Synthesis and biological activity of new quinoxaline antibiotics of echinomycin analogues

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 2, 2004, Pages 541-544

  Kim, Yun Bong ^a   Kim, Yong Hae ^a   Park, Ju Youn ^b   Kim, Soo Kie ^b  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

^b Yonsei University Wonju College of Medicine   (South Korea)

Author keywords

Active VRE; Anticancer; Apoptosis; Echinomycin

Indexed keywords

ANTINEOPLASTIC ANTIBIOTIC; ECHINOMYCIN; QUINOXALINE DERIVATIVE;

ANIMAL CELL; ANTIBIOTIC RESISTANCE; ARTICLE; CHORIOCARCINOMA; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; DRUG MECHANISM; DRUG SYNTHESIS; ENTEROCOCCUS; EUKARYOTE; HUMAN; HUMAN CELL; MINIMUM INHIBITORY CONCENTRATION; MOUSE; NONHUMAN; PROKARYOTE; TUMOR CELL LINE;

EUKARYOTA; PROKARYOTA;

EID: 0346729859     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2003.09.086     Document Type: Article

References (37)

1. (a) Otsuka H., Shoji J., Kawano K., Kyogoku Y. J. Antibiotics. 29:1976;107
2. (b) Martin D.A., Mizsak S.A., Biles C., Meulman P.A. J. Antibiotics. 28:1975;332.
3. Shoji J., Katakiri K. J. Antibiotics Ser. A. 14:1961;335.
4. Mutssuura S. J. Antibiotics Ser. A. 18:1965;335.
5. Waring M.J., Makoff A. Mol. Pharmacol. 10:1974;214.
6. (a) Waring M.J., Wakelin L.P.G. Nature. 252:1974;653
7. (b) Waring M.J., Wakelin L.P.G. Biochem. J. 157:1976;721.
8. (a) Kuroya M., Ishida N. J. Antibiotics Ser. A. 14:1961;324
9. (b) Mutssuura S. J. Antibiotics Ser. A. 18:1965;43.
10. (a) Ciardelli T.L., Chakravarty P.K., Olsen R.K. J. Am. Chem. Soc. 100:1978;7684
11. (b) Ciardelli T.L., Olsen R.K. J. Am. Chem. Soc. 99:1977;2806
12. (c) Chakravarty P.K., Olsen R.K. Tetrahedron Lett. 19:1978;1613
13. (d) Chew W.Y., Hsu R.K., Olsen R.K. J. Org. Chem. 40:1975;3110
14. (e) Dhaon M.K., Gardner J.H., Olsen R.K. Tetrahedron. 38:1982;57
15. (f) Shin M., Inouye K., Otsuka H. Bull. Chem. Soc. Jpn. 57:1984;2203
16. (g) Shin M., Inouye K., Higuchi N., Kyogoku Y. Bull. Chem. Soc. Jpn. 57:1984;2211
17. (h) Boger D.L., Ichikawa S. J. Am. Chem. Soc. 122:2000;2956
18. (i) Boger D.L., Lee J.K. J. Org. Chem. 65:2000;5996.
19. Park Y.S., Kim Y.H. Bioorg. Med. Chem. Lett. 8:1998;731.
20. Van Veen A.G., Hyman A.J. Recl. Yrav. Chim. Pays-Bas. 54:1935;493.
21. Corey E.J., Bhattacharyya S. Tetrahedron Lett. 18:1977;3919.
22. (a) McDermott J.R., Benoiton N.L. Can. J. Chem. 51:1973;1915
23. (b) Cheung S.T., Benoiton N.L. Can. J. Chem. 55:1977;2987.
24. (a) McElvain S.M., Nelson J.W. J. Am. Chem. Soc. 64:1942;1825
25. (b) Undhein K., Eidem A. Acta Chem. Scand. 24:1970;3129
26. (c) Veber D.F., Milkowski J.D., Varga S.L., Denkewalter R.G., Hirschmann R. J. Am. Chem. Soc. 94:1972;5456
27. (d) Schmir G.L. J. Am. Chem. Soc. 87:1965;2743
28. (e) Chakravarty P.K., Olsen R.K. J. Org. Chem. 43:1978;1270.
29. Hendrickson J.B., Kandall C. Tetrahedron Lett. 11:1970;343.
30. Kamber B. Helv. Chim. Acta. 54:1971;927.
31. Woods T.S., Klayman D.L. J. Org. Chem. 39:1974;3716.
32. Ueki M., Ikeo T., Hokari K., Nakamura K., Saeki A., Komatsu H. Bull. Chem. Soc. Jpn. 72:1999;829.
33. Koppel H.C., Honigberg I.L., Springer R.H., Cheng C.C. J. Org. Chem. 28:1963;1119.
34. 50 values were determined by plotting the logarithm of the drug concentration versus the growth rate of the treated cells.
35. The 1a and 1b were synthesized for attenuating immune cell toxicity, and then 2-4 were synthesized for increasing hydrophobicity (1a,b).
36. (a) Waring M.J., Wakelin L.P.G. Nature. 252:1974;653
37. (b) Waring M.J. Path. Biol. 40:1992;1022.