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Volumn 48, Issue 12, 2005, Pages 3980-3990

Structure-based characterization and optimization of novel hydrophobic binding interactions in a series of pyrrolidine influenza neuraminidase inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

4 ACETAMIDO 5 AMINO 3 (1 ETHYLPROPOXY) 1 CYCLOHEXENE 1 CARBOXYLIC ACID; AMINE; ESTER; OSELTAMIVIR; PERAMIVIR; PRODRUG; SIALIDASE; SIALIDASE INHIBITOR; UNCLASSIFIED DRUG; ZANAMIVIR;

EID: 20444378860     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm049276y     Document Type: Article
Times cited : (64)

References (35)
  • 2
    • 0037095588 scopus 로고    scopus 로고
    • Pandemic planning
    • Snacken, R. Pandemic planning. Vaccine 2002, 20, S88-S90.
    • (2002) Vaccine , vol.20
    • Snacken, R.1
  • 4
    • 0036831479 scopus 로고    scopus 로고
    • Influenza. Past, present, and future
    • Regan, S. F.; Fowler, C. Influenza. Past, present, and future. J. Gerontol. Nursing 2002, 28, 30-37.
    • (2002) J. Gerontol. Nursing , vol.28 , pp. 30-37
    • Regan, S.F.1    Fowler, C.2
  • 5
    • 0037273046 scopus 로고    scopus 로고
    • Neuraminidase inhibitors in pediatric patients: Potential place in influenza therapy
    • Noyola, D. E. Neuraminidase inhibitors in pediatric patients: Potential place in influenza therapy. Pediatr. Drugs 2003, 5, 125-131.
    • (2003) Pediatr. Drugs , vol.5 , pp. 125-131
    • Noyola, D.E.1
  • 6
    • 0036651804 scopus 로고    scopus 로고
    • New millennium antivirals against pandemic and epidemic influenza: The neuraminidase inhibitors
    • Oxford, J. S.; Novelli, P.; Sefton, A.; Lambkin, R. New millennium antivirals against pandemic and epidemic influenza: The neuraminidase inhibitors. Antiviral Chem. Chemother. 2002, 13, 205-217
    • (2002) Antiviral Chem. Chemother. , vol.13 , pp. 205-217
    • Oxford, J.S.1    Novelli, P.2    Sefton, A.3    Lambkin, R.4
  • 7
    • 0027287506 scopus 로고
    • Rational design of potent sialidase-based inhibitors of influenza virus replication
    • von Itzstein, M.; Wu, W. Y.; Kok, G. B.; Pegg, M. S.; Dyason, J. C. et al. Rational design of potent sialidase-based inhibitors of influenza virus replication [comment]. Nature 1993, 363, 418-423.
    • (1993) Nature , vol.363 , pp. 418-423
    • Von Itzstein, M.1    Wu, W.Y.2    Kok, G.B.3    Pegg, M.S.4    Dyason, J.C.5
  • 8
    • 0030875781 scopus 로고    scopus 로고
    • 'Flu' and structure-based drug design
    • Wade, R. C. 'Flu' and structure-based drug design. Structure 1997, 5, 1139-1145.
    • (1997) Structure , vol.5 , pp. 1139-1145
    • Wade, R.C.1
  • 9
    • 0037938782 scopus 로고    scopus 로고
    • Effectiveness of neuraminidase inhibitors in treatment and prevention of influenza A and B: Systematic review and meta-analyses of randomised controlled trials
    • Cooper, N. J.; Button, A. J.; Abrams, K. R.; Wailoo, A.; Turner, D., et al. Effectiveness of neuraminidase inhibitors in treatment and prevention of influenza A and B: Systematic review and meta-analyses of randomised controlled trials. Br. Med. J. 2003, 326, 1235.
    • (2003) Br. Med. J. , vol.326 , pp. 1235
    • Cooper, N.J.1    Button, A.J.2    Abrams, K.R.3    Wailoo, A.4    Turner, D.5
  • 10
    • 0042662780 scopus 로고    scopus 로고
    • Review of the use of neuraminidase inhibitors for prophylaxis of influenza
    • Kirkbride, H. A.; Watson, J. Review of the use of neuraminidase inhibitors for prophylaxis of influenza [review]. Communicable Dis. Public Health 6 (2), 123-7.
    • Communicable Dis. Public Health , vol.6 , Issue.2 , pp. 123-127
    • Kirkbride, H.A.1    Watson, J.2
  • 11
    • 0037279614 scopus 로고    scopus 로고
    • Treatment of epidemic and pandemic influenza with neuraminidase and M2 proton channel inhibitors
    • Oxford, J. S.; Bossuyt, S.; Balasingam, S.; Mann., A.; Novelli, P.; Lambkin, R. Treatment of epidemic and pandemic influenza with neuraminidase and M2 proton channel inhibitors. Clin. Microbiol. 2003, 9, 1-14.
    • (2003) Clin. Microbiol. , vol.9 , pp. 1-14
    • Oxford, J.S.1    Bossuyt, S.2    Balasingam, S.3    Mann, A.4    Novelli, P.5    Lambkin, R.6
  • 12
    • 0034536708 scopus 로고    scopus 로고
    • RWJ-270201 BioCryst Pharmaceuticals/Johnson & Johnson
    • Barnard, D. L. RWJ-270201 BioCryst Pharmaceuticals/Johnson & Johnson. Curr. Opin. Invest. Drugs 2000, 1, 421-424.
    • (2000) Curr. Opin. Invest. Drugs , vol.1 , pp. 421-424
    • Barnard, D.L.1
  • 13
    • 0035969782 scopus 로고    scopus 로고
    • RWJ-270201 (BCX-1812): A novel neuraminidase inhibitor for influenza
    • Young, D.; Fowler, C.; Bush, K. RWJ-270201 (BCX-1812): A novel neuraminidase inhibitor for influenza. Philos. Trans. R. Soc. London Ser. B 2001, 356, 1905-1913.
    • (2001) Philos. Trans. R. Soc. London Ser. B , vol.356 , pp. 1905-1913
    • Young, D.1    Fowler, C.2    Bush, K.3
  • 14
    • 0032796258 scopus 로고    scopus 로고
    • Neuraminidase inhibitors as anti-influenza virus agents
    • Kim, C. U.; Chen, X.; Mendel, D. B. Neuraminidase inhibitors as anti-influenza virus agents. Antiviral Chem. Chemother. 1999, 10, 141-154.
    • (1999) Antiviral Chem. Chemother. , vol.10 , pp. 141-154
    • Kim, C.U.1    Chen, X.2    Mendel, D.B.3
  • 15
    • 0034084227 scopus 로고    scopus 로고
    • Discovery and development of GS 4104 (oseltamivir): An orally active influenza neuraminidase inhibitor
    • Lew, W.; Chen, X.; Kim, C. U. Discovery and development of GS 4104 (oseltamivir): An orally active influenza neuraminidase inhibitor. Curr. Med. Chem. 2000, 7, 663-672.
    • (2000) Curr. Med. Chem. , vol.7 , pp. 663-672
    • Lew, W.1    Chen, X.2    Kim, C.U.3
  • 16
    • 0034699492 scopus 로고    scopus 로고
    • BCX-1812 (RWJ-270201): Discovery of a novel, highly potent, orally active, and selective influenza neuraminidase inhibitor through structure-based drug design
    • Babu, Y. S.; Chand, P.; Bantia, S.; Kotian, P.; Dehghani, A., et al. BCX-1812 (RWJ-270201): Discovery of a novel, highly potent, orally active, and selective influenza neuraminidase inhibitor through structure-based drug design. J. Med. Chem. 2000, 43, 3482-3486.
    • (2000) J. Med. Chem. , vol.43 , pp. 3482-3486
    • Babu, Y.S.1    Chand, P.2    Bantia, S.3    Kotian, P.4    Dehghani, A.5
  • 17
    • 0028500713 scopus 로고
    • Synthesis of transition-state analogues as potential inhibitors of sialidase from Influenza virus
    • Driguez, P. A.; Barrere, B.; Quash, G.; Doutheau, A. Synthesis of transition-state analogues as potential inhibitors of sialidase from Influenza virus. Carbohydr. Res. 1994, 262, 297-310.
    • (1994) Carbohydr. Res. , vol.262 , pp. 297-310
    • Driguez, P.A.1    Barrere, B.2    Quash, G.3    Doutheau, A.4
  • 18
    • 0033897803 scopus 로고    scopus 로고
    • Resistance of influenza viruses to neuraminidase inhibitors - A review
    • McKimm-Breschkin, J. L. Resistance of influenza viruses to neuraminidase inhibitors - A review. Antiviral Res. 2000, 47, 1-17.
    • (2000) Antiviral Res. , vol.47 , pp. 1-17
    • McKimm-Breschkin, J.L.1
  • 19
    • 0036027825 scopus 로고    scopus 로고
    • Detection of influenza virus resistance to neuraminidase inhibitors by an enzyme inhibition assay
    • Gubareva, L. V.; Webster, R. G.; Hayden, F. G. Detection of influenza virus resistance to neuraminidase inhibitors by an enzyme inhibition assay. Antiviral Res. 2002, 53, 47-61.
    • (2002) Antiviral Res. , vol.53 , pp. 47-61
    • Gubareva, L.V.1    Webster, R.G.2    Hayden, F.G.3
  • 20
    • 0034773748 scopus 로고    scopus 로고
    • Characterization of an influenza A (H3N2) virus resistant to the cyclopentane neuraminidase inhibitor RWJ-270201
    • Smee, D. F.; Sidwell, R. W.; Morrison, A. C.; Bailey, K. W.; Baum, E. Z.; et al. Characterization of an influenza A (H3N2) virus resistant to the cyclopentane neuraminidase inhibitor RWJ-270201. Antiviral Res. 2001, 52, 251-259.
    • (2001) Antiviral Res. , vol.52 , pp. 251-259
    • Smee, D.F.1    Sidwell, R.W.2    Morrison, A.C.3    Bailey, K.W.4    Baum, E.Z.5
  • 21
    • 0037469141 scopus 로고    scopus 로고
    • Influenza neuraminidase inhibitors: Structure-based design of a novel inhibitor series
    • Stoll, V.; Stewart, K. D.; Maring, C. J.; Muchmore, S.; Giranda, V. et al. Influenza neuraminidase inhibitors: Structure-based design of a novel inhibitor series. Biochemistry 2003, 42, 718-727.
    • (2003) Biochemistry , vol.42 , pp. 718-727
    • Stoll, V.1    Stewart, K.D.2    Maring, C.J.3    Muchmore, S.4    Giranda, V.5
  • 22
    • 0037016983 scopus 로고    scopus 로고
    • 1,3-Dipolar cycloaddition reactions of ester-stabilized azomethine ylides with acrolein: A one-pot regio- and stereoselective synthesis of N-substituted 4-formyl-5-vinyl proline carboxylates
    • Gu, Y. G.; Xu, Y.; Krueger, A. C.; Madigan, D.; Sham, H., L. 1,3-Dipolar cycloaddition reactions of ester-stabilized azomethine ylides with acrolein: A one-pot regio- and stereoselective synthesis of N-substituted 4-formyl-5-vinyl proline carboxylates. Tetrahedron Lett. 2002, 43, 955-957.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 955-957
    • Gu, Y.G.1    Xu, Y.2    Krueger, A.C.3    Madigan, D.4    Sham, H.5
  • 23
    • 0029003145 scopus 로고
    • Three-dimensional structure of the complex of 4-guanidino-Neu5Ac2en and influenza virus neuraminidase
    • Varghese, J. N.; Epa, V. C.; Colman, P. M. Three-dimensional structure of the complex of 4-guanidino-Neu5Ac2en and influenza virus neuraminidase. Protein Sci. 1995, 4, 1081-1087.
    • (1995) Protein Sci. , vol.4 , pp. 1081-1087
    • Varghese, J.N.1    Epa, V.C.2    Colman, P.M.3
  • 25
    • 20444430612 scopus 로고    scopus 로고
    • Pitfalls in the biochemical evaluation of influenza neuraminidase inhibitors
    • Kati, W. M.; Saldivar, A.; Maring, C. J.; Madigan, D. L.; Gu, Y.-G. et al. Pitfalls in the Biochemical Evaluation of Influenza Neuraminidase Inhibitors. Antiviral Res. 2000, 46, A59.
    • (2000) Antiviral Res. , vol.46
    • Kati, W.M.1    Saldivar, A.2    Maring, C.J.3    Madigan, D.L.4    Gu, Y.-G.5
  • 27
    • 0035080983 scopus 로고    scopus 로고
    • Comparison of the anti-influenza virus activity of RWJ-270201 with those of oseltamivir and zanamivir
    • Bantia, S.; Parker, C. D.; Ananth, S. L.; Horn, L. L.; Andries, K., et al. Comparison of the anti-influenza virus activity of RWJ-270201 with those of oseltamivir and zanamivir. Antimicrob. Agents Chemother. 2001, 45, 1162-1167.
    • (2001) Antimicrob. Agents Chemother. , vol.45 , pp. 1162-1167
    • Bantia, S.1    Parker, C.D.2    Ananth, S.L.3    Horn, L.L.4    Andries, K.5
  • 28
    • 0035190544 scopus 로고    scopus 로고
    • Comparison of the activities of zanamivir, oseltamivir, and RWJ-270201 against clinical isolates of influenza virus and neuraminidase inhibitor-resistant variants
    • Gubareva, L. V.; Webster, R. G.; Hayden, F. G. Comparison of the activities of zanamivir, oseltamivir, and RWJ-270201 against clinical isolates of influenza virus and neuraminidase inhibitor-resistant variants. Antimicrob. Agents Chemother. 2001, 45, 3403-3408.
    • (2001) Antimicrob. Agents Chemother. , vol.45 , pp. 3403-3408
    • Gubareva, L.V.1    Webster, R.G.2    Hayden, F.G.3
  • 30
    • 0036210594 scopus 로고    scopus 로고
    • In vitro characterization of A-315675, a highly potent inhibitor of A and B strahl influenza virus neuraminidases and influenza virus replication
    • Kati, W. M.; Montgomery, D.; Carrick, R.; Gubareva, L.; Maring, C., et al. In vitro characterization of A-315675, a highly potent inhibitor of A and B strahl influenza virus neuraminidases and influenza virus replication. Antimicrob. Agents Chemother. 2002, 46, 1014-1021.
    • (2002) Antimicrob. Agents Chemother. , vol.46 , pp. 1014-1021
    • Kati, W.M.1    Montgomery, D.2    Carrick, R.3    Gubareva, L.4    Maring, C.5
  • 31
    • 0036091649 scopus 로고    scopus 로고
    • In vitro selection and characterization of influenza A (A/N9) virus variants resistant to a novel neuraminidase inhibitor, A-315675
    • Molla, A.; Kati, W.; Carrick, R.; Steffy, K.; Shi, Y., et al. In Vitro Selection and Characterization of Influenza A (A/N9) Virus Variants Resistant to a Novel Neuraminidase Inhibitor, A-315675. J. Virol. 2002, 76, 5380-5386.
    • (2002) J. Virol. , vol.76 , pp. 5380-5386
    • Molla, A.1    Kati, W.2    Carrick, R.3    Steffy, K.4    Shi, Y.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.