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Volumn 44, Issue 52, 2003, Pages 9259-9262

Noviose mimics of the coumarin inhibitors of gyrase B

Author keywords

Antibiotics; Coumarin; Noviose; Structure activity

Indexed keywords

5',5' DIMETHYLCYCLOHEXANE; ANTIBIOTIC AGENT; COUMARIN DERIVATIVE; GYRASE INHIBITOR; PIPERIDINE; UNCLASSIFIED DRUG;

EID: 0344441317     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.076     Document Type: Article
Times cited : (21)

References (20)
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    • Klich, M.; Laurin, P.; Musicki, B.; Schio, L. WO 9747634, 1998; Chem. Abstr. 1998, 128, 75634 Chartreaux, F.; Klich, M.; Schio, L. EP 894805, 1999; Chem. Abstr. 1999, 130, 125344.
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    • Klich, M.1    Laurin, P.2    Musicki, B.3    Schio, L.4
  • 2
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    • EP 894805
    • Klich, M.; Laurin, P.; Musicki, B.; Schio, L. WO 9747634, 1998; Chem. Abstr. 1998, 128, 75634 Chartreaux, F.; Klich, M.; Schio, L. EP 894805, 1999; Chem. Abstr. 1999, 130, 125344.
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    • Chartreaux, F.1    Klich, M.2    Schio, L.3
  • 6
    • 0026015132 scopus 로고
    • For a review of DNA gyrase structure and function, see: (a) Reece, R. J. ; Maxwell, A. Crit. Rev. Biochem. Mol. Biol. 1991, 26, 335-375; (b) Levine, C.; Hiasa, H.; Marians, K. J. Biochim. Biophys. Acta 1998, 1400, 29-43; (c) Berger, J. M. Biochim. Biophys. Acta 1998, 1400, 3-18; (d) Maxwell, A. Biochem. Soc. Trans. 1999, 27, 48-53.
    • (1991) Crit. Rev. Biochem. Mol. Biol. , vol.26 , pp. 335-375
    • Reece, R.J.1    Maxwell, A.2
  • 7
    • 0032189275 scopus 로고    scopus 로고
    • For a review of DNA gyrase structure and function, see: (a) Reece, R. J. ; Maxwell, A. Crit. Rev. Biochem. Mol. Biol. 1991, 26, 335-375; (b) Levine, C.; Hiasa, H.; Marians, K. J. Biochim. Biophys. Acta 1998, 1400, 29-43; (c) Berger, J. M. Biochim. Biophys. Acta 1998, 1400, 3-18; (d) Maxwell, A. Biochem. Soc. Trans. 1999, 27, 48-53.
    • (1998) J. Biochim. Biophys. Acta , vol.1400 , pp. 29-43
    • Levine, C.1    Hiasa, H.2    Marians, K.3
  • 8
    • 0032189653 scopus 로고    scopus 로고
    • For a review of DNA gyrase structure and function, see: (a) Reece, R. J. ; Maxwell, A. Crit. Rev. Biochem. Mol. Biol. 1991, 26, 335-375; (b) Levine, C.; Hiasa, H.; Marians, K. J. Biochim. Biophys. Acta 1998, 1400, 29-43; (c) Berger, J. M. Biochim. Biophys. Acta 1998, 1400, 3-18; (d) Maxwell, A. Biochem. Soc. Trans. 1999, 27, 48-53.
    • (1998) Biochim. Biophys. Acta , vol.1400 , pp. 3-18
    • Berger, J.M.1
  • 9
    • 0032973659 scopus 로고    scopus 로고
    • For a review of DNA gyrase structure and function, see: (a) Reece, R. J. ; Maxwell, A. Crit. Rev. Biochem. Mol. Biol. 1991, 26, 335-375; (b) Levine, C.; Hiasa, H.; Marians, K. J. Biochim. Biophys. Acta 1998, 1400, 29-43; (c) Berger, J. M. Biochim. Biophys. Acta 1998, 1400, 3-18; (d) Maxwell, A. Biochem. Soc. Trans. 1999, 27, 48-53.
    • (1999) Biochem. Soc. Trans. , vol.27 , pp. 48-53
    • Maxwell, A.1
  • 10
    • 33748588737 scopus 로고    scopus 로고
    • In this publication, the authors used a somewhat similar approach based on a series of spiro 5′,5′-dimethylcyclohexane acetals bearing different biphenyl systems as a coumarin replacement.
    • Bell, W.; Block, M. H.; Cook, C.; Grant, A. J.; Timms, D. J. Chem. Soc., Perkin Trans. 1 1997, 2789-2801. In this publication, the authors used a somewhat similar approach based on a series of spiro 5′,5′- dimethylcyclohexane acetals bearing different biphenyl systems as a coumarin replacement.
    • (1997) J. Chem. Soc., Perkin Trans. 1 , pp. 2789-2801
    • Bell, W.1    Block, M.H.2    Cook, C.3    Grant, A.J.4    Timms, D.5
  • 11
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    • The thermodynamic equilibrium between the α-methyl coumeroside and β-methyl coumeroside that favours the α-anomer is largely determined by the anomeric effect. See: Wick A.E., Blount J.F., Leimgruber W. Tetrahedron. 32:1976;2057-2065.
    • (1976) Tetrahedron , vol.32 , pp. 2057-2065
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  • 12
    • 0001772690 scopus 로고
    • Lipkowitz, K. B.; Boyd, D. B., Eds.; Approaches to Empirical Force Fields; VCH: New York, Chapter 4.
    • The relative energies of the conformers 3-6 were minimized with the Insight/Discoverer software applying the CVFF forcefield and conjugate gradient method. See: Dinur, U.; Hagler, A. T. In Reviews of Computational Chemistry; Lipkowitz, K. B.; Boyd, D. B., Eds.; Approaches to Empirical Force Fields; VCH: New York, 1991; Vol 2, Chapter 4.
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    • Dinur, U.1    Hagler, A.T.2
  • 20
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    • note
    • Recently, we accomplished the synthesis of a 4′-desmethoxy analogue of RU79115 and the results of its biological activity confirmed the importance of this group in conferring a good inhibitory potency to the analogues. These findings will be published in due course.


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