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Volumn 18, Issue 17, 2008, Pages 4774-4778

Synthesis of a C-glucosylated cyclopropylamide and evaluation as a glycogen phosphorylase inhibitor

Author keywords

Acyl migration; C Glycoside; Cyclopropane; Glycogen phosphorylase; Nitrile; Titanium

Indexed keywords

CYCLOPROPYLAMIDE; ENZYME INHIBITOR; GLYCOGEN PHOSPHORYLASE INHIBITOR; TITANIUM; UNCLASSIFIED DRUG;

EID: 50049117181     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.07.098     Document Type: Article
Times cited : (13)

References (38)
  • 13
    • 34250703215 scopus 로고    scopus 로고
    • For a review, see:
    • For a review, see:. Bertus P., and Szymoniak J. Synlett 4 (2007) 1346
    • (2007) Synlett , vol.4 , pp. 1346
    • Bertus, P.1    Szymoniak, J.2
  • 25
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    • note
    • -3; S = 1.118 R/wR = 0.050/0.057 for 1693 parameters and 14319 reflections with I > 2σ(I), R/wR = 0.0571/0.0662 for all 16391 independent reflections measured in the range 1.082°-27.893°. CCDC 686021 contains the supplementary crystallographic data for this molecule. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
  • 26
    • 50049107102 scopus 로고    scopus 로고
    • note
    • 6 calcd 346.1267, found 346.1270.
  • 29
    • 50049106236 scopus 로고    scopus 로고
    • note
    • The intensities were collected at 150 K on a Nonius KappaCCD diffractometer using graphite-monochromated MoKα radiation (λ = 0.71073 Å). The data collection was carried out by the COLLECT program (see Ref. 32) and cell parameters refinement and the data reduction were achieved with DENZO/SCALEPACK (see Ref. 33). The crystal structure was solved by direct methods with SIR97 (see Ref. 34). Because the data were collected with molybdenum radiation, there were no measurable anomalous differences; as a consequence it was admissible to merge Friedel pairs of reflections. All non-hydrogen atoms were refined anisotropically by full-matrix least-squares calculations based on F using CRYSTALS (see Ref. 35). The H atoms were located in a difference Fourier map and repositioned geometrically. The H atoms positions and Uiso were then refined using soft restraints on the bond lengths and angles to regularize their geometry (C-H in the range 0.93-0.98 Å, O-H = 0.82 Å and Uiso(H) = 1.2-1.5 times equiv of the adjacent atom). In the last cycles of the refinement, they were refined using a riding model. The absolute configuration of the structure was obtained with a quick data collection using Cu radiation by examining the Flack parameter. The molecular and crystal structure drawings were prepared with DIAMOND (see Ref. 36).
  • 30
    • 50049088580 scopus 로고    scopus 로고
    • Allen, F. H.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. International Tables for Crystallography, 3rd ed.; Kluwer Academic Publishers: Dordrecht, Netherlands, 2006; Vol. C, Chapter 9.5, pp 790-811.
    • Allen, F. H.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. International Tables for Crystallography, 3rd ed.; Kluwer Academic Publishers: Dordrecht, Netherlands, 2006; Vol. C, Chapter 9.5, pp 790-811.
  • 31
    • 50049093298 scopus 로고    scopus 로고
    • note
    • 50 values were determined in the presence of 4 mM α-d-glucose-1-phosphate, 1 mM AMP, 1% glycogen, and varying concentrations of the inhibitor.
  • 32
    • 50049089545 scopus 로고    scopus 로고
    • Nonius. COLLECT. Nonius BV, D., The Netherlands, 1997-2001.
    • Nonius. COLLECT. Nonius BV, D., The Netherlands, 1997-2001.
  • 33
    • 0031059866 scopus 로고    scopus 로고
    • Otwinowski, Z.; Minor, W.; Carter, C. W., Jr.; Sweet, R. M., Eds.; Academic Press: New York, 1997; Vol. 276, p 307.
    • Otwinowski, Z.; Minor, W.; Carter, C. W., Jr.; Sweet, R. M., Eds.; Academic Press: New York, 1997; Vol. 276, p 307.
  • 36
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    • Brandenburg, K. P. H. DIAMOND. Version 3. Crystal Impact GbR, Postfach 1251, D-53002 Bonn, Germany, 1996.
    • Brandenburg, K. P. H. DIAMOND. Version 3. Crystal Impact GbR, Postfach 1251, D-53002 Bonn, Germany, 1996.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.