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Volumn 74, Issue 1, 2009, Pages 197-205

Six-membered ring phosphates and phosphonates as model compounds for cyclic phosphate prodrugs: Is the anomeric effect involved in the selective and spontaneous cleavage of cyclic phosphate prodrugs?

Author keywords

[No Author keywords available]

Indexed keywords

ANOMERIC EFFECTS; ANTITUMOR AGENTS; ARYL GROUPS; AS MODELS; BIOLOGICAL ACTIVITIES; BOND CLEAVAGES; CHEMICAL EQUATIONS; CYCLIC PHOSPHATES; ELECTRONIC NATURES; HETEROCYCLIC RINGS; LIVER DISEASES; MODE OF ACTIONS; PHOSPHONATES; PRODRUGS; PYRIDYL GROUPS; SIMPLE MODELS;

EID: 58149296142     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8017473     Document Type: Article
Times cited : (18)

References (48)
  • 3
    • 58149308918 scopus 로고    scopus 로고
    • Bentrude, W. G.; Setzer, W. N. Stereospecificity in 31P-Element Coupling: Proton-Phosphorus Coupling In Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis; Verkade, J. G., Quin, L. D., Eds; VCH: Weinheim, 1987.
    • Bentrude, W. G.; Setzer, W. N. Stereospecificity in 31P-Element Coupling: Proton-Phosphorus Coupling In Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis; Verkade, J. G., Quin, L. D., Eds; VCH: Weinheim, 1987.
  • 4
    • 0038401589 scopus 로고
    • Steric and Stereoelectronic Effects in 1,3,2-Dioxaphosphorinanes
    • Juaristi, E, Ed, VCH: New York
    • Bentrude, W. G. Steric and Stereoelectronic Effects in 1,3,2-Dioxaphosphorinanes. In Methods in Stereochemical Analysis; Juaristi, E., Ed.; VCH: New York, 1995.
    • (1995) Methods in Stereochemical Analysis
    • Bentrude, W.G.1
  • 19
    • 58149308920 scopus 로고    scopus 로고
    • Erion suggested that the prodrug cleavage proceeds via an initial oxidation at C4 (see ref 12, and Hu suggested that an electron-donating group in the aromatic ring facilitates the prodrug cleavage see ref 16, however, no fundamental explanations for the selective prodrug cleavage were given
    • Erion suggested that the prodrug cleavage proceeds via an initial oxidation at C4 (see ref 12), and Hu suggested that an electron-donating group in the aromatic ring facilitates the prodrug cleavage (see ref 16), however, no fundamental explanations for the selective prodrug cleavage were given.
  • 26
    • 58149292341 scopus 로고    scopus 로고
    • 3,2-dioxaphosphorinane rings into a chair conformation that orients the phenyl group equatorially
    • The phenyl group placed at the C4 position has been used to lock the spontaneous chair-chair equilibrium of 1
    • The phenyl group placed at the C4 position has been used to lock the spontaneous chair-chair equilibrium of 1,3,2-dioxaphosphorinane rings into a chair conformation that orients the phenyl group equatorially. See refs 27-31.
    • See refs , pp. 27-31
  • 32
    • 58149280915 scopus 로고    scopus 로고
    • It is important to mention that in this work, the C4 position of the 1,3,2-dioxaphosphorinane nomenclature corresponds to the C5′ position of xylofuranose nomenclature.
    • It is important to mention that in this work, the C4 position of the 1,3,2-dioxaphosphorinane nomenclature corresponds to the C5′ position of xylofuranose nomenclature.
  • 33
    • 58149306454 scopus 로고    scopus 로고
    • Crystallographic data were deposited in Cambridge Crystallographic Data Base (CCDC-660542).
    • Crystallographic data were deposited in Cambridge Crystallographic Data Base (CCDC-660542).
  • 37
    • 58149294112 scopus 로고    scopus 로고
    • Crystallographic data were deposited in Cambridge Crystallographic Data Base (CCDC-660543).
    • Crystallographic data were deposited in Cambridge Crystallographic Data Base (CCDC-660543).
  • 38
    • 58149314653 scopus 로고    scopus 로고
    • 31P-NMR after purification by column chromatography.
    • 31P-NMR after purification by column chromatography.
  • 39
    • 58149303369 scopus 로고    scopus 로고
    • It is well documented that cyclic phosphates undergo hydrolysis in protic media or basic conditions see refs 7 and 34, however, the cyclic phosphates 4d, 6d, and 7d showed to be resistant to hydrolysis in methanol
    • It is well documented that cyclic phosphates undergo hydrolysis in protic media or basic conditions (see refs 7 and 34), however, the cyclic phosphates 4d, 6d, and 7d showed to be resistant to hydrolysis in methanol.
  • 44
    • 58149316720 scopus 로고    scopus 로고
    • Fully spectroscopic characterization is provided in the Supporting Information
    • Fully spectroscopic characterization is provided in the Supporting Information.
  • 47
    • 58149277827 scopus 로고    scopus 로고
    • Crystallographic data were deposited in Cambridge Crystallographic Data Base (CCDC-687297).
    • Crystallographic data were deposited in Cambridge Crystallographic Data Base (CCDC-687297).
  • 48
    • 58149300319 scopus 로고    scopus 로고
    • First, phosphorylation, then spontaneous conversion (in situ), and finally removal of the phosphate group with lithium aluminium hydride (LAH): (Chemical Equation Presented)
    • First, phosphorylation, then spontaneous conversion (in situ), and finally removal of the phosphate group with lithium aluminium hydride (LAH): (Chemical Equation Presented)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.