R.S.2
  • 14
    • 0026690437 scopus 로고
    • Inhibition of dihydroorotate dehydrogenase activity by brequinar sodium
    • S.-F. Chen, F.W. Perrella, and D.L. Behrens Inhibition of dihydroorotate dehydrogenase activity by brequinar sodium Cancer Res. 52 1992 3521 3527
    • (1992) Cancer Res. , vol.52 , pp. 3521-3527
    • Chen, S.-F.1    Perrella, F.W.2    Behrens, D.L.3
  • 16
    • 0034650342 scopus 로고    scopus 로고
    • Structures of human dihydroorotate dehydrogenase in complex with antiproliferative agents
    • DOI 10.1016/S0969-2126(00)00077-0
    • S.P. Liu, E.A. Neidhardt, T.H. Grossman, T. Ocain, and J. Clardy Structures of human dihydroorotate dehydrogenase in complex with antiproliferative agents Struct. Fold. Des. 8 2000 25 33 (Pubitemid 30051339)
    • (2000) Structure , vol.8 , Issue.1 , pp. 25-33
    • Liu, S.1    Neidhardt, E.A.2    Grossman, T.H.3    Ocain, T.4    Clardy, J.5
  • 17
    • 34147113829 scopus 로고    scopus 로고
    • NO-donor COX-2 inhibitors. New nitrooxy-substituted 1,5-diarylimidazoles endowed with COX-2 inhibitory and vasodilator properties
    • DOI 10.1021/jm0607247
    • K. Chegaev, L. Lazzarato, P. Tosco, C. Cena, E. Marini, B. Rolando, P.-A. Carrupt, R. Fruttero, and A. Gasco NO-donor COX-2 inhibitors. New nitrooxy-substituted 1,5-diarylimidazoles endowed with COX-2 inhibitory and vasodilator properties J. Med. Chem. 50 2007 1449 1457 (and references therein reported) (Pubitemid 46564368)
    • (2007) Journal of Medicinal Chemistry , vol.50 , Issue.7 , pp. 1449-1457
    • Chegaev, K.1    Lazzarato, L.2    Tosco, P.3    Cena, C.4    Marini, E.5    Rolando, B.6    Carrupt, P.-A.7    Fruttero, R.8    Gasco, A.9
  • 18
    • 77952758403 scopus 로고    scopus 로고
    • Nitrooxymethyl-substituted analogues of rofecoxib: Synthesis and pharmacological characterization
    • (and references therein reported)
    • D. Boschi, C. Cena, A. Di Stilo, B. Rolando, P. Manzini, R. Fruttero, and A. Gasco Nitrooxymethyl-substituted analogues of rofecoxib: synthesis and pharmacological characterization Chem. Biodivers. 7 2010 1173 1182 (and references therein reported)
    • (2010) Chem. Biodivers. , vol.7 , pp. 1173-1182
    • Boschi, D.1    Cena, C.2    Di Stilo, A.3    Rolando, B.4    Manzini, P.5    Fruttero, R.6    Gasco, A.7
  • 19
    • 79952077671 scopus 로고    scopus 로고
    • Nitrooxyacyl derivatives of salicylic acid: Aspirin-like molecules that covalently inactivate cyclooxygenase-1
    • (and references therein reported)
    • C. Cena, P. Tosco, E. Marini, L. Lazzarato, M. Piccinini, C. Ramondetti, E. Lupino, R. Fruttero, and A. Gasco Nitrooxyacyl derivatives of salicylic acid: aspirin-like molecules that covalently inactivate cyclooxygenase-1 ChemMedChem 6 2011 523 530 (and references therein reported)
    • (2011) ChemMedChem , vol.6 , pp. 523-530
    • Cena, C.1    Tosco, P.2    Marini, E.3    Lazzarato, L.4    Piccinini, M.5    Ramondetti, C.6    Lupino, E.7    Fruttero, R.8    Gasco, A.9
  • 21
    • 77952721574 scopus 로고    scopus 로고
    • T.N.Johansen, 4-Hydroxy-1,2,5-oxadiazol-3-yl moiety as bioisoster of the carboxy function. Synthesis, ionization constants, and molecular pharmacological characterization at ionotropic glutamate receptors of compounds related to glutamate and its homologues
    • M.L. Lolli, C. Giordano, D.S. Pickering, B. Rolando, K.B. Hansen, A. Foti, A. Contreras-Sanz, A. Amir, R. Fruttero, A. Gasco, and B. Nielsen T.N.Johansen, 4-Hydroxy-1,2,5-oxadiazol-3-yl moiety as bioisoster of the carboxy function. Synthesis, ionization constants, and molecular pharmacological characterization at ionotropic glutamate receptors of compounds related to glutamate and its homologues J. Med. Chem. 53 2010 4110 4118
    • (2010) J. Med. Chem. , vol.53 , pp. 4110-4118
    • Lolli, M.L.1    Giordano, C.2    Pickering, D.S.3    Rolando, B.4    Hansen, K.B.5    Foti, A.6    Contreras-Sanz, A.7    Amir, A.8    Fruttero, R.9    Gasco, A.10    Nielsen, B.11
  • 22
    • 0346256826 scopus 로고    scopus 로고
    • Discovery of a novel series of DHODH inhibitors by a docking procedure and QSAR refinement
    • DOI 10.1016/j.bmcl.2003.10.021
    • J. Leban, W. Saeb, G. Garcia, R. Baumgartner, and B. Kramer Discovery of a novel series of DHODH inhibitors by a docking procedure and QSAR refinement Bioorg. Med. Chem. Lett. 14 2004 55 58 (Pubitemid 38010193)
    • (2004) Bioorganic and Medicinal Chemistry Letters , vol.14 , Issue.1 , pp. 55-58
    • Leban, J.1    Saeb, W.2    Garcia, G.3    Baumgartner, R.4    Kramer, B.5
  • 24
    • 0034823624 scopus 로고    scopus 로고
    • Recombinant expression of n-terminal truncated mutants of the membrane bound mouse, rat and human flavoenzyme dihydroorotate dehydrogenase: A versatile tool to rate inhibitor effects?
    • DOI 10.1046/j.1432-1327.2001.02061.x
    • A. Ullrich, W. Knecht, M. Fries, and M. Loffler Recombinant expression of N-terminal truncated mutants of the membrane bound mouse, rat and humanflavoenzyme dihydroorotate dehydrogenase - A versatile tool to rate inhibitor effects? Eur. J. Biochem. 268 2001 1861 1868 (Pubitemid 32862722)
    • (2001) European Journal of Biochemistry , vol.268 , Issue.6 , pp. 1861-1868
    • Ullrich, A.1    Knecht, W.2    Fries, M.3    Loffler, M.4
  • 30
    • 84857233159 scopus 로고    scopus 로고
    • 2010.11 Chemical Computing Group Inc Montreal, Quebec, Canada
    • MOE Version 2010.11 2010 Chemical Computing Group Inc Montreal, Quebec, Canada
    • (2010) MOE Version
  • 31
    • 84961980477 scopus 로고    scopus 로고
    • Quantum mechanical continuum solvation models
    • J. Tomasi, B. Mennucci, and R. Cammi Quantum mechanical continuum solvation models Chem. Rev. 105 2005 2999 3094
    • (2005) Chem. Rev. , vol.105 , pp. 2999-3094
    • Tomasi, J.1    Mennucci, B.2    Cammi, R.3
  • 33
    • 84857239036 scopus 로고    scopus 로고
    • The Protein Data Bank; (Accessed 11 July 2011)
    • The Protein Data Bank; http://www.rcsb.org/ (Accessed 11 July 2011).
  • 35
    • 0001398008 scopus 로고    scopus 로고
    • How well does a restrained electrostatic potential (RESP) model perform in calculating conformational energies of organic and biological molecules?
    • J. Wang, P. Cieplak, and P.A. Kollman How well does a restrained electrostatic potential (RESP) model perform in calculating conformational energies of organic and biological molecules? J. Comput. Chem. 21 2000 1049 1074
    • (2000) J. Comput. Chem. , vol.21 , pp. 1049-1074
    • Wang, J.1    Cieplak, P.2    Kollman, P.A.3
  • 36
    • 0033198021 scopus 로고    scopus 로고
    • A molecular dynamics simulation of the flavin mononucleotide-RNA aptamer complex
    • DOI 10.1002/(SICI)1097-0282(199909)50:3<287::AID-BIP5>3.0.CO;2-G
    • C. Schneider, and J. Sühnel A molecular dynamics simulation of the flavin mononucleotide-RNA aptamer complex Biopolymers 50 1999 287 302 (Pubitemid 29334304)
    • (1999) Biopolymers , vol.50 , Issue.3 , pp. 287-302
    • Schneider, C.1    Suhnel, J.2


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