Effective discrimination of antimalarial potency of artemisinin compounds based on quantum chemical calculations of their reaction mechanism

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 7, 2006, Pages 2082-2088

  Tonmunphean, Somsak ^a   Parasuk, Vudhichai ^a   Kokpol, Sirirat ^a  

^a CHULALONGKORN UNIVERSITY   (Thailand)

Author keywords

Antimalarial activity; Endoperoxide; Mechanism of action; Transition state

Indexed keywords

ARTEMISININ; CARBON; HYDROGEN; OXYGEN; RADICAL;

ANTIMALARIAL ACTIVITY; ARTICLE; CALCULATION; DRUG DISCRIMINATION; DRUG POTENCY; GEOMETRY; KINETICS; QUANTUM CHEMISTRY; REACTION ANALYSIS; THERMODYNAMICS;

ANIMALS; ANTIMALARIALS; ARTEMISININS; KINETICS; MOLECULAR CONFORMATION; PLASMODIUM FALCIPARUM; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; QUANTUM THEORY; STEREOISOMERISM; THERMODYNAMICS;

EID: 32844466920     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.07.003     Document Type: Article

References (18)

1. Roll Back Malaria, World Health Organization, and UNICEF, World Malaria Report 2005.
2. S. Tonmunphean, V. Parasuk, and S. Kokpol Quant. Struct.-Act. Rel. 19 2000 475
3. S. Tonmunphean, S. Kokpol, and V. Parasuk J. Sci. Res. Chula. Univ. 29 2004 1
4. S.R. Krungkrai, and Y. Yuthavong Trans. R. Soc. Trop. Med. Hyg. 81 1987 710
5. A. Brossi, B. Venugopalan, L.D. Gerpe, H.J. Yeh, J.L. Flippen-Anderson, P. Buchs, X.D. Luo, W. Milhous, and W. Peters J. Med. Chem. 31 1988 645
6. S.R. Meshnick Int. J. Parasitol. 32 2002 1655 and references therein
7. S.R. Meshnick, Y.-Z. Yang, V. Lima, F. Kuypers, S. Kamchonwongpaisan, and Y. Yuthavong Antimicrob. Agents Chemother. 37 1993 1108
8. S. Kamchonwongpaisan, and S.R. Meshnick Gen. Pharmacol. 27 1996 587
9. W. Asawamahasakda, I. Ittarat, Y.-M. Pu, H. Ziffer, and S.R. Meshnick Antimicrob. Agents Chemother. 38 1994 1854
10. G.H. Posner, and C.H. Oh J. Am. Chem. Soc. 114 1992 8328
11. S. Tonmunphean, V. Parasuk, and S. Kokpol J. Mol. Struct. (THEOCHEM) 724 2005 99
12. M.A. Avery, S. Mehrotra, T.L. Johnson, J.D. Bonk, J.A. Vroman, and R. Miller J. Med. Chem. 39 1996 4149
13. J. Gu, K. Chen, H. Jiang, and J. Leszczynski J. Mol. Struct. (THEOCHEM) 491 1999 57
14. J. Gu, K. Chen, H. Jiang, and J. Leszczynski J. Phys. Chem. A 103 1999 9364
15. W.-M. Wu, Y. Wu, W.-L. Wu, Z.-J. Yao, C-M. Zhou, Y. Li, and F. Shan J. Am. Chem. Soc. 120 1998 3316
16. S. Tonmunphean, V. Parasuk, and S. Kokpol J. Mol. Model. 7 2001 26
17. S. Humbel, S. Sieber, and K. Morokuma J. Chem. Phys. 105 1996 1959
18. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, Jr., J. A.; 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.; Salvador, P.; Dannenberg, J. J.; 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.; 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.11, Gaussian: Pittsburgh PA, 2001.