Synthesis and antimalarial efficacy of aza-fused rhodacyanines in vitro and in the P. berghei mouse model

Journal of Medicinal Chemistry

Volumn 49, Issue 15, 2006, Pages 4795-4798

  Takasu, Kiyosei ^a   Pudhom, Khanitha ^a,b,c   Kaiser, Marcel ^d   Brun, Reto ^d   Ihara, Masataka ^a,b  

^a TOHOKU UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c CHULALONGKORN UNIVERSITY   (Thailand)

^d SWISS TROPICAL AND PUBLIC HEALTH INSTITUTE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMALARIAL AGENT; AZARHODACYANINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIMALARIAL ACTIVITY; ARTICLE; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM;

ANIMALS; ANTIMALARIALS; AZA COMPOUNDS; CELL LINE; DRUG RESISTANCE; MALARIA; MICE; PLASMODIUM BERGHEI; PLASMODIUM FALCIPARUM; PYRIDINIUM COMPOUNDS; THIAZOLES;

EID: 33746729457     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0606241     Document Type: Article

References (17)

1. The World Health Report 2002, World Health Organization (WHO), http://www.who.int/whr/2002/en/.
2. Peters, W. Antimalarial Drug Resistance: An Increasing Problem. Br. Med. Bull. 1982, 38, 187-192.
3. Wernsdorfer, W. H.; Pyne, D. The Dynamics of Drug Resistance in Plasmodium falciparum. Pharmacol. Ther. 1991, 50, 95-121.
4. Rosenthal, P. J.; Miller, L. H. In Antimalarial Chemotherapy; Rosenthal, P. J., Ed.; Humana Press: Totowa, NJ, 2001; pp 3-15.
5. Go, M.-L. Novel Antiplasmodial Agents. Med. Res. Rev. 2003, 23, 456-487.
6. Thayer, A. M. Fighting Malaria. Chem. Eng. News 2005, 83 (43) 69-82.
7. Kawakami, M.; Koya, K.; Ukai, T.; Tatsuta, N.; Ikegawa, A.; Ogawa, K.; Shishido, T.; Chen, L. B. Synthesis and Evaluation of Novel Rhodacyanine Dyes That Exhibit Antitumor Activity. J. Med. Chem. 1997, 40, 3151-3160.
8. Chen, L. B. Mitochondrial Menmrane Potential in Living Cells. Annu. Rev. Cell Biol. 1988, 4, 155-181.
9. Takasu, K.; Shimogama, T.; Saiin, C.; Kim, H.-S.; Wataya, Y.; Brun, R.; Ihara, M. Synthesis and Evaluation of β-Carbolinium Cations as New Antimalarial Agents Based on π-Delocalized Lipophilic Cation (DLC) Hypothesis. Chem. Pharm. Bull. 2005, 53, 653-661.
10. Takasu, K.; Inoue, H.; Kim, H.-S.; Suzuki, M.; Shishido, T.; Wataya, Y.; Ihara, M. Rhodacyanine Dyes as Antimalarials. 1. Preliminary Evaluation of Their Activity and Toxicity. J. Med. Chem. 2002, 45, 995-998.
11. Takasu, K.; Terauchi, H.; Inoue, H.; Kim, H.-S.; Wataya, Y.; Ihara, M. Parallel Synthesis of Antimalarial Rhodacyanine Dyes by the Combination of Three Components in One Pot. J. Comb. Chem. 2003, 5, 211-214.
12. Takasu, K.; Morisaki, D.; Kaiser, M.; Brun, R.; Ihara, M. Syntheses and Biological Activities of Structurally Stiff Rhodacyanines as Novel Antimalarial Candidates. Heterocycles 2005, 66, 161-166.
13. Ikegawa, A.; Ukai, T.; Kawakami, M. Water-Soluble Thiazolidinone Merocyanines. JP Patent 06220053, 1994; Chem. Abstr. 123:172637.
14. Sahu, M.; Garnik, B. K.; Behera, R. Influence of Substituents on the Synthesis of Thiazolidinones. Indian J. Chem. 1987, 26B, 779-781.
15. We do not assign all the geometries of synthetic azarhodacyanines in this study. Although there are several possible geometrical isomers of azarhodacyanines, the structures shown in the schemes and charts are depicted as a single geometrical isomer. It is well-known that the conjugated double bonds, such as the merocyanine and cyanine moieties, can be easily isomerized in the solution and that the trans geometrical isomers would be thermodynamic products.
16. Desjardins, R. E.; Canfield, C. J.; Haynes, J. D.; Chulay, J. D. Antimicrob. Agents Chemother. 1979, 16, 710-718.
17. Peters, W.; Portus, J. H.; Robinson, B. L. The Chemotherapy of Rodent Malaria XXII. The Value of Drug Resistant Strains of Plasmodium berghei in Screening for Blood Schizontocidal Activity. Ann. Trop. Med. Parasitol. 1975, 69, 155-171.