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Volumn 11, Issue 9, 1999, Pages 694-700

Chiral discrimination of the analgesic cizolirtine by using cyclodextrins: A 1H NMR study on the solution structures of their host-guest complexes

Author keywords

cyclodextrin; cyclodextrin; cyclodextrin; Enantiorecognition; Heptakis(2,3 di O methyl) cyclodextrin; Host guest; ROESY

Indexed keywords

ANALGESIC AGENT; BETA CYCLODEXTRIN; CIZOLIRTINE; CYCLODEXTRIN DERIVATIVE; METHANOL; UNCLASSIFIED DRUG;

EID: 0345035475     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1999)11:9<694::AID-CHIR5>3.0.CO;2-W     Document Type: Article
Times cited : (22)

References (35)
  • 3
    • 84985609923 scopus 로고
    • Cyclodextrin inclusion compounds in research and industry
    • Saenger W. Cyclodextrin inclusion compounds in research and industry. Angew Chem Int Ed Engl 1980;19:344-362.
    • (1980) Angew Chem Int Ed Engl , vol.19 , pp. 344-362
    • Saenger, W.1
  • 4
    • 0004031703 scopus 로고
    • Chichester: Ellis Horwood
    • nd ed. Chichester: Ellis Horwood; 1991.
    • (1991) nd Ed.
    • Allenmark, S.1
  • 6
    • 0028593480 scopus 로고
    • Enantiomeric differentiation of a wide range of pharmacologically active substances by capillary electrophoresis using modified β-cyclodextrins
    • Aumatell A, Wells RJ, Wong DKY. Enantiomeric differentiation of a wide range of pharmacologically active substances by capillary electrophoresis using modified β-cyclodextrins. J Chromatogr A 1994;686: 293-307.
    • (1994) J Chromatogr A , vol.686 , pp. 293-307
    • Aumatell, A.1    Wells, R.J.2    Wong, D.K.Y.3
  • 7
    • 0028875384 scopus 로고
    • Evaluation of the use of cyclodextrins in chiral separation of basic drug substances by capillary electrophoresis
    • Bjornsdottir I, Hansen SH. Evaluation of the use of cyclodextrins in chiral separation of basic drug substances by capillary electrophoresis. Chirality 1995;7:219-225.
    • (1995) Chirality , vol.7 , pp. 219-225
    • Bjornsdottir, I.1    Hansen, S.H.2
  • 8
    • 0028839349 scopus 로고
    • Rapid chiral separation methods development-mediated capillary electrophoresis for acidic and basic compounds
    • Guttman A, Brunet S, Jurado C, Cooke N. Rapid chiral separation methods development-mediated capillary electrophoresis for acidic and basic compounds. Chirality 1995;7:409-414.
    • (1995) Chirality , vol.7 , pp. 409-414
    • Guttman, A.1    Brunet, S.2    Jurado, C.3    Cooke, N.4
  • 9
    • 0031081663 scopus 로고    scopus 로고
    • Selectivity in capillary electrophoresis: Application to chiral separations with cyclodextrins
    • Lelievre F, Gareil P, Jardy A Selectivity in capillary electrophoresis: application to chiral separations with cyclodextrins. Anal Chem 1997; 69:385-392.
    • (1997) Anal Chem , vol.69 , pp. 385-392
    • Lelievre, F.1    Gareil, P.2    Jardy, A.3
  • 10
    • 0000022380 scopus 로고
    • Cyclodextrins as chiral nuclear magnetic resonance shift reagents
    • MacNicol DD, Rycroft DS. Cyclodextrins as chiral nuclear magnetic resonance shift reagents. Tetrahedron Lett 1977;25:2173-2176.
    • (1977) Tetrahedron Lett , vol.25 , pp. 2173-2176
    • MacNicol, D.D.1    Rycroft, D.S.2
  • 12
    • 84989603742 scopus 로고
    • Cyclodextrins as chiral complexing agents in water and their application to optical purity measurements
    • Greatbanks D, Pickford R. Cyclodextrins as chiral complexing agents in water and their application to optical purity measurements. Magn Reson Chem 1987;25:208-215.
    • (1987) Magn Reson Chem , vol.25 , pp. 208-215
    • Greatbanks, D.1    Pickford, R.2
  • 14
    • 0029958605 scopus 로고    scopus 로고
    • NMR investigation of the interaction of (+)- and (-)-flurbiprofen with β-cyclodextrin
    • Salvadori P, Uccello-Barretta G, Balzano F, Bertucci C, Chiavacci C. NMR investigation of the interaction of (+)- and (-)-flurbiprofen with β-cyclodextrin. Chirality 1996;8:423-429.
    • (1996) Chirality , vol.8 , pp. 423-429
    • Salvadori, P.1    Uccello-Barretta, G.2    Balzano, F.3    Bertucci, C.4    Chiavacci, C.5
  • 15
    • 0030965831 scopus 로고    scopus 로고
    • Chiral discrimination by NMR spectroscopy of ephedrine and N-methylephedrine induced by β-cyclodextrin, heptakis(2,3-di-O-acetyl)β-cyclodextrin and heptakis(6-O-acetyl)β-cyclodextrin
    • Holzgrabe U, Mallwitz H, Branch SK, Jefferies TM, Wiese M. Chiral discrimination by NMR spectroscopy of ephedrine and N-methylephedrine induced by β-cyclodextrin, heptakis(2,3-di-O-acetyl)β-cyclodextrin and heptakis(6-O-acetyl)β-cyclodextrin. Chirality 1997;9:211-219.
    • (1997) Chirality , vol.9 , pp. 211-219
    • Holzgrabe, U.1    Mallwitz, H.2    Branch, S.K.3    Jefferies, T.M.4    Wiese, M.5
  • 17
    • 0345072980 scopus 로고
    • Drug Data Report 1990;12:347.
    • (1990) Drug Data Report , vol.12 , pp. 347
  • 18
    • 0032904430 scopus 로고    scopus 로고
    • Optical resolution and enantiomeric purity determination of the analgesic cizolirtine
    • Torrens A, Castrillo JA, Frigola J, Salgado L, Redondo J. Optical resolution and enantiomeric purity determination of the analgesic cizolirtine. Chirality 1999;11:63-69.
    • (1999) Chirality , vol.11 , pp. 63-69
    • Torrens, A.1    Castrillo, J.A.2    Frigola, J.3    Salgado, L.4    Redondo, J.5
  • 20
    • 0003494644 scopus 로고
    • Molecular complexes. Part 18. A nuclear magnetic resonance adaptation of the continuous variation (Job) method of stoichiometry determination
    • Homer J, Perry MC. Molecular complexes. Part 18. A nuclear magnetic resonance adaptation of the continuous variation (Job) method of stoichiometry determination. J Chem Soc Faraday Trans 1 1986;82: 533-543.
    • (1986) J Chem Soc Faraday Trans 1 , vol.82 , pp. 533-543
    • Homer, J.1    Perry, M.C.2
  • 21
    • 77956856355 scopus 로고
    • NMR Studies of the structure and properties of cyclodextrins and their inclusion complexes
    • London: Academic Press
    • Inoue Y. NMR Studies of the structure and properties of cyclodextrins and their inclusion complexes In: Annual reports on NMR spectroscopy, vol 27. London: Academic Press; 1993. p 59-101.
    • (1993) Annual Reports on NMR Spectroscopy , vol.27 , pp. 59-101
    • Inoue, Y.1
  • 22
    • 0011491177 scopus 로고
    • Structure determination of a tetrasaccharide: Transient nuclear Overhauser effects in the rotating frame
    • Bothner-By AA, Stevens RL, Lee JT, Warren CD, Jeanloz RW. Structure determination of a tetrasaccharide: transient nuclear Overhauser effects in the rotating frame. J Am Chem Soc 1984;106:811-813.
    • (1984) J Am Chem Soc , vol.106 , pp. 811-813
    • Bothner-By, A.A.1    Stevens, R.L.2    Lee, J.T.3    Warren, C.D.4    Jeanloz, R.W.5
  • 23
    • 5144229966 scopus 로고
    • Practical aspects of two-dimensional transverse NOE spectroscopy
    • Bax A, Davis DG. Practical aspects of two-dimensional transverse NOE spectroscopy. J Magn Reson 1985;63:207-213.
    • (1985) J Magn Reson , vol.63 , pp. 207-213
    • Bax, A.1    Davis, D.G.2
  • 25
    • 84994921904 scopus 로고
    • 1H NMR chiral analysis of benzhydrylamine derivatives using β-cyclodextrin-solution geometry of host-guest complexes as determined by 1D NOE and ROESY experiments
    • 1H NMR chiral analysis of benzhydrylamine derivatives using β-cyclodextrin-solution geometry of host-guest complexes as determined by 1D NOE and ROESY experiments. Magn Reson Chem 1995;33:104-109.
    • (1995) Magn Reson Chem , vol.33 , pp. 104-109
    • Redondo, J.1    Frigola, J.2    Torrens, A.3    Lupón, P.4
  • 26
    • 33751154975 scopus 로고
    • Positive or adverse effects of methylation on the inclusion behavior of cyclodextrins. A comparative NMR study using pheromone constituents of the olive fruit fly
    • Botsi A, Yannakopoulou K, Perly B, Hadjoudis E. Positive or adverse effects of methylation on the inclusion behavior of cyclodextrins. A comparative NMR study using pheromone constituents of the olive fruit fly. J Org Chem 1995;60:4017-4023.
    • (1995) J Org Chem , vol.60 , pp. 4017-4023
    • Botsi, A.1    Yannakopoulou, K.2    Perly, B.3    Hadjoudis, E.4
  • 27
    • 0000609240 scopus 로고
    • NMR and fluorescence studies of cyclodextrin complexes with guest molecules containing both phenyl and naphthyl units
    • Schneider H-J, Blatter T, Simova S. NMR and fluorescence studies of cyclodextrin complexes with guest molecules containing both phenyl and naphthyl units. J Am Chem Soc 1991;113:1996-2000.
    • (1991) J Am Chem Soc , vol.113 , pp. 1996-2000
    • Schneider, H.-J.1    Blatter, T.2    Simova, S.3
  • 28
    • 37049083729 scopus 로고
    • High field NMR techniques and molecular modelling study of the inclusion complexes of the nootropic drug tenilsetam (CAS-997) in cyclodextrins
    • Amato ME, Djedaïni-Pilard F, Perly B, Scarlata G. High field NMR techniques and molecular modelling study of the inclusion complexes of the nootropic drug tenilsetam (CAS-997) in cyclodextrins. J Chem Soc Perkin Trans 1992;2:2065-2069.
    • (1992) J Chem Soc Perkin Trans , vol.2 , pp. 2065-2069
    • Amato, M.E.1    Djedaïni-Pilard, F.2    Perly, B.3    Scarlata, G.4
  • 29
    • 0003095853 scopus 로고
    • Complexation of ephedrine with β-cyclodextrin: An NMR spectroscopy study
    • Ndou T, Mukundan S Jr, Warner IM. Complexation of ephedrine with β-cyclodextrin: an NMR spectroscopy study. J Incl Phenom 1993;15: 9-25.
    • (1993) J Incl Phenom , vol.15 , pp. 9-25
    • Ndou, T.1    Mukundan S., Jr.2    Warner, I.M.3
  • 30
    • 0030024977 scopus 로고    scopus 로고
    • 1H NMR and molecular modeling study on the inclusion complex β-cyclodextrin-indomethacin
    • 1H NMR and molecular modeling study on the inclusion complex β-cyclodextrin-indomethacin. J Org Chem 1996;61:909-914.
    • (1996) J Org Chem , vol.61 , pp. 909-914
    • Fronza, G.1    Mele, A.2    Redenti, E.3    Ventura, P.4
  • 31
    • 0031848416 scopus 로고    scopus 로고
    • The application of selective ROE experiments to study solution structures of cyclomaltooligosaccharide derivatives and complexes
    • Forgo P, Dsouza VT. The application of selective ROE experiments to study solution structures of cyclomaltooligosaccharide derivatives and complexes. Carbohydr Res 1998;306:473-478.
    • (1998) Carbohydr Res , vol.306 , pp. 473-478
    • Forgo, P.1    Dsouza, V.T.2
  • 32
    • 0001410909 scopus 로고    scopus 로고
    • Determination of the inclusion geometry for the β-cyclodextrin/benzoic acid complex by NMR and molecular modeling
    • Salvatierra D, Jaime C, Virgili A, Sánchez-Ferrando F. Determination of the inclusion geometry for the β-cyclodextrin/benzoic acid complex by NMR and molecular modeling. J Org Chem 1996;61:9578-9581.
    • (1996) J Org Chem , vol.61 , pp. 9578-9581
    • Salvatierra, D.1    Jaime, C.2    Virgili, A.3    Sánchez-Ferrando, F.4
  • 33
    • 0002496179 scopus 로고    scopus 로고
    • Mechanisms for chiral recognition by cyclodextrins
    • Kano K. Mechanisms for chiral recognition by cyclodextrins. J Phys Org Chem 1997;10:286-291.
    • (1997) J Phys Org Chem , vol.10 , pp. 286-291
    • Kano, K.1
  • 34
    • 0000648129 scopus 로고    scopus 로고
    • The principle of maximum chiral discrimination: Chiral recognition in per-methyl-β-cyclodextrin
    • Lipkowitz KB, Coner R, Peterson MA, Morreale A, Shackelford J. The principle of maximum chiral discrimination: chiral recognition in per-methyl-β-cyclodextrin. J Org Chem 1998;63:732-745.
    • (1998) J Org Chem , vol.63 , pp. 732-745
    • Lipkowitz, K.B.1    Coner, R.2    Peterson, M.A.3    Morreale, A.4    Shackelford, J.5
  • 35
    • 0029761804 scopus 로고    scopus 로고
    • Detailed experimental and theoretical analysis of chiral discrimination: Enantioselective binding of R/S methyl mandelate by β-cyclodextrin
    • Lipkowitz KB, Stoehr CM. Detailed experimental and theoretical analysis of chiral discrimination: enantioselective binding of R/S methyl mandelate by β-cyclodextrin. Chirality 1996;8:341-350.
    • (1996) Chirality , vol.8 , pp. 341-350
    • Lipkowitz, K.B.1    Stoehr, C.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.