메뉴 건너뛰기




Volumn 45, Issue 23, 2002, Pages 4954-4957

Discovery of γ-lactam hydroxamic acids as selective inhibitors of tumor necrosis factor α converting enzyme: Design, synthesis, and structure-activity relationships

Author keywords

[No Author keywords available]

Indexed keywords

DIPEPTIDYL CARBOXYPEPTIDASE; GAMMA LACTAM DERIVATIVE; HYDROXAMIC ACID; TUMOR NECROSIS FACTOR ALPHA;

EID: 0037038311     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0255670     Document Type: Article
Times cited : (126)

References (25)
  • 2
    • 0033168031 scopus 로고    scopus 로고
    • Therapeutical. Potential and strategies for inhibiting tumor necrosis factor- α
    • (b) Newton, R. C.; Decicco, C. P. Therapeutical. Potential and strategies for inhibiting tumor necrosis factor- α. J. Med. Chem. 1999, 42, 2295-2314.
    • (1999) J. Med. Chem. , vol.42 , pp. 2295-2314
    • Newton, R.C.1    Decicco, C.P.2
  • 8
    • 0035846068 scopus 로고    scopus 로고
    • Discovery of macrocyclic hydroxamic acids containing biphenylmethyl derivatives at P1′, a series of selective TNF-α converting enzyme inhibitors with potent cellular activity in the inhibition of TNF-α release
    • (b) Xue, C.-B.; He, X.; Corbett, R. L.; Roderick, J.; Wasserman, Z. R.; Liu, R.-Q.; Jaffee, B. D.; Covington, M. B.; Qian, M.; Trzaskos, J. M.; Newton, R. C.; Magolda, R. L.; Wexler, R. R.; Decicco, C. P. Discovery of Macrocyclic Hydroxamic Acids Containing Biphenylmethyl Derivatives at P1′, a Series of Selective TNF-α Converting enzyme inhibitors with potent cellular activity in the inhibition of TNF-α release. J. Med. Chem. 2001, 44, 3351-3354.
    • (2001) J. Med. Chem. , vol.44 , pp. 3351-3354
    • Xue, C.-B.1    He, X.2    Corbett, R.L.3    Roderick, J.4    Wasserman, Z.R.5    Liu, R.-Q.6    Jaffee, B.D.7    Covington, M.B.8    Qian, M.9    Trzaskos, J.M.10    Newton, R.C.11    Magolda, R.L.12    Wexler, R.R.13    Decicco, C.P.14
  • 11
    • 0037156343 scopus 로고    scopus 로고
    • Anthranilate sulfonamide hydroxamate TACE inhibitors. Part 1: Structure-based design of novel acetylenic p1′ groups
    • (c) Chen, J. M.; Jin, G.; Sung, A.; Levin, J. I. Anthranilate sulfonamide hydroxamate tace inhibitors. Part 1: Structure-based design of novel acetylenic p1′ groups. Bioorg. Med. Chem. Lett. 2002, 12, 1195-1198.
    • (2002) Bioorg. Med. Chem. Lett. , vol.12 , pp. 1195-1198
    • Chen, J.M.1    Jin, G.2    Sung, A.3    Levin, J.I.4
  • 14
    • 17944389351 scopus 로고    scopus 로고
    • PCT Int. Appl. WO 9732846
    • During the course of this work, a patent application disclosing unrelated lactam-based MMP inhibitors was published: Jacobsen, E. J. PCT Int. Appl. WO 9732846. After completion of this work, another series of unrelated lactam-based MMP inhibitors was published: Robinson, R. P.; Laird, E. R.; Blake, J. F.; Bordner, J.; Donahue, K. M.; Lopresti-Morrow, L. L.; Mitchell, P. G.; Reese, M. R.; Reeves, L. M.; Stam, E. J.; Yocum, S. A. Structure-based design and synthesis of a potent matrix metalloproteinase-13 inhibitors based on pyrrolidinone scaffold. J. Med. Chem. 2000, 43, 2293-2296.
    • Jacobsen, E.J.1
  • 15
    • 17944389351 scopus 로고    scopus 로고
    • Structure-based design and synthesis of a potent matrix metalloproteinase-13 inhibitors based on pyrrolidinone scaffold
    • During the course of this work, a patent application disclosing unrelated lactam-based MMP inhibitors was published: Jacobsen, E. J. PCT Int. Appl. WO 9732846. After completion of this work, another series of unrelated lactam-based MMP inhibitors was published: Robinson, R. P.; Laird, E. R.; Blake, J. F.; Bordner, J.; Donahue, K. M.; Lopresti-Morrow, L. L.; Mitchell, P. G.; Reese, M. R.; Reeves, L. M.; Stam, E. J.; Yocum, S. A. Structure-based design and synthesis of a potent matrix metalloproteinase-13 inhibitors based on pyrrolidinone scaffold. J. Med. Chem. 2000, 43, 2293-2296.
    • (2000) J. Med. Chem. , vol.43 , pp. 2293-2296
    • Robinson, R.P.1    Laird, E.R.2    Blake, J.F.3    Bordner, J.4    Donahue, K.M.5    Lopresti-Morrow, L.L.6    Mitchell, P.G.7    Reese, M.R.8    Reeves, L.M.9    Stam, E.J.10    Yocum, S.A.11
  • 18
    • 0032491208 scopus 로고    scopus 로고
    • Solution structure of the catalytic domain of human stromelysin-1 complexed to a potent, nonpeptidic inhibitor
    • (b) Li, Y.-C.; Zhang, X.; Melton, R.; Ganu, V.; Gonnella, N. C. Solution structure of the catalytic domain of human stromelysin-1 complexed to a potent, nonpeptidic inhibitor. Biochemistry 1998, 37, 14048-14056.
    • (1998) Biochemistry , vol.37 , pp. 14048-14056
    • Li, Y.-C.1    Zhang, X.2    Melton, R.3    Ganu, V.4    Gonnella, N.C.5
  • 19
    • 0035965133 scopus 로고    scopus 로고
    • Crystal structure of human macrophage elastase (MMP-12) in complex with a hydroxamic acid inhibitor
    • (c) Nar, H.; Werle, K.; Bauer, M. M. T.; Dollinger, H.; Jung, B. Crystal structure of human macrophage elastase (MMP-12) in complex with a hydroxamic acid inhibitor. J. Mol. Biol. 2001, 312, 743-751.
    • (2001) J. Mol. Biol. , vol.312 , pp. 743-751
    • Nar, H.1    Werle, K.2    Bauer, M.M.T.3    Dollinger, H.4    Jung, B.5
  • 21
    • 0011114507 scopus 로고    scopus 로고
    • note
    • Selectivity profile was assessed using MMP-1 as a representative with a shallow S1′ pocket and using MMP-2 and -9 with deep S1′ pockets. Details of the assays are described in ref 4a.
  • 22
    • 0011149471 scopus 로고    scopus 로고
    • note
    • Details of pTACE and WBA are described in ref 4a.
  • 24
    • 0038541768 scopus 로고    scopus 로고
    • Intracellular maturation and localization of the tumour necrosis factor α convertase (TACE)
    • Schlondorff, J.; Becherer, J. D.; Blobel, C. P. Intracellular maturation and localization of the tumour necrosis factor α convertase (TACE). Biochem. J. 2000, 347, 131-138.
    • (2000) Biochem. J. , vol.347 , pp. 131-138
    • Schlondorff, J.1    Becherer, J.D.2    Blobel, C.P.3
  • 25
    • 0033957404 scopus 로고    scopus 로고
    • Direct plasma sample injection in multiple -component LC-MS-MS assays for high-throughput pharmacokinetic screening
    • Wu, J.-T.; Zeng, H.; Qian, M.; Brogdon, B. L.; Unger, S. E. Direct plasma sample injection in multiple -component LC-MS-MS assays for high-throughput pharmacokinetic screening. Anal. Chem. 2000, 72, 61-67.
    • (2000) Anal. Chem. , vol.72 , pp. 61-67
    • Wu, J.-T.1    Zeng, H.2    Qian, M.3    Brogdon, B.L.4    Unger, S.E.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.