Efficient synthesis of ribonucleotide reductase inhibitors 3- aminopyridine-2-carboxaldehyde thiosemicorbazone (3-AP) and 3-amino-4- methylpyridine-2-carboxaldehyde thiosemicarbazone (3-AMP) via palladium mediated cross-coupling reactions

Tetrahedron

Volumn 54, Issue 3-4, 1998, Pages 393-400

  Li, Jun ^a,b   Chen, Shu Hui ^a   Li, Xiuyan ^a   Niu, Chuansheng ^a   Doyle, Terrence W ^a  

^a Vion Pharmaceuticals Incorporated   (United States)

^b BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 AMINOPYRIDINE; PALLADIUM; RIBONUCLEOTIDE REDUCTASE; THIOSEMICARBAZONE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; ENZYME SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0032518830     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10298-8     Document Type: Article

References (27)

1. 2. (a) Cory, J.G.; Chiba, P. Combination Chemotherapy Directed at the Components of Nucleoside Diphosphate Reductase. In Inhibitors of ribonucleoside Diphosphate Reductase Activity; Cory, J. G.; Cory, A. M., Eds.; Pergamon Press: Oxford, 1989; pp 245-264.
2. (b) Lien, E. J., Ribonucleotide Reductase Inhibitors as Anticancer and Antiviral Agents, in Progress in Drug research.; Jucker, E., Ed.; Birkhauser Verlag: Basel, 1987; Vol. 31, pp101.
3. 3. Krakoff, I. H.; Brown, N. C.; Reichard, P. Cancer Res. 1968, 28, 1559
4. 4. (a) Sartorelli, A. C.; Agrawal, K. C. ACS Symp. Ser. 1976, No. 30, 1.
5. (b)Agrawal, K. C.; Sartorelli, A. C. The Chemistry and Biological activity of the a-(N)-Heterocyclic Carboxaldehyde Thiosemicarbazones. In Progress in Medicinal Chemistry; Ellis, G. P., West, G. B., Eds.; Elsevier/North-Holland Biomedical Press: New York, 1978; Vol 15, pp321-356
6. 5. (a) Cohen, E. A.; Gaudreau, P.; Brazeau, P.; Langelier, Y. Nature, 1986, 321, 441.
7. (b) Dutia, B. M.; Frame, M. C.; Subak-Sharpe, J. H.; Clark, W. H.; Marsden, H. S. Nature, 1986, 321, 439.
8. 6. (a) Elford, H. L.; Wampler, G. L.; Van't Riet, B. Cancer Res. 1979, 39, 844.
9. (b)Van't Riet, B.; Wampler, G. L.; Elford, H. L. J. Med. Chem. 1979, 22, 589.
10. 7. (a) Thei.; Larson, B. Hobbs, J.; Eckstein, F. J. Biol. Chem. 1976, 251, 1398.
11. (b) Tai, A. W.; Lien, E. J.; lai, M. M. C.; Khwaja, T. A. J. Med. Chem. 1984, 27, 236.
12. (c)Weckbecker, G.; Lien, E. J.; Cory, J. G. Biochem. Pharmacol. 1988, 37, 529.
13. (d) Cory, J. G.; Cory, A. H.; raber, N. K.; Narayanan, A.; Schneller, S. W. Adv. Enzyme Reg. 1993, 33, 129.
14. 8. (a)Wang, Y.; Liu, M. C.; Lin, T. S.; Sartorelli, A. C. J. Med. Chem. 1992, 35, 3667.
15. (b) Liu, M. C.; Lin, T. S.; Sartorelli, A. C. Ibid. 1992, 35, 3672.
16. (c) Liu, M. C.; Lin, T. S.; Penketh, P.; Sartorelli, A. C. Ibid. 1995, 38, 4234.
17. (d) Liu, M. C.; Lin, T. S.; Cory, J. G.; Cory, A. H.; Sartorelli, A. C. Ibid. 1996, 39, 2586.
18. 9. (a) Stille, J. K. Angew. Chem. Int. Ed. 1986, 25, 508.
19. (b) Dehmlow, E. V.; Sleegers, A. Liebigs Ann. Chem. 1992. 953.
20. (c) Rocca, P; Marsais, F.; Godard, A.; Queguiner, G. Tetrahedron 1993, 49, 3325.
21. 10. Callighan, R. H.; Wilt, M.; H. J. Org. Chem. 1961, 26, 4912.
22. 11. (a) Hodgson, H. H.; Ward, E. R. J. Chem. Soc. 1945, 663.
23. (b) Hodgson, H. H.; Birtwell, S. J. Chem. Soc. 1944, 75.
24. 12. (a) Sandosham, J.; Undheim, K. Heterocycles 1994, 37, 501.
25. (b) Maguire, M.P.; Sheets, K. R.; McVety, K.; Spada, A. P.; Ziberstein, A. J. Med. Chem. 1994, 37, 2129.
26. 13. Gersch, B.; Lehn, J-M.; Grell, E. Tetrahedron Lett. 1996, 37, 2213
27. 14. Heck, R. F. Palldium Reagents in Organic Synthesis; Academic Press:San Diego, USA , 1985; Chapter 6.