Parallel synthesis of antimalarial rhodacyanine dyes by the combination of three components in one pot

Journal of Combinatorial Chemistry

Volumn 5, Issue 3, 2003, Pages 211-214

  Takasu, Kiyosei ^a   Terauchi, Hiroki ^a   Inoue, Hiroshi ^a   Kim, Hye Sook ^b   Wataya, Yusuke ^b   Ihara, Masataka ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMALARIAL AGENT; ANTINEOPLASTIC AGENT; DYE; RHODACYANINE DYE; UNCLASSIFIED DRUG;

ANTIMALARIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL COMPOSITION; DRUG MECHANISM; DRUG SYNTHESIS; PLASMODIUM FALCIPARUM; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

ANTIMALARIALS; COLORING AGENTS; MOLECULAR STRUCTURE; PYRIDINIUM COMPOUNDS; THIAZOLES;

EID: 0141563671     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc020119z     Document Type: Article

References (21)

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10. MKT-077, one of rhodacyanine dyes, has been subjected to phase I clinical investigation for the treatment of solid tumors. (a) Propper, D. J.; Braybrooke, J. P.; Taylor, D. J.; Lodi, R.; Styles, P.; Cramer, J. A.; Collins, W. C. J.; Levitt, N. C.; Talbot, D. C.; Ganesan, T. S.; Harris, A. L. Ann. Oncol. 1999, 10, 923-927. (b) Britten, C. D.; Rowinsky, E. K.; Baker, S. D.; Weiss, G. R.; Smith, L.; Stephenson, J.; Rothenberg, M.; Smetzer, L.; Cramer, J.; Collins, W.; Von Hoff, D. D.; Eckhardt, S. A. Clin. Cancer Res. 2000, 6, 42-49.
11. MKT-077, one of rhodacyanine dyes, has been subjected to phase I clinical investigation for the treatment of solid tumors. (a) Propper, D. J.; Braybrooke, J. P.; Taylor, D. J.; Lodi, R.; Styles, P.; Cramer, J. A.; Collins, W. C. J.; Levitt, N. C.; Talbot, D. C.; Ganesan, T. S.; Harris, A. L. Ann. Oncol. 1999, 10, 923-927. (b) Britten, C. D.; Rowinsky, E. K.; Baker, S. D.; Weiss, G. R.; Smith, L.; Stephenson, J.; Rothenberg, M.; Smetzer, L.; Cramer, J.; Collins, W.; Von Hoff, D. D.; Eckhardt, S. A. Clin. Cancer Res. 2000, 6, 42-49.
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15. Only limited applications to the combinatorial synthesis in the dye chemistry have been reported. For examples, see: (a) merocyanines: Würthner, F.; Sens, R.; Etzbach, K.-H.; Seybold, G. Angew. Chem. Int. Ed. 1999, 38, 1649-1652. (b) cyanines: Iacsson, J.; Westman, G. Tetrahedron Lett. 2001, 42, 3207-3210. (c) courmarine-type OLED: Schiedel, M.-C.; Briehn, C. A.; Bäuerle, P. Angew. Chem. Int. Ed. 2001, 40, 4677-4680. (d) azo dyes: Merrington, J. M.; James, M.; Bradley, M. Chem. Commun. 2002, 140-141. (e) conjugated polymer-type OLED: Lavastre, O.; Illitchev, I.; Jegou, G.; Dixneuf, P. H. J. Am. Chem. Soc. 2002, 124, 5278-5279.
16. Only limited applications to the combinatorial synthesis in the dye chemistry have been reported. For examples, see: (a) merocyanines: Würthner, F.; Sens, R.; Etzbach, K.-H.; Seybold, G. Angew. Chem. Int. Ed. 1999, 38, 1649-1652. (b) cyanines: Iacsson, J.; Westman, G. Tetrahedron Lett. 2001, 42, 3207-3210. (c) courmarine-type OLED: Schiedel, M.-C.; Briehn, C. A.; Bäuerle, P. Angew. Chem. Int. Ed. 2001, 40, 4677-4680. (d) azo dyes: Merrington, J. M.; James, M.; Bradley, M. Chem. Commun. 2002, 140-141. (e) conjugated polymer-type OLED: Lavastre, O.; Illitchev, I.; Jegou, G.; Dixneuf, P. H. J. Am. Chem. Soc. 2002, 124, 5278-5279.
17. Only limited applications to the combinatorial synthesis in the dye chemistry have been reported. For examples, see: (a) merocyanines: Würthner, F.; Sens, R.; Etzbach, K.-H.; Seybold, G. Angew. Chem. Int. Ed. 1999, 38, 1649-1652. (b) cyanines: Iacsson, J.; Westman, G. Tetrahedron Lett. 2001, 42, 3207-3210. (c) courmarine-type OLED: Schiedel, M.-C.; Briehn, C. A.; Bäuerle, P. Angew. Chem. Int. Ed. 2001, 40, 4677-4680. (d) azo dyes: Merrington, J. M.; James, M.; Bradley, M. Chem. Commun. 2002, 140-141. (e) conjugated polymer-type OLED: Lavastre, O.; Illitchev, I.; Jegou, G.; Dixneuf, P. H. J. Am. Chem. Soc. 2002, 124, 5278-5279.
18. Only limited applications to the combinatorial synthesis in the dye chemistry have been reported. For examples, see: (a) merocyanines: Würthner, F.; Sens, R.; Etzbach, K.-H.; Seybold, G. Angew. Chem. Int. Ed. 1999, 38, 1649-1652. (b) cyanines: Iacsson, J.; Westman, G. Tetrahedron Lett. 2001, 42, 3207-3210. (c) courmarine-type OLED: Schiedel, M.-C.; Briehn, C. A.; Bäuerle, P. Angew. Chem. Int. Ed. 2001, 40, 4677-4680. (d) azo dyes: Merrington, J. M.; James, M.; Bradley, M. Chem. Commun. 2002, 140-141. (e) conjugated polymer-type OLED: Lavastre, O.; Illitchev, I.; Jegou, G.; Dixneuf, P. H. J. Am. Chem. Soc. 2002, 124, 5278-5279.
19. Only limited applications to the combinatorial synthesis in the dye chemistry have been reported. For examples, see: (a) merocyanines: Würthner, F.; Sens, R.; Etzbach, K.-H.; Seybold, G. Angew. Chem. Int. Ed. 1999, 38, 1649-1652. (b) cyanines: Iacsson, J.; Westman, G. Tetrahedron Lett. 2001, 42, 3207-3210. (c) courmarine-type OLED: Schiedel, M.-C.; Briehn, C. A.; Bäuerle, P. Angew. Chem. Int. Ed. 2001, 40, 4677-4680. (d) azo dyes: Merrington, J. M.; James, M.; Bradley, M. Chem. Commun. 2002, 140-141. (e) conjugated polymer-type OLED: Lavastre, O.; Illitchev, I.; Jegou, G.; Dixneuf, P. H. J. Am. Chem. Soc. 2002, 124, 5278-5279.
20. Although there are several possible geometrical isomers of rhodacyanines 1 and merocyanines 4, the structures shown in the Schemes are depicted as a single geometrical isomer. It is well-known that the conjugated double bonds can be easily isomerized in the solution, and the trans geometrical isomers are usually thermodynamic products.
21. Kim, H.-S.; Shibata, Y.; Wataya, Y.; Tsuchiya, K.; Ma-suyama, A.; Nojima, M. J. Med. Chem. 1999, 42, 2604-2609.