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0032758392
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Recent advances in matrix metalloproteinase inhibitor research
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Michaelides, M. R.; Curtin, M. L. Recent Advances in Matrix Metalloproteinase Inhibitor Research. Curr. Pharm. Des. 1999, 5, 787-819.
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(1999)
Curr. Pharm. Des.
, vol.5
, pp. 787-819
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Michaelides, M.R.1
Curtin, M.L.2
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2
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0001651169
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Design and therapeutic application of matrix metalloproteinase inhibitors
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Whittaker, M.; Floyd, C. D.; Brown, P.; Gearing, A. J. H. Design and Therapeutic Application of Matrix Metalloproteinase Inhibitors. Chem. Rev. 1999, 2735-2776.
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(1999)
Chem. Rev.
, pp. 2735-2776
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Whittaker, M.1
Floyd, C.D.2
Brown, P.3
Gearing, A.J.H.4
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4
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0031657033
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New drugs on the horizon: Matrix metalloproteinase inhibitors
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Rothenberg, M. L.; Nelson, A. R.; Hande, K. R. New Drugs on the Horizon: Matrix Metalloproteinase Inhibitors. Oncologist 1998, 3, 271-274.
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(1998)
Oncologist
, vol.3
, pp. 271-274
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Rothenberg, M.L.1
Nelson, A.R.2
Hande, K.R.3
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5
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0031799439
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Matrix metalloproteinase inhibitors in arthritis
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Bottomley, K. M.; Johnson, W. H.; Walter, D. S. Matrix Metalloproteinase Inhibitors in Arthritis. J. Enzyme Inhib. 1998, 13, 79-101.
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(1998)
J. Enzyme Inhib.
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, pp. 79-101
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Bottomley, K.M.1
Johnson, W.H.2
Walter, D.S.3
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6
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15644374838
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Discovery of CGS 27023A, a non-peptidic, potent and orally active stromelysin inhibitor that blocks cartilage degradation in rabbits
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MacPherson, L. J.; Bayburt, E. K.; Capparelli, M. P.; Carroll, B. J.; Goldstein, R.; Justice, M. R.; Zhu, L.; Hu, S.; Melton, R. A.; Fryer, L.; Goldberg, R. L.; Doughty, J. R.; Spirito, S.; Blancuzzi, V.; Wilson, D.; O'Byrne, E. M.; Ganu, V.; Parker, D. T. Discovery of CGS 27023A, A Non-Peptidic, Potent and Orally Active Stromelysin Inhibitor That Blocks Cartilage Degradation in Rabbits. J. Med. Chem. 1997, 40, 2525-2532.
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(1997)
J. Med. Chem.
, vol.40
, pp. 2525-2532
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MacPherson, L.J.1
Bayburt, E.K.2
Capparelli, M.P.3
Carroll, B.J.4
Goldstein, R.5
Justice, M.R.6
Zhu, L.7
Hu, S.8
Melton, R.A.9
Fryer, L.10
Goldberg, R.L.11
Doughty, J.R.12
Spirito, S.13
Blancuzzi, V.14
Wilson, D.15
O'Byrne, E.M.16
Ganu, V.17
Parker, D.T.18
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7
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0343396739
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During the course of this work, patent applications disclosing unrelated pyrrolidinone-based MMP inhibitors were published: (a) Jacobsen, E. J. PCT Int. Appl. WO 97/32846.
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PCT Int. Appl. WO 97/32846
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Jacobsen, E.J.1
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9
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0028047686
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Structure of the catalytic domain of fibroblast collagenase complexed with an inhibitor
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Lovejoy, B.; Cleasby, A.; Hassell, A. M.; Longley, K.; Luther, M. A.; Weigl, D.; McGeehan, G.; McElroy, A. B.; Drewry, D.; Lambert, M. H.; Jordan, S. R. Structure of the Catalytic Domain of Fibroblast Collagenase Complexed with an Inhibitor. Science 1994, 263, 375-377.
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(1994)
Science
, vol.263
, pp. 375-377
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Lovejoy, B.1
Cleasby, A.2
Hassell, A.M.3
Longley, K.4
Luther, M.A.5
Weigl, D.6
McGeehan, G.7
McElroy, A.B.8
Drewry, D.9
Lambert, M.H.10
Jordan, S.R.11
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10
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0028382506
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Structure of the catalytic domain of human fibroblast collagenase complexed with an inhibitor
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Borkakoti, N.; Winkler, F. K.; Williams, D. H.; D'Arcy, A.; Broadhurst, M. J.; Brown, P. A.; Johnson, W. H.; Murray, E. J. Structure of the Catalytic Domain of Human Fibroblast Collagenase Complexed with an Inhibitor. Nat. Struct. Biol. 1994, 1, 106-110.
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(1994)
Nat. Struct. Biol.
, vol.1
, pp. 106-110
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Borkakoti, N.1
Winkler, F.K.2
Williams, D.H.3
D'Arcy, A.4
Broadhurst, M.J.5
Brown, P.A.6
Johnson, W.H.7
Murray, E.J.8
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11
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0028805811
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Stromelysin-1: Three-dimensional structure of the inhibited catalytic domain and of the C-truncated proenzyme
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Becker, J. W.; Marcy, A. I.; Rokosz, L. L.; Axel, M. G.; Burbaum, J. J.; Fitzgerald, P. M. D.; Cameron, P. M.; Esser, C. K.; Hagmann, W. K.; Hermes, J. D.; Springer, J. P. Stromelysin-1: Three-dimensional Structure of the Inhibited Catalytic Domain and of the C-Truncated Proenzyme. Protein Sci. 1995, 4, 1966-1976.
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(1995)
Protein Sci.
, vol.4
, pp. 1966-1976
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Becker, J.W.1
Marcy, A.I.2
Rokosz, L.L.3
Axel, M.G.4
Burbaum, J.J.5
Fitzgerald, P.M.D.6
Cameron, P.M.7
Esser, C.K.8
Hagmann, W.K.9
Hermes, J.D.10
Springer, J.P.11
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12
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0029030448
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Matrilysin-inhibitor complexes: Common themes among metalloproteases
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Browner, M. F.; Smith, W. W.; Castelhano, A. L.; Matrilysin-Inhibitor Complexes: Common Themes among Metalloproteases. Biochemistry 1995, 34, 6602-6610.
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(1995)
Biochemistry
, vol.34
, pp. 6602-6610
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Browner, M.F.1
Smith, W.W.2
Castelhano, A.L.3
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13
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0028382512
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1′ specificity pocket
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1′ Specificity Pocket. Nat. Struct. Biol. 1994, 1, 119-123.
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(1994)
Nat. Struct. Biol.
, vol.1
, pp. 119-123
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Stams, T.1
Spurlino, J.C.2
Smith, D.L.3
Wahl, R.C.4
Ho, T.F.5
Qoronfleh, M.W.6
Banks, T.M.7
Rubin, B.8
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14
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0028838862
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Structure determination and analysis of human neutrophil collagenase complexed with a hydroxamate inhibitor
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Grams, F.; Crimmin, M.; Hinnes, L.; Huxley, P.; Pieper, M.; Tschesche, H.; Bode, W. Structure Determination and Analysis of Human Neutrophil Collagenase Complexed with a Hydroxamate Inhibitor. Biochemistry 1995, 34, 14012-14020.
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(1995)
Biochemistry
, vol.34
, pp. 14012-14020
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Grams, F.1
Crimmin, M.2
Hinnes, L.3
Huxley, P.4
Pieper, M.5
Tschesche, H.6
Bode, W.7
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15
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0033048045
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Crystal structures of MMP-1 and -13 reveal the structural basis for selectivity of collagenase inhibitors
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Lovejoy, B.; Welch, A. R.; Carr, S.; Luong, C.; Broka, C.; Hendricks, R. T.; Campbell, J. A.; Walker, K. A. M.; Martin, R.; Van Wart, H.; Browner, M. F. Crystal Structures of MMP-1 and -13 Reveal the Structural Basis for Selectivity of Collagenase Inhibitors. Nat. Struct. Biol. 1999, 6, 217-221.
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(1999)
Nat. Struct. Biol.
, vol.6
, pp. 217-221
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Lovejoy, B.1
Welch, A.R.2
Carr, S.3
Luong, C.4
Broka, C.5
Hendricks, R.T.6
Campbell, J.A.7
Walker, K.A.M.8
Martin, R.9
Van Wart, H.10
Browner, M.F.11
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16
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0028324076
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The X-ray crystal structure of the catalytic domain of human neutrophil collagenase inhibited by a substrate analogue reveals the essentials for catalysis and specificity
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Bode, W.; Reinemer, P.; Huber, R.; Kleine, T.; Schnierer, Tschesche, H. The X-ray Crystal Structure of the Catalytic Domain of Human Neutrophil Collagenase Inhibited by a Substrate Analogue Reveals the Essentials for Catalysis and Specificity. EMBO J. 1994, 13, 1263-1269.
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(1994)
EMBO J.
, vol.13
, pp. 1263-1269
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Bode, W.1
Reinemer, P.2
Huber, R.3
Kleine, T.4
Schnierer, T.H.5
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17
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0342961312
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We did not have access to an X-ray crystal structure of MMP-13. The model, based on MMP-8, was built using the program COMPOSER and minimized using the AMBER all-atom force field as implemented in the Sybyl program. (Sybyl 6.3, Rev 3A; Tripos Inc., 1699 Hanley Rd, Suite 303, St. Louis, MO 63144.)
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We did not have access to an X-ray crystal structure of MMP-13. The model, based on MMP-8, was built using the program COMPOSER and minimized using the AMBER all-atom force field as implemented in the Sybyl program. (Sybyl 6.3, Rev 3A; Tripos Inc., 1699 Hanley Rd, Suite 303, St. Louis, MO 63144.)
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18
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0342961311
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Unpublished information
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Blake, J. F. Unpublished information.
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Blake, J.F.1
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19
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0032491208
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Solution structure of the catalytic domain of human stromelysin-1 complexed to a potent, nonpeptidic inhibitor
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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.
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(1998)
Biochemistry
, vol.37
, pp. 14048-14056
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Li, Y.-C.1
Zhang, X.2
Melton, R.3
Ganu, V.4
Gonnella, N.C.5
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20
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0025985753
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Asymmetric synthesis from α-amino acids; some reactions of (S)-pyroglutamate
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The (S) enantiomer is known: (a) Woo, K.-C.; Jones, K. Asymmetric Synthesis from α-Amino Acids; Some Reactions of (S)-Pyroglutamate. Tetrahedron Lett. 1991, 6949-6952.
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(1991)
Tetrahedron Lett.
, pp. 6949-6952
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Woo, K.-C.1
Jones, K.2
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21
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0025797354
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Synthesis of four diastereomeric L-2-(carboxycyclopropyl)glycines. Conformationally constrained L-glutamate analogues
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(b) Shimamoto, K.; Ishida, M.; Shinozaki, H.; Ohfune, Y. Synthesis of Four Diastereomeric L-2-(Carboxycyclopropyl)glycines. Conformationally Constrained L-Glutamate Analogues. J. Org. Chem. 1991, 56, 4167-4176.
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(1991)
J. Org. Chem.
, vol.56
, pp. 4167-4176
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Shimamoto, K.1
Ishida, M.2
Shinozaki, H.3
Ohfune, Y.4
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22
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0026500938
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Direct α-iodination of cycloalkenones
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Johnson, C. R.; Adams, J. P.; Braun, M. P.; Senanayake, C. B. W.; Wovkulich, P. M.; Uskokovic, M. R. Direct α-Iodination of Cycloalkenones. Tetrahedron Lett. 1992, 33, 917-918.
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(1992)
Tetrahedron Lett.
, vol.33
, pp. 917-918
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Johnson, C.R.1
Adams, J.P.2
Braun, M.P.3
Senanayake, C.B.W.4
Wovkulich, P.M.5
Uskokovic, M.R.6
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23
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0000397348
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Directed ortho metalation of neopentyl benzoates with LDA: Preparation of arylboronic acids
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In the Suzuki couplings of 8, the arylboronic acids were preferably generated from the corresponding diethanolamine complexes; see: Caron, S.; Hawkins, J. M. Directed Ortho Metalation of Neopentyl Benzoates with LDA: Preparation of Arylboronic Acids. J. Org. Chem. 1998, 63, 2054-2055.
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(1998)
J. Org. Chem.
, vol.63
, pp. 2054-2055
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Caron, S.1
Hawkins, J.M.2
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24
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0342527117
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note
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3/toluene/ reflux), long reaction times ( > 12 h) gave appreciable racemization. The use of 8 instead of the corresponding bromo lactam was preferred because the higher coupling rate allowed reaction times to be shortened to about 1 h, thus minimizing racemization as determined by chiral HPLC (ee's > 98%).
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25
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0343832422
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note
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1H NMR spectra of 6a-e to the spectrum of 6f showed a common pattern of chemical shifts and coupling constants for the pyrrolidinone ring protons. The pattern was clearly distinguishable from that exhibited by 12. (24) Retention of the N-BOC group was essential for the success of the subsequent oxidation.
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26
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0032560829
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A novel chromium trioxide catalyzed oxidation of primary alcohols to the carboxylic acids
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Zhao, M.; Li, J.; Song, Z.; Desmond, R.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. A Novel Chromium Trioxide Catalyzed Oxidation of Primary Alcohols to the Carboxylic Acids. Tetrahedron Lett. 1998, 39, 5323-5326.
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(1998)
Tetrahedron Lett.
, vol.39
, pp. 5323-5326
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Zhao, M.1
Li, J.2
Song, Z.3
Desmond, R.4
Tschaen, D.M.5
Grabowski, E.J.J.6
Reider, P.J.7
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28
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0342961305
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note
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3 oxidation.
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29
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0032712582
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Crystal structure of the stromelysin catalytic domain at 2.0 ä resolution: Inhibitor-induced conformational changes
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Chen, L.; Rydel, T. J.; Gu, F.; Dunaway, C. M.; Pikul, S.; Dunham, K. M.; Barnett, B. L. Crystal Structure of the Stromelysin Catalytic Domain at 2.0 Ä Resolution: Inhibitor-Induced Conformational Changes. J. Mol. Biol. 1999, 293, 545-557.
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(1999)
J. Mol. Biol.
, vol.293
, pp. 545-557
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Chen, L.1
Rydel, T.J.2
Gu, F.3
Dunaway, C.M.4
Pikul, S.5
Dunham, K.M.6
Barnett, B.L.7
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30
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0033587024
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Homology modeling of gelatinase catalytic domains and docking simulations of novel sulfonamide inhibitors
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Kiyama, R.; Tamura, Y.; Watanabe, F.; Tsuzuki, H.; Ohtani, M.; Yodo, M. Homology Modeling of Gelatinase Catalytic Domains and Docking Simulations of Novel Sulfonamide Inhibitors. J. Med. Chem. 1999, 42, 1723-1738.
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(1999)
J. Med. Chem.
, vol.42
, pp. 1723-1738
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Kiyama, R.1
Tamura, Y.2
Watanabe, F.3
Tsuzuki, H.4
Ohtani, M.5
Yodo, M.6
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31
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0342527111
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note
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The isomer 12 was obtained via treatment of the intermediate corresponding to 10 with DBU (3.5 equiv) in toluene at room temperature. The epimeric product was then advanced to 12 in the usual way.
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32
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0343396728
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note
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2.
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33
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0032543517
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Rational design and combinatorial evaluation of enzyme inhibitor scaffolds: Identification of novel inhibitors of matrix metalloproteinases
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Szardenings, A. K.; Harris, D.; Lam, S.; Shi, L.; Tien, D.; Wang, Y.; Patel, D. V.; Navre, M.; Campbell, D. A. Rational Design and Combinatorial Evaluation of Enzyme Inhibitor Scaffolds: Identification of Novel Inhibitors of Matrix Metalloproteinases. J. Med. Chem. 1998, 41, 2194-2200.
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(1998)
J. Med. Chem.
, vol.41
, pp. 2194-2200
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Szardenings, A.K.1
Harris, D.2
Lam, S.3
Shi, L.4
Tien, D.5
Wang, Y.6
Patel, D.V.7
Navre, M.8
Campbell, D.A.9
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