Separation of maxi-K channel opening 3-substitued-4-arylquinolinone atropisomers by enantioselective supercritical fluid chromatography

Journal of Pharmaceutical and Biomedical Analysis

Volumn 48, Issue 4, 2008, Pages 1120-1126

  Qian Cutrone, Jingfang ^a   Dasgupta, Bireshwar ^a   Kozlowski, Edward S ^a   Dalterio, Richard ^a   Wang Iverson, David ^a   Vrudhula, Vivekananda M ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

3 substitued 4 arylquinolinone; Atropisomer separation; Drug discovery; Maxi K channel opener; Supercritical fluid chromatography

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POTASSIUM CHANNEL AFFECTING AGENT; QUINOLINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SCREENING; ENANTIOSELECTIVITY; HYDROPHILICITY; HYDROPHOBICITY; ISOMER; PRIORITY JOURNAL; SEPARATION TECHNIQUE; SUPERCRITICAL FLUID CHROMATOGRAPHY;

ALCOHOLS; CHROMATOGRAPHY, SUPERCRITICAL FLUID; DRUG DESIGN; LARGE-CONDUCTANCE CALCIUM-ACTIVATED POTASSIUM CHANNELS; MOLECULAR STRUCTURE; QUINOLONES; STEREOISOMERISM; TEMPERATURE; TIME FACTORS;

EID: 57849147568     PISSN: 07317085     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jpba.2008.08.029     Document Type: Article

References (32)

1. Gribkoff V.K., Dworetzky S.I., and Starrett Jr. J.E. Neuroscientist 7 (2001) 166-177
2. Kurachi Y., Jan L.Y., and Lazdunzki M. Potassium Ion Channels: Molecular Structure, Function, and Diseases (1999), Academic Press, San Diego, CA
3. Shieh C., Coghlan M., Sullivan J.P., and Gopalakrishnan M. Pharmacol. Rev. 52 (2000) 557-593
4. P. Hewawasam, J.E. Starrett Jr., US Patent 2001/6184231.
5. Hewawasam P., Fan W., Ding M., Flint K., Cook D., Goggins G.D., Myers R.A., Gribkoff V.K., Boissard C.G., Dworetzky S.I., Starrett Jr. J.E., and Lodge N.J. J. Med. Chem. 46 (2003) 2819-2822
6. Vrudhula V.M., Dasgupta B., Boissard C.G., Gribkoff V.K., Santone K., Dalterio R.A., Lodge N.J., and Starrett Jr. J.E. Bioorg. Med. Chem. Lett. 15 (2005) 4286-4290
7. Boy K.M., Guernon J.M., Sit S.Y., Xie K., Hewawasam P., Boissard C.G., Dworetzky S.I., Natale J., Gribkoff V.K., Lodge N.J., and Starrett Jr. J.E. Bioorg. Med. Chem. Lett. 14 (2004) 5089-5093
8. Eliel E.L., Allinger N.L., Angyal S., and Morrison G.A. Conformational Analysis (1965), Interscience Publisher, New York
9. Vrudhula V.M., Dasgupta B., Qian-Cutrone J., Kozlowski E.S., Boissard C.G., Dworetzky S.I., Wu D., Gao Q., Kimura R., Gribkoff V.K., and Starrett Jr. J.E. J. Med. Chem. 50 (2007) 1050-1057
10. Welch W.M., Erwing F.E., Huang J., Mennitti F.S., pagnozzi M.J., Kelly K., Seymour P.A., Guanowsky V., Guhan S., Guinn M.R., Critchett D., Lazzaro J., Ganong A.H., DeVries K.M., Staigers T.L., and Chenard B.L. Bioorg. Med. Chem. Lett. 11 (2001) 177-181
11. Salvadori P., Bertucci C., Ascoli G., Uccello-Barretta G., and Rossi E. Chirality 9 (1997) 495-505
12. Gilman N.W., Rosen P., Earley J.V., Cook C.M., Blount J.F., and Todaro L.J. J. Org. Chem. 58 (1993) 3285-3298
13. Dreikorn B.A., Jourdan G.P., Hall H.R., Deeter J.B., and Jones N. J. Agric. Food Chem. 38 (1990) 549-552
14. Blakemore P.R., Kilner C., and Milicevic S.D. J. Org. Chem. 71 (2006) 8212-8218
15. Shi Y., Huang M.H., Macor J.E., and Hughes D.E. J. Chromatogr. A 1078 (2005) 67-73
16. Berger T.A. Packed Column SFC (1995), The Royal Society of Chemistry, Cambridge, UK
17. In: Anton K., and Berger C. (Eds). Supercritical Fluid Chromatography with Packed Columns: Techniques and Application (1998), Marcel Dekker, Inc., New York
18. In: Subramanian G. (Ed). Chiral Separation Techniques: A practical Approach. 3rd, completely revised and updated edition (2006), Wiley-VCH, Weinheim
19. Yaku K., and Morishita F. J. Biochem. Biophys. Methods 43 (2000) 59-76
20. White C. J. Chromatogr. A 1074 (2005) 163-173
21. White C., and Burnett J. J. Chromatogr. A 1074 (2005) 175-185
22. Terfloth G. J. Chromatogr. A 906 (2001) 301-307
23. Taylor L.T. Anal. Chem. 80 (2008) 4285-4294
24. Zhang Y., Wu D., Wang-Iverson D.B., and Tymiak A.A. Drug Discov. Today 10 (2005) 571-577
25. Maftouh M., Granier-Loyaux C., Chavana E., Marini J., Pradines A., Vander Heyden Y., and Picard C. J. Chromatogr. A 1088 (2005) 67-81
26. Kramal C.M., Zhou D., Byrne N., and McConnell O. J. Chromatogr. A 1100 (2005) 108-115
27. Nogle L., Mann C.W., Watts Jr. W.L., and Zhang Y. J. Pharm. Biomed. Anal. 40 (2006) 901-909
28. Toribio L., Alonso C., Del Nozel M.J., Bernal J.L., and Martin M.T. J. Chromatogr. A 1137 (2006) 30-35
29. Del Nozel M.J., Toribio L., Bernal J.L., Nieto E.M., and Jimenez J.J. J. Biochem. Biophys. Methods 54 (2002) 339-345
30. Wu D., Leith L., Balasubramanian B., Palcic T., and Wang-Iverson D. Am. Lab. 38 (2006) 24-26
31. Ye Y.K., Lynam K.G., and Stringham R.W. J. Chromatogr. A 1041 (2004) 211-217
32. Stringham R.W. J. Chromatogr. A 1070 (2005) 163-170