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http://dx.doi.org/10.5012/bkcs.2006.27.9.1359

Synthesis of New Anthracycline Derivatives Containing Lactic or Stearic Acid Moiety  

Rho, Young S. (Department of Chemistry, Chonbuk National University)
Kim, Wan-Joong (Department of Chemistry, Chonbuk National University)
Yoo, Dong-Jin (Department of Chemistry, Seonam University)
Publication Information
Abstract
Novel anthracycline analogues 2-9 as potential anticancer agents were synthesized from daunomycin (1a) and doxorubicin (1b). Compounds 2, 6, and 7 were prepared by the nucleophilic displacement type esterification of a 14-bromodaunomycin (1c) with a sodium lactate, and stearic acid, respectively. Compounds 3-5 and 7-9 were prepared by the reaction of either daunomycin (1a) or doxorubicin (1b) with L-lactic and stearic acids in the presence of EDCI/PP reagents.
Keywords
Daunomycin; Doxorubicin; Anthracycline derivatives; Lactic acid; Stearic acid;
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1 Hortobagyi, G. N. Drugs 1997, 54, 1
2 Levin, Y.; Sela, B.-A. US Patent 4256632, 1981
3 Lee, M. G.; Yang, J. Drugs of the Future 1996, 21, 782
4 Arcamone, F.; Franceschi, G.; Minghetti, A.; Penco, S.; Redaelli, S. J. Med. Chem. 1974, 17, 335   DOI
5 Arcamone, F.; Franceschi, G.; Penco, S. US Patent 3803124, 1974
6 Rho, Y. S.; Kim, G. I.; Kim, W.-J.; Park, S. H.; Yoo, D. J.; Kang, H. S.; Chung, S. R. Bull. Korean Chem. Soc. 2001, 22, 587
7 Rho, Y. S.; Kim, W.-J.; Park, S. H.; Yoo, D. J.; Kang, H. S.; Chung, S. R. Bull. Korean Chem. Soc. 2001, 22, 963
8 Rho, Y. S.; Kim, S. Y.; Cho, I.; Kang, H. S.; Yoo, D. J.; Cheong, C. Bull. Korean Chem. Soc. 1998, 19, 1059   DOI
9 Hauser, F. M.; Hewawasam, P.; Rho, Y. S. J. Org. Chem. 1989, 54, 5110   DOI
10 Rho, Y. S.; Park, S.; Kim, S. Y.; Cho, I.; Lee, C.; Kang, H. S.; Cheong, C. Bull. Korean Chem. Soc. 1998, 19, 74
11 Rho, Y. S.; Choi, Y.; Kim, G.; Sin, H.; Yoo, D. J.; Kim, S. H.; Cheong, C. Bull. Korean Chem. Soc. 1999, 20, 551
12 Rho, Y. S.; Ko, H. K.; Sin, H.; Yoo, D. J. Bull. Korean Chem. Soc. 1999, 20, 1517
13 Rho, Y. S.; Park, S. C.; Kang, H. S. Novel Anthracycline Derivatives and Their Preparation. US Patent (09/674,673), EU Patent (99 919679.3), JPN Patent (2000-547095), KOR Patent (2000-7012427)
14 Umezawa, H.; Takeuchi, T.; Naganawa, H.; Tatsuta, K. US Patent 4360664, 1982
15 Dhaon, M. K.; Olsen, R. K.; Ramasamy, K. J. Org. Chem. 1982, 47, 1962   DOI
16 Akaji, K.; Kuriyama, N.; Kiso, Y. Tetrahedron Lett. 1994, 35, 3315   DOI   ScienceOn
17 Lavie, Y.; Cao, H.-T.; Bursten, S. L.; Giuliano, A. E.; Cabot, M. C. J. Biological Chem. 1996, 271(32), 19530   DOI   ScienceOn
18 Rho, Y. S.; Park, S. H.; Kim, W.-J.; Kim, G. I.; Yoo, D. J.; Kang, H. S.; Chung, S. R. Synth. Commun. 2002, 32(13), 1961   DOI   ScienceOn
19 Rho, Y. S.; Park, J.; Kim, G.; Kim, H.; Sin, H.; Suh, P. W.; Yoo, D. J. Synth. Commun. 2004, 34(9), 1703
20 Rho, Y. S.; Kim, S. Y.; Kim, W.-J.; Yun, Y. K.; Sin, H. S.; Yoo, D. J. Synth. Commun. 2004, 34(19), 3497   DOI   ScienceOn
21 Armerigo, W. L. F.; Perrin, D. D. Purification of Laboratory Chemicals, 4th Ed.; Oxford: Butterworth-Heinemann, 1996
22 Hudson, D. J. Org. Chem. 1988, 53, 617   DOI
23 Rho, Y. S.; Ko, H. K.; Kim, W.-J.; Yoo, D. J.; Kang, H. S. Bull. Korean Chem. Soc. 2000, 21, 774
24 Rho, Y. S.; Kim, W. -J.; Park, S. H.; Yoo, D. J.; Kang, H. S.; Chung, S. R. Bull. Korean Chem. Soc. 2001, 22, 581
25 Mettler, F. P.; Young, D. M.; Ward, J. M. Cancer Res. 1977, 37, 2705
26 Desai, M. C.; Stephens Stramiello, L. M. Tetrahedron Lett. 1993, 34, 7685   DOI   ScienceOn
27 Ducep, J.-B.; Farge, D.; Ponsinet, G.; Reisdorf, D. US Patent 4225589, 1980
28 Priebe, W. Anthracycline Antibiotics, New Analogues, Methods of Delivery, and Mechanisms of Action; American Chemical Society: Washington DC, 1995