Confirmation of the structure of (3S)-3-hydroxyquinine: Synthesis and X-ray crystal structure of its 9-aceto analogue

Journal of Natural Products

Volumn 68, Issue 6, 2005, Pages 942-944

  Srirama Sarma, P V V ^a   Han, Dongmei ^a   Deschamps, Jefferey R ^b   Cook, James M ^a  

^a UNIVERSITY OF WISCONSIN MILWAUKEE   (United States)

^b NAVAL RESEARCH LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXYQUININE; 3 HYDROXYQUININE 9 ACETATE; QUININE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHROMATOGRAPHY; CRYSTAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TRANSFORMATION; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR OVERHAUSER EFFECT; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; QUINIDINE; QUININE; STEREOISOMERISM;

CINCHONA PUBESCENS;

EID: 22544485650     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np050015g     Document Type: Article

References (17)

1. White, N. J. Clin. Pharmacokin. 1985, 10, 187-215.
2. List, A. F. Leukemia 1996, 10, 937-942.
3. Barrow, S. E.; Taylor, A. A.; Horning, E. C.; Horning, M. G. J. Chromatogr. 1980, 181, 219-226.
4. Wanwimolruk, S.; Wong, S. M.; Zhang, H.; Coville, P. F.; Walker, R. J. J. Pharm. Pharmacol. 1995, 47, 957-963.
5. Guengerich, F. P.; Muller-Enoch, D. M.; Blair, I. A. Mol. Pharmacol. 1986, 30, 287-295.
6. Zhao, X. J.; Yokoyama, H.; Chiba, K.; Wanwimolruk, S.; Ishizaki, T. J. Pharmacol. Exp. Ther. 1996, 279, 1327-1334.
7. Zhang, H.; Coville, P. F.; Walker, R. J.; Miners, J. O.; Birkett, D. J.; Wanwimolruck, S. Br. J. Clin. Pharmacol. 1997, 43, 245-252.
8. Carroll, F. I.; Philip, A.; Coleman, M. C. Tetrahedron Lett. 1976, 21, 1757-1760.
9. Diaz-Arauzo, H. Synthesis, High-Resolution NMR Spectroscopy of the Metabolites of Quinine and Quinidine and Antibody-Mediated Platelet Destruction. M.S. Thesis, University of Wisconsin-Milwaukee, WI, 1988.
10. Mirghani, R. A.; Ericsson, O.; Gustafsson, L. L. J. Chromatogr. B 1998, 708, 209-216.
11. Bannon, P.; Yu, P.; Cook, J. M.; Roy, L.; Villeneuve, J. P. J. Chromatogr. B 1998, 715, 387-393.
12. Mirghani, R. A.; Ericsson, O.; Cook, J. M.; Yu, P.; Gustafsson, L. L. J. Chromatogr. B 2001, 754, 57-64.
13. Diaz-Arauzo, H.; Cook, J. M.; Christie, D. J. J. Nat. Prod. 1990, 53, 112-124.
14. Yu, P.; Wang, T.; Li, J.; Cook, J. M. J. Org. Chem. 2000, 65, 3173-3191.
15. Brodie, B. B.; Baer, J. E.; Craig, L. C. J. Biol. Chem. 1951, 188, 567-581.
16. Cambridge Crystallographic Database, 12 Union Road, Cambridge CBZ 1EZ, UK (deposit@ccdc.cam.ac.uk).
17. SHELXTL v6.10; Bruker AXS Inc.: Madison, WI, 2000.