Revealing Atropisomer Axial Chirality in Drug Discovery

ChemMedChem

Volumn 6, Issue 3, 2011, Pages 505-513

  Laplante, Steven R ^a   Edwards, Paul J ^a   Fader, Lee D ^a   Jakalian, Araz ^a   Hucke, Oliver ^a  

^a BOEHRINGER INGELHEIM CANADA LTD   (Canada)

Author keywords

Atropisomers; Axial hindrance; Chiral axis; Chirality; Drug discovery

Indexed keywords

LAQUINIMOD;

ARTICLE; CHIRALITY; CONTROLLED STUDY; DATA BASE; DIASTEREOISOMER; DRUG DESIGN; DRUG DEVELOPMENT; NONHUMAN; PRIORITY JOURNAL; QUANTUM MECHANICS; RACEMIC MIXTURE; STEREOISOMERISM; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION;

COMBINATORIAL CHEMISTRY TECHNIQUES; DATABASES, FACTUAL; DRUG EVALUATION, PRECLINICAL; PHARMACEUTICAL PREPARATIONS; QUANTUM THEORY; STEREOISOMERISM; THERMODYNAMICS;

EID: 79952083884     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.201000485     Document Type: Article

References (44)

1. M. Eichelbaum, A. S. Gross, Adv Drug Res. 1996, 28, 1-64;
2. R. J. Crossley, Chirality and the Biological Activity of Drugs, CRC Press, Boca Raton, 1995;
3. R. R. Shah, J. M. Midgley, S. K. Branch, Adverse Drug React. Toxicol. Rev. 1998, 17, 145-190.
4. G. Blaschke, H. P. Kraft, K. Fickentscher, F. Köhler, Arzneim.-Forsch. 1979, 29, 1640-1642;
5. S. Fabro, R. L. Smith, R. T. Williams, Nature 1967, 215, 296-297;
6. M. Reist, P.-A. Carrupt, E. Francotte, B. Testa, Chem. Res. Toxicol. 1998, 11, 1521-1528;
7. T. Eriksson, S. Bjorkman, B. Roth, A. Fyge, P. Hoglund, Chirality 1995, 7, 44-52.
8. I. Agranat, H. Caner, J. Caldwell, Nat. Rev. Drug Discovery 2002, 1, 753-768;
9. A. M. Rouhi, Chem. Eng. News 2003, 81, (18), 56-61.
10. J. Clayden, W. J. Moran, P. J. Edwards, S. R. LaPlante, Angew. Chem. 2009, 121, 6516-6520; Angew. Chem. Int. Ed. 2009, 48, 6398-6401.
11. M. Oki, Topics in Stereochemistry 1983, 14, 1-81.
12. Examples (and references within) of molecular systems in which atropisomers have been noted to be implicated.
13. J. L. Gustafson, D. Lim, S. J. Miller, Science 2010, 328, 1251-1255;
14. I. Kania-Korwel, M. H. M. E. El-Komy, P. Veng-Pedersen, H.-J. Lehmler, Environ. Sci. Technol. 2010, 44, 2828-2835;
15. D. Vizitiu, B. J. Halden, R. P. Lemieux, Chem. Commun. 1997, 1123-1124;
16. B. A. Dreikorn, G. P. Jourdan, H. R. Hall, J. B. Deeter, N. J. Jones, J. Agric. Food Chem. 1990, 38, 549-552;
17. A. Jamshidi, S. Hunter, S. Hazrati, S. Harrad, Environ. Sci. Technol. 2007, 41, 2153-2158;
18. G. Bringmann, D. Menche, Acc. Chem. Res. 2001, 34, 615-624;
19. J. Clayden, S. P. Fletcher, J. J. W. McDouall, S. J. M. Rowbottom, J. Am. Chem. Soc. 2009, 131, 5331-5343;
20. R. D. Stipanovic, L. S. Puckhaber, J. Liu, A. A. Bell, J. Agric. Food Chem. 2009, 57, 566-571.
21. Y. S. Zhou, L. K. Tay, D. Hughes, S. Donahue, J. Clin. Pharmacol. 2004, 44, 680-688.
22. J. Clayden, Chem. Commun. 2004, 127-135.
23. S. D. Guile, J. R. Bantick, D. R. Cheshire, M. E. Cooper, A. M. Davis, D. K. Donald, R. Evans, C. Eyssade, D. D. Ferguson, S. Hill, R. Hutchinson, A. H. Ingall, L. P. KingstonMartin, B. P. Martin, R. T. Mohammed, C. Murray, M. W. D. Perry, R. H. Reynolds, P. V. Thorne, D. J. Wilkinson, J. Withnall, Bioorg. Med. Chem. Lett. 2006, 16, 2260-2265.
24. Department of Health and Human Services, U.S. Food and Drug Administration, FDA's Policy Statement for the Development of New Stereoisomeric Drugs, WashingtonDC, 1992: (Last accessed: December 22, 2010);
25. S. Miller, Chirality 2006, Busan, Korea, June 26, 2006 [ (Last accessed: December 22, 2010)].
26. P. Eveleigh, E. C. Hulme, C. Schudt, N. J. M. Birdsall, Mol. Pharmacol. 1989, 35, 477-483.
27. R. J. Friary, M. Spangler, R. Osterman, L. Schulman, J. H. Schwerdt, Chirality 1996, 8, 364-371.
28. I. Fitos, J. Visy, F. Zsila, Z. Bikádi, G. Mády, M. Simonyi, Biochem. Pharmacol. 2004, 67, 679-688;
29. N. Trendafilova, G. Bauer, T. Mihaylov, Chem. Phys. 2004, 302, 95-104;
30. L. Afzelius, I. Zamora, M. Ridderström, T. B. Andersson, A. Karlén, C. M. Masimirembwa, Mol. Pharmacol. 2001, 59, 909-919.
31. G. Comi, A. Pulizzi, M. Rovaris, O. Abramsky, T. Arbizu, A. Boiko, R. Gold, E. Havrdova, S. Komoly, K. Selmaj, B. Sharrack, M Filippi, Lancet 2008, 371, 2085-2095;
32. C. Polman, F. Barkhof, M. Sandberg-Wollheim, A. Linde, O. Nordle, T. Nederman, Neurology 2005, 64, 987-991;
33. K. Jansson, T. Fristedt, A. Olsson, B. Svensson, S. Jönsson, J. Org. Chem. 2006, 71, 1658-1667.
34. M. Dooley, B. Jarvis, Drugs 2000, 59, 1169-1186;
35. T. Arbughi, F. Bertani, R. Celeste, P. Tirone, J. Chromatography B 1999, 729, 323-332;
36. A. Gallotti, F. Uggeri, A. Favilla, M. Cabrini, C. DeHaen, Eur. J. Radiol. 1994, 18, S1-S12;
37. W. Seitz, J.-Q. JiangWeber, B. J. Lloyd, M. Maier, D. Maier, Environ. Chem. 2006, 3, 35-39.
38. E. Azanli, R. Rothchild, A.-M. Sapse, Spectrosc. Lett. 2002, 35, 257-274;
39. H.-Y. Yun, S.-P. Lee, H. H. Jeong, Y.-R. Yoon, S. J. Sohn, S. K. Kim, W. Kang, K.-I. Kwon, Talanta 2007, 73, 635-643;
40. Y. Yamada, M. Otsuka, J. Tani, T. Oine, Chem. Pharm. Bull. 1983, 31, 1158-1165;
41. F. Prost, W. Thormann, Electrophoresis 2003, 24, 2598-2607;
42. Y. MacHida, H. Nishi, K. Nakamura, H. Nakai, T. Sato, J. Chromatogr. A 1998, 805, 85-92.
43. W. Gao, J. Kang, J. Chromatogr. A 2006, 1108, 145-148;
44. J. Jin, H. Sun, H. Wei, G. Liu, Invest. New Drugs 2006, 25, 95-105.