-
1
-
-
0000824034
-
-
Fields, B. N., Knipe, D. M., Howley, P. M., et al., Eds.; Lippincott-Raven Publishers: Philadelphia, Chapter 23
-
(a) Couch, R. B. In Fields Virology, 3rd ed.; Fields, B. N., Knipe, D. M., Howley, P. M., et al., Eds.; Lippincott-Raven Publishers: Philadelphia, 1996; Vol. 1, Chapter 23, pp 713-734.
-
(1996)
Fields Virology, 3rd Ed.
, vol.1
, pp. 713-734
-
-
Couch, R.B.1
-
2
-
-
0026803235
-
-
(b) McKinlay, M. A.; Pevear, D. C.; Rossmann, M. G. Annu. Rev. Microbiol. 1992, 46, 635.
-
(1992)
Annu. Rev. Microbiol.
, vol.46
, pp. 635
-
-
McKinlay, M.A.1
Pevear, D.C.2
Rossmann, M.G.3
-
4
-
-
0002871857
-
-
Mandell, G. L., Douglas, R. G., Bennett, J. E., Eds.; John Wiley & Sons: New York, Chapter 38
-
(d) Gwaltney, J. M. In Principles and Practices of Infectious Diseases; Mandell, G. L., Douglas, R. G., Bennett, J. E., Eds.; John Wiley & Sons: New York, 1985; Chapter 38, pp 351-355.
-
(1985)
Principles and Practices of Infectious Diseases
, pp. 351-355
-
-
Gwaltney, J.M.1
-
5
-
-
0002546256
-
-
Evans, A. S., Ed.; Plenum Publishing Corp.: New York, Chapter 20
-
(e) Gwaltney, J. M. In Viral Infections of Humans; Evans, A. S., Ed.; Plenum Publishing Corp.: New York, 1982; Chapter 20, pp 491-517.
-
(1982)
Viral Infections of Humans
, pp. 491-517
-
-
Gwaltney, J.M.1
-
6
-
-
0000327130
-
-
Fields, B. N., Knipe, D. M., Howley, P. M., et al., Eds.; Lippincott-Raven Publishers: Philadelphia, Chapter 21
-
(a) Rueckert, R. R. In Fields Virology, 3rd ed.; Fields, B. N., Knipe, D. M., Howley, P. M., et al., Eds.; Lippincott-Raven Publishers: Philadelphia, 1996; Vol. 1, Chapter 21, pp 609-654.
-
(1996)
Fields Virology, 3rd Ed.
, vol.1
, pp. 609-654
-
-
Rueckert, R.R.1
-
8
-
-
0025370822
-
Substrate requirements of human rhinovirus 3C protease for peptide cleavage in vitro
-
(a) Cordingley, M. G.; Callahan, P. L.; Sardana, V. V.; Garsky, V. M.; Colonno, R. J. Substrate Requirements of Human Rhinovirus 3C Protease for Peptide Cleavage in Vitro. J. Biol. Chem. 1990, 265, 9062-9065.
-
(1990)
J. Biol. Chem.
, vol.265
, pp. 9062-9065
-
-
Cordingley, M.G.1
Callahan, P.L.2
Sardana, V.V.3
Garsky, V.M.4
Colonno, R.J.5
-
9
-
-
0024468899
-
Hydrolysis of a series of synthetic peptide substrates by the human rhinovirus 14 3C proteinase, cloned and expressed in Escherichia coli
-
(b) Orr, D. C.; Long, A. C.; Kay, J.; Dunn, B. M.; Cameron, J. M. Hydrolysis of a Series of Synthetic Peptide Substrates by the Human Rhinovirus 14 3C Proteinase, Cloned and Expressed in Escherichia coli. J. Gen. Virol. 1989, 70, 2931-2942.
-
(1989)
J. Gen. Virol.
, vol.70
, pp. 2931-2942
-
-
Orr, D.C.1
Long, A.C.2
Kay, J.3
Dunn, B.M.4
Cameron, J.M.5
-
10
-
-
0024431580
-
Cleavage of small peptides in vitro by human rhinovirus 14 3C protease expressed in Escherichia coli
-
(c) Cordingley, M. G.; Register, R. B.; Callahan, P. L.; Garsky, V. M.; Colonno, R. J. Cleavage of Small Peptides In Vitro by Human Rhinovirus 14 3C Protease Expressed in Escherichia coli. J. Virol. 1989, 63, 5037-5045.
-
(1989)
J. Virol.
, vol.63
, pp. 5037-5045
-
-
Cordingley, M.G.1
Register, R.B.2
Callahan, P.L.3
Garsky, V.M.4
Colonno, R.J.5
-
11
-
-
0014211618
-
On the size of the active site in proteases. I. Papain
-
2′, etc.) is described in the following: Schechter, I.; Berger, A. On the Size of the Active Site in Proteases. I. Papain. Biochem. Biophys. Res. Commun. 1967, 27, 157-162.
-
(1967)
Biochem. Biophys. Res. Commun.
, vol.27
, pp. 157-162
-
-
Schechter, I.1
Berger, A.2
-
12
-
-
14444272282
-
Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 1. Michael acceptor structure-activity studies
-
Dragovich, P. S.; Webber, S. E.; Babine, R. E.; Fuhrman, S. A.; Patick, A. K.; Matthews, D. A.; Lee, C. A.; Reich, S. R.; Prins, T. J.; Marakovits, J. T.; Littlefield, E. S.; Zhou, R.; Tikhe, J.; Ford, C. E.; Wallace, M. B.; Meador, J. W., III; Ferre, R. A.; Brown, E. L.; Binford, S. L.; Harr, J. E. V.; DeLisle, D. M.; Worland, S. T. Structure-Based Design, Synthesis, and Biological Evaluation of Irreversible Human Rhinovirus 3C Protease Inhibitors. 1. Michael Acceptor Structure-Activity Studies. J. Med. Chem. 1998, 41, 2806-2818.
-
(1998)
J. Med. Chem.
, vol.41
, pp. 2806-2818
-
-
Dragovich, P.S.1
Webber, S.E.2
Babine, R.E.3
Fuhrman, S.A.4
Patick, A.K.5
Matthews, D.A.6
Lee, C.A.7
Reich, S.R.8
Prins, T.J.9
Marakovits, J.T.10
Littlefield, E.S.11
Zhou, R.12
Tikhe, J.13
Ford, C.E.14
Wallace, M.B.15
Meador J.W. III16
Ferre, R.A.17
Brown, E.L.18
Binford, S.L.19
Harr, J.E.V.20
DeLisle, D.M.21
Worland, S.T.22
more..
-
13
-
-
15144354736
-
Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 2. Peptide structure-activity studies
-
Dragovich, P. S.; Webber, S. E.; Babine, R. E.; Fuhrman, S. A.; Patick, A. K.; Matthews, D. A.; Reich, S. H.; Marakovits, J. T.; Prins, T. J.; Zhou, R.; Tikhe, J.; Littlefield, E. S.; Bleckman, T. M.; Wallace, M. B.; Little, T. L.; Ford, C. E.; Meador, J. W., III; Ferre, R. A.; Brown, E. L.; Binford, S. L.; DeLisle, D. M.; Worland, S. T. Structure-Based Design, Synthesis, and Biological Evaluation of Irreversible Human Rhinovirus 3C Protease Inhibitors. 2. Peptide Structure-Activity Studies. J. Med. Chem. 1998, 41, 2819-2834.
-
(1998)
J. Med. Chem.
, vol.41
, pp. 2819-2834
-
-
Dragovich, P.S.1
Webber, S.E.2
Babine, R.E.3
Fuhrman, S.A.4
Patick, A.K.5
Matthews, D.A.6
Reich, S.H.7
Marakovits, J.T.8
Prins, T.J.9
Zhou, R.10
Tikhe, J.11
Littlefield, E.S.12
Bleckman, T.M.13
Wallace, M.B.14
Little, T.L.15
Ford, C.E.16
Meador J.W. III17
Ferre, R.A.18
Brown, E.L.19
Binford, S.L.20
DeLisle, D.M.21
Worland, S.T.22
more..
-
14
-
-
0032474754
-
Synthesis and evaluation of peptidyl michael acceptors that inactivate human rhinovirus 3C protease and inhibit virus replication
-
A similar series of HRV 3CP inhibitors has also recently been described. See: Kong, J.-s.; Venkatraman, S.; Furness, K.; Nimkar, S.; Shepherd, T. A.; Wang, Q. M.; Aubé, J.; Hanzlik, R. P. Synthesis and Evaluation of Peptidyl Michael Acceptors That Inactivate Human Rhinovirus 3C Protease and Inhibit Virus Replication. J. Med. Chem. 1998, 41, 2579-2587.
-
(1998)
J. Med. Chem.
, vol.41
, pp. 2579-2587
-
-
Kong, J.-S.1
Venkatraman, S.2
Furness, K.3
Nimkar, S.4
Shepherd, T.A.5
Wang, Q.M.6
Aubé, J.7
Hanzlik, R.P.8
-
15
-
-
0033535579
-
Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 3. Structure-activity studies of ketomethylene-containing peptidomimetics
-
Preceding paper in this issue. Dragovich, P. S.; Prins, T. J.; Zhou, R.; Fuhrman, S. A.; Patick, A. K.; Matthews, D. A.; Ford, C. E.; Meador, J. W., III; Ferre, R. A.; Worland, S. T. Structure-Based Design, Synthesis, and Biological Evaluation of Irreversible Human Rhinovirus 3C Protease Inhibitors. 3. Structure-Activity Studies of Ketomethylene-Containing Peptidomimetics. J. Med. Chem. 1999, 42, 1203-1212.
-
(1999)
J. Med. Chem.
, vol.42
, pp. 1203-1212
-
-
Dragovich, P.S.1
Prins, T.J.2
Zhou, R.3
Fuhrman, S.A.4
Patick, A.K.5
Matthews, D.A.6
Ford, C.E.7
Meador J.W. III8
Ferre, R.A.9
Worland, S.T.10
-
16
-
-
0344212198
-
-
note
-
All amino acids described in the text are L-isomers unless otherwise noted.
-
-
-
-
17
-
-
0345506027
-
-
note
-
Note that the reduction in the antiviral potency of 2 (or 3) relative to 1 was not nearly as great as the loss in 3CP inhibition activity. This observation suggested that Gln amide N-alkylation may result in improved cell permeability properties.
-
-
-
-
18
-
-
0345074479
-
-
note
-
obs/[I] values approximate changes in ligand-3CP binding affinity and that the anti-3CP activities of cis-and trans-Z are similar to those displayed by compounds 1 and 3, respectively.
-
-
-
-
19
-
-
26044455503
-
Cis-trans energy difference for the peptide bond in the gas phase and in aqueous solution
-
and references therein
-
Jorgensen, W. L.; Gao, J. Cis-Trans Energy Difference for the Peptide Bond in the Gas Phase and in Aqueous Solution. J. Am. Chem. Soc. 1988, 110, 4212-4216 and references therein.
-
(1988)
J. Am. Chem. Soc.
, vol.110
, pp. 4212-4216
-
-
Jorgensen, W.L.1
Gao, J.2
-
20
-
-
0344212196
-
-
note
-
50 values.
-
-
-
-
21
-
-
0344212195
-
-
Unpublished results
-
5 for the glutamine-derived molecule 1 (Matthews, D. A. Unpublished results).
-
-
-
Matthews, D.A.1
-
22
-
-
0032987794
-
Solid-phase synthesis of irreversible human rhinovirus 3C protease inhibitors. 1. Optimization of tripeptideg incorporating n-terminal amides
-
in press
-
Dragovich, P. S.; Zhou, R.; Skalitzky, D. J.; Fuhrman, S. A.; Patick, A. K.; Ford, C. E.; Meador, J. W., III; Worland, S. T. Solid-Phase Synthesis of Irreversible Human Rhinovirus 3C Protease Inhibitors. 1. Optimization of Tripeptideg Incorporating N-Terminal Amides. Bioorg. Med. Chem., in press.
-
Bioorg. Med. Chem.
-
-
Dragovich, P.S.1
Zhou, R.2
Skalitzky, D.J.3
Fuhrman, S.A.4
Patick, A.K.5
Ford, C.E.6
Meador J.W. III7
Worland, S.T.8
-
23
-
-
0344212194
-
-
Manuscript in preparation
-
90 of approximately 0.10 μM. Full details of these experiments will be presented elsewhere (Patick, A. K. Manuscript in preparation).
-
-
-
Patick, A.K.1
-
24
-
-
0026502172
-
In vitro activity of pirodavir (R 77975), a substituted phenoxy-pyridazinamine with broad-spectrum antipicornaviral activity
-
Andries, K.; Dewindt, B.; Snoeks, J.; Willebrords, R.; Van Eemeren, K.; Stokbroekx, R.; Janssen, P. A. J. In Vitro Activity of Pirodavir (R 77975), a Substituted Phenoxy-Pyridazinamine with Broad-Spectrum Antipicornaviral Activity. Antimicrob. Agents Chemother. 1992, 36, 100-107.
-
(1992)
Antimicrob. Agents Chemother.
, vol.36
, pp. 100-107
-
-
Andries, K.1
Dewindt, B.2
Snoeks, J.3
Willebrords, R.4
Van Eemeren, K.5
Stokbroekx, R.6
Janssen, P.A.J.7
-
25
-
-
0028930769
-
Picornavirus inhibitors: Trifluoromethyl substitution provides a global protective effect against hepatic metabolism
-
(a) Diana, G. D.; Rudewicz, P.; Pevear, D. C.; Nitz, T. J.; Aldous, S. C.; Aldous, D. J.; Robinson, D. T.; Draper, T.; Dutko, F. J.; Aldi, C.; Gendron, G.; Oglesby, R. C.; Volkots, D. L.; Reuman, M.; Bailey, T. R.; Czerniak, R.; Block, T.; Roland, R.; Oppermann, J. Picornavirus Inhibitors: Trifluoromethyl Substitution Provides a Global Protective Effect against Hepatic Metabolism. J. Med. Chem. 1995, 38, 1355-1371.
-
(1995)
J. Med. Chem.
, vol.38
, pp. 1355-1371
-
-
Diana, G.D.1
Rudewicz, P.2
Pevear, D.C.3
Nitz, T.J.4
Aldous, S.C.5
Aldous, D.J.6
Robinson, D.T.7
Draper, T.8
Dutko, F.J.9
Aldi, C.10
Gendron, G.11
Oglesby, R.C.12
Volkots, D.L.13
Reuman, M.14
Bailey, T.R.15
Czerniak, R.16
Block, T.17
Roland, R.18
Oppermann, J.19
-
27
-
-
0344643789
-
-
note
-
The α,β-unsaturated carboxylic acids corresponding to the compounds in Table 3 are assumed to exhibit drastically reduced antirhinoviral activity by analogy to data obtained for inhibitor 1. See ref 5 for additional details.
-
-
-
-
28
-
-
0344643788
-
-
note
-
The assumption that rat plasma degradation of 11 primarily affords the corresponding α,β-unsaturated carboxylic acid is based on the related degradation of compound 1. See ref 5 for additional details.
-
-
-
-
29
-
-
0000598486
-
Using a convenient, quantitative model for torsional entropy to establish qualitative trends for molecular processes that restrict conformational freedom
-
Mammen, M.; Shakhnovich, E. I.; Whitesides, G. M. Using a Convenient, Quantitative Model for Torsional Entropy To Establish Qualitative Trends for Molecular Processes That Restrict Conformational Freedom. J. Org. Chem. 1998, 83, 3168-3175.
-
(1998)
J. Org. Chem.
, vol.83
, pp. 3168-3175
-
-
Mammen, M.1
Shakhnovich, E.I.2
Whitesides, G.M.3
-
30
-
-
0026690381
-
Total synthesis and absolute configuration of bengamide A
-
Chida, N.; Tobe, T.; Okada, S.; Ogawa, S. Total Synthesis and Absolute Configuration of Bengamide A. J. Chem. Soc., Chem. Commun. 1992, 1064-1066.
-
(1992)
J. Chem. Soc., Chem. Commun.
, pp. 1064-1066
-
-
Chida, N.1
Tobe, T.2
Okada, S.3
Ogawa, S.4
-
31
-
-
0001071065
-
Lithium-initiated imide formation. A simple method for N-acylation of 2-oxazolidinones and bornane-2,10-Sultam
-
Ho, G.-J.; Mathre, D. Lithium-Initiated Imide Formation. A Simple Method for N-Acylation of 2-Oxazolidinones and Bornane-2,10-Sultam. J. Org. Chem. 1995, 60, 2271-2273.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 2271-2273
-
-
Ho, G.-J.1
Mathre, D.2
-
32
-
-
0001607161
-
Assignment of stereochemistry in the oligomycin/rutamycin/ cytovaricin family of antibiotics. Asymmetric synthesis of the rutamycin spiroketal synthon
-
and references therein
-
Evans, D. A.; Rieger, D. L.; Jones, T. K.; Kaldor, S. W. Assignment of Stereochemistry in the Oligomycin/Rutamycin/ Cytovaricin Family of Antibiotics. Asymmetric Synthesis of the Rutamycin Spiroketal Synthon. J. Org. Chem. 1990, 55, 6260-6268 and references therein.
-
(1990)
J. Org. Chem.
, vol.55
, pp. 6260-6268
-
-
Evans, D.A.1
Rieger, D.L.2
Jones, T.K.3
Kaldor, S.W.4
-
33
-
-
0344643785
-
-
note
-
1H NMR spectra of 18 and subsequent synthetic intermediates.
-
-
-
-
34
-
-
84989478646
-
Activated dimethyl sulfoxide: Useful reagents for synthesis
-
(a) Mancuso, A. J.; Swern, D. Activated Dimethyl Sulfoxide: Useful Reagents for Synthesis. Synthesis 1981, 165-185.
-
(1981)
Synthesis
, pp. 165-185
-
-
Mancuso, A.J.1
Swern, D.2
-
35
-
-
85082551132
-
Oxidation of alcohols by activated dimethyl sulfoxide and related reactions: An update
-
(b) Tidwell, T. T. Oxidation of Alcohols by Activated Dimethyl Sulfoxide and Related Reactions: An Update. Synthesis 1990, 857-870.
-
(1990)
Synthesis
, pp. 857-870
-
-
Tidwell, T.T.1
-
36
-
-
0026084964
-
Stereocontrolled addition of propionate homoenolate equivalents to chiral α-amino aldehydes
-
(c) DeCamp, A. E.; Kawaguchi, A. T.; Volante, R. P.; Shinkai, I. Stereocontrolled Addition of Propionate Homoenolate Equivalents to Chiral α-Amino Aldehydes. Tetrahedron Lett. 1991, 32, 1867-1870.
-
(1991)
Tetrahedron Lett.
, vol.32
, pp. 1867-1870
-
-
DeCamp, A.E.1
Kawaguchi, A.T.2
Volante, R.P.3
Shinkai, I.4
-
37
-
-
0001702466
-
A new amidoalkynylation using alkynylzinc reagent
-
and references therein
-
Mori, S.; Iwakura, H.; Takechi, S. A New Amidoalkynylation Using Alkynylzinc Reagent. Tetrahedron Lett. 1988, 29, 5391-5394 and references therein.
-
(1988)
Tetrahedron Lett.
, vol.29
, pp. 5391-5394
-
-
Mori, S.1
Iwakura, H.2
Takechi, S.3
-
38
-
-
0021985341
-
A convenient synthesis of 4-unsubstituted β-lactams
-
and references therein
-
Overman, L. E.; Osawa, T. A Convenient Synthesis of 4-Unsubstituted β-Lactams. J. Am. Chem. Soc. 1985, 107, 1698-1701 and references therein.
-
(1985)
J. Am. Chem. Soc.
, vol.107
, pp. 1698-1701
-
-
Overman, L.E.1
Osawa, T.2
-
39
-
-
0344212192
-
-
note
-
During the preparation of 6, the diastereomeric excess of the allylic alkylation product corresponding to 18 was also not rigorously determined. See ref 25 above.
-
-
-
-
40
-
-
14444269890
-
1 glutamine isosteric replacements
-
1 Glutamine Isosteric Replacements. J. Med. Chem. 1998, 41, 2786-2805.
-
(1998)
J. Med. Chem.
, vol.41
, pp. 2786-2805
-
-
Webber, S.E.1
Okano, K.2
Little, T.L.3
Reich, S.H.4
Xin, Y.5
Fuhrman, S.A.6
Matthews, D.A.7
Hendrickson, T.F.8
Love, R.A.9
Patick, A.K.10
Meador J.W. III11
Ferre, R.A.12
Brown, E.L.13
Ford, C.E.14
Binford, S.L.15
Worland, S.T.16
-
41
-
-
84986437005
-
MacroModel-an integrated software system for modeling organic and bioorganic molecules using molecular mechanics
-
Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. MacroModel-An Integrated Software System for Modeling Organic and Bioorganic Molecules Using Molecular Mechanics. J. Comput. Chem. 1990, 11, 440-467.
-
(1990)
J. Comput. Chem.
, vol.11
, pp. 440-467
-
-
Mohamadi, F.1
Richards, N.G.J.2
Guida, W.C.3
Liskamp, R.4
Lipton, M.5
Caufield, C.6
Chang, G.7
Hendrickson, T.8
Still, W.C.9
|