Febrifugine analogue compounds: Synthesis and antimalarial evaluation

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 2, 2012, Pages 927-932

  Zhu, Shuren ^a   Chandrashekar, Gudise ^a   Meng, Li ^a   Robinson, Katie ^a   Chatterji, Dipsanker ^b  

^a Radix Pharmaceuticals Inc   (United States)

^b CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

Antimalarial; Febrifugine; Natural products; Preclinical evaluation

Indexed keywords

3 [2 (3 BENZYLOXY PYRROLIDIN 2 YL) 2 OXO ETHYL] 3H PYRIDO[3,2 D]PYRIMIDIN 4 ONE; 3 [2 (3 ETHOXY PYRROLIDIN 2 YL) 2 OXO ETHYL] 5 FLUORO 3H QUINAZOLIN 4 ONE; 3 [2 (3 HYDROXY PYRROLIDIN 2 YL) 2 OXO ETHYL] 3H PYRIDO[3,2 D]PYRIDINE 4 ONE; 3 [2 (3 HYDROXY PYRROLIDIN 2 YL) 2 OXO ETHYL] 3H PYRIDO[3,2 D]PYRIMIDINE 4 ONE; 3 [2 (3 HYDROXY PYRROLIDIN 2 YL) 2 OXO ETHYL] 3H PYRIDO[4,3 D]PYRIDINE 4 ONE; 3 [2 (3 HYDROXY PYRROLIDIN 2 YL) 2 OXO ETHYL] 3H QUINAZOLIN 4 ONE; 3 [2 (3 HYDROXY PYRROLIDIN 2 YL) 2 OXO ETHYL] 5 TRIFLUOROMETHYL 3H QUINAZOLIN 4 ONE; 3 [2 (3 HYDROXY PYRROLIDIN 2 YL) 2 OXO ETHYL] 5 TRUFLUOROMETHYL 3H QUINAZOLIN 4 ONE; 3 [2 (3 HYDROXY PYRROLIDIN 2 YL) 2 OXO ETHYL]3H PYRIDO[3,2 D]PYRIMIDIN 4 ONE; 3 [2 (3 ISOPROXY PYRROLIDIN 2 YL) 2 OXO ETHYL] 5 TRIFLUOROMETHYL 3H QUINAZOLIN 4 ONE; 3 BENZYLOXY 2 [1 HYDROXY 2 (4 OXO 4H QUINAZOLIN 3 YL)ETHYL] PYRROLIDINE 1 CARBOXYLIC ACID BENZYL ESTER; 3 BENZYLOXY 2 OXIRANYL PYRROLIDINE 1 CARBOXYLIC ACID BENZYL ESTER; 5 FLUORO 3 [2 (3 HYDROXY PYRROLIDIN 2 YL) 2 OXO ETHYL] 3H QUINAZOLIN 4 ONE; CHLOROQUINE; FEBRIFUGINE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIMALARIAL ACTIVITY; ARTICLE; DRUG EFFICACY; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; FUNGAL STRAIN; LIPOPHILICITY; MALARIA FALCIPARUM; NONHUMAN; PLASMODIUM BERGHEI INFECTION; PLASMODIUM FALCIPARUM; TREATMENT RESPONSE;

ANIMALS; ANTIMALARIALS; AOTUS TRIVIRGATUS; DRUG EVALUATION, PRECLINICAL; MALARIA; PIPERIDINES; PLASMODIUM FALCIPARUM; QUINAZOLINES;

DICHROA FEBRIFUGA; PLASMODIUM FALCIPARUM;

EID: 84855821637     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.11.053     Document Type: Article

References (26)

1. World Health Organization: World Malaria Report 2010.
2. P.A. Winstanley Parasitol. Today 16 2000 146
3. J.B. Koepfly, J.F. Mead, and J.A. Brockman Jr J. Am. Chem. Soc. 69 1947 1837
4. J.B. Koepfly, J.F. Mead, and J.A. Brockman Jr J. Am. Chem. Soc. 71 1949 1048
5. F. Ablondi, S. Gordon, J. Morton II, and J.H. Williams J. Org. Chem. 17 1952 14
6. R.I. Hewitt, W.S. Wallace, E.R. Gill, and J.H. Williams Am. J. Trop. Med. Hyg. 1 1952 768
7. M. Kato, H. Inaba, H. Itahana, E. Ohara, K. Nakamura, S. Uesato, H. Inouye, and T. Fujita Shoyakugaku Zasshi 44 1990 288
8. S. Zhu, L. Meng, Q. Zhang, and L. Wei Bioorg. Med. Chem. Lett. 16 2006 1854
9. S. Zhu, Q. Zhang, C. Gudise, L. Wei, E. Smith, and Y. Zeng Bioorg. Med. Chem. 17 2009 4496
10. S. Zhu, J. Wang, G. Chandrashekar, E. Smith, X. Liu, and Y. Zhang Eur. J. Med. Chem. 45 2010 3864
11. D. Koch, S. Maechling, and S. Blechert Tetrahedron 63 2007 7112
12. S.V. Ley, J. Norman, W.P. Griffith, and S.P. Marsden Synthesis 1994 639
13. E.J. Williams, P.W. Kenny, J.G. Kettle, and P.G. Mwashimba Tetrahedron Lett. 45 2004 3737
14. F.R. Alexandre, A. Berecibar, and T. Besson Tetrahedron Lett. 43 2002 3911
15. W.L.F. Armarego, and J.I.C. Smith J. Chem. Soc. B 1967 449
16. F.S. Gibson, S.C. Bergmeier, and H. Rapoport J. Org. Chem. 59 1994 3216
17. R.E. Desjardins, C.J. Canfield, D.E. Haynes, and J.D. Chulay Antimicrob. Agents Chemother. 16 1979 710
18. J.D. Chulay, J.D. Haynes, and C.L. Diggs Exp. Parasitol. 55 1983 138
19. W.K. Milhous, N.F. Weatherly, J.H. Bowdre, and R.E. Desjardins Antimicrob. Agents Chemother. 27 1985 525
20. Q. Li, L.H. Xie, T.O. Johnson, Y. Si, A.S. Haeberlea, and P.J. Weina Trans. R Soc. Trop. Med. Hyg. 101 2007 104
21. G.S. Dow, Y. Chen, K.T. Andrews, D. Caridha, L. Gerena, M. Gettayacamin, J. Johnson, Q. Li, V. Melendez, N. Obaldia III, T.N. Tran, and A.P. Kozikowski Antimicrob. Agents Chemother. 52 2008 3467
22. J. Berman, L. Brown, R. Miller, S.L. Andersen, P. McGreevy, B.G. Schuster, W. Ellis, A. Ager, and R. Rossan Antimicrob. Agents Chemother. 38 1994 1753
23. R.N. Rossan, J.S. Harper III, D.E. Davidson Jr, A. Escajadillo, and H.A. Christensen Am. J. Trop. Med. Hyg. 34 1985 1037
24. L.H. Schmidt Antimicrob. Agents Chemother. 16 1979 475
25. L.H. Schmidt, J. Rasco, and D. Vaughan Antimicrob. Agents Chemother. 13 1978 1011
26. The National Academies Press. Guide for the care and use of laboratory animals. Eighth Edition, 2011. The National Academies Press, Washington, DC.