Ab initio quantum chemical analysis of stereoelectronic properties may explain in vitro antileishmanial activity of some macrocyclic bisbenzylisoquinoline alkaloids

International Journal of Quantum Chemistry

Volumn 75, Issue 6, 1999, Pages 995-1002

  Bhattacharjee, Apurba K ^a  

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

Author keywords

Ab initio quantum chemical; Antileishmanial activity; Bisbenzylisoquinolines; Stereoelectronic properties

Indexed keywords

EID: 0005160786     PISSN: 00207608     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1097-461x(1999)75:6<995::aid-qua3>3.0.co;2-%23     Document Type: Article

References (25)

1. Pitzer, K. K.; Werbovetz, K. A.; Brendle, J. J.; Scovill, J. P. J Med Chem 1998, 41, 4885-4889.
2. WHO Report, Disease sheet: Leishmaniasis, 1997.
3. Iwu, M. M.; Jackson, J. E.; Schuster, B. G. Parasitology Today 1994, 10, 65-68.
4. Anon. Public Health Laboratory Service, Malaria Reference Laboratory Report; London School of Hygiene and Tropical Medicine, 1990.
5. Ashford, R. W.; Desjeux, P.; deRaadt, P. Parasitology Today 1992, 8, 104-105.
6. Chang, K. P.; Fong, D.; Bray, R. S. In Biology of Leishmania and Leishmaniasis: Elsevier Biomedical Press: Amsterdam, 1985, Vol. 1, pp. 1-50.
7. Bryceson, A. In Therapy in Man: The Leishmaniases in Biology and Medicine, Clinical Aspects and Control; Peters, W.; Killick-Kendrick, R., Ed.; Academic: New York, 1987, Vol. 2, pp. 847-907.
8. Croft, S. L. Trends Pharmacol Sci 1988, 9, 376-381.
9. Olliaro, P. L.; Bryceson, A. D. M. Parasitology Today 1993, 9, 323-328.
10. Al-Majali, O.; Routh, H. B.; Abuloham, O.; Bhowmik, K. R.; Muhsen, M.; Hebeheba, H. Int J Dermatol 1997, 36, 460-462.
11. Velasco-Castrejon, O.; Walton, B. C.; Rivas-Sanchez, B.; Garcia, M. F.; Lazaro, G. J.; Hobart, O.; Roldan, S.; Floriani-Verdugo, J.; Munguia-Saldana, A.; Berzaluce, R. Am J Trop Med Hyg 1997, 57, 309-312.
12. Schiff, P. L. J Nat Products 1991, 34, 645-648.
13. Fournet, A.; Munoz, V.; Manjon, A. M.; Angelo, A. M. A.; Hocquemiller, R.; Cortes, D.; Cave, A.; Bruneton, J. J Ethnopharmacol 1988, 24, 327-335.
14. Karelson, M.; Lobanov, V. S.; Katritzky, A. R. Chem Rev 1996, 96, 1027-1044.
15. Boyd, D. B. In Reviews in Computational Chemistry; Indiana University-Purdue University at Indianapolis (IUPUI), 1997.
16. O'Neill, P. M.; Willock, D. J.; Hawley, S. R.; Bray, P. G.; Storr, R. C.; Ward, S. A.; Park, B. K. J Med Chem 1997, 40, 437-448.
17. Bhattacharjee, A. K.; Karle, J. M. Bioorg Med Chem 1998, 6, 1927-1933.
18. Bhattacharjee, A. K.; Karle, J. M. J Med Chem 1996, 39, 4622.
19. Bhattacharjee, A. K.; Pundlik, S. S.; Cadre, S. R. Cancer Investigation 1997, 15, 531-541.
20. Bhattacharjee, A. K.; Majumdar, D.; Guha, S. J Chem Soc Perkin Trans 2 1992, 805-809.
21. Dewar, M. J. S.; Zoebisch, E. G.; Horsley, E. F.; Stewart, J. J. P. J Am Chem Soc 1985, 107, 3902-3909.
22. SPARTAN version 5.1, Wavefunction, Inc., 18401 Von Karman Ave., #370, Irvine, CA 92715.
23. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T. A.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94 (Revision A.1), Gaussian Inc., Pittsburgh, PA, 1995.
24. Dixon, R. W.; Leonard, J. M.; Hehre, W. J. Israel J Chem 1993, 33, 427-434.
25. Pearson, R. G. J. J Org Chem 1989, 54, 1423-1430.