메뉴 건너뛰기




Volumn 42, Issue 7, 1999, Pages 1213-1224

Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 4. Incorporation of P1 lactam moieties as L-glutamine replacements

Author keywords

[No Author keywords available]

Indexed keywords

3 [(5' METHYLISOXAZOLE 3' CARBONYL)VALYL PSI PHENYLALANYL (4F) [PYRROLALANYL]]PROPENOIC ACID ETHYL ESTER; 3 [(5' METHYLISOXAZOLE 3' CARBONYL)VALYLPHENYLALANYL (4F) [PYRROLALANYL]]PROPENOIC ACID ETHYL ESTER; CYSTEINE; GLUTAMINE; LACTAM; PIRODAVIR; PLECONARIL; PROTEINASE INHIBITOR; RUPINTRIVIR; UNCLASSIFIED DRUG;

EID: 0033535596     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9805384     Document Type: Article
Times cited : (190)

References (41)
  • 1
    • 0000824034 scopus 로고    scopus 로고
    • 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
  • 4
    • 0002871857 scopus 로고
    • 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 scopus 로고
    • 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 scopus 로고    scopus 로고
    • 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 scopus 로고
    • 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 scopus 로고
    • 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 scopus 로고
    • 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 scopus 로고
    • 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
  • 14
    • 0032474754 scopus 로고    scopus 로고
    • 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 scopus 로고    scopus 로고
    • 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 scopus 로고    scopus 로고
    • note
    • All amino acids described in the text are L-isomers unless otherwise noted.
  • 17
    • 0345506027 scopus 로고    scopus 로고
    • 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 scopus 로고    scopus 로고
    • 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 scopus 로고
    • 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 scopus 로고    scopus 로고
    • note
    • 50 values.
  • 21
    • 0344212195 scopus 로고    scopus 로고
    • Unpublished results
    • 5 for the glutamine-derived molecule 1 (Matthews, D. A. Unpublished results).
    • Matthews, D.A.1
  • 23
    • 0344212194 scopus 로고    scopus 로고
    • 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
  • 27
    • 0344643789 scopus 로고    scopus 로고
    • 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 scopus 로고    scopus 로고
    • 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 scopus 로고    scopus 로고
    • 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
  • 31
    • 0001071065 scopus 로고
    • 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 scopus 로고
    • 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 scopus 로고    scopus 로고
    • note
    • 1H NMR spectra of 18 and subsequent synthetic intermediates.
  • 34
    • 84989478646 scopus 로고
    • 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 scopus 로고
    • 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 scopus 로고
    • 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 scopus 로고
    • 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 scopus 로고
    • 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 scopus 로고    scopus 로고
    • 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.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.