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Volumn 132, Issue 32, 2010, Pages 11223-11233

Conformations, conformational preferences, and conformational exchange of N′-substituted N -acylguanidines: Intermolecular interactions hold the key

Author keywords

[No Author keywords available]

Indexed keywords

ACCEPTOR PROPERTIES; ALKYL SUBSTITUENT; AS-LIGANDS; BIOISOSTERES; BIOLOGICAL TARGETS; BIOLOGICALLY ACTIVE COMPOUNDS; BISPHOSPHONATES; CONFORMATIONAL EXCHANGE; CONFORMATIONAL PREFERENCES; EXCHANGE RATES; G PROTEIN COUPLED RECEPTORS; INTERMOLECULAR INTERACTIONS; LIGAND-RECEPTOR INTERACTIONS; MECHANISM OF ACTION; MICROSOLVATION; MOLECULAR BASIS; MOLECULAR LEVELS; PHARMACOKINETICS AND PHARMACODYNAMICS; PROTONATED; RATIONAL DESIGN; SOLVENT MOLECULES; STRUCTURAL FEATURE;

EID: 77955561472     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja103756y     Document Type: Article
Times cited : (19)

References (51)
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    • CCDC 686506 contains the supplementary crystallographic data for the compound shown in Figure 2 (available free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif).
  • 40
    • 77956378844 scopus 로고    scopus 로고
    • in press (published online Jul 18, doi: 10.1002/mrc.2648).
    • Kleinmaier, R. and Gschwind, R. M. Magn. Reson. Chem. 2010, in press (published online Jul 18, doi: 10.1002/mrc.2648).
    • (2010) Magn. Reson. Chem.
    • Kleinmaier, R.1    Gschwind, R.M.2
  • 41
    • 77955571489 scopus 로고    scopus 로고
    • + for 4b •Boc-Asp-OBn and 4b •TFA showed that the broadening of the signals in Figure 7 is dominated by the exchange rate and that the different chemical shift dispersions affect the exchange rates only marginally. According to these simulations, at 210 K the rate constant for the conformational exchange is increased by a factor of 30 when going from the strong H-bond acceptor Boc-Asp-OBn to the much weaker TFA as anions.
    • + for 4b •Boc-Asp-OBn and 4b •TFA showed that the broadening of the signals in Figure 7 is dominated by the exchange rate and that the different chemical shift dispersions affect the exchange rates only marginally. According to these simulations, at 210 K the rate constant for the conformational exchange is increased by a factor of 30 when going from the strong H-bond acceptor Boc-Asp-OBn to the much weaker TFA as anions.
  • 43
    • 77955577725 scopus 로고    scopus 로고
    • DOSY spectra of 4a •DCA at 300 K and 4d •DCA at 270 K showed identical diffusion coefficients for the anion and the cation. Due to the fast exchange of the NH protons in acylguanidines, the positions of the anions could not be verified by NOESY cross peaks.
    • DOSY spectra of 4a •DCA at 300 K and 4d •DCA at 270 K showed identical diffusion coefficients for the anion and the cation. Due to the fast exchange of the NH protons in acylguanidines, the positions of the anions could not be verified by NOESY cross peaks.
  • 44
    • 77955571027 scopus 로고    scopus 로고
    • 13C chemical shifts of the carboxylic carbons of alkali salts of the acids used here (see Supporting Information).
    • 13C chemical shifts of the carboxylic carbons of alkali salts of the acids used here (see Supporting Information).
  • 48
    • 77955585086 scopus 로고
    • Wavefunction, Inc.: Irvine, CA.
    • Spartan; Wavefunction, Inc.: Irvine, CA, 1991-2007.
    • (1991) Spartan


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