N-aryl sulfonyl homocysteine hydroxamate inhibitors of matrix metalloproteinases: Further probing of the S1, S1′, and S2′ pockets

Journal of Medicinal Chemistry

Volumn 44, Issue 19, 2001, Pages 3066-3073

  Hanessian, S ^a   Moitessier, N ^a   Gauchet, C ^a   Viau, M ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CGS 27023A; CIPEMASTAT; COLLAGENASE 3; GELATINASE A; GELATINASE B; HOMOCYSTEINE; HYDROXAMIC ACID DERIVATIVE; INTERSTITIAL COLLAGENASE; MARIMASTAT; MATRIX METALLOPROTEINASE INHIBITOR; PRINOMASTAT; STROMELYSIN; SULFONYL HOMOCYSTEINE HYDROXAMATE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME INHIBITION; IC 50; MOLECULAR MODEL; STRUCTURE ACTIVITY RELATION;

COLLAGENASES; HOMOCYSTEINE; HYDROXAMIC ACIDS; MATRIX METALLOPROTEINASE 1; MATRIX METALLOPROTEINASE 13; MATRIX METALLOPROTEINASE 2; MATRIX METALLOPROTEINASE 3; MATRIX METALLOPROTEINASE 9; METALLOENDOPEPTIDASES; MODELS, MOLECULAR; PROTEASE INHIBITORS; PROTEIN BINDING; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0035855835     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm010097f     Document Type: Article

References (40)

1. Protease inhibitors: Current status and future prospects
2. Design and therapeutic application of matrix metalloproteinase inhibitors
3. Recent advances in matrix metalloproteinase inhibitors research
4. Emerging therapeutic advances for the development of second generation matrix metalloproteinase inhibitors
5. Recent advances in matrix metalloproteinase inhibitor research
6. Design and synthesis of the Cartilage Protective Agent (CPA, Ro32-3555)
7. Discovery of CGS 27023A, a non-peptidic, potent, and orally active stromelysin inhibitor that blocks cartilage degradation in rabbits
8. Bioactive conformation of a potent stromelysin inhibitor determined by X-nucleus filtered and multidimensional NMR spectroscopy
9. Crystal structure of the stromelysin catalytic domain at 2.0 Å resolution: Inhibitor-induced conformational change
10. Crystal structures of MMP-1 and MMP-13 reveal the structural basis for selectivity of collagenase inhibitors
11. Discovery of potent, achiral matrix metalloproteinase inhibitors
12. 1′-biphenylethyl carboxyalkyl dipeptides
13. Structure determination and analysis of human neutrophil collagenase complexed with a hydroxamate inhibitor
14. Synthesis of conformationally constrained potential inhibitors of mammalian metalloproteinases
15. Tetrahydrofuran as a scaffold for peptidomimetics. Application to the design and synthesis of conformationally constrained metalloproteinase inhibitors
16. 2′ pockets of matrix metalloproteinases. A niche for potent acyclic sulfonamide inhibitors
17. A computational procedure for determining energetically favorable binding sites on biologically important macromolecules
18. New hydrogen-bond potentials for use in determining energetically favorable binding sites in molecules of known structure
19. Further development of hydrogen bond functions for use in determining energetically favorable binding sites on molecules of known structure. 1. Ligand probe groups with the ability to form two hydrogen bonds
20. Further development of hydrogen bond functions for use in determining energetically favorable binding sites on molecules of known structure. 1. Ligand probe groups with the ability to form more than two hydrogen bonds
21. Affinity and selectivity of matrix metalloproteinase inhibitors: A chemometrical study from the perspective of ligands and proteins
22. Automated docking using a lamarckian genetic algorithm and an empirical binding free energy function
23. Design and synthesis of MMP inhibitors guided by molecular modeling. Overview of the available structural data, comparative docking study and design of potentially selective inhibitors
24. Complementarity of combinatorial chemistry and structure-based ligand design - Application to the discovery of novel inhibitors of matrix metalloproteinases
25. Synthesis of hydroxamic esters via alkoxyaminocarbonylation of β-dicarbonyl compounds
26. Highly selective and orally active inhibitors of type IV collagenase (MMP-9 and MMP-2): N-sulfonylamino acid derivatives
27. What can we learn from molecular recognition in protein-ligand complexes for the design of new drugs?
28. Homology modeling of gelatinase catalytic domains and docking simulations of novel sulfonamide inhibitors
29. A new force field for molecular mechanical simulation of nucleic acids and proteins
30. - exchange reaction and gas phase protonation of polyethers
31. Crystal structure of MMP-1 and -13 reveal the structural basis for selectivity of collagenase inhibitors
32. Discovery of potent, achiral matrix metalloproteinase inhibitors