1H-NMR determination of the enantiomeric excess of the antiarrhythmic drug Mexiletine by using mandelic acid analogues as chiral solvating agents

Arkivoc

Volumn 2004, Issue 5, 2004, Pages 5-25

  Carbonara, Giuseppe ^a   Carocci, Alessia ^a   Fracchiolla, Giuseppe ^a   Franchini, Carlo ^a   Lentini, Giovanni ^a   Loiodice, Fulvio ^a   Tortorella, Paolo ^a  

^a UNIVERSITY OF BARI   (Italy)

Author keywords

2 phenoxyphenylacetic acid; 1H NMR analyses; Chiral Solvating Agent; Mexiletine

Indexed keywords

2 (4 CHLOROPHENOXY) 2 PHENYLACETIC ACID; 2 (4 CHLOROPHENOXY)PROPIONIC ACID; 2 (4 CHLOROPHENYL) 2 PHENOXYACETIC ACID; 2 (4 METHOXYPHENOXY) 2 PHENYLACETIC ACID; 2 (4 METHOXYPHENYL) 2 PHENOXYACETIC ACID; 2 ARYLOXY 2 ARYLACETIC ACID; 2 PHENOXY 2 PHENYLACETIC ACID; ANTIARRHYTHMIC AGENT; MANDELIC ACID DERIVATIVE; MEXILETINE; NAPROXEN; SOLVENT; UNCLASSIFIED DRUG;

ARTICLE; CAPILLARY ELECTROPHORESIS; CHIRALITY; CONCENTRATION (PARAMETERS); DIASTEREOISOMER; ENANTIOMER; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; STOICHIOMETRY; STRUCTURE ANALYSIS; TEMPERATURE SENSITIVITY;

EID: 2942677308     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (95)

1. Fenster, P. E.; Comess, K. A. Pharmacotherapy 1986, 6, 1-9.
2. Rüdel, R.; Lehmann-Horn, F. Physiol. Rev. 1985, 65, 310-356.
3. Kalso, E.; Tramer, M. R.; McQuay, H. J.; Moore, R. A. Eur. J. Pain 1998, 2, 3-14.
4. (a) Turgeon, J.; Uprichard, A. C. G.; Bélanger, P. M.; Harron, D. W. G.; Grech-Bélanger, O. J. Pharm. Pharmacol. 1991, 43, 630-635.
5. (b) Hill, R. J.; Duff, H. J.; Sheldon, R. S. Mol. Pharmacol. 1988, 34, 659-663.
6. (c) De Luca, A.; Natuzzi, F.; Lentini, G.; Franchini, C.; Tortorella, V. ; Conte Camerino, D. Naunyn-Schmiedebergs Arch. Pharmacol. 1995, 352, 653-661.
7. (d) De Luca, A.; Natuzzi, F.; Falcone, G.; Duranti, A.; Lentini, G.; Franchini, C.; Tortorella, V.; Conte Camerino, D. Naunyn-Schmiedebergs Arch. Pharmacol. 1997, 356, 777-787.
8. (e) Clarke, D. E.; Lyles, G. A.; Calligham, B. A. Biochem. Pharmacol. 1982, 31, 27-35.
9. (f) Sinnott, C. J.; Garfield, J. M.; Zeitlin, A.; Teo, S.; Wu, M. D.; Chen, J. H.; Shafer, S. L.; Strichartz, G. R. J. Pain 2000, 1, 128-137.
10. Wu, W. P.; Nordmark, J., Wiesenfeld-Hallin, Z. Eur. J. Pain 2000, 4, 409-412.
11. (a) De Luca, A.; Pierno, S.; Natuzzi, F.; Franchini, C.; Duranti, A.; Lentini, G.; Tortorella, V.; Jockusch, H.; Conte Camerino, D. J. Pharmacol. Exp. Ther. 1997, 282, 93-100.
12. (b) Desaphy, J.-F.; Conte Camerino, D.; Franchini, C.; Lentini, G.; Tortorella, V.; De Luca, A. Br. J. Pharmacol. 1999, 128, 1165-1174.
13. (c) De Luca, A.; Natuzzi, F.; Desaphy, J.-F.; Loni, G.; Lentini, G.; Franchini, C.; Tortorella, V.; Conte Camerino, D. Mol. Pharmacol. 2000, 57, 268-277.
14. (a) Franchini, C.; Cellucci, C.; Corbo, F.; Lentini, G.; Scilimati, A.; Tortorella, V.; Stasi, F. Chirality 1994, 6, 590-595.
15. (b) Carocci, A.; Franchini, C.; Lentini, G.; Loiodice, F.; Tortorella, V. Chirality 2000, 12, 103-106.
16. (c) Carocci, A.; Catalano, A.; Corbo, F.; Duranti, A.; Amoroso, R.; Franchini, C.; Lentini, G.; Tortorella, V. Tetrahedron: Asymmetry 2000, 11, 3619-3634.
17. Hedeland, M.; Holmin, S.; Nygård, M.; Pettersson, C. J. Chromatogr. A 1999, 864, 1-16.
18. Loughhead, D. G.; Flippin, L. A.; Weikert, R. J. J. Org. Chem. 1999, 64, 3373-3375.
19. (a) Lanchote, V. L.; Cesarino, E. J.; Santos, V. J.; Mere, Y. A. Jr.; Santos, S. R. C. J. Chirality 1999, 11, 29-32.
20. (b) Lanchote, V. L.; Bonato, P. S.; Cesarino, E. J.; Mere, Y. A. Jr.; Santos, S. R. C. J.; Bertucci, C.Chirality 1997, 9, 732-738.
21. (c) Santos, V. J.; Dreossi, S. A. C.; Cesarino, E. J.; Santos, S. R. C. J.; Lanchote, V. L. Boll. Chim. Farm. 1997, 136, 130.
22. (d) Abolfathi, Z.; Bélanger, P. M.; Gilbert, M.; Rouleau, J. R.; Turgeon, J. J. Chromatogr. B 1992, 579, 366-370.
23. (e) Labbé, L.; Abolfathi, Z.; Robitaille, N. M.; St-Maurice, F.; Gilbert, M.; Turgeon, J. Ther. Drug Monit. 1999, 21, 191-199.
24. (f) Abolfathi, Z.; Fiset, C.; Gilbert, M.; Moerike, K.; Bélanger, P. M.; Turgeon, J. J. Pharmacol. Exp. Ther. 1993, 266, 1196-1201.
25. (g) Lanchote, V. L.; Cesarino, E. J.; Santos, V. J.; Moraes Junior, A. V.; Zanardi, A. M. T.; Santos, S. R. C. J. Eur. J. Drug Metab. Pharmacokinet. 1998, 23, 259-266.
26. Lanchote, V. L.; Bonato, P. S.; Dreossi, S. A. C.; Gonçalves, P. V. B.; Cesarino, E. J.; Bertucci, C. J. Chromatogr., B 1996, 685, 281-289.
27. Desai, D. M.; Gal, J. J. Chromatogr. 1993, 629, 215-228.
28. (a) Freitag, D. G.; Foster, R. T.; Coutts, R. T.; Pickard, M. A.; Pasutto, F. M. Drug Metab. Dispos. 1997, 25, 685-692.
29. (b) Freitag, D. G.; Foster, R. T.; Coutts, R. T.; Pasutto, F. J. Chromatogr, B. 1993, 616, 253-259.
30. Nishi, H.; Nakamura, K.; Nakai, H.; Sato, T. J. Chromatogr., A 1997, 757, 225-235.
31. Büschges, R.; Linde, H.; Mutschler, E.; Spahn-Langguth, H. J. Chromatogr., A 1996, 725, 323-334.
32. Booth, T. D.; Wainer, I. W. J. Chromatogr., A 1996, 741, 205-211.
33. Fieger, H.; Wainer, I. W. J. Pharm. Biomed. Anal. 1993, 11, 1173-1179.
34. Aav, R.; Parve, O.; Pehk, T.; Claesson, A.; Martin, I. Tetrahedron: Asymmetry 1999, 10, 3033-3038.
35. Büschges, R.; Devant, R.; Mutschler, E.; Spahn-Langguth, H. J. Pharm. Biomed. Anal. 1996, 15, 201-220.
36. Henriksson, H.; Jonsson, S.; Isaksson, R.; Pettersson, G. Chirality 1995, 7, 415-424.
37. Fukushima, T.; Kato, M.; Santa, T.; Imai, K. Analyst 1995, 120, 381-383.
38. Kleidernigg, O. P.; Lindner, W. Chromatographia 1997, 44, 465-472.
39. (a) Kwok, D. K. W.; Igwemezie, L.; Kerr, C. R.; McErlane, K. M. J. Chromatogr., B 1994, 661, 271-280.
40. (b) Kwok, D. W.; Kerr, C. R.; McErlane, K. M. Xenobiotica, 1995, 25, 1127-1142.
41. Igwemezie, L.; Beatch, G. N.; Walker, M. J. A.; McErlane, K. M. Xenobiotica 1991, 21, 1153-1158.
42. Josefsson, M.; Carlsson, B.; Norlander, B. Chromatographia 1993, 37, 129-132.
43. Grech-Bélanger, O.; Turgeon, J.; Gilbert, M. J. Chromatogr., B 1985, 337, 172-177.
44. Gal, J.; Desai, D. M.; Meyer-Lehnert, S. Chirality 1990, 2, 43-51.
45. (a) Igwemezie, L.; Kerr, C. R.; McErlane, K. M. Xenobiotica 1989, 19, 677-682.
46. (b) McErlane, K. M.; Igwemezie, L.; Kerr, C. R. J. Chromatogr., B 1987, 415, 335-346.
47. (c) McErlane, K. M.; Igwemezie, L.; Kerr, C. R. Res. Commun. Chem. Pathol. Pharmacol. 1987, 56, 141-144.
48. Uzunov, D.; Stoev, G. J. Chromatogr. 1993, 645, 233-239.
49. Yang, Q.; Sun, Z. P. Yaoxue Xuebao 1988, 23, 921-926; Chem. Abstr. 1989, 110, 219195.
50. Yang, Q.; Sun, Z. P. Yaoxue Xuebao 1988, 23, 921-926; Chem. Abstr. 1989, 110, 219195.
51. Weller, O.; Schulze, J.; König, W. A. J. Chromatogr. 1987, 403, 263-270.
52. Zhou, Y.; Sun, Z.-P. J. Chromatogr. 1990, 508, 220-224.
53. Martin, E.; Quinke, K.; Spahn, H.; Mutschler, E. Chirality 1989, 1, 223-234.
54. Zhou, Y.; Sun, Z.-P. Yaoxue Xuebao 1991, 26, 701-704; Chem. Abstr. 1992, 116, 91538.
55. Zhou, Y.; Sun, Z.-P. Yaoxue Xuebao 1991, 26, 701-704; Chem. Abstr. 1992, 116, 91538.
56. Wilson, J. M.; Hoch, K.; Blake, J.; Lindsay, W.; Smith, E. Clin. Chem. 1989, 35, 1178-1179.
57. Zhou, Y.; Sun, Z. P.; Lin, K. J. Liq. Chromatogr. 1990, 13, 875-885.
58. (a) Wang, S.-J.; Mao, H.-Q.; Zeng, S. J. Chin. Pharm. Sci. 1998, 7, 201-204.
59. (b) Wang, S.-J.; Mao, H.-Q.; Zeng, S. Zhongguo Yaoxue Zazhi 1997, 32(suppl.), 6-8; Chem. Abstr. 1998, 130, 118998.
60. (b) Wang, S.-J.; Mao, H.-Q.; Zeng, S. Zhongguo Yaoxue Zazhi 1997, 32(suppl.), 6-8; Chem. Abstr. 1998, 130, 118998.
61. Grech-Bélanger, O.; Turgeon, J.; Gilbert, M. Br. J. Clin. Pharmacol. 1986, 21, 481-487.
62. Knoche, B.; Gehrcke, B.; König, W. A.; Wainer, I. W. Chirality 1996, 8, 30-34.
63. König, W. A.; Lutz, S.; Wenz, G.; Von der Bey, E. J. High Resolut. Chromatogr. Chromatogr. Commun. 1988, 11, 506-509.
64. Li, G.; Lin, X.; Zhu, C.; Wu, P.; Guan, Y. Fenxi Huaxue 2000, 28, 1287-1280; Chem. Abstr. 2000, 134, 9443.
65. Li, G.; Lin, X.; Zhu, C.; Wu, P.; Guan, Y. Fenxi Huaxue 2000, 28, 1287-1280; Chem. Abstr. 2000, 134, 9443.
66. Lin, X.; Li, G.; Zhu, C.; Wu, P.; Guang, Y. Fenxi Ceshi Xuebao 2000, 19, 20-23; Chem. Abstr. 2000, 133, 256916.
67. Lin, X.; Li, G.; Zhu, C.; Wu, P.; Guang, Y. Fenxi Ceshi Xuebao 2000, 19, 20-23; Chem. Abstr. 2000, 133, 256916.
68. Li, G.; Lin, X.; Zhu, C.; Hao, A.; Guan, Y. Anal. Chim. Acta 2000, 421, 27-34.
69. Proksa, B.; Proksová, A. Pharmazie 2000, 55, 393-394.
70. Bjørnsdottir, I.; Hansen, S. H. Chirality 1995, 7, 219-225.
71. Kang, J.; Ou, Q. J. Chromatogr., A 1998, 795, 394-398.
72. Tanaka, Y.; Terabe, S. Chromatographia 1997, 44, 119-128.
73. Stalcup, A. M.; Gahm, K. H. Anal. Chem. 1996, 68, 1360-1368.
74. Lin, X.; Li, G.; Zhu, C.; Wu, P.; Guan, Y. Sepu 2001, 19, 109-111; Chem. Abstr. 2001, 135, 127319.
75. Lin, X.; Li, G.; Zhu, C.; Wu, P.; Guan, Y. Sepu 2001, 19, 109-111; Chem. Abstr. 2001, 135, 127319.
76. Srinivas, N. R.; Igwemezie, L. N. Biomed. Chromatogr. 1992, 6, 163-167.
77. Weinberger, R. Practical Capillary Electrophoresis; Academic: New York, 2000; Chapters 2 and 10.
78. Otsuka, K.; Honda, S.; Kato, J.; Terabe, S.; Kimata, K.; Tanaka, N. J. Pharm. Biomed. Anal. 1998, 17, 1177-1190.
79. Whitesides, G. M.; Lewis, D. W. J. Am. Chem Soc. 1970,92, 6979-6980.
80. (a) Parker, D. Chem. Rev. 1991, 91, 1441-1457.
81. (b) Prestat, G.; Marchand, A.; Lebreton, J.; Guingant, A.; Pradère, J.-P. Tetrahedron: Asymmetry 1995, 9, 197-201.
82. (c) Chinchilla, R.; Foubelo, F.; Nájera, C.; Yus, M. Tetrahedron: Asymmetry 1995, 6, 1877-1880.
83. (d) Parker, D.; Taylor, R. J. Tetrahedron 1987, 43, 5451-5456.
84. (e) Villani, F. J., Jr.; Costanzo, M. J.; Inners, R. R.; Mutter, M. S.; McClure, D. E. J. Org. Chem. 1986, 51, 3715-3718.
85. (f) Benson, S. C.; Cai, P.; Colon, M.; Haiza, M. A.; Tokles, M.; Snyder, J. K. J. Org. Chem. 1988, 53, 5335-5341.
86. (g) Baxter, C. A. R.; Richards, H. C. Tetrahedron Lett. 1972, 32, 3357-3358.
87. (h) Fulwood, R.; Parker, D. J. Chem. Soc. Perkin Trans. 2 1994, 1, 57-64.
88. Aboul-Enein, H.-Y.; Médonné, S.; Rotchild, R. Spectrosc. Lett. 1991, 24, 909-930.
89. Aboul-Enein, H.-Y.; Rotchild, R.; Sinnema, A. Spectrosc. Lett. 1992, 25, 1367-1385.
90. (a) Bettoni, G.; Ferorelli, S.; Loiodice, F.; Tangari, N.; Tortorella, V.; Gasparrini, F.; Misiti, D.; Villani, C. Chirality 1992, 4, 193-203.
91. (b) Rangwala, S. M.; O'Brien, M. L.; Tortorella, V.; Longo, A.; Loiodice, F.; Noonan, D. J.; Feller, D. R. Chirality 1997, 9, 37-47.
92. Berardi, F.; Loiodice, F.; Fracchiolla, G.; Colabufo, N. A.; Perrone, R. ; Tortorella, V. J. Med. Chem. 2003, 46, 2117-2124.
93. Görög, S.; Gazdag, M. J. Chromatogr., B 1994, 659, 51-84.
94. Franchini, C.; Corbo, F.; Lentini, G.; Bruno, G.; Scilimati A.; Tortorella, V.; Conte-Camerino, D.; De Luca, A. J. Med. Chem. 2000,43, 3792-3798.
95. Koh, K.; Durst, T. J. Org. Chem. 1994, 59, 4683-4686.