메뉴 건너뛰기




Volumn 11, Issue 7, 1999, Pages 529-535

1H NMR studies of drugs with achiral and chiral lanthanide shift reagents: Applications to the anticonvulsant pheneturide

Author keywords

(2 phenylbutyryl) urea; Analysis; Enantiomers; Ethylphenacemide; Eu(FOD)3; Eu(HFC)3; N (aminocarbonyl) ethylbenzeneacetamide; One and two dimensional 1H NMR; Stereoisomers

Indexed keywords

ANTICONVULSIVE AGENT; PHENETURIDE; DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; LANTHANIDE; UREA;

EID: 0032589196     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1999)11:7<529::AID-CHIR3>3.0.CO;2-K     Document Type: Article
Times cited : (7)

References (31)
  • 1
    • 84984088486 scopus 로고
    • Synthesis of the antipodes of pheneturide [α-phenyl-α-ethylacetylurea]. Synthesis of a radioactive (+)-pheneturide labeled with carbon-14
    • Gold-Aubert P. Synthesis of the antipodes of pheneturide [α-phenyl-α-ethylacetylurea]. Synthesis of a radioactive (+)-pheneturide labeled with carbon-14. Helv Chim Acta 1958;41:1512-1515.
    • (1958) Helv Chim Acta , vol.41 , pp. 1512-1515
    • Gold-Aubert, P.1
  • 3
    • 0345050672 scopus 로고
    • The psychotherapeutic effects of the optical antipodes of pheneturide
    • publ.
    • Gold-Aubert P. The psychotherapeutic effects of the optical antipodes of pheneturide. Proc Int Congr Neuro-Pharm, 1st, Rome 1958;313-317 (publ. 1959).
    • (1958) Proc Int Congr Neuro-Pharm, 1st, Rome , pp. 313-317
    • Gold-Aubert, P.1
  • 4
    • 25944437957 scopus 로고
    • α-Ethyl-α-phenylacetylureas for treatment of epilepsy
    • Br 864,536 (Sapos SA) Apr. 6, 1961
    • Gold-Aubert P. α-Ethyl-α-phenylacetylureas for treatment of epilepsy. Br 864,536 (Sapos SA) Apr. 6, 1961; Chem Abstr 1961;55:19156a.
    • (1961) Chem Abstr , vol.55
    • Gold-Aubert, P.1
  • 5
    • 0023661777 scopus 로고
    • Separation of racemic pharmaceuticals by high-performance liquid chromatography on silica gel modified with carbohydrate residues
    • Welder O, Schulze J, König WA. Separation of racemic pharmaceuticals by high-performance liquid chromatography on silica gel modified with carbohydrate residues. J Chromatogr 1987;403:263-270.
    • (1987) J Chromatogr , vol.403 , pp. 263-270
    • Welder, O.1    Schulze, J.2    König, W.A.3
  • 6
    • 0023886225 scopus 로고
    • Separation of the enantiomers of pheneturide in serum by high-performance liquid chromatography
    • Wad N. Separation of the enantiomers of pheneturide in serum by high-performance liquid chromatography. J Liq Chromatogr 1988;11 (5):1107-1116.
    • (1988) J Liq Chromatogr , vol.11 , Issue.5 , pp. 1107-1116
    • Wad, N.1
  • 7
    • 0021190076 scopus 로고
    • Acylureas: A new class of barbitu-rate-like bacterial cytochrome P-450 inducers
    • Ruettinger RT, Kim B-H, Fulco AJ. Acylureas: a new class of barbitu-rate-like bacterial cytochrome P-450 inducers. Biochim Biophys Acta 1984;801(3):372-380.
    • (1984) Biochim Biophys Acta , vol.801 , Issue.3 , pp. 372-380
    • Ruettinger, R.T.1    Kim, B.-H.2    Fulco, A.J.3
  • 8
    • 0010632993 scopus 로고
    • Ethylphenacemide and phenacemide: Conformational similarities to diphenylhydantoin and stereochemical basis of anticonvulsant activity
    • Camerman A, Camerman N. Ethylphenacemide and phenacemide: conformational similarities to diphenylhydantoin and stereochemical basis of anticonvulsant activity. Proc Natl Acad Sci USA. 1977;74(3): 1264-1266.
    • (1977) Proc Natl Acad Sci USA , vol.74 , Issue.3 , pp. 1264-1266
    • Camerman, A.1    Camerman, N.2
  • 9
    • 0022472943 scopus 로고
    • Conformational analysis of clinically active anticonvulsant drugs
    • Wong MG, Defina JA, Andrews PR. Conformational analysis of clinically active anticonvulsant drugs. J Med Chem 1986;29(4):562-572.
    • (1986) J Med Chem , vol.29 , Issue.4 , pp. 562-572
    • Wong, M.G.1    Defina, J.A.2    Andrews, P.R.3
  • 12
    • 0001166795 scopus 로고
    • The determination of enantiomeric purity using chiral lanthanide shift reagents
    • McCreary MD, Lewis DW, Wernick DL, Whitesides GM. The determination of enantiomeric purity using chiral lanthanide shift reagents. J Am Chem Soc 1974;96(4):1038-1054.
    • (1974) J Am Chem Soc , vol.96 , Issue.4 , pp. 1038-1054
    • McCreary, M.D.1    Lewis, D.W.2    Wernick, D.L.3    Whitesides, G.M.4
  • 13
    • 0009832235 scopus 로고
    • Direct determination of enantiomeric compositions with optically active nuclear magnetic resonance lanthanide shift reagents
    • Goering HL, Eikenberry JN, Koermer GS, Lattimer CJ. Direct determination of enantiomeric compositions with optically active nuclear magnetic resonance lanthanide shift reagents. J Am Chem Soc 1974;96(5):1493-1501.
    • (1974) J Am Chem Soc , vol.96 , Issue.5 , pp. 1493-1501
    • Goering, H.L.1    Eikenberry, J.N.2    Koermer, G.S.3    Lattimer, C.J.4
  • 14
    • 0027322825 scopus 로고
    • Chiral discrimination by NMR spectroscopy
    • Casy AF. Chiral discrimination by NMR spectroscopy. Trends in Analytical Spectroscopy 1993;12(4):185-189.
    • (1993) Trends in Analytical Spectroscopy , vol.12 , Issue.4 , pp. 185-189
    • Casy, A.F.1
  • 15
    • 0344188411 scopus 로고
    • The use of nuclear magnetic resonance in the analysis of chiral compounds
    • June 20-24; Gargano (BS): Palazzo Feltrinelli, Univ. degli Studi di Milano
    • Uccello-Barretta G. The use of nuclear magnetic resonance in the analysis of chiral compounds. XIX Summer School "A. Corbella," Seminars in Organic Synthesis; 1994 June 20-24; Gargano (BS): Palazzo Feltrinelli, Univ. degli Studi di Milano. p 53-78.
    • (1994) XIX Summer School "A. Corbella," Seminars in Organic Synthesis , pp. 53-78
    • Uccello-Barretta, G.1
  • 18
    • 0000237404 scopus 로고
    • NMR determination of enantiomeric purity
    • Parker D. NMR determination of enantiomeric purity. Chem Rev 1991;91(7):1441-1457.
    • (1991) Chem Rev , vol.91 , Issue.7 , pp. 1441-1457
    • Parker, D.1
  • 19
    • 0001491583 scopus 로고    scopus 로고
    • - tions in drugs. Use of achiral and chiral lanthanide shift reagents with mecloqualone, an axially chiral drug of abuse. Rigorous definition of spin systems
    • and references cited therein
    • - tions in drugs. Use of achiral and chiral lanthanide shift reagents with mecloqualone, an axially chiral drug of abuse. Rigorous definition of spin systems. Spectrosc Lett 1998;31(2):419-440, and references cited therein.
    • (1998) Spectrosc Lett , vol.31 , Issue.2 , pp. 419-440
    • Benshafrut, R.1    Bynum, K.2    Rothchild, R.3
  • 20
    • 0010128164 scopus 로고    scopus 로고
    • Analysis of hindered rotation and magnetic anisotropy by NMR. Models for drugs and agricultural compounds. The Diels-Alder adduct of phencyclone with N-carbamoylmaleimide
    • Bynum K, Rothchild R. Analysis of hindered rotation and magnetic anisotropy by NMR. Models for drugs and agricultural compounds. The Diels-Alder adduct of phencyclone with N-carbamoylmaleimide. Spectrosc Lett 1997;30(4):727-749.
    • (1997) Spectrosc Lett , vol.30 , Issue.4 , pp. 727-749
    • Bynum, K.1    Rothchild, R.2
  • 24
    • 0003490590 scopus 로고
    • An introduction to lanthanide shift reagents
    • Morrill TC, editors. New York: VCH Publishers. Chapter 1
    • Morrill TC. An introduction to lanthanide shift reagents. In: Morrill TC, editors. Lanthanide shift reagents in stereochemical analysis. New York: VCH Publishers; 1986. Chapter 1. p 1-17.
    • (1986) Lanthanide Shift Reagents in Stereochemical Analysis , pp. 1-17
    • Morrill, T.C.1
  • 25
    • 0003451947 scopus 로고
    • Boca Raton, FL: CRC Press
    • Wenzel TJ. NMR shift reagents. Boca Raton, FL: CRC Press; 1987. p 11-12.
    • (1987) NMR Shift Reagents , pp. 11-12
    • Wenzel, T.J.1
  • 26
    • 0345482217 scopus 로고
    • Lanthanide-induced effects in proton NMR spectra. VIII. Scavenging effects: A problem and a solution
    • Shapiro BL, Shapiro MJ, Godwin AD, Johnston MD, Jr. Lanthanide-induced effects in proton NMR spectra. VIII. Scavenging effects: a problem and a solution. J Magn Reson 1972;8(4):402-405.
    • (1972) J Magn Reson , vol.8 , Issue.4 , pp. 402-405
    • Shapiro, B.L.1    Shapiro, M.J.2    Godwin, A.D.3    Johnston M.D., Jr.4
  • 27
    • 0003451947 scopus 로고
    • Boca Raton, FL: CRC Press
    • Wenzel TJ. NMR shift reagents. Boca Raton, FL: CRC Press; 1987. p 23-25, 178-180.
    • (1987) NMR Shift Reagents , pp. 23-25
    • Wenzel, T.J.1
  • 28
    • 0003490590 scopus 로고
    • The nature of the LSR-substrate complex
    • Morrill TC, editor. New York: VCH Publishers. Chapter 3
    • Raber DJ. The nature of the LSR-substrate complex. In: Morrill TC, editor. Lanthanide shift reagents in stereochemical analysis. New York: VCH Publishers; 1986. Chapter 3. p 55-105.
    • (1986) Lanthanide Shift Reagents in Stereochemical Analysis , pp. 55-105
    • Raber, D.J.1
  • 29
    • 0042533707 scopus 로고
    • Structure elucidation with lanthanide-induced shifts. 8. Geometry of europium-ketone complexes
    • Raber DJ, Janks CM, Johnston MD Jr, Raber NK. Structure elucidation with lanthanide-induced shifts. 8. Geometry of europium-ketone complexes. J Am Chem Soc 1980;102(21):6591-6594.
    • (1980) J Am Chem Soc , vol.102 , Issue.21 , pp. 6591-6594
    • Raber, D.J.1    Janks, C.M.2    Johnston M.D., Jr.3    Raber, N.K.4
  • 30
    • 0000817366 scopus 로고
    • Isotropic nuclear resonance shifts
    • McConnell HM, Robertson RE. Isotropic nuclear resonance shifts. J Chem Phys 1958;29(6):1361-1365.
    • (1958) J Chem Phys , vol.29 , Issue.6 , pp. 1361-1365
    • McConnell, H.M.1    Robertson, R.E.2
  • 31
    • 0024346179 scopus 로고
    • Stability of phenobarbital N-glucosides: Identification of hydrolysis products and kinetics of decomposition
    • see esp. p 460 and Fig. 4A on p 463
    • Vest FB, Soine WH, Westkaemper RB, Soine PJ. Stability of phenobarbital N-glucosides: identification of hydrolysis products and kinetics of decomposition. Pharm Res 1989;6(6):458-465, [see esp. p 460 and Fig. 4A on p 463].
    • (1989) Pharm Res , vol.6 , Issue.6 , pp. 458-465
    • Vest, F.B.1    Soine, W.H.2    Westkaemper, R.B.3    Soine, P.J.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.