Synthesis of 2-azabicyclo [3.2.2]nonanes from bicyclo [2.2.2]octan-2-ones and their activities against Trypanosoma brucei rhodesiense and Plasmoduim falciparum K1

Journal of Pharmacy and Pharmaceutical Sciences

Volumn 8, Issue 3, 2005, Pages 578-585

  Seebacher, Werner ^a   Weis, Robert ^a   Kaiser, Marcel ^b   Brun, Reto ^b   Saf, Robert ^a  

^a UNIVERSITY OF GRAZ   (Austria)

^b SWISS TROPICAL AND PUBLIC HEALTH INSTITUTE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

(7,8 DIPHENYL 2 AZABICYCLO[3.2.2]NON 5 YL)DIMETHYLAMINE; 1 (7,8 DIPHENYL 2 AZABICYCLO[3.2.2]NON 5 YL)MORPHOLINE; 1 (7,8 DIPHENYL 2 AZABICYCLO[3.2.2]NON 5 YL)PIPERIDINE; 1 (7,8 DIPHENYL 2 AZABICYCLO[3.2.2]NON 5 YL)PYRROLIDINE; 5 (1 MORPHOLINYL) 7,8 DIPHENYL 2 AZABICYCLO[3.2.2]NONAN 3 ONE; 5 DIMETHYLAMINO 7,8 DIPHENYL 2 AZABICYCLO[3.2.2]NONAN 3 ONE; 7,8 DIPHENYL 5 (1 PIPERIDYL) 2 AZABICYCLO[3.2.2]NONAN 3 ONE; 7,8 DIPHENYL 5 (1 PYRROLIDYL) 2 AZABICYCLO[3.2.2]NONAN 3 ONE; ANTIMALARIAL AGENT; ANTIPROTOZOAL AGENT; ANTITRYPANOSOMAL AGENT; ARTEMISIN; AZABICYCLO[3.2.2]NONANE DERIVATIVE; BICYCLO[2.2.2]OCTAN 2 ONE DERIVATIVE; CHLOROQUINE; MEFLOQUINE; MELARSOPROL; PYRIMETHAMINE; SURAMIN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIMALARIAL ACTIVITY; ANTIPROTOZOAL ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; IC 50; IN VITRO STUDY; IN VIVO STUDY; MALE; MOUSE; NONHUMAN; PARASITEMIA; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; TRYPANOSOMA BRUCEI; TRYPANOSOMA RHODESIENSE;

ANIMALS; BICYCLO COMPOUNDS, HETEROCYCLIC; CELLS, CULTURED; HUMANS; MALARIA, FALCIPARUM; MALE; MICE; OCTANOLS; PLASMODIUM FALCIPARUM; TRYPANOSOMA BRUCEI RHODESIENSE; TRYPANOSOMIASIS, AFRICAN;

EID: 31544463315     PISSN: 14821826     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (27)

1. Burri, C., Nkunku, S., Merolle, A., Smith, T., Blum, J., Brun, R., Efficacy of new, concise schedule for melarsoprol in treatment of sleeping sickness caused by Trypanosoma brucei gambiense: a randomised trial. Lancet, 355:1419-1425, 2000.
2. Barrett, M.P., Burchmore, R.J.S., Stich, A., Lazzari, J.O., Frasch, A.C., Cazzulo, J.J., Krishna, S., The trypanosomiases. Lancet, 362:1469-1480, 2003.
3. World Health Organization, Human African Trypanosomiasis Treatment and Drug Resistance Network. Report of the first meeting. Geneva, World Health Organization, 14-15 April 1999, WHO/CDS/CSR/EDC/99.5. WHO:Geneva 1999.
4. Agbo, E.C., Majiwa, P.A.O., Büscher, P., Claassen, E., te Pas, M.F.W., Trypanosoma brucei genomics and the challenge of identifying drug and vaccine targets. Trends in Microbiology, 11:322-329, 2003.
5. Jennings, F.W., Rodgers, J., Bradley, B., Gettinby, G., Kennedy, P.G.E., Murray, M., Human African trypanosomiasis: Potential therapeutic benefits of an alternative suramine and melarsoprol regimen. Parasit Int, 51:381-388, 2002.
6. Berger, B.J., Carter, N.S., Fairlamb, A.H., Characterisation of pentamidine-resistant Trypanosoma brucei brucei. Mol Biochem Parasitol 69:289-298, 1995.
7. Barrett, M.P., The fall and rise of sleeping sickness. Lancet, 353:1113-1114, 1999.
8. Anene, B.M., Onah, D.N., Nawa, Y., Drug resistance in pathogenic African trypanosomes: what hopes for the future ? Vet Parasitol, 96:83-100, 2001.
9. Matovu, E., Seebeck, T., Enyaru, J.C.K., Kaminsky, R., Drug resistance in Trypanosoma brucei spp., the causative agents of sleeping sickness in man and nagana in cattle. Microbes Infect, 3:763-770, 2001.
10. Webster, D., Hill, A.V., Progress with Malaria vaccines. Bull World Health Organ, 81:902-909, 2003.
11. Newton, C.R.J.C., Krishna, S., Severe falciparum Malaria in Children: Current understanding of Pathophysiology and Supportive Treatment. Pharmacol Ther, 79:1-53, 1998.
12. Hyde, J.E., Mechanisms of resistance of Plasmodium falciparum to antimalarial drugs. Microbes Infect, 4:165-174, 2002.
13. Winstanley, P.A., Ward, S.A., Snow, R.W., Clinical status and implications of antimalarial drug resistance. Microbes Infect, 4:157-164, 2002.
14. Wongsrichanalai, C., Pickard, A. L., Wernsdorfer, E.H., Meshnik, S.R., Epidemiology of drug resistant malaria. Lancet Infect Dis, 2:209-218, 2002.
15. Tanser, F.C., le Suer, D., The application of geographical information systems to public health problems in Africa. Int J Health Geogr, 1:4, 2002.
16. Loutan, L., Malaria: still a threat to travellers. Int J Antimicrob. Agents, 21:158-163, 2003.
17. Meshnick, S.R., Artemisinin: mechanisms of action, resistance and toxicity. Int J Parasit, 32:1655-1660, 2002.
18. Sharma, P., Kumar, A., Pant, P., Prakash, S., Presumptive artemether resistance in a patient with mixed malarial infection. J Assoc Physicians India, 51: 233, 2003.
19. Turner, G.D., Artemether resistant P.falciparum. Cent Afr J Med, 41:263, 1995.
20. Wiesner, J., Ortmann, R., Jomaa, H., Schlitzer, M., Neue Antimalaria-Wirkstoffe. Angew Chem, 115:5432-5451, 2003.
21. Yang, H.L., Gao, B.H., Huang, K.G., Monitoring of sensitivity of artesunate-resistant Plasmodium falciparum to pyronaridine. Zhonggou Ji Sheng Chong Xue Yu Ji Sheng Chong Bing Za Zhi 18:320-321, 2000.
22. Weis, R., Schweiger, K., Seebacher, W., Belaj, F., One-pot synthesis of 4-Aminobicyclo[2.2.2]octan-2-ones. Tetrahedron 54:14015-14022, 1998.
23. Weis, R., Brun, R., Saf, R., Seebacher, W., 4-Aminobicyclo[2.2.2]octanone Derivatives with Antiprotozoal Activities. Monatsh Chem, 134:1019-1026, 2003.
24. Seebacher, W., Brun, R., Saf, R., Weis, R., 4-Aminobicyclo[2.2.2]octanone Derivatives with Antiplasmodial and Antitrypanosomal Activities. Monatsh Chem, 134:1411-1420, 2003.
25. Matile, H., Pink, J.R.L., Plasmodium falciparum malaria parasite cultures and their use in immunology, in: Lefkovits, I., Pernis, B., (eds.), Immunological Methods. Academic Press, San Diego, pp. 221-234, 1990.
26. Baltz, T., Baltz, D., Giroud, C., Crockett, J., Cultivation in a semi-defined medium of animal infective forms of Trypanosoma brucei, T. equiperdum, T. evansi, T. rhodesiense and T. gambiense. EMBO J, 4: 1273-1277, 1985.
27. Räz, B., Iten, M., Grether-Bühler, Y., Kaminsky, R., Brun, R., The Alamar Blue assay to determine drug sensitivity of African trypanosomes (T. b. rhodesiense and T. b. gambiense) in vitro. Acta Trop, 68: 139-147, 1997.