A spectroscopic and computational study of an electrocyclized photo-degradation product of 6-(2-(5-chloro-2-(2,4-difluorobenyzloxy)phenyl) cyclopent-1-enyl)picolinic acid

Journal of Molecular Structure

Volumn 984, Issue 1-3, 2010, Pages 246-261

  Vogt, Frederick G ^a   Wu, Lianming ^a   Olsen, Mark A ^a   Clark, William M ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

Density functional theory; Electrocyclization; Mass spectrometry; Nuclear magnetic resonance; Smiles rearrangement; UV Visible spectroscopy

Indexed keywords

ACCURATE MASS; COMPUTATIONAL STUDIES; DFT METHOD; DRUG CANDIDATES; ELECTROCYCLIZATION; EXCHANGEABLE PROTONS; EXPERIMENTAL DATA; EXPERIMENTAL VALUES; LC-MS N; NMR ANALYSIS; NUCLEAR OVERHAUSER EFFECTS; PICOLINIC ACID; PREPARATIVE CHROMATOGRAPHY; SMILES REARRANGEMENT; STOPPED FLOW; STRUCTURAL ASSIGNMENTS; STRUCTURAL IDENTIFICATION; TIME-DEPENDENT DFT; TRANSITION STATE; UV VISIBLE SPECTROSCOPY; UV-VISIBLE;

ACIDS; DENSITY FUNCTIONAL THEORY; ELECTROSPRAY IONIZATION; EXPERIMENTS; INFRARED SPECTROPHOTOMETERS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTODEGRADATION; RESONANCE; SPECTRUM ANALYSIS; ULTRAVIOLET SPECTROSCOPY;

NUCLEAR MAGNETIC RESONANCE;

EID: 78649333774     PISSN: 00222860     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molstruc.2010.09.036     Document Type: Article

References (58)

1. R. Nageswara Rao, and V. Nagaraju J. Pharm. Biomed. Anal. 33 2003 335 377
2. S. Ahuja Adv. Drug Deliv. Rev. 59 2007 3 11
3. International Conference on Harmonisation, Guidance for Industry, ICH Q3A (R2), Impurities in New Drug Substances, Proceedings of the International Conference on Harmonization, EMEA, London, 2006.
4. D. Jacobson-Kram, and T. McGovern Adv. Drug Deliv. Rev. 59 2007 38 42
5. A.K. Basak, A.S. Raw, A.H. Al Hakim, S. Furness, N.I. Samaan, D.S. Grill, H.B. Patel, R.F. Powers, and L. Yu Adv. Drug Deliv. Rev. 59 2007 64 72
6. M.P. Argentine, P.K. Owens, and B.A. Olsen Adv. Drug Deliv. Rev. 59 2007 12 28
7. J.T. Carstensen Drug Stability: Principles and Practices 1990 Marcel-Dekker New York
8. International Conference on Harmonisation, Guidance for Industry, ICH Q1B, Stability Testing of New Drug Substances and Products, Proceedings of the International Conference on Harmonization, EMEA, London, 1996.
9. L. Wu, T.Y. Hong, and F.G. Vogt J. Pharm. Biomed. Anal. 44 2007 763 772
10. M. Matsuo, Y. Machida, H. Furuichi, K. Nakamura, and Y. Takeda Drug Stabil. 1 1996 179 187
11. M.A. Olsen, P.G. Cummings, S. Kennedy-Gabb, B.M. Wagner, G.R. Nicol, and B. Munson Anal. Chem. 72 2000 5070 5078
12. G. Terfloth Preparative isolation of impurities R. Smith, M. Webb, Analysis of Drug Impurities 2007 Wiley-Blackwell New York
13. J.C. Lindon, J.K. Nicholson, and I.D. Wilson Prog. NMR Spectrosc. 29 1996 1 49
14. S.X. Peng, B. Borah, R.L.M. Dobson, Y.D. Liu, and S. Pikul J. Pharm. Biomed. Anal. 20 1999 75 89
15. W. Feng, H. Liu, G. Chen, R. Malchow, F. Bennett, E. Lin, B. Pramanik, and T.M. Chan J. Pharm. Biomed. Anal. 25 2001 545 557
16. G.J. Sharman, and I.C. Jones Magn. Reson. Chem. 41 2003 448 454
17. M. Spraul, A.S. Freund, R.E. Nast, R.S. Withers, W.E. Maas, and O. Corcoran Anal. Chem. 75 2003 1546 1551
18. C. Pan, F. Liu, Q. Ji, W. Wang, D. Drinkwater, and R. Vivilecchia J. Pharm. Biomed. Anal. 40 2006 581 590
19. G.S. Walker, and T.N. O'Connell Exp. Opin. Drug Metab. Toxicol. 4 2008 1295 1305
20. E.J. Delaney Reg. Toxicol. Pharm. 49 2007 107 124
21. T. McGovern, and D. Jacobson-Kram Trends Anal. Chem. 25 2006 790 795
22. S.C. McKeown, A. Hall, G. M.P. Giblin, O. Lorthioir, R. Blunt, X.Q. Lewell, R.J. Wilson, S.H. Brown, A. Chowdhury, T. Coleman, S.P. Watson, I.P. Chessell, A. Pipe, N. Clayton, and P. Goldsmith Bioorg. Med. Chem. Lett. 16 2006 4767 4771
23. H. Kawahara, T. Sakamoto, S. Takeda, H. Onodera, J. Imaki, and R. Ogawa Anesth. Analg. 93 2001 1012
24. D. Neuhaus, I.M. Ismail, and C.W. Chung J. Magn. Reson. A 118 1996 256 263
25. R.E. Hurd J. Magn. Reson. 87 1990 422 428
26. D. Neuhaus, and M.P. Williamson The Nuclear Overhauser Effect in Structural and Conformational Analysis second ed. 2000 Wiley-VCH New York
27. L.E. Kay, P. Keifer, and T. Saarinen J. Am. Chem. Soc. 114 1991 151 170
28. J. Schleucher, M. Schwendinger, M. Sattler, P. Schmidt, O. Schedletzky, S.J. Glaser, O.W. Sorenson, and C. Griesinger J. Biomol. NMR 4 1994 301 306
29. A. Tannus, and M. Garwood NMR Biomed. 10 1997 424 434
30. S. Braun, H.O. Kalinowski, and S. Berger 150 and More Basic NMR Experiments second ed. 1998 Wiley-VCH New York
31. T.A. Halgren J. Comp. Chem. 17 1996 490 519
32. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople Gaussian 03, Revision D.02 2004 Gaussian, Inc. Wallingford, CT
33. A.D. Becke J. Chem. Phys. 98 1993 5648 5652
34. M. Kaupp, M. Bühl, V.G. Malkin, Calculation of NMR and EPR Parameters: Theory and Applications 2004 Wiley-VCH Weinheim
35. W. Koch, and M.C. Holthausen A Chemist's Guide to Density Functional Theory 2001 Wiley-VCH Weinheim
36. P.R. Rablen, S.A. Pearlman, and J. Finkbiner J. Phys. Chem. A 103 1999 7357 7363
37. M. Cossi, G. Scalmani, N. Rega, and V. Barone J. Chem. Phys. 117 2002 43 54
38. M.T. Cancs, B. Mennucci, and J. Tomasi J. Chem. Phys. 107 1997 3032 3041
39. B. Mennucci, and J. Tomasi J. Chem. Phys. 106 1997 5151 5158
40. R. Bauernschmitt, and R. Ahlrichs Chem. Phys. Lett. 256 1996 454 464
41. R.E. Stratmann, G.E. Scuseria, and M.J. Frisch J. Chem. Phys. 109 1998 8218 8224
42. C. Peng, and H.B. Schlegel Israel J. Chem. 33 1994 449 454
43. C. Peng, P.Y. Ayala, H.B. Schlegel, and M.J. Frisch J. Comp. Chem. 17 1996 49 56
44. H.O. Kalinowski, S. Berger, and S. Braun Carbon-13 NMR Spectroscopy 1991 New York Wiley pp. 522
45. J.R. Cheeseman, G.W. Trucks, T.A. Keith, and M.J. Frisch J. Chem. Phys. 104 1996 5497 5509
46. F.G. Vogt, G.P. Spoors, Q. Su, Y.W. Andemichael, H. Wang, T.C. Potter, and D.J. Minick J. Mol. Struct. 797 2006 5 24
47. A. Gryff-Keller, and S. Molchanov Mol. Phys. 102 2004 1903 1908
48. L. Wu, D.Q. Liu, and F.G. Vogt Rapid Commun. Mass Spectrom. 20 2006 2614 2620
49. A.A. Levy, H.C. Rains, and S. Smiles J. Chem. Soc. 1931 3264 3269
50. H.-Y. Wang, X. Zhang, R. Qian, Y.-L. Guo, and L. Lu Rapid Commun. Mass Spectrom. 20 2006 2773 2776
51. L. Wu, L. Zhou, F.G. Vogt, and D.Q. Liu J. Pharm. Biomed. Anal. 51 2010 577 582
52. H.-Y. Wang, X. Zhang, Y.-L. Guo, Q.-H. Tang, and L. Lu J. Am. Soc. Mass Spectrom. 17 2006 253 263
53. H.-Y. Wang, X. Zhang, Y.-L. Guo, X.-C. Dong, Q.-H. Tang, and L. Lu Rapid Commun. Mass Spectrom. 19 2005 1696 1702
54. H.-Y. Wang, Y.-L. Guo, and L. Lu J. Am. Soc. Mass Spectrom. 15 2004 1820 1832
55. R.E. March Quadrupole ion trap mass spectrometers R.A. Meyers, Encyclopedia of Analytical Chemistry 2000 Wiley Chichester
56. A. Gilbert Cyclization of stilbene and its derivatives W. Horspool, F. Lenci, The CRC Handbook of Organic Photochemistry and Photobiology second ed. 2004 CRC Press Boca Raton (Chapter 33)
57. F.A. Carey, and R.J. Sundberg Advanced Organic Chemistry, Part A fourth ed. 2000 Kluwer/Plenum New York pp. 747-753
58. C. Carra, T. Bally, T.A. Jenny, and A. Albini Photochem. Photobiol. Sci. 1 2002 38 44