메뉴 건너뛰기




Volumn 50, Issue 1, 2007, Pages 21-39

Synthesis and biological evaluation of quinoline salicylic acids as P-selectin antagonists

Author keywords

[No Author keywords available]

Indexed keywords

2 (4 CHLOROPHENYL) 3 HYDROXY 8 PHENYLQUINOLINE 4 CARBOXYLIC ACID; CARRAGEENAN; CYTOCHROME P450; DIHYDROOROTATE DEHYDROGENASE; DIHYDROOROTATE DEHYDROGENASE INHIBITOR; GLYCOPROTEIN; PADGEM PROTEIN; PROTEIN INHIBITOR; QUINOLINE DERIVATIVE; SALICYLIC ACID DERIVATIVE; SIALYL LEWIS X ANTIGEN; UNCLASSIFIED DRUG;

EID: 33846217395     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0602256     Document Type: Article
Times cited : (128)

References (62)
  • 1
    • 0027982876 scopus 로고
    • Traffic signals for lymphocyte recirculation and leukocyte emigration: The multistep paradigm
    • Springer, T. A. Traffic signals for lymphocyte recirculation and leukocyte emigration: the multistep paradigm. Cell 1994, 76, 301-314.
    • (1994) Cell , vol.76 , pp. 301-314
    • Springer, T.A.1
  • 3
    • 0029922156 scopus 로고    scopus 로고
    • Adhesion Molecules in Auto Immune Disease
    • (a) McMurray, R. W. Adhesion Molecules in Auto Immune Disease. Semin. Arthritis Rheum. 1996, 25, 215-233.
    • (1996) Semin. Arthritis Rheum , vol.25 , pp. 215-233
    • McMurray, R.W.1
  • 4
    • 0029919175 scopus 로고    scopus 로고
    • Soluble forms of P-selectin and intercellular adhesion molecule-3 in synovial fluids
    • (b) Hosaka, S.; Shah, M. R.; Pope, R. M.; Koch, A. E. Soluble forms of P-selectin and intercellular adhesion molecule-3 in synovial fluids. Clin. Immunol. Immunopathol. 1996, 78, 276-282.
    • (1996) Clin. Immunol. Immunopathol , vol.78 , pp. 276-282
    • Hosaka, S.1    Shah, M.R.2    Pope, R.M.3    Koch, A.E.4
  • 7
    • 0037061647 scopus 로고    scopus 로고
    • Kaila, N.; Chen, L.; Thomas, B. E., IV; Tsao, D.; Tam, S.; Bedard, P. W.; Camphausen, R. T.; Alvarez, J. C.; Ullas, G. Beta-C-mannosides as selectin inhibitors. J. Med. Chem. 2002, 45, 1563-1566.
    • Kaila, N.; Chen, L.; Thomas, B. E., IV; Tsao, D.; Tam, S.; Bedard, P. W.; Camphausen, R. T.; Alvarez, J. C.; Ullas, G. Beta-C-mannosides as selectin inhibitors. J. Med. Chem. 2002, 45, 1563-1566.
  • 10
    • 0035937574 scopus 로고    scopus 로고
    • Searching for medicines sweet spot
    • (a) Alper, J. Searching for medicines sweet spot. Science 2001, 291, 2338-2343.
    • (2001) Science , vol.291 , pp. 2338-2343
    • Alper, J.1
  • 12
    • 0037904051 scopus 로고    scopus 로고
    • Development of synthetic pan-selectin antagonists: A new treatment strategy for chronic inflammation in asthma
    • (a) Aydt, E.; Wolff, G. Development of synthetic pan-selectin antagonists: a new treatment strategy for chronic inflammation in asthma. Pathobiology 2003, 70, 297-301.
    • (2003) Pathobiology , vol.70 , pp. 297-301
    • Aydt, E.1    Wolff, G.2
  • 13
    • 18144414334 scopus 로고    scopus 로고
    • Selectin antagonists: Therapeutic potential in asthma and COPD
    • (b) Romano, S. J., Selectin antagonists: therapeutic potential in asthma and COPD. Treat. Respir. Med. 2005, 4, 85-94
    • (2005) Treat. Respir. Med , vol.4 , pp. 85-94
    • Romano, S.J.1
  • 14
    • 0035927435 scopus 로고    scopus 로고
    • Development of potent non-carbohydrate imidazole-based small molecule selectin inhibitors with antiinflammatory activity
    • Slee, D. H.; Romano, S.; Yu, J.; Nguyen, T. N.; John, J. K.; Raheja, N. K.; Axe, F. U.; Jones, T. K.; Ripka, W. C. Development of potent non-carbohydrate imidazole-based small molecule selectin inhibitors with antiinflammatory activity. J. Med. Chem. 2001, 44, 2094-2107.
    • (2001) J. Med. Chem , vol.44 , pp. 2094-2107
    • Slee, D.H.1    Romano, S.2    Yu, J.3    Nguyen, T.N.4    John, J.K.5    Raheja, N.K.6    Axe, F.U.7    Jones, T.K.8    Ripka, W.C.9
  • 15
    • 0035205557 scopus 로고    scopus 로고
    • Inhibition of P-selectin specific cell adhesion by a low molecular weight, non-carbohydrate compound, KF38789
    • Ohta, S.; Inujima, Y.; Abe, M.; Uosaki, Y.; Sato, S.; Miki, I. Inhibition of P-selectin specific cell adhesion by a low molecular weight, non-carbohydrate compound, KF38789. Inflammation Res. 2001, 50, 544-551.
    • (2001) Inflammation Res , vol.50 , pp. 544-551
    • Ohta, S.1    Inujima, Y.2    Abe, M.3    Uosaki, Y.4    Sato, S.5    Miki, I.6
  • 16
    • 0036117531 scopus 로고    scopus 로고
    • Schön, M. P.; Krahn, T.; Schön, M.; Rodriguez, M.-L.; Antonicek, H.; Schultz, J. E.; Ludwig, R. J.; Thomas, M.; Zollner, T. M.; Bischoff, E.; Bremm, K.-D.; Schramm, M.; Henninger, K.; Kaufmann, R.; Gollnick, H. P. M.; Parker, C. M.; Boehncke, W.-H. Efomycine M, a new specific inhibitor of selectin, impairs leukocyte adhesion and alleviates cutaneous inflammation. Nature Med. 2002, 8, 366-372.
    • Schön, M. P.; Krahn, T.; Schön, M.; Rodriguez, M.-L.; Antonicek, H.; Schultz, J. E.; Ludwig, R. J.; Thomas, M.; Zollner, T. M.; Bischoff, E.; Bremm, K.-D.; Schramm, M.; Henninger, K.; Kaufmann, R.; Gollnick, H. P. M.; Parker, C. M.; Boehncke, W.-H. Efomycine M, a new specific inhibitor of selectin, impairs leukocyte adhesion and alleviates cutaneous inflammation. Nature Med. 2002, 8, 366-372.
  • 17
    • 19944392268 scopus 로고    scopus 로고
    • Inhibitors of membrane receptors involved with leukocyte extravasation
    • Bendas, G. Inhibitors of membrane receptors involved with leukocyte extravasation. Mini-Rev. Med. Chem. 2005, 5, 575-584.
    • (2005) Mini-Rev. Med. Chem , vol.5 , pp. 575-584
    • Bendas, G.1
  • 18
    • 33846194411 scopus 로고    scopus 로고
    • The ELISA evaluates the binding of a PSGL-1 fusion protein, which consists of the functional N-terminal region of PSGL-1 fused to the Fc region of IgG1, to immobilized soluble P-selectin, which is preincubated with the test compound.
    • The ELISA evaluates the binding of a PSGL-1 fusion protein, which consists of the functional N-terminal region of PSGL-1 fused to the Fc region of IgG1, to immobilized soluble P-selectin, which is preincubated with the test compound.
  • 19
    • 0000588587 scopus 로고    scopus 로고
    • Selectin-Carbohydrate Interactions: From Natural ligands to designed mimics
    • (a) Simanek, E. E.; McGarvey, G. J.; Jablonowski, J. A.; Wong, C.-H. Selectin-Carbohydrate Interactions: From Natural ligands to designed mimics. Chem. Rev. 1998, 98, 833-862.
    • (1998) Chem. Rev , vol.98 , pp. 833-862
    • Simanek, E.E.1    McGarvey, G.J.2    Jablonowski, J.A.3    Wong, C.-H.4
  • 20
    • 0036846759 scopus 로고    scopus 로고
    • Design and synthesis of sialyl Lewis x mimics as E- and P-selectin inhibitors
    • (b) Kaila, N.; Thomas, B. E., IV. Design and synthesis of sialyl Lewis x mimics as E- and P-selectin inhibitors. Med. Res. Rev. 2002, 22, 566-601.
    • (2002) Med. Res. Rev , vol.22 , pp. 566-601
    • Kaila, N.1    Thomas, B.2    IV, E.3
  • 22
    • 0033618074 scopus 로고    scopus 로고
    • Versatile functionalization of polylysine: Synthesis, characterization, and use of neoglycoconjugates
    • Thoma, G.; Patton, J. T.; Magnani, J. L.; Ernst, B.; Ohrlein, R.; Duthaler, R. O. Versatile functionalization of polylysine: synthesis, characterization, and use of neoglycoconjugates. J. Am. Chem. Soc. 1999, 121, 5919-5929.
    • (1999) J. Am. Chem. Soc , vol.121 , pp. 5919-5929
    • Thoma, G.1    Patton, J.T.2    Magnani, J.L.3    Ernst, B.4    Ohrlein, R.5    Duthaler, R.O.6
  • 23
    • 0037061647 scopus 로고    scopus 로고
    • Kaila, N.; Chen, L.; Thomas, B. E., IV; Tsao, D.; Tam, S.; Bedard, P. W.; Camphausen, R. T.; Alvarez, J. C.; Ullas, G. β-C-Mannosides as selectin inhibitors. J. Med. Chem. 2002, 45, 1563-1566.
    • Kaila, N.; Chen, L.; Thomas, B. E., IV; Tsao, D.; Tam, S.; Bedard, P. W.; Camphausen, R. T.; Alvarez, J. C.; Ullas, G. β-C-Mannosides as selectin inhibitors. J. Med. Chem. 2002, 45, 1563-1566.
  • 25
    • 0028728698 scopus 로고
    • Recent developments in transferred NOE methods
    • (b) Ni, F. Recent developments in transferred NOE methods. Prog. Nucl. Magn. Reson. Spectrosc. 1994, 26, 517-606.
    • (1994) Prog. Nucl. Magn. Reson. Spectrosc , vol.26 , pp. 517-606
    • Ni, F.1
  • 26
    • 0030917461 scopus 로고    scopus 로고
    • Screening mixtures for biological activity by NMR
    • (c) Meyer, B.; Thomas, W.; Peters, T. Screening mixtures for biological activity by NMR. Eur. J. Biochem. 1997, 246, 705-709.
    • (1997) Eur. J. Biochem , vol.246 , pp. 705-709
    • Meyer, B.1    Thomas, W.2    Peters, T.3
  • 28
    • 3342879982 scopus 로고
    • The synthesis of 3-hydroxycinchoninic acid and certain of its derivatives
    • (a) Cragoe, E. J.; Robb, C. M.; Bealor, M. D. The synthesis of 3-hydroxycinchoninic acid and certain of its derivatives. J. Org. Chem. 1953 18, 552-560.
    • (1953) J. Org. Chem , vol.18 , pp. 552-560
    • Cragoe, E.J.1    Robb, C.M.2    Bealor, M.D.3
  • 29
    • 0342420241 scopus 로고
    • The synthesis of 3-hydroxy-2-phenylquinoline-4,8-dicarboxylic acid and certain of its derivatives
    • (b) Cragoe, E. J.; Bealor, M. D.; Robb, C. M.; Ziegler, C.; Sprague, J. M. The synthesis of 3-hydroxy-2-phenylquinoline-4,8-dicarboxylic acid and certain of its derivatives. J. Org. Chem. 1953, 18, 561-569.
    • (1953) J. Org. Chem , vol.18 , pp. 561-569
    • Cragoe, E.J.1    Bealor, M.D.2    Robb, C.M.3    Ziegler, C.4    Sprague, J.M.5
  • 30
    • 84977246376 scopus 로고
    • Isonitrosoacetanilides and their condensation to form isatin derivatives
    • (a) Sandmeyer, T. Isonitrosoacetanilides and their condensation to form isatin derivatives. Helv. Chim. Acta. 1919, 2, 234-242.
    • (1919) Helv. Chim. Acta , vol.2 , pp. 234-242
    • Sandmeyer, T.1
  • 31
    • 0029963648 scopus 로고    scopus 로고
    • Induction of a ferroelectric Sc* liquid crystal phase by an atropisomeric dopant derived from 4,4′-dihydroxy-2,2′-dimethyl-6,6′- dinitrobiphenyl
    • (b) Yang, K.; Campbell, B.; Birch, G.; Williams, V. E.; Lemieux, R. P. Induction of a ferroelectric Sc* liquid crystal phase by an atropisomeric dopant derived from 4,4′-dihydroxy-2,2′-dimethyl-6,6′- dinitrobiphenyl. J. Am. Chem. Soc. 1996 118, 9557-9561.
    • (1996) J. Am. Chem. Soc , vol.118 , pp. 9557-9561
    • Yang, K.1    Campbell, B.2    Birch, G.3    Williams, V.E.4    Lemieux, R.P.5
  • 32
    • 33846224959 scopus 로고    scopus 로고
    • Marvel, C. S.; Hiers, G. S. Isatin Org. Synth. 1925, V, 71-74.
    • (c) Marvel, C. S.; Hiers, G. S. Isatin Org. Synth. 1925, V, 71-74.
  • 34
    • 0034733102 scopus 로고    scopus 로고
    • Efficient synthesis of novel 3-(het)arylanthranilic acids via a Suzuki cross-coupling reaction of 7-iodoisatin with (het)arylboronic acids in water
    • Lisowski, V.; Robba, M.; Rault, S. Efficient synthesis of novel 3-(het)arylanthranilic acids via a Suzuki cross-coupling reaction of 7-iodoisatin with (het)arylboronic acids in water. J. Org. Chem. 2000, 65, 4193-4194.
    • (2000) J. Org. Chem , vol.65 , pp. 4193-4194
    • Lisowski, V.1    Robba, M.2    Rault, S.3
  • 35
    • 0032499980 scopus 로고    scopus 로고
    • A facile protocol for the convenient preparation of amino-substituted α-bromo- and α,α-dibromo arylmethyl ketones
    • Diwu, Z.; Beachdel C.; Klaubert, D. H. A facile protocol for the convenient preparation of amino-substituted α-bromo- and α,α-dibromo arylmethyl ketones Tetrahedron Lett. 1998, 39, 4987-4990.
    • (1998) Tetrahedron Lett , vol.39 , pp. 4987-4990
    • Diwu, Z.1    Beachdel, C.2    Klaubert, D.H.3
  • 36
    • 33846201441 scopus 로고    scopus 로고
    • It is well-demonstrated in the literature that due to the nature of the selectin biology this high IC50 translates to in vivo efficacy. 5
    • 5
  • 37
    • 33846188727 scopus 로고    scopus 로고
    • This compound was studied as an anti-inflammatory agent at Lederle
    • This compound was studied as an anti-inflammatory agent at Lederle.
  • 39
    • 0033170743 scopus 로고    scopus 로고
    • Expression and characterization of E. coli-produced soluble, functional human dihydroorotate dehydrogenase: A potential target for immunosuppression
    • (a) Neidhardt, E. A.; Punreddy, S. R.; McLean, J. E.; Hedstrom, L.; Grossman, T. H. Expression and characterization of E. coli-produced soluble, functional human dihydroorotate dehydrogenase: a potential target for immunosuppression J. Mol. Microbiol. Biotechnol. 1999, 1, 183-188.
    • (1999) J. Mol. Microbiol. Biotechnol , vol.1 , pp. 183-188
    • Neidhardt, E.A.1    Punreddy, S.R.2    McLean, J.E.3    Hedstrom, L.4    Grossman, T.H.5
  • 40
    • 0029793899 scopus 로고    scopus 로고
    • Functional expression of a fragment of human dihydroorotate dehydrogenase by means of baculovirus expression vector system, and kinetic investigation of purified recombinant enzyme
    • (b) Knecht, W.; Bergjohann, U.; Gonski, S.; Kirschbaum, B.; Loffler, M. Functional expression of a fragment of human dihydroorotate dehydrogenase by means of baculovirus expression vector system, and kinetic investigation of purified recombinant enzyme. Eur. J. Biochem. 1996, 240, 292-301.
    • (1996) Eur. J. Biochem , vol.240 , pp. 292-301
    • Knecht, W.1    Bergjohann, U.2    Gonski, S.3    Kirschbaum, B.4    Loffler, M.5
  • 41
    • 33846187861 scopus 로고    scopus 로고
    • 50s from cell interaction assays are lower and more biologically relevant because they incorporate physiological flow rates and selectin densities and are under nonequilibrium conditions.
    • 50s from cell interaction assays are lower and more biologically relevant because they incorporate physiological flow rates and selectin densities and are under nonequilibrium conditions.
  • 43
    • 0024812605 scopus 로고    scopus 로고
    • This animal model has been used to demonstrate the antiarthritic potential of agents such as methotrexate or nonsteroidal antiinflammatory agents NSAIDS, Kerwar, S. S, Oronsky, A. L. Methotrexate in rheumatoid arthritis: studies with animal models. Adv. Enzyme Regul. 1989, 29, 247-265
    • This animal model has been used to demonstrate the antiarthritic potential of agents such as methotrexate or nonsteroidal antiinflammatory agents (NSAIDS). Kerwar, S. S.; Oronsky, A. L. Methotrexate in rheumatoid arthritis: studies with animal models. Adv. Enzyme Regul. 1989, 29, 247-265.
  • 44
    • 0030906896 scopus 로고    scopus 로고
    • The role of E- and P-selectin in neutrophil and monocyte migration in adjuvant-induced arthritis in the rat
    • Walter, U. M.; Issekutz, A. C. The role of E- and P-selectin in neutrophil and monocyte migration in adjuvant-induced arthritis in the rat. Eur. J. Immunol. 1997, 27, 1498-1505.
    • (1997) Eur. J. Immunol , vol.27 , pp. 1498-1505
    • Walter, U.M.1    Issekutz, A.C.2
  • 45
    • 0033574172 scopus 로고    scopus 로고
    • Recombinant soluble form of PSGL-1 accelerates thrombolysis and prevents reocclusion in a porcine model
    • Kumar, A.; Villani, M. P.; Patel, U. K.; Keith, J. C., Jr.; Schaub, R. G. Recombinant soluble form of PSGL-1 accelerates thrombolysis and prevents reocclusion in a porcine model. Circulation 1999, 99, 1363-1369.
    • (1999) Circulation , vol.99 , pp. 1363-1369
    • Kumar, A.1    Villani, M.P.2    Patel, U.K.3    Keith Jr., J.C.4    Schaub, R.G.5
  • 46
    • 0037525986 scopus 로고    scopus 로고
    • Pharmacokinetics, pharmacodynamics, allometry, and dose selection of rPSGL - Ig for phase I trial
    • Khor, P. S.; Mccarthy, K.; Dupont, M.; Murray, K.; Timony, G. Pharmacokinetics, pharmacodynamics, allometry, and dose selection of rPSGL - Ig for phase I trial. J. Pharmacol. Exp. Ther. 2000, 293, 618-624.
    • (2000) J. Pharmacol. Exp. Ther , vol.293 , pp. 618-624
    • Khor, P.S.1    Mccarthy, K.2    Dupont, M.3    Murray, K.4    Timony, G.5
  • 47
    • 14444268539 scopus 로고    scopus 로고
    • Novel Synthetic inhibitors of selectin-mediated cell adhesion: Synthesis of 1,6-bis[3-(3- carboxymethylphenyl)-4-(2-α-D-mannopyranosyloxy)phenyl]hexane (TBC1269)
    • Kogan, T. P.; Dupre, B.; Bui, H.; McAbee, K. L.; Kassir, J. M.; Scott, I. L.; Hu, X.; Vanderslice, P.; Beck, P. J.; Dixon, R. A. F. Novel Synthetic inhibitors of selectin-mediated cell adhesion: synthesis of 1,6-bis[3-(3- carboxymethylphenyl)-4-(2-α-D-mannopyranosyloxy)phenyl]hexane (TBC1269). J. Med. Chem. 1998, 41, 1099-1111.
    • (1998) J. Med. Chem , vol.41 , pp. 1099-1111
    • Kogan, T.P.1    Dupre, B.2    Bui, H.3    McAbee, K.L.4    Kassir, J.M.5    Scott, I.L.6    Hu, X.7    Vanderslice, P.8    Beck, P.J.9    Dixon, R.A.F.10
  • 51
    • 0035077761 scopus 로고    scopus 로고
    • Positioning of the carboxamide side chain in 11-oxo-11H- indeno[1,2-b]quinolinecarboxamide anticancer agents: Effects on cytotoxicity
    • Deady, L. W.; Desneves, J.; Kaye, A. J.; Finlay, G. J.; Baguley, B. C.; Denny, W. A. Positioning of the carboxamide side chain in 11-oxo-11H- indeno[1,2-b]quinolinecarboxamide anticancer agents: effects on cytotoxicity. Bioorg. Med. Chem. 2001, 9, 445-452.
    • (2001) Bioorg. Med. Chem , vol.9 , pp. 445-452
    • Deady, L.W.1    Desneves, J.2    Kaye, A.J.3    Finlay, G.J.4    Baguley, B.C.5    Denny, W.A.6
  • 52
    • 0026100365 scopus 로고
    • Potential antitumor agents. 61. Structure-activity relationships for in vivo colon 38 activity among disubstituted 9-oxo-9H-xanthene-4-acetic acids
    • Rewcastle, G. W.; Atwell, G. J.; Zhuang, L.; Baguley, B. C.; Denny, W. A. Potential antitumor agents. 61. Structure-activity relationships for in vivo colon 38 activity among disubstituted 9-oxo-9H-xanthene-4-acetic acids. J. Med. Chem. 1991, 34, 217-222.
    • (1991) J. Med. Chem , vol.34 , pp. 217-222
    • Rewcastle, G.W.1    Atwell, G.J.2    Zhuang, L.3    Baguley, B.C.4    Denny, W.A.5
  • 53
    • 0035157254 scopus 로고    scopus 로고
    • A method for the simultaneous evaluation of the activities of seven major human drug-metabolizing cytochrome P450s using an in vitro cocktail of probe substrates and fast gradient liquid chromatography tandem mass spectrometry
    • Dierks, E. A.; Stams, K. R.; Lim, H.; Cornelius, G.; Zhang, H.; Ball, S.E. A method for the simultaneous evaluation of the activities of seven major human drug-metabolizing cytochrome P450s using an in vitro cocktail of probe substrates and fast gradient liquid chromatography tandem mass spectrometry. Drug Metab. Dispos. 2001, 29, 23-29.
    • (2001) Drug Metab. Dispos , vol.29 , pp. 23-29
    • Dierks, E.A.1    Stams, K.R.2    Lim, H.3    Cornelius, G.4    Zhang, H.5    Ball, S.E.6
  • 55
    • 0028885684 scopus 로고
    • A sulfated peptide segment at the amino terminus of PSGL-1 is critical for P-selectin binding
    • (b) Sako, D.; Comess, K. M.; Barone, K. M.; Camphausen, R. T.; Cumming, D. A.; Shaw, G. D. A sulfated peptide segment at the amino terminus of PSGL-1 is critical for P-selectin binding. Cell 1995, 83, 323-331.
    • (1995) Cell , vol.83 , pp. 323-331
    • Sako, D.1    Comess, K.M.2    Barone, K.M.3    Camphausen, R.T.4    Cumming, D.A.5    Shaw, G.D.6
  • 56
    • 0032701484 scopus 로고    scopus 로고
    • Improving biosensor analysis
    • Myszka, D. G. Improving biosensor analysis. J. Mol. Recognit. 1999, 12, 279-284.
    • (1999) J. Mol. Recognit , vol.12 , pp. 279-284
    • Myszka, D.G.1
  • 57
    • 67249094291 scopus 로고
    • Carrageenan-induced edema in hind paw of rat as an assay for antiinflammatory drugs
    • Winter, C. A.; Risley, E. A.; Nuss, G. W. Carrageenan-induced edema in hind paw of rat as an assay for antiinflammatory drugs. Proc. Soc. Exp. Biol. Med. 1962, 111, 544-547.
    • (1962) Proc. Soc. Exp. Biol. Med , vol.111 , pp. 544-547
    • Winter, C.A.1    Risley, E.A.2    Nuss, G.W.3
  • 60
    • 8644242950 scopus 로고    scopus 로고
    • Zhang, Y.; Hegen, M.; Xu, J.; Keith, J. C., Jr.; Jin, G.; Du, X.; Cummons, T.; Sun, L. H.; Zhu, Y.; Rao, V. R.; Wang, Q.; Xu, W.; Cowling, R.; Nickerson-Nutter, C. L.; Gibbons, J.; Skotnicki, J.; Lin, L. L.; Levin, J. Characterization of (2R,3S)-2-({4-(2-butynyloxy0phenyl]-sulfonyl} amino)-N-3-dihydroxybutanamide (TMI-2), a potent and selective inhibitor of TNF-α converting enzyme (TACE). Int. J. Immunopharmacol. 2004, 4, 1845-1857.
    • Zhang, Y.; Hegen, M.; Xu, J.; Keith, J. C., Jr.; Jin, G.; Du, X.; Cummons, T.; Sun, L. H.; Zhu, Y.; Rao, V. R.; Wang, Q.; Xu, W.; Cowling, R.; Nickerson-Nutter, C. L.; Gibbons, J.; Skotnicki, J.; Lin, L. L.; Levin, J. Characterization of (2R,3S)-2-({4-(2-butynyloxy0phenyl]-sulfonyl} amino)-N-3-dihydroxybutanamide (TMI-2), a potent and selective inhibitor of TNF-α converting enzyme (TACE). Int. J. Immunopharmacol. 2004, 4, 1845-1857.
  • 62
    • 20444387545 scopus 로고    scopus 로고
    • Mewshaw, R. E.; Edsall, R. J., Jr.; Yang, C.; Manas, E. S.; Xu, Z. B.; Henderson, R. A.; Keith, J. C., Jr.; Harris, H. A. ERβ ligands. 3. Exploiting two binding orientations of the 2-phenyl-naphthalene scaffold to achieve ERβ selectivity. J. Med. Chem. 2005, 48, 3953-3979.
    • Mewshaw, R. E.; Edsall, R. J., Jr.; Yang, C.; Manas, E. S.; Xu, Z. B.; Henderson, R. A.; Keith, J. C., Jr.; Harris, H. A. ERβ ligands. 3. Exploiting two binding orientations of the 2-phenyl-naphthalene scaffold to achieve ERβ selectivity. J. Med. Chem. 2005, 48, 3953-3979.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.