Crystal structure of the potent bisquinoline antimalarial agent (±)-trans-N1,N2-bis(7-chloroquinolin-4-yl) cyclohexane-1,2-diamine dimethanesulfonate salt hydrate in relation to its biological properties

Journal of Chemical Crystallography

Volumn 32, Issue 5-6, 2002, Pages 133-139

  Karle, Jean M ^a   Bhattacharjee, Apurba K ^a   Vennerstrom, Jonathan L ^b  

^a WALTER REED ARMY INSTITUTE OF RESEARCH   (United States)

^b UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

Author keywords

Antimalarial agent; Bisquinoline; Hematin polymerization; Phototoxicity

Indexed keywords

ANTIMALARIAL AGENT; CHLOROQUINE; N,N BIS(7 CHLOROQUINOLIN 4 YL)CYCLOHEXANE 1,2 DIAMINE DIMETHANESULFONATE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; CRYSTALLIZATION; DRUG POTENCY; ELECTRICITY; HYDROGEN BOND; PHARMACOPHORE; POLYMERIZATION; PREDICTION; PROTON TRANSPORT; QUANTUM CHEMISTRY;

HOMO;

EID: 0036275729     PISSN: 10741542     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1015602002694     Document Type: Article

References (14)

1. Vennerstrom, J.L.; Ellis, W.Y.; Ager, A.L.; Andersen, S.L.; Gerena, L.; Milhous, W.K. J. Med. Chem. 1992, 35, 2129.
2. Basco, L.K.; Andersen, S.L.; Milhous, W.K.; Le Bras, J.; Vennerstrom, J.L. Am. J. Trop. Med. Hyg. 1994, 50, 200.
3. Ridley, R.G.; Matile, H.; Jaquet, C.; Dorn, A.; Hofheinz, W.; Leupin, W. ; Masciadri, R.; Theil, F.; Richter, W.F.; Girometta, M.; Guenzi, A.; Urwyler, H.; Gocke, E.; Potthast, J.; Csato, M.; Thomas, A.; Peters, W. Antimicrob. Agents Chemother. 1997, 41, 677.
4. Raynes, K. Int. J. Parasitol. 1999, 29, 367.
5. Dorn, A.; Vippagunta, S.R.; Matile, H.; Bubendorf, A.; Vennerstrom, J.L. ; Ridley, R. G. Biochem. Pharmacol. 1998, 55, 737.
6. Sheldrick, G.M. SHELXTL software; University of Göttingen: Germany, 1990.
7. Sheldrick, G.M. SHELX-97; University of Göttingen: Germany, 1997.
8. Spartan SGI, Version 5.1.3OpenGL; Wavefunction: Irvine, CA, 1998.
9. Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Zakrzewski, V.G.; Montgomery, J.A., Jr.; Stratmann, R.E.; Burant, J.C.; Dapprich, S.; Millam, J.M.; Daniels, A.D.; Kudin, K.N.; Strain, M.C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G.A.; Ayala, P.Y.; Cui, Q.; Morokuma, K.; Malick, D.K.; Rabuck, A.D.; Raghavachari, K.; Foresman, J.B.; Cioslowski, J.; Ortiz, J.V.; Baboul, A.G.; Stefanov, B.B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R.L.; Fox, D.J.; Keith, T.; Al-Laham, M.A.; Peng, C.Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P.M.W.; Johnson, B.; Chen, W.; Wong, M.W.; Andres, J.L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E.S.; Pople, J.A. Gaussian 98, Revision A.7; Gaussian: Pittsburgh, PA, 1998.
10. Box, V.G.S.; Yu, H.W. J. Chem. Ed. 1997, 74, 1293.
11. Vippagunta, S.R.; Dorn, A.; Matile, H.; Bhattacharjee, A.K.; Karle, J.M. ; Ellis, W.Y.; Ridley, R.G.; Vennerstrom, J.L. J. Med. Chem. 1999, 42, 4630.
12. Ismail, F.M.D.; Dascombe, M.J.; Carr, P.; North, S.E. J. Pharm. Pharmacol. 1996, 48, 841.
13. Foley, M.; Tilley, L. Pharmacol. Ther. 1998, 79, 55.
14. Raynes, K. Int. J. Parasitol. 1999, 29, 367.