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Volumn 53, Issue 2, 2010, Pages 573-585

Discovery of 4-[(2S)-2-{[4-(4-Chlorophenoxy)phenoxy]methyl}-1-pyrrolidinyl] butanoic acid (DG-051) as a novel leukotriene A4 hydrolase inhibitor of leukotriene B4 biosynthesis

Author keywords

[No Author keywords available]

Indexed keywords

4 [2 [[4 (4 CHLOROPHENOXY)PHENOXY]METHYL] 1 PYRROLIDINYL]BUTANOIC ACID; DG 051; LEUKOTRIENE A4 HYDROLASE; LEUKOTRIENE B4; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 77249161707     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm900838g     Document Type: Article
Times cited : (59)

References (59)
  • 1
    • 10744220794 scopus 로고    scopus 로고
    • Helgadottir, A.; Manolescu, A.; Thorleifsson, G.; Jonsdottir, H.; Thorsteinsdottir, U.; Samani, N. J.; Gretarsdottir, S.; Johannsson, H.; Gudmundsson, G.; Grant, S. F. A.; Sveinbjornsdottir, S.; Valdimarsson, E. M.; Matthiasson, S. E.; Gudmundsdottir, O; Gurney, M.; Sainz, J.; Thorhallsdottir; Andresdottir, M.; Frigge, M. L.; Gudnason, V.; Kong, A.; Topol, E. J.; Thorgeirsson, G.; Gulcher, J. R.; Hakonarson, H.; Stefansson, K. The gene encoding 5-lipoxygenase activating protein confers risk of myocardial infarction and stroke. Nat. Genet. 2004, 36, 233-239.
    • Helgadottir, A.; Manolescu, A.; Thorleifsson, G.; Jonsdottir, H.; Thorsteinsdottir, U.; Samani, N. J.; Gretarsdottir, S.; Johannsson, H.; Gudmundsson, G.; Grant, S. F. A.; Sveinbjornsdottir, S.; Valdimarsson, E. M.; Matthiasson, S. E.; Gudmundsdottir, O; Gurney, M.; Sainz, J.; Thorhallsdottir; Andresdottir, M.; Frigge, M. L.; Gudnason, V.; Kong, A.; Topol, E. J.; Thorgeirsson, G.; Gulcher, J. R.; Hakonarson, H.; Stefansson, K. The gene encoding 5-lipoxygenase activating protein confers risk of myocardial infarction and stroke. Nat. Genet. 2004, 36, 233-239.
  • 2
    • 29444444748 scopus 로고    scopus 로고
    • Helgadottir, A.; Manolescu, A.; Helgason, A.; Thorleifsson, G.; Thorsteinsdottir, U.; Gudbjartsson, D. F.; Gretarsdottir, S.; Magnusson, K. P.; Gudmundsson, G.; Hicks, A.; Jonsson, T.; Grant, S. F. A.; Sainz, J.; O'Brien, S. J.; Sveinbjornsdottir, S.; Valdimarsson, E. M.; Matthiasson, S. E.; Levey, A. I.; Abramson, J. L.; Reilly, M.; Vaccarino, V.; Wolfe, M.; Gudnason, V.; Quyyumi, A. A.; Topol, E. J.; Rader, D. J.; Thorgeirsson, G.; Gulcher, J. R.; Hakonarson, H.; Kong, A.; Stefansson, K. A variant of the gene encoding leukotriene A4 hydrolase confers ethnicity-specific risk of myocardial infarction. Nat. Genet. 2006, 38, 68-74.
    • Helgadottir, A.; Manolescu, A.; Helgason, A.; Thorleifsson, G.; Thorsteinsdottir, U.; Gudbjartsson, D. F.; Gretarsdottir, S.; Magnusson, K. P.; Gudmundsson, G.; Hicks, A.; Jonsson, T.; Grant, S. F. A.; Sainz, J.; O'Brien, S. J.; Sveinbjornsdottir, S.; Valdimarsson, E. M.; Matthiasson, S. E.; Levey, A. I.; Abramson, J. L.; Reilly, M.; Vaccarino, V.; Wolfe, M.; Gudnason, V.; Quyyumi, A. A.; Topol, E. J.; Rader, D. J.; Thorgeirsson, G.; Gulcher, J. R.; Hakonarson, H.; Kong, A.; Stefansson, K. A variant of the gene encoding leukotriene A4 hydrolase confers ethnicity-specific risk of myocardial infarction. Nat. Genet. 2006, 38, 68-74.
  • 3
    • 33646174211 scopus 로고    scopus 로고
    • Atherosclerosis is an inflammatory disorder after all
    • Meng, C. Q. Atherosclerosis is an inflammatory disorder after all. Curr. Top. Med. Chem 2006, 6, 93-102.
    • (2006) Curr. Top. Med. Chem , vol.6 , pp. 93-102
    • Meng, C.Q.1
  • 7
    • 0025164256 scopus 로고
    • Leukotrienes and other products of the 5-lipoxygenase pathway. Biochemistry and relation to pathology in human diseases
    • (a) Lewis, R. A.; Austen, K. F.; Soberman, R. J. Leukotrienes and other products of the 5-lipoxygenase pathway. Biochemistry and relation to pathology in human diseases. N. Engl. J. Med. 1990, 232, 645-655.
    • (1990) N. Engl. J. Med , vol.232 , pp. 645-655
    • Lewis, R.A.1    Austen, K.F.2    Soberman, R.J.3
  • 9
    • 0031037332 scopus 로고    scopus 로고
    • Pharmacology of leukotriene receptor antagonists and 5-lipoxygenase inhibitors in the management of asthma
    • (c) Drazen, J. M. Pharmacology of leukotriene receptor antagonists and 5-lipoxygenase inhibitors in the management of asthma. Pharmacotherapy 1997, 17, S22-S30.
    • (1997) Pharmacotherapy , vol.17
    • Drazen, J.M.1
  • 10
    • 0020073093 scopus 로고
    • The leukotrienes in allergy and inflammation
    • (d) Marx, J. L. The leukotrienes in allergy and inflammation. Science 1982, 215, 1380-1383.
    • (1982) Science , vol.215 , pp. 1380-1383
    • Marx, J.L.1
  • 12
    • 33646484781 scopus 로고    scopus 로고
    • Shao, W. H.; Del, Prete, A.; Bock, C. B.; Haribabu, B. Targeted disruption of leukotriene B4 receptors BLT1 and BLT2: a critical role for BLT1 in collagen-induced arthritis in mice. J. Immunol. 2006, 176 (10), 6254-6261.
    • (f) Shao, W. H.; Del, Prete, A.; Bock, C. B.; Haribabu, B. Targeted disruption of leukotriene B4 receptors BLT1 and BLT2: a critical role for BLT1 in collagen-induced arthritis in mice. J. Immunol. 2006, 176 (10), 6254-6261.
  • 14
    • 0036598241 scopus 로고    scopus 로고
    • New treatments for COPD
    • (h) Barnes, P. J. New treatments for COPD. Nat. Rev. Drug Discovery 2002, 1 (6), 437-446.
    • (2002) Nat. Rev. Drug Discovery , vol.1 , Issue.6 , pp. 437-446
    • Barnes, P.J.1
  • 15
    • 0036308390 scopus 로고    scopus 로고
    • Arandomized, placebo-controlled trial of a leukotriene synthesis inhibitor in patients with COPD
    • (i) Gompertz, S.; Stockley, R.A.Arandomized, placebo-controlled trial of a leukotriene synthesis inhibitor in patients with COPD. Chest 2002 122 (1), 289-294.
    • (2002) Chest , vol.122 , Issue.1 , pp. 289-294
    • Gompertz, S.1    Stockley, R.A.2
  • 17
    • 4544296118 scopus 로고    scopus 로고
    • T-cell trafficking in asthma: Lipid mediators grease the way
    • (k) Luster, A. D.; Tager, A. M. T-cell trafficking in asthma: lipid mediators grease the way. Nat. Rev. Immunol. 2004, 4 (9), 711-724.
    • (2004) Nat. Rev. Immunol , vol.4 , Issue.9 , pp. 711-724
    • Luster, A.D.1    Tager, A.M.2
  • 18
    • 25444447952 scopus 로고    scopus 로고
    • Absence of leukotriene B4 receptor 1 confers resistance to airway hyperresponsiveness and Th2?type immune responses
    • (l) Terawaki, K.; Yokomizo, T.; Nagase, T.; Toda, A.; Taniguchi, M.; Hashizume, K..; et al. Absence of leukotriene B4 receptor 1 confers resistance to airway hyperresponsiveness and Th2?type immune responses. J. Immunol. 2005, 175 (7), 4217-4225.
    • (2005) J. Immunol , vol.175 , Issue.7 , pp. 4217-4225
    • Terawaki, K.1    Yokomizo, T.2    Nagase, T.3    Toda, A.4    Taniguchi, M.5    Hashizume, K.6
  • 19
    • 34247392438 scopus 로고    scopus 로고
    • Pharmacological modulation of the leukotriene pathway in allergic airway disease
    • (m) Montuschi, P.; Sala, A.; Dahlen, S. E.; Folco, G. Pharmacological modulation of the leukotriene pathway in allergic airway disease. Drug Discovery Today 2007, 12 (9-10), 404-412.
    • (2007) Drug Discovery Today , vol.12 , Issue.9-10 , pp. 404-412
    • Montuschi, P.1    Sala, A.2    Dahlen, S.E.3    Folco, G.4
  • 21
    • 0025879425 scopus 로고
    • Effect of zileuton (A-64077) on the 5-lipoxygenase activity of human whole blood ex vivo
    • (b) Sirois, P.; Borgeat, P.; Lauziere, M.; Dube, L.; Rubin, P. R.; Kesterson, J. Effect of zileuton (A-64077) on the 5-lipoxygenase activity of human whole blood ex vivo. Agents Actions 1991, 34, 117-120.
    • (1991) Agents Actions , vol.34 , pp. 117-120
    • Sirois, P.1    Borgeat, P.2    Lauziere, M.3    Dube, L.4    Rubin, P.R.5    Kesterson, J.6
  • 22
    • 0028888059 scopus 로고    scopus 로고
    • Labelle, M.; Belley, M.; Gareau, Y.; Gauthier, J. Y.; Guay, D.; Gordon, R.; Grossman, S. G.; Jones, T. R.; Leblanc, Y.; McAuliffe, M.; McFarlane, C.; Masson, P.; Metters, K. M.; Ouimet, N.; Patrick, D. H.; Piechuta, H.; Rochette, C.; Sawyer, N.; Xiang, Y. B.; Pickett, C. B.; Ford-Hutchinson, A. W.; Zamboni, R. J.; Young, R. N. Discovery of MK-0476, a potent and orally active leukotriene D4 receptor antagonist devoid of peroxisomal enzyme induction. Bioorg. Med. Chem. Lett. 1995, 5 (3), 283-288.
    • Labelle, M.; Belley, M.; Gareau, Y.; Gauthier, J. Y.; Guay, D.; Gordon, R.; Grossman, S. G.; Jones, T. R.; Leblanc, Y.; McAuliffe, M.; McFarlane, C.; Masson, P.; Metters, K. M.; Ouimet, N.; Patrick, D. H.; Piechuta, H.; Rochette, C.; Sawyer, N.; Xiang, Y. B.; Pickett, C. B.; Ford-Hutchinson, A. W.; Zamboni, R. J.; Young, R. N. Discovery of MK-0476, a potent and orally active leukotriene D4 receptor antagonist devoid of peroxisomal enzyme induction. Bioorg. Med. Chem. Lett. 1995, 5 (3), 283-288.
  • 23
    • 0025300626 scopus 로고
    • Evolution of a Series of Peptidoleukotriene Antagonists: Synthesis and Structure/Activity Relationships of 1,3,5-Substituted Indoles and Indazoles
    • Matassa, V. G.; Maduskuie, T. P.; Shapiro,H. S.; Hesp, B.; Snyder, D. W.; Aharony, D.; Krell, R. D.; Keith, R. A. Evolution of a Series of Peptidoleukotriene Antagonists: Synthesis and Structure/Activity Relationships of 1,3,5-Substituted Indoles and Indazoles. J. Med. Chem. 1990, 33, 1781-1790.
    • (1990) J. Med. Chem , vol.33 , pp. 1781-1790
    • Matassa, V.G.1    Maduskuie, T.P.2    Shapiro, H.S.3    Hesp, B.4    Snyder, D.W.5    Aharony, D.6    Krell, R.D.7    Keith, R.A.8
  • 24
    • 0024368596 scopus 로고
    • Enzymes involved in the biosynthesis of leukotriene B4
    • Samuelsson, B.; Funk, C. D. Enzymes involved in the biosynthesis of leukotriene B4. J. Biol. Chem. 1989, 264, 19469-19472.
    • (1989) J. Biol. Chem , vol.264 , pp. 19469-19472
    • Samuelsson, B.1    Funk, C.D.2
  • 25
    • 0025164256 scopus 로고
    • Leukotrienes and other products of the 5-lipoxygenase pathway. Biochemistry and relation to pathology in human diseases
    • (a) Lewis, R. A.; Austen, K. F.; Soberman, R. J. Leukotrienes and other products of the 5-lipoxygenase pathway. Biochemistry and relation to pathology in human diseases. N. Engl. J. Med. 1990, 232, 645-655.
    • (1990) N. Engl. J. Med , vol.232 , pp. 645-655
    • Lewis, R.A.1    Austen, K.F.2    Soberman, R.J.3
  • 26
    • 33750102847 scopus 로고    scopus 로고
    • Therapeutic options for 5-lipoxygenase inhibitors
    • (b) Werz, O.; Steinhilber, D. Therapeutic options for 5-lipoxygenase inhibitors. Pharmacol. Ther. 2006, 112, 701-718.
    • (2006) Pharmacol. Ther , vol.112 , pp. 701-718
    • Werz, O.1    Steinhilber, D.2
  • 27
    • 0035093238 scopus 로고    scopus 로고
    • Enhanced production of leukotrienes by peripheral leukocytes and specific IgE antibodies in patients with chronic obstructive pulmonary disease
    • Mitsunobu, F.; Mifune, T.; Hosaki, Y.; Ashida, K.; Tsugeno, H.; Okamoto, M.; Takata, S.; Tanizaki, Y. Enhanced production of leukotrienes by peripheral leukocytes and specific IgE antibodies in patients with chronic obstructive pulmonary disease. J. Allergy Clin. Immunol. 2001, 107, 492-498.
    • (2001) J. Allergy Clin. Immunol , vol.107 , pp. 492-498
    • Mitsunobu, F.1    Mifune, T.2    Hosaki, Y.3    Ashida, K.4    Tsugeno, H.5    Okamoto, M.6    Takata, S.7    Tanizaki, Y.8
  • 28
    • 0029665739 scopus 로고    scopus 로고
    • 4 hydrolase in peripheral leukocytes of patients with atopic dermatitis
    • 4 hydrolase in peripheral leukocytes of patients with atopic dermatitis. Arch. Dermatol. Res. 1996, 288, 168-172.
    • (1996) Arch. Dermatol. Res , vol.288 , pp. 168-172
    • Okano-Mitani, H.1    Ikai, K.2    Imamura, S.3
  • 29
    • 0019217271 scopus 로고
    • Lipoxygenation of arachidonic acid as a source of polymorphonuclear leukocyte chemotactic factors in synovial fluid and tissue in rheumatoid arthritis and spondyloarthritis
    • Klickstein, L. B.; Shapleigh, C.; Geotzl, E. J. Lipoxygenation of arachidonic acid as a source of polymorphonuclear leukocyte chemotactic factors in synovial fluid and tissue in rheumatoid arthritis and spondyloarthritis. J. Clin. Invest. 1980, 66, 1166-1170.
    • (1980) J. Clin. Invest , vol.66 , pp. 1166-1170
    • Klickstein, L.B.1    Shapleigh, C.2    Geotzl, E.J.3
  • 32
    • 0032478676 scopus 로고    scopus 로고
    • Effects of SA6541, a leukotriene A4 hydrolase inhibitor, and indomethacin on carrageenan-induced murine dermatitis
    • (c) Tsuji, F.; Miyake, Y.; Enomoto, H.; Horiuchi, M.; Mita, S. Effects of SA6541, a leukotriene A4 hydrolase inhibitor, and indomethacin on carrageenan-induced murine dermatitis. Eur. J. Pharmacol. 1998, 346, 81-85.
    • (1998) Eur. J. Pharmacol , vol.346 , pp. 81-85
    • Tsuji, F.1    Miyake, Y.2    Enomoto, H.3    Horiuchi, M.4    Mita, S.5
  • 39
    • 46849089254 scopus 로고    scopus 로고
    • Recent developments in fragment-based drug discovery
    • Congreve, M.; Chessari, G.; Tisi, D.; Woodhead, A. J. Recent developments in fragment-based drug discovery. J. Med. Chem. 2008, 51, 3661-3689.
    • (2008) J. Med. Chem , vol.51 , pp. 3661-3689
    • Congreve, M.1    Chessari, G.2    Tisi, D.3    Woodhead, A.J.4
  • 42
    • 0033773899 scopus 로고    scopus 로고
    • Discovering novel ligands for macromolecules using X-ray crystallographic screening
    • Nienaber, V. L.; Greer, J. Discovering novel ligands for macromolecules using X-ray crystallographic screening. Nat. Biotechnol. 2000, 18, 1105-1108.
    • (2000) Nat. Biotechnol , vol.18 , pp. 1105-1108
    • Nienaber, V.L.1    Greer, J.2
  • 44
    • 17044403086 scopus 로고    scopus 로고
    • Ligand efficiency indices as guideposts for drug discovery
    • Abad-Zapatero, C.; Metz, J. T. Ligand efficiency indices as guideposts for drug discovery. Drug Discovery Today 2005, 10, 464-469.
    • (2005) Drug Discovery Today , vol.10 , pp. 464-469
    • Abad-Zapatero, C.1    Metz, J.T.2
  • 47
    • 0035146853 scopus 로고    scopus 로고
    • Crystal structure of human leukotriene A(4) hydrolase, a bifunctional enzyme in inflammation
    • (a) Thunnissen, M. M.; Nordlund, P.; Haeggstrom, J. Z. Crystal structure of human leukotriene A(4) hydrolase, a bifunctional enzyme in inflammation. Nat. Struct. Biol. 2001, 8, 131-135.
    • (2001) Nat. Struct. Biol , vol.8 , pp. 131-135
    • Thunnissen, M.M.1    Nordlund, P.2    Haeggstrom, J.Z.3
  • 48
    • 0036778551 scopus 로고    scopus 로고
    • Structures of leukotriene A4 hydrolase in complex with captopril and two competitive tight-binding inhibitors
    • (b) Thunnissen, M. M.; Andersson, G. M.; Samuelsson, B.; Wong, B.; Haeggström, C. H.; Crystal, J. Z. Structures of leukotriene A4 hydrolase in complex with captopril and two competitive tight-binding inhibitors. FASEB J. 2002, 16, 1648-1650.
    • (2002) FASEB J , vol.16 , pp. 1648-1650
    • Thunnissen, M.M.1    Andersson, G.M.2    Samuelsson, B.3    Wong, B.4    Haeggström, C.H.5    Crystal, J.Z.6
  • 50
    • 77249173362 scopus 로고    scopus 로고
    • A 1.9 A resolution structure, 3FUD.pdb that contains a fragment bound on the surface of LTA4Hfar from the active site see ref 21, was used as reference for unligated active site topology
    • 4Hfar from the active site (see ref 21), was used as reference for unligated active site topology.
  • 51
    • 77249157962 scopus 로고    scopus 로고
    • Cerep; http://www.cerep.fr/cerep/users/pages/catalog/Profiles/catalog. asp.
  • 52
    • 0029992559 scopus 로고    scopus 로고
    • Such a transformation has in fact been reported for SC-57461. Yuan, J. H.; Birkmeier, J.; Yang, D. C.; Hribar, J. D.; Liu, N.; Bible, R.; Hajdu, E.; Rock, M.; Schoenhard, G. Isolation and identification of metabolites of leukotriene A4 hydrolase inhibitor SC-57461 in rats. Drug Metab. Dispos. 1996, 24, 1124-1133.
    • Such a transformation has in fact been reported for SC-57461. Yuan, J. H.; Birkmeier, J.; Yang, D. C.; Hribar, J. D.; Liu, N.; Bible, R.; Hajdu, E.; Rock, M.; Schoenhard, G. Isolation and identification of metabolites of leukotriene A4 hydrolase inhibitor SC-57461 in rats. Drug Metab. Dispos. 1996, 24, 1124-1133.
  • 53
    • 0035523337 scopus 로고    scopus 로고
    • Metabolism profiling and cytochrome P450 inhibition and induction
    • Yan, Z.; Caldwell, G. W. Metabolism profiling and cytochrome P450 inhibition and induction. Drug Discovery Curr. Top. Med. Chem. 2001, 1, 403-425.
    • (2001) Drug Discovery Curr. Top. Med. Chem , vol.1 , pp. 403-425
    • Yan, Z.1    Caldwell, G.W.2
  • 56
    • 5144228478 scopus 로고    scopus 로고
    • Palladium-catalyzed amination of aryl iodides
    • Wolfe, J. P.; Buchwald, S. L. Palladium-catalyzed amination of aryl iodides. J. Org. Chem. 1996, 61, 1133-1135.
    • (1996) J. Org. Chem , vol.61 , pp. 1133-1135
    • Wolfe, J.P.1    Buchwald, S.L.2
  • 57
    • 0029019760 scopus 로고
    • N-Acyl-2-substituted-1,3-thiazolidineas, new class of non-narcotic antitussive agents: Studies leading to the discovery of ethyl 2-[(2-methoxyphenoxy)methyl]-3-oxothiazolidine-3-propanoate
    • Gandolfi, C. A.; Di-Domenico, R.; Spinelli, S.; Gallico, L.; Fiocchi, L.; Lotto, A.; Menta, E.; Borghi, A.; Rosa, C. D.; Tognella, S. N-Acyl-2-substituted-1,3-thiazolidineas, new class of non-narcotic antitussive agents: Studies leading to the discovery of ethyl 2-[(2-methoxyphenoxy)methyl]-3-oxothiazolidine-3-propanoate. J. Med. Chem. 1995, 38, 508-525.
    • (1995) J. Med. Chem , vol.38 , pp. 508-525
    • Gandolfi, C.A.1    Di-Domenico, R.2    Spinelli, S.3    Gallico, L.4    Fiocchi, L.5    Lotto, A.6    Menta, E.7    Borghi, A.8    Rosa, C.D.9    Tognella, S.10
  • 58
    • 0344391956 scopus 로고    scopus 로고
    • Palladium charcol-catlysed Suzuki-Miyaura coupling to obatin arylpyridines and arylquinolines
    • Tagat, T.; Nishida, M. Palladium charcol-catlysed Suzuki-Miyaura coupling to obatin arylpyridines and arylquinolines. J. Org. Chem. 2003, 68, 9412-9415.
    • (2003) J. Org. Chem , vol.68 , pp. 9412-9415
    • Tagat, T.1    Nishida, M.2
  • 59
    • 0242543883 scopus 로고    scopus 로고
    • N-Dimethyl glycine-promoted Ullmann coupling reaction of phenols and aryl halides
    • Ma, D.; Qian, C. N,N-Dimethyl glycine-promoted Ullmann coupling reaction of phenols and aryl halides. Org. Lett. 2003, 5 (21), 3799-3802.
    • (2003) Org. Lett , vol.5 , Issue.21 , pp. 3799-3802
    • Ma, D.1    Qian, C.N.2


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