Synthesis of daunorubicin analogues containing truncated aromatic cores and unnatural monosaccharide residues

Journal of Organic Chemistry

Volumn 72, Issue 8, 2007, Pages 2917-2928

  Fan, Eric ^a   Shi, Wei ^a   Lowary, Todd L ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC MOIETIES; CARDIOTOXICITY; DAUNORUBICIN ANALOGUES;

ANTIBIOTICS; CYTOTOXICITY; GLUCOSE; GLYCOSYLATION; KETONES; SYNTHESIS (CHEMICAL);

AROMATIC COMPOUNDS;

1,2,3,4 TETRAHYDROANTHRACENE; 4 AMINO 2,3,6 TRIDEOXYHEXOPYRANOSE; ACOSAMINE; ANTHRACENE DERIVATIVE; ANTHRACYCLINE ANTIBIOTIC AGENT; ANTINEOPLASTIC AGENT; AROMATIC COMPOUND; BENZOPYRAN DERIVATIVE; CARBOHYDRATE; DAUNORUBICIN DERIVATIVE; DAUNOSAMINE; DOXORUBICIN; MONOSACCHARIDE; NAPHTHALENE DERIVATIVE; NORBORNENE DERIVATIVE; TETRALIN; THIOGLYCOSIDE; UNCLASSIFIED DRUG;

ARTICLE; CARDIOTOXICITY; CELL STRAIN MCF 7; CHEMICAL REACTION; CONCENTRATION (PARAMETERS); CYTOTOXICITY; DRUG STRUCTURE; GLYCOSYLATION; HUMAN; HUMAN CELL; IC 50; REACTION ANALYSIS; SYNTHESIS;

ANTHRACYCLINES; ANTIBIOTICS, ANTINEOPLASTIC; BREAST NEOPLASMS; CELL LINE, TUMOR; CELL SURVIVAL; DAUNORUBICIN; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MONOSACCHARIDES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34247273640     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062542q     Document Type: Article

References (52)

1. (a) Cassinelli, F.; Orezzi, P. G. Microbiol. 1963, 11, 167-174.
2. (b) Di Marco, A.; Gaetani, M.; Orezzi, P.; Scarpinato, B. M.; Silvestrini, R.; Soldati, M.; Dasdia, T.; Valentini, L. Nature 1964, 201, 706-707.
3. (c) Di Marco, A.; Gaetani, M.; Dorigotti, L.; Soldati, M.; Bellini, O. Cancer Chemother. Rep. 1964, 38, 31-38.
4. (a) Weiss, R. B. Semin. Oncol. 1992, 19, 670-686.
5. (b) Arcamone, F. M. Anthracyclines. In Anticancer Agents from Natural Products; Cragg, G. M., Kingston, D. G. I., Newman, D. J., Eds.; CRC Press: Boca Raton, FL, 2005; pp 299-320.
6. Robert, J. Drugs 1993, 45, 20-30.
7. Borchmann, P.; Huebel, K.; Schnell, R.; Engert, A. Int. J. Clin. Pharmacol. Ther. 1997, 35, 80-83.
8. Recent examples: (a) Guano, F.; Pourquier, P.; Tinelli, S.; Binaschi, M.; Bigioni, M.; Animati, F.; Manzani, S.; Zunino, F.; Kohlhagen, G.; Pommier, Y.; Capranico, G. Mol. Pharmacol. 1999, 56, 77-84.
9. (b) Zunino, F.; Pratesi, G.; Perego, P. Biochem. Pharmacol. 2001, 61, 933-938.
10. (c) Cipollone, A.; Berettoni, M.; Bigioni, M.; Binaschi, M.; Cermele, C.; Monteagudo, E.; Olivieri, L.; Palomba, D.; Animati, F.; Goso, C.; Maggi, C. A. Bioorg. Med. Chem. 2002, 10, 1459-1470.
11. (d) Portugal, J.; Cashman, D. J.; Trent, J. O.; Ferrer-Miralles, N.; Przewloka, T.; Fokt, I.; Priebe, W.; Chaires, J. B. J. Med. Chem. 2005, 48, 8209-8219.
12. (e) Zhang, G.; Fang, L.; Zhu, L.; Aimiuwu, J. E.; Shen, J.; Cheng, H.; Muller, M. T.; Lee, G. E.; Sun, D.; Wang, P. G. J. Med. Chem. 2005, 48, 5269-5278.
13. (f) Fang, L.; Zhang, G.; Li, C.; Zheng, X.; Zhu, L.; Xiao, J. J.; Szakacs, G.; Nadas, J.; Chan, K. K.; Wang, P. G.; Sun, D. J. Med. Chem. 2006, 49, 932-941.
14. (g) Zhang, G.; Fang, L.; Zhu, L.; Zhong, Y.; Wang, P. G.; Sun, D. J. Med. Chem. 2006, 49, 1792-1799.
15. (h) Horton, D.; Khare, A. Carbohydr. Res. 2006, 341, 2631-2640.
16. Champoux, J. J. Annu. Rev. Biochem. 2001, 70, 369-413.
17. (a) Zunino, F.; Capranico, G. Anti-Cancer Drug Des. 1990, 5, 307-317.
18. (b) Fortune, J. M. Osheroff, N. Prog. Nucleic Acid Res. Mol. Biol. 2000, 64, 221-253.
19. (a) Wang, A. H. J.; Ughetto, G.; Quigley, G. J.; Rich, A. Biochemistry 1987, 26, 1152-1163.
20. (b) Frederick, C. A.; Williams, L. D.; Ughetto, G.; van der Marel, G. A.; van Boom, J. H.; Rich, A.; Wang, A. H. J. Biochemistry 1990, 29, 2538-2549.
21. (c) Yang, D.; Wang, A. H. J. Biochemistry 1994, 33, 6595-6604.
22. (d) Qu, X.; Wan, C.; Becker, H. C.; Zhong, D.; Zewail, A. H. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 14212-14217.
23. (e) Cashman, D. J.; Kellogg, G. E. J. Med. Chem. 2004, 47, 1360-1374.
24. Ng, R.; Better, N.; Green, M. D. Semin. Oncol. 2006, 33, 2-14.
25. Minotti, G.; Menna, P.; Salvatorelli, E.; Cairo, G.; Gianni, L. Pharmacol. Rev. 2004, 56, 185-229.
26. (a) Doroshow, J. H.; Locker, G. Y.; Myers, C. E. J. Clin. Invest. 1980, 65, 128-135.
27. (b) Kalyanaraman, B.; Joseph, J.; Kalivendi, S.; Wang, S.; Konorev, E.; Kotamraju, S. Mol. Cell. Biochem. 2002, 234/235, 119-124.
28. (a) Dyong, I.; Hermann, R. Tetrahedron Lett. 1981, 22, 4225-4226.
29. (b) Dyong, I.; Hermann, R. Liebigs Ann. Chem. 1986, 545-550.
30. (c) Scheeren, J. W.; De Bie, J. F. M.; De Vos, D. Preparation of Antitumor Anthracyclines and Their Intermediates. European Patent 475473, 1992.
31. Momose, T.; Ozaki, Y. Chem. Pharm. Bull. 1976, 24, 1631-1636.
32. Stiles, M.; Miller, R. G.; Burckhardt, U. J. Am. Chem. Soc. 1963, 85, 1792-1797.
33. Lautens, M.; Rovis, T. J. Org. Chem. 1997, 62, 5246-5247.
34. Imamoto, T.; Takiyama, N.; Nakamura, K.; Hatajima, T.; Kamiya, Y. J. Am. Chem. Soc. 1989, 111, 4392-4398.
35. Fan, E.; Lowary, T. L.; Ferguson, M. J. Acta Crystallogr., Sect. E 2005, 61, o4295-o4296.
36. Hon, Y. S.; Lin, S. W.; Lu, L.; Chen, Y. J. Tetrahedron 1995, 17, 5019-5034.
37. (a) Lehoullier, C. S.; Gribble, G. W. J. Org. Chem. 1983, 48, 2364-2366.
38. (b) Hart, H.; Bashir-Hashemi, A.; Luo, J.; Meador, M. A. Tetrahedron 1986, 42, 1641-1654.
39. Yu, W.; Mei, Y.; Kang, Y.; Hua, Z.; Jin, Z. Org. Lett. 2004, 6, 3217-3219.
40. Renneberg, B.; Li, Y.-M.; Laatsch, H.; Fiebig, H.-H. Carbohydr. Res. 2000, 329, 861-872.
41. Hollenbeak, K. H.; Kuehne, M. E. Tetrahedron 1974, 30, 2307-2316.
42. Yadav, J. S.; Reddy, B. V. S.; Murthy, C. V. S. R.; Kumar, G. M. Synlett 2000, 1450-1451.
43. Brimacombe, J. S.; Doner, L. W.; Rollins, A. J. J. Chem. Soc., Perkin Trans. 1 1972, 2977-2979.
44. Konradsson, P.; Udodong, U. E.; Fraser-Reid, B. Tetrahedron Lett. 1990, 31, 4313-3416.
45. Lear, M. J.; Yoshimura, F.; Hirama, M. Angew. Chem., Int. Ed. 2001, 40, 946-949.
46. (a) Corey, E. J.; Carpino, P. J. Am. Chem. Soc. 1989, 111, 5472-5474.
47. (b) Demchenko, A. V.; Rousson, E.; Boons, G.-J. Tetrahedron Lett. 1999, 40, 6523-6526.
48. (c) Crich, D.; Wai, W.; Dai, Z. J. Org. Chem. 2000, 65, 1291-1297.
49. (d) Cheng, Y.-P.; Chen, H.-T.; Lin, C.-C. Tetrahedron Lett. 2002, 43, 7721-7723.
50. (e) De Meo, C.; Kamat, M. N.; Demchenko, A. V. Eur. J. Org. Chem. 2005, 706-711.
51. (a) Cory, A. H.; Owen, T. C.; Barltrop, J. A.; Cory, J. G. Cancer Commun. 1991, 3, 207-212.
52. (b) Barltrop, J. A.; Owen, T. C.; Cory, A. H.; Cory, J. G. Bioorg. Med. Chem. Lett. 1991, 1, 611-614.