메뉴 건너뛰기




Volumn 11, Issue 7, 1999, Pages 602-608

Resolution of some 4-benzofurazanyl and 4-benzofuroxanyl 1,4- dihydropyridine derivatives by chiral HPLC on Whelk-O1 and some polysaccharide chiral stationary phases

Author keywords

1,4 dihydropyridines; Analytical and semipreparative chiral HPLC; Benzofurazane; Benzofuroxane; Cluster analysis

Indexed keywords

4 BENZOFURAZANYL; 4 BENZOFUROXANYL 1,4 DIHYDROPYRIDINE; DIHYDROPYRIDINE DERIVATIVE; FURAZAN DERIVATIVE; POLYSACCHARIDE; UNCLASSIFIED DRUG;

EID: 0032764609     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1999)11:7<602::AID-CHIR14>3.0.CO;2-Q     Document Type: Article
Times cited : (5)

References (30)
  • 1
    • 0024477866 scopus 로고
    • 2+ channel ligands: Structure-function relationship of the 1,4-dihydropyridines
    • 2+ Channel ligands: Structure-function relationship of the 1,4-dihydropyridines. Med Res Rev 1989; 9:123-180.
    • (1989) Med Res Rev , vol.9 , pp. 123-180
    • Triggle, D.J.1    Langs, D.A.2    Janis, R.A.3
  • 2
    • 0030030361 scopus 로고    scopus 로고
    • Benzofurazanyl- and benzofuroxanyl-1,4-dihydropyridines: Synthesis, structure and calcium entry blocker activities
    • Gasco AM, Ermondi G, Fruttero R, Gasco A. Benzofurazanyl- and benzofuroxanyl-1,4-dihydropyridines: Synthesis, structure and calcium entry blocker activities. Eur J Med Chem. 1996;31:3-10.
    • (1996) Eur J Med Chem. , vol.31 , pp. 3-10
    • Gasco, A.M.1    Ermondi, G.2    Fruttero, R.3    Gasco, A.4
  • 3
    • 0026342780 scopus 로고
    • 1,4-Dihydropyridines: Effects of chirality and conformation on the calcium antagonist and calcium agonist activities
    • Goldmann S, Stoltefuss J. 1,4-Dihydropyridines: Effects of chirality and conformation on the calcium antagonist and calcium agonist activities. Angew Chem, Int Ed Engl 1991;30:1559-1578.
    • (1991) Angew Chem, Int Ed Engl , vol.30 , pp. 1559-1578
    • Goldmann, S.1    Stoltefuss, J.2
  • 4
    • 0028918956 scopus 로고
    • Stereoselective pharmacokinetics of dihydropyridine calcium antagonists
    • Tokuma Y, Noguchi H. Stereoselective pharmacokinetics of dihydropyridine calcium antagonists. J Chromatogr 1995;694:181-193.
    • (1995) J Chromatogr , vol.694 , pp. 181-193
    • Tokuma, Y.1    Noguchi, H.2
  • 5
    • 0033594337 scopus 로고    scopus 로고
    • Synthesis and voltage-clamp studies of methyl 1,4-dihydro-2,6-dimethyl-5-nitro-4-benzofurazanylpyridine-3-carboxylate racemates and enantiomers and their benzofuroxanyl analogues
    • in press
    • Visentin S, Amiel P, Gasco AM, Fruttero R, Roussel C, Giusta L, Carbone E, Gasco A. Synthesis and voltage-clamp studies of methyl 1,4-dihydro-2,6-dimethyl-5-nitro-4-benzofurazanylpyridine-3-carboxylate racemates and enantiomers and their benzofuroxanyl analogues. J Med Chem, in press.
    • J Med Chem
    • Visentin, S.1    Amiel, P.2    Gasco, A.M.3    Fruttero, R.4    Roussel, C.5    Giusta, L.6    Carbone, E.7    Gasco, A.8
  • 6
    • 0031928079 scopus 로고    scopus 로고
    • Structure and substituent effect on chiral separation of some 4a-methyl-2,3,4,4a-tetrahydro-1H-fluorene derivatives and 4a-methyl-1,2,3,4,4a,9a-hexahydrofluorene-9-one derivatives on CTA-I and Chiralcel OJ chiral stationary phases
    • (a) Roussel C, Suteu C, Shaimi L, Soufiaoui M. Structure and substituent effect on chiral separation of some 4a-methyl-2,3,4,4a-tetrahydro-1H-fluorene derivatives and 4a-methyl-1,2,3,4,4a,9a-hexahydrofluorene-9-one derivatives on CTA-I and Chiralcel OJ chiral stationary phases. Chirality 1998;10:522-527.
    • (1998) Chirality , vol.10 , pp. 522-527
    • Roussel, C.1    Suteu, C.2    Shaimi, L.3    Soufiaoui, M.4
  • 7
    • 0344188136 scopus 로고    scopus 로고
    • Note: The chemical name and the structure of the chiral selector of all the chiral stationary phases actually used or quoted in this article under their trade name: Chiralcel OJ, Chiralpak AS, Chiralcel OD-H, Chiralpak AD, (R,R)-Whelk-O1, Chiralcel OF, Chiral-AGP, Cyclobond I, Cyclobond I SP, Cyclobond I RSP, Chiralpak OT(+), Ultron ES-OVM, Sumichiral OA-2500 as well as the suppliers are displayed
    • (b) Note: The chemical name and the structure of the chiral selector of all the chiral stationary phases actually used or quoted in this article under their trade name: Chiralcel OJ, Chiralpak AS, Chiralcel OD-H, Chiralpak AD, (R,R)-Whelk-O1, Chiralcel OF, Chiral-AGP, Cyclobond I, Cyclobond I SP, Cyclobond I RSP, Chiralpak OT(+), Ultron ES-OVM, Sumichiral OA-2500 as well as the suppliers are displayed at http://chirbase.u-3mrs.fr/chirbase/database.html.
  • 8
    • 33751143092 scopus 로고    scopus 로고
    • Inversion of optically active dihydropyridines by oxidation and electroreduction
    • Straub A, Gohrt A. Inversion of optically active dihydropyridines by oxidation and electroreduction. Angew Chem, Int Ed Engl 1996;35: 2662-2664.
    • (1996) Angew Chem, Int Ed Engl , vol.35 , pp. 2662-2664
    • Straub, A.1    Gohrt, A.2
  • 9
    • 0029739166 scopus 로고    scopus 로고
    • Fluorenone 1,4-dihydropyridine derivatives with cardiodepressant activity: Enantiomeric separation by chiral HPLC and conformational aspects
    • Caccamese S, Chillemi R, Principato G. Fluorenone 1,4-dihydropyridine derivatives with cardiodepressant activity: Enantiomeric separation by chiral HPLC and conformational aspects. Chirality 1996;8: 281-290.
    • (1996) Chirality , vol.8 , pp. 281-290
    • Caccamese, S.1    Chillemi, R.2    Principato, G.3
  • 10
    • 0030914742 scopus 로고    scopus 로고
    • Synthesis of two optically active calcium channel antagonists labelled at carbon-11 for in vivo cardiac PET imaging
    • Dolle F, Hinnen F, Valette H, Fuseau C, Duval R, Peglion JL, Crouzel C. Synthesis of two optically active calcium channel antagonists labelled at carbon-11 for in vivo cardiac PET imaging. Bioorg Med Chem 1997;5:749-764.
    • (1997) Bioorg Med Chem , vol.5 , pp. 749-764
    • Dolle, F.1    Hinnen, F.2    Valette, H.3    Fuseau, C.4    Duval, R.5    Peglion, J.L.6    Crouzel, C.7
  • 11
    • 0030957177 scopus 로고    scopus 로고
    • Semipreparative chromatographic purification of the enantiomers of S-(-)-amlodipine and R-(+)-amlodipine
    • Luksa J, Josic D, Podobnik B, Furlan B, Kremser M. Semipreparative chromatographic purification of the enantiomers of S-(-)-amlodipine and R-(+)-amlodipine. J Chromatogr B 1997;693:367-375.
    • (1997) J Chromatogr B , vol.693 , pp. 367-375
    • Luksa, J.1    Josic, D.2    Podobnik, B.3    Furlan, B.4    Kremser, M.5
  • 12
    • 0344619702 scopus 로고    scopus 로고
    • Automated chiral HPLC screening compounds enantiomeric separation
    • Poster 165 ISCD'1994 Stockholm. Letter, W.S., Automated column selection switching systems
    • (a) Wright AG. Automated chiral HPLC screening compounds enantiomeric separation. Poster 165 ISCD'1994 Stockholm. Letter, W.S., Automated column selection switching systems. LC-GC Mag Sep Sci 1997;15:205-209.
    • (1997) LC-GC Mag Sep Sci , vol.15 , pp. 205-209
    • Wright, A.G.1
  • 13
    • 0344188134 scopus 로고    scopus 로고
    • Information on Chirbase is available
    • (b) Information on Chirbase is available at http:// chirbase.u-3mrs.fr.
  • 14
    • 0021269849 scopus 로고
    • Rotational barriers of 4-aryl-1,4-dihydropyridines (Ca antagonists)
    • Goldmann S, Geiger W. Rotational barriers of 4-aryl-1,4-dihydropyridines (Ca antagonists). Angew Chem, Int Ed Engl 1994;23:301-302. Gallo R, Roussel C, Berg U. Quantitative analysis of steric effects in heteroaromatics. Adv Heterocycl Chem 1988;43:173-298.
    • (1994) Angew Chem, Int Ed Engl , vol.23 , pp. 301-302
    • Goldmann, S.1    Geiger, W.2
  • 15
    • 0006441248 scopus 로고
    • Quantitative analysis of steric effects in heteroaromatics
    • Goldmann S, Geiger W. Rotational barriers of 4-aryl-1,4-dihydropyridines (Ca antagonists). Angew Chem, Int Ed Engl 1994;23:301-302. Gallo R, Roussel C, Berg U. Quantitative analysis of steric effects in heteroaromatics. Adv Heterocycl Chem 1988;43:173-298.
    • (1988) Adv Heterocycl Chem , vol.43 , pp. 173-298
    • Gallo, R.1    Roussel, C.2    Berg, U.3
  • 16
    • 0027276809 scopus 로고
    • Sensitive determination of enantiomers of amino acids derivatized with the fluorogenic reagent 4-fluoro-7-nitro-2,1,3-benzoxadiazole separated on Pirkle-type column Sumichiral OA-2500(S)
    • Imai K, Kukushima T, Uzu S. Sensitive determination of enantiomers of amino acids derivatized with the fluorogenic reagent 4-fluoro-7-nitro-2,1,3-benzoxadiazole separated on Pirkle-type column Sumichiral OA-2500(S). Biomed Chromatogr 1993;7:177-178. Kato M, Fukushima T, Santa T, Homma H, Imai K. Determination of D-amino-acid derivatized with 4-fluoro-7-nitro-2,1,3-benzoxadiazole (NBD-F) in wine samples by high performance liquid chromatography. Biomed Chromatogr 1995; 9:193-194. Toyo'oka T, Liu YM. Development of optically active fluorescent Edman-type reagents. Analyst 1995;120:385-390.
    • (1993) Biomed Chromatogr , vol.7 , pp. 177-178
    • Imai, K.1    Kukushima, T.2    Uzu, S.3
  • 17
    • 0029081622 scopus 로고
    • Determination of D-amino-acid derivatized with 4-fluoro-7-nitro-2,1,3-benzoxadiazole (NBD-F) in wine samples by high performance liquid chromatography
    • Imai K, Kukushima T, Uzu S. Sensitive determination of enantiomers of amino acids derivatized with the fluorogenic reagent 4-fluoro-7-nitro-2,1,3-benzoxadiazole separated on Pirkle-type column Sumichiral OA-2500(S). Biomed Chromatogr 1993;7:177-178. Kato M, Fukushima T, Santa T, Homma H, Imai K. Determination of D-amino-acid derivatized with 4-fluoro-7-nitro-2,1,3-benzoxadiazole (NBD-F) in wine samples by high performance liquid chromatography. Biomed Chromatogr 1995; 9:193-194. Toyo'oka T, Liu YM. Development of optically active fluorescent Edman-type reagents. Analyst 1995;120:385-390.
    • (1995) Biomed Chromatogr , vol.9 , pp. 193-194
    • Kato, M.1    Fukushima, T.2    Santa, T.3    Homma, H.4    Imai, K.5
  • 18
    • 37049072102 scopus 로고
    • Development of optically active fluorescent Edman-type reagents
    • Imai K, Kukushima T, Uzu S. Sensitive determination of enantiomers of amino acids derivatized with the fluorogenic reagent 4-fluoro-7-nitro-2,1,3-benzoxadiazole separated on Pirkle-type column Sumichiral OA-2500(S). Biomed Chromatogr 1993;7:177-178. Kato M, Fukushima T, Santa T, Homma H, Imai K. Determination of D-amino-acid derivatized with 4-fluoro-7-nitro-2,1,3-benzoxadiazole (NBD-F) in wine samples by high performance liquid chromatography. Biomed Chromatogr 1995; 9:193-194. Toyo'oka T, Liu YM. Development of optically active fluorescent Edman-type reagents. Analyst 1995;120:385-390.
    • (1995) Analyst , vol.120 , pp. 385-390
    • Toyo'oka, T.1    Liu, Y.M.2
  • 19
    • 0031561759 scopus 로고    scopus 로고
    • Some recent HPLC separations of enantiomers of pharmaceuticals compounds and other compounds using the Whelk O1 chiral stationary phase
    • Welch CJ, Szczerba T, Perrin SC. Some recent HPLC separations of enantiomers of pharmaceuticals compounds and other compounds using the Whelk O1 chiral stationary phase. J Chromatogr A 1997;758: 93-98.
    • (1997) J Chromatogr A , vol.758 , pp. 93-98
    • Welch, C.J.1    Szczerba, T.2    Perrin, S.C.3
  • 20
    • 84989525730 scopus 로고
    • Highly enantioselective epoxidation of 2,2-dimethylchromenes
    • The chromatographic data were kindly provided by the authors
    • Hatayama A, Hosoya N, Irie R, Ito Y, Katsuki T. Highly enantioselective epoxidation of 2,2-dimethylchromenes. Synlett 1992;407-409. The chromatographic data were kindly provided by the authors.
    • (1992) Synlett , pp. 407-409
    • Hatayama, A.1    Hosoya, N.2    Irie, R.3    Ito, Y.4    Katsuki, T.5
  • 21
    • 0025339805 scopus 로고
    • Optical resolution of dihydropyridine enantiomers by HPLC using phenylcarbamates of polysaccharides as CSPs
    • Okamoto Y, Aburatani R, Hatada K, Honda M, Inotsume N, Nakano M. Optical resolution of dihydropyridine enantiomers by HPLC using phenylcarbamates of polysaccharides as CSPs. J Chromatogr 1990;513: 375-378.
    • (1990) J Chromatogr , vol.513 , pp. 375-378
    • Okamoto, Y.1    Aburatani, R.2    Hatada, K.3    Honda, M.4    Inotsume, N.5    Nakano, M.6
  • 22
    • 0002445850 scopus 로고
    • Tris(chloro-disubstituted methyl-disubstituted phenylcarbamates) cellulose
    • Chankvetadze B, Yashima E, Okamoto Y. Tris(chloro-disubstituted methyl-disubstituted phenylcarbamates) cellulose. Chem Lett 1993;4: 617-620.
    • (1993) Chem Lett , vol.4 , pp. 617-620
    • Chankvetadze, B.1    Yashima, E.2    Okamoto, Y.3
  • 23
    • 0025316762 scopus 로고
    • Enantioselective determination of Felodipine and other chiral dihydropyridine calcium entry blockers in human plasma
    • Soons PA, Roosemalen MCM, Breimer DD. Enantioselective determination of Felodipine and other chiral dihydropyridine calcium entry blockers in human plasma. J Chromatogr Biomed Applic 1990;528: 343-356.
    • (1990) J Chromatogr Biomed Applic , vol.528 , pp. 343-356
    • Soons, P.A.1    Roosemalen, M.C.M.2    Breimer, D.D.3
  • 24
    • 0027076204 scopus 로고
    • Design of chiral liquid chromatographic separations of calcium antagonists on γ1-acid glycoprotein and ovomucoid columns
    • De Lorenzi E, Fell AF, Caccialanza G, Massolini G, Kitsos M. Design of chiral liquid chromatographic separations of calcium antagonists on γ1-acid glycoprotein and ovomucoid columns. J Pharm Biomed Anal 1992;10:909-915.
    • (1992) J Pharm Biomed Anal , vol.10 , pp. 909-915
    • De Lorenzi, E.1    Fell, A.F.2    Caccialanza, G.3    Massolini, G.4    Kitsos, M.5
  • 26
    • 84985287201 scopus 로고
    • Enantiomeric separation of isradipine and related compounds by liquid chromatography with a chiral stationary phase
    • Küsters E, Dosenbach C, Gerber G. Enantiomeric separation of isradipine and related compounds by liquid chromatography with a chiral stationary phase. J High Res Chromatogr 1991;14:769-771.
    • (1991) J High Res Chromatogr , vol.14 , pp. 769-771
    • Küsters, E.1    Dosenbach, C.2    Gerber, G.3
  • 27
    • 0026656169 scopus 로고
    • Enzymatic synthesis of optically active 2-carbamoyloxymethyl-1,4-dihydropyridines: R(+) S(-)NB 818
    • Ebiike H, Maruyama K, Achiwa K. Enzymatic synthesis of optically active 2-carbamoyloxymethyl-1,4-dihydropyridines: R(+) S(-)NB 818. Tetrahedron: Asymmetry 1992;3:1153-1156.
    • (1992) Tetrahedron: Asymmetry , vol.3 , pp. 1153-1156
    • Ebiike, H.1    Maruyama, K.2    Achiwa, K.3
  • 28
    • 0027280542 scopus 로고
    • Protease-catalyzed enantioselective synthesis of optically active 1,4-dihydropyridines
    • Hirose Y, Kariya K, Sasaki I, Kurono Y, Achiwa K. Protease-catalyzed enantioselective synthesis of optically active 1,4-dihydropyridines. Tetrahedron Lett 1993;34:3441-3444.
    • (1993) Tetrahedron Lett , vol.34 , pp. 3441-3444
    • Hirose, Y.1    Kariya, K.2    Sasaki, I.3    Kurono, Y.4    Achiwa, K.5
  • 29
    • 0028059322 scopus 로고
    • Separation of optical isomers of a new 1,4-dihydropyridine calcium channel blocker (LF 2.0254) by liquid and supercritical fluid chromatography
    • Siret L, Macaudiere P, Bargmann-Leyder N, Tambute A, Caude M, Gougeon E. Separation of optical isomers of a new 1,4-dihydropyridine calcium channel blocker (LF 2.0254) by liquid and supercritical fluid chromatography. Chirality 1994;6:440-445.
    • (1994) Chirality , vol.6 , pp. 440-445
    • Siret, L.1    Macaudiere, P.2    Bargmann-Leyder, N.3    Tambute, A.4    Caude, M.5    Gougeon, E.6
  • 30
    • 0026476140 scopus 로고
    • Drastic solvent effect in lipase-catalyzed enantioselective hydrolysis of prochiral 1,4-dihydropyridines
    • Hirose Y, Kariya K, Sasaki I, Kurono Y, Ebiike H, Achiwa K. Drastic solvent effect in lipase-catalyzed enantioselective hydrolysis of prochiral 1,4-dihydropyridines. Tetrahedron Lett. 1992;33:7157-7160.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 7157-7160
    • Hirose, Y.1    Kariya, K.2    Sasaki, I.3    Kurono, Y.4    Ebiike, H.5    Achiwa, K.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.