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Spectroscopy Letters
An International Journal for Rapid Communication
Volume 26, 1993 - Issue 4
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Original Articles

NMR Studies of Drugs. Use of Lanthanide Shift Reagents in Polar Solvent with Thalidomide

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Pages 597-619 | Received 20 Oct 1992, Accepted 27 Nov 1992, Published online: 17 Feb 2007

References

  • Blakeslee , S. April 10 1990 . Scorned thalidomide researched anew , April 10 , C3 The New York Times .
  • Melmon , K. L. , Gilman , A. G. and Mayer , S. E. 1980 . “ Principles of therapeutics ” . In Goodman and Gilman's The Pharmacological Basis of Therapeutics , 6th ed , Edited by: Gilman , A. G. , Goodman , L. S. and Gilman , A. 40 – 55 . New York, Toronto, London : Macmillan .
  • Mandell , G. L. 1980 . “ Sande Antimicrobial M. A. agents. Drugs used in the chemotherapy of tuberculosis and leprosy ” . In Goodman and Gilman's The Pharmacological Basis of Therapeutics , 6th ed. , Edited by: Gilman , A. G. , Goodman , L. S. and Gilman , A. 1200 – 1221 . New York, Toronto, London : Macmillan . and references cited therein
  • Vogelsang , G. B. , Farmer , E. R. , Hess , A. D. , Altamonte , V. , Beschorner , W. E. , Jabs , D. A. , Corio , R. L. , Levin , L. S. , Colvin , O. M. , Wingard , J. R. and Santos , G. W. 1992 . Thalidomide for the treatment of chronic graft-versus-host disease. . N. Engl. J. Med. , 326 ( 16 ) : 1055 – 1058 . and references cited therein
  • Field , E. O. , Gibbs , J. E. , Tucker , D. F. and Hellmann , K. 1966 . Effect of thalidomide on the graft versus host reaction. . Nature , 211 ( 5055 ) : 1308 – 1310 .
  • Shealy , Y. F. , Opliger , C. E. and Montgomery , J. A. 1968 . Synthesis of D- and L-thalidomide and related studies. . J. Pharm. Sci. , 57 ( 5 ) : 757 – 764 .
  • Shealy , Y. F. , Opliger , C. E. and Montgomery , J. A. 1965 . D- and L-thalidomide. . Chem. Ind. (London) , 24 : 1030 – 1031 .
  • Casini , G. and Ferappi , M. 1964 . Preparation of one optical antipode of 2-phthalimidoglutarimide. . Farmaco (Pavia) Ed. Sci. , 19 ( 6 ) : 563 – 565 .
  • Fabro , S. , Smith , R. L. and Williams , R. T. 1967 . Toxicity and teratogenicity of optical isomers of thalidomide. . Nature , 215 ( 5098 ) : 296
  • Borghi , S. , Botre , C. , Cicconetti , P. and Mazzeo , P. 1966 . Interaction of d- and 1-2-phthalimidoglutarimide with DNA and RNA. Farmaco Ed. Sci. . 21 ( 10 ) : 723 – 727 .
  • Ockenfels , H. and Köhler , F. 1970 . The L-isomer as the teratogenic principle of N-phthalyl-D L-glutamic acid. . Experientia , 26 ( 11 ) : 1236 – 1237 .
  • Ockenfels , H. , Köhler , F. and Meise , W. 1976 . Teratogenic effect and stereospecificity of a thalidomide metabolite. . Pharmazie , 31 ( 7 ) : 492 – 493 .
  • Ockenfels , H. , Köhler , F. and Meise , W. 1977 . Teratogenic effect of N-phthaloyl-L-aspartic acid on the mouse. . Arzneim. -Forsch./Drug Res. , 27 ( 1 ) : 126 – 128 .
  • Blaschke , G. , Kraft , H. P. , Fickentscher , K. and Köhler , F. 1979 . Chromatographic separation of racemic thalidomide and teratogenic activity of its enantiomers. . Arzneim.-Forsch./Drug Res. , 29 (II) (10) : 1640 – 1642 .
  • DeCamp , W. 1989 . The FDA perspective on the development of stereoisomers. . Chirality , 1 ( 1 ) : 2 – 6 .
  • Soudijn , W. 1983 . “ Advantages and disadvantages in the application of bioactive racemates or specific isomers as drugs ” . In Stereochemistry and Biological Activity of Drugs , Edited by: Ariëns , E. J. , Soudijn , W. and Timmermans , P. B.M.W.M. 89 – 102 . Oxford, London, Edinburgh, Boston, Melbourne : Blackwell Scientific .
  • Brown , J. R. 1990 . Stereochemical principles. . Drug Information J. , 24 : 117 – 120 .
  • Blaschke , G. , Kraft , H. P. and Markgraf , H. 1980 . Chromatographic resolutions of racemates. X. Optical resolution of thalidomide and other glutarimide derivatives. . Chem. Ber. , 113 ( 6 ) : 2318 – 2322 .
  • Blaschke , G. 1980 . Chromatographic resolution of racemates. . Angew. Chem. Int. Ed. Engl. , 19 ( 1 ) : 13 – 24 .
  • Blaschke , G. , Bröker , W. and Fraenkel , W. 1986 . Chromatographic separation of racemates. 15. HPLC separation of enantiomers on silica gel-bound optically active polyamides. . Angew. Chem. Int. Ed. Engl. , 25 ( 9 ) : 830 – 831 .
  • Blaschke , G. 1986 . Chromatographic resolution of chiral drugs on polyamides and cellulose triacetate. . J. Liq. Chromatogr. , 9 (2&3) : 341 – 368 .
  • Kinkel , J. N. , Fraenkel , W. and Blaschke , G. 1987 . The separation of enantiomers on polymer coated chiral silica gels. . Kontakte (Darmstadt) , 1 : 3 – 14 .
  • Rosini , C. , Bertucci , C. , Pini , D. , Altemura , P. and Salvadori , P. 1987 . Chiral stationary phases based on Cinchona alkaloids for the HPLC resolution of racemates. . Chromatographia , 24 : 671 – 676 .
  • Aboul-Enein , H. Y. and Islam , M. R. 1991 . Direct HPLC separation of thalidomide enantiomers using cellulose tris-4-methylphenyl benzoate chiral stationary phase. . J. Liq. Chromatogr. , 14 ( 4 ) : 667 – 673 .
  • Cockerill , A. F. , Davies , G. L. O. , Harden , R. C. and Rackham , D. M. 1973 . Lanthanide shift reagents for nuclear magnetic resonance spectroscopy. . Chem. Rev. , 73 ( 6 ) : 553 – 588 .
  • Morrill , T. C. , ed. 1986 . Lanthanide Shift Reagents in Stereochemical Analysis , New York : VCH .
  • Wenzel , T. J. 1987 . NMR Shift Reagents , New York : VCH .
  • Schurig , V. 1985 . Current methods for determination of enantiomeric compositions (Part 2): NMR spectroscopy with chiral lanthanide shift reagents. Kontakte (Darmstadt) . : 22 – 36 .
  • Eberhart , S. and Rothchild , R. 1983 . Optical purity determination and proton NMR spectral simplification with lanthanide shift reagents. Glutethimide, 3-ethyl-3-phenyl-2, 6-piperidinedione. . Appl. Spectrosc. , 37 ( 3 ) : 292 – 296 .
  • Hatzis , A. , Rothchild , R. and Simons , P. 1987 . 1H NMR spectral simplification with achiral and chiral lanthanide shift reagents. V. Aminoglutethimide, 3-(4-aminophenyl)-3-ethyl-2, 6-piperidinedione. . Anal. Chim. Acta , 194 : 211 – 219 .
  • Goering , H. L. , Eikenberry , J. N. , Koermer , G. S. and Lattimer , C. J. 1974 . Direct determination of enantiomeric compositions with optically active nuclear magnetic resonance lanthanide shift reagents. . J. Am. Chem. Soc. , 96 ( 5 ) : 1493 – 1501 .
  • McCreary , M. D. , Lewis , D. W. , Wernick , D. L. and Whitesides , G. M. 1974 . The determination of enantiomeric purity using chiral lanthanide shift reagents. . J. Am. Chem. Soc. , 96 ( 4 ) : 1038 – 1054 .
  • Sweeting , L. M. , Crans , D. C. and Whitesides , G. M. 1987 . Determination of enantiomeric purity of polar substrates with chiral lanthanide NMR shift reagents in polar solvents. . J. Org. Chem. , 52 ( 11 ) : 2273 – 2276 . and reference 4 cited therein
  • Rothchild , R. , Braddock , S. , Traviglia , S. and Venkatasubban , K. S. 1992 . NMR studies of drugs. 5-Methyl-5-phenylhydantoin. Applications of lanthanide shift reagents in polar solvents to a non-chelating substrate. . Submitted to Spectrosc. Lett. ,

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