Determining the absolute configuration of (+)-mefloquine HCl, the side-effect-reducing enantiomer of the antimalaria drug lariam

Journal of the American Chemical Society

Volumn 134, Issue 6, 2012, Pages 3080-3083

  Schmidt, Manuel ^a   Sun, Han ^a   Rogne, Per ^b,c   Scriba, Gerhard K E ^d   Griesinger, Christian ^a   Kuhn, Lars T ^b,c   Reinscheid, Uwe M ^a  

^a MAX PLANCK INSTITUTE FOR BIOPHYSICAL CHEMISTRY   (Germany)

^b EUROPEAN NEUROSCIENCE INSTITUTE   (Germany)

^c Deutsche Forschungsgemeinschaft   (Germany)

^d FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATION; ADENOSINE RECEPTOR; ADVERSE SIDE EFFECTS; ANOMALOUS X-RAY DIFFRACTION; CD SPECTRA; DENSITY FUNCTIONAL THEORY CALCULATIONS; ENANTIOSELECTIVE SYNTHESIS; EXPERIMENTAL VALUES; HUMAN BRAIN; OPTICAL ROTATORY DISPERSION; OVERHAUSER EFFECT; RESIDUAL DIPOLAR COUPLINGS; SCALAR COUPLING; STRUCTURAL MODELS;

CHIRALITY; ENANTIOMERS; MODEL STRUCTURES; OPTICAL ROTATION; X RAY DIFFRACTION;

MALARIA CONTROL;

ANTIMALARIAL AGENT; MEFLOQUINE;

ARTICLE; CIRCULAR DICHROISM; DENSITY FUNCTIONAL THEORY; DRUG STRUCTURE; ENANTIOMER; ENANTIOSELECTIVITY; MALARIA; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OPTICAL ROTATORY DISPERSION; X RAY DIFFRACTION;

ANTIMALARIALS; BRAIN; CIRCULAR DICHROISM; HUMANS; HYDROCHLORIC ACID; MAGNETIC RESONANCE SPECTROSCOPY; MEFLOQUINE; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OPTICAL ROTATORY DISPERSION; RECEPTORS, PURINERGIC P1; TEMPERATURE; X-RAY DIFFRACTION;

EID: 84863414511     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja209050k     Document Type: Article

References (30)

1. Karle, J. M.; Olmeda, R.; Gerena, L.; Milhous, W. K. Exp. Parasitol. 1993, 76, 345-351
2. Fletcher, A.; Shepherd, R. U.S. Patent 6,664,397, 2003.
3. Croft, A. M. J.; World, M. J. Lancet 1996, 347, 326-326
4. Gullahorn, G. M.; Bohman, H. R.; Wallace, M. R. Lancet 1993, 341, 632-632
5. Carroll, F. I.; Blackwell, J. T. J. Med. Chem. 1974, 17, 210-219
6. Karle, J. M.; Karle, I. L. Antimicrob. Agents Chemother. 2002, 46, 1529-1534
7. Trost, B. M.; Brindle, C. S. Chem. Soc. Rev. 2010, 39, 1600-1632
8. Hoye, T. R.; Jeffrey, C. S.; Shao, F. Nat. Protoc. 2007, 2, 2451-2458
9. Xie, Z. X.; Zhang, L. Z.; Ren, X. J.; Tang, S. Y.; Li, Y. Chin. J. Chem. 2008, 26, 1272-1276
10. Gargiulo, V.; Morando, M. A.; Silipo, A.; Nurisso, A.; Perez, S.; Imberty, A.; Canada, F. J.; Parilli, M.; Jimenez-Barbero, J.; De Castro, C. Glycobiology 2010, 20, 1208-1216
11. Frank, A. T.; Stelzer, A. C.; Al-Hashimi, H. M.; Andricioaei, I. Nucleic Acids Res. 2009, 37, 3670-3679
12. Gabel, F.; Simon, B.; Nilges, M.; Petoukhov, M.; Svergun, D.; Sattler, M. J. Biomol. NMR 2008, 41, 199-208
13. Lange, O. F.; Lakomek, N. A.; Fares, C.; Schröder, G. F.; Walter, K. F. A.; Becker, S.; Meiler, J.; Grubmüller, H.; Griesinger, C.; de Groot, B. L. Science 2008, 320, 1471-1475
14. Thiele, C. M.; Marx, A.; Berger, R.; Fischer, J.; Biel, M.; Giannis, A. Angew. Chem., Int. Ed. 2006, 45, 4455-4460
15. Schütz, A.; Junker, J.; Leonov, A.; Lange, O.; Molinski, T.; Griesinger, C. J. Am. Chem. Soc. 2007, 129, 15114-15115
16. Sun, H.; dAuvergne, E. J.; Reinscheid, U. M.; Dias, L. C.; Andrade, C. K. Z.; Rocha, R. O.; Griesinger, C. Chem.-Eur. J. 2011, 17, 1811-1817
17. Tønnesen, H. H.; Grislingaas, A.-L. Int. J. Pharm. 1990, 60, 157-162
18. Go, M.-L.; Lee, H.-S.; Ngiam, T.-L. Biol. Pharm. Bull. 1993, 16, 668-674
19. Frisch, M. J.; Gaussian 09, revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
20. Mennucci, B.; Tomasi, J. J. Chem. Phys. 1997, 106, 5151-5158
21. MSpin. Mestrelab Research SL: Santiago de Compostela, Spain; http://www.mestrelab.com.
22. Hallwass, F.; Schmidt, M.; Sun, H.; Mazur, A.; Kummerlöwe, G.; Luy, B.; Navarro-Vázquez, A.; Griesinger, C.; Reinscheid, U. M. Angew. Chem., Int. Ed. 2011, 50, 9487-9490
23. Polavarapu, P. L. Chirality 2008, 20, 664-672
24. Petrovic, A. G.; Navarro-Vázquez, A.; Alonso-Gómez, J. L. Curr. Org. Chem. 2010, 14, 1612-1628
25. Bringmann, G.; Bruhn, T.; Maksimenka, K.; Hemberger, Y. Eur. J. Org. Chem. 2009, 2717-2727
26. Autschbach, J. Chirality 2009, 21, E116-E152
27. Bürgi, T.; Baiker, A. J. Am. Chem. Soc. 1998, 120, 12920-12926
28. Urakawa, A.; Meier, D. M.; Rüegger, H.; Baiker, A. J. Phys. Chem. A 2008, 112, 7250-7255
29. Keiser, J.; Chollet, J.; Xiao, S.-H.; Mei, J.-Y.; Jiao, P.-Y.; Utzinger, J.; Tanner, M. PLoS Neglected Trop. Dis. 2009, 3 e350
30. Jayaprakash, S.; Iso, Y.; Wan, B.; Franzblau, S. G.; Kozikowski, A. P. ChemMedChem 2006, 1, 593-597