Novel class of cyclophosphamide prodrug: Cyclophosphamide spiropiperaziniums (CPSP)

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 14, 2006, Pages 3727-3730

  Sun, Qi ^a   Li, Run Tao ^a   Guo, Wei ^a   Cui, Jing Rong ^a   Cheng, Tie Ming ^a   Ge, Ze Mei ^a  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

Author keywords

Anti cancer; Cyclophosphamide; Cyclophosphamide spiro piperaziniums; Prodrug; Synthesis

Indexed keywords

ANTINEOPLASTIC AGENT; CYCLOPHOSPHAMIDE; CYCLOPHOSPHAMIDE DERIVATIVE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTINEOPLASTIC AGENTS; CYCLOPHOSPHAMIDE; INHIBITORY CONCENTRATION 50; MICE; PIPERAZINES; PRODRUGS; SPIRO COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33746572074     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2006.04.049     Document Type: Article

References (34)

1. Sladek N.E. Pharmacol. Ther. 37 (1998) 301
2. Friedman O.M., Myles A., and Colvin M. Adv. Cancer Chemother. 1 (1979) 143
3. Sladek N.E. Cancer Res. 32 (1972) 1848
4. Connors T.A., Cox P.J., Farmer P.B., Foster A.B., and Jarman M. Biochem. Pharmacol. 23 (1974) 115
5. Brock N., Stekar J., Pohl J., Niemeyer U., and Scheffler G. Arzneim-Forsch. Drug Res. 29 (1979) 659
6. Eibl, H.; Kolar, C.; Seiler, F. R. Eur. Pat. Appl. EP72531, 1982.
7. Moon K.-Y., Shirota F.N., Baturay N., and Kwon Ch.-H. J. Med. Chem. 38 (1995) 848
8. Engel, J.; Kleemann, A.; Niemeyer, U. Ger. Offen., DE3505482, 1985.
9. Scheffler, G.; Niemeyer, U.; Brock, N. U.S. 4618692, 1986.
10. Boyd V.L., Zon G., Himes V.L., Stalick J.K., Mighell A.D., and Secor H.V. J. Med. Chem. 23 (1980) 372
11. Brandt J.A., Ludeman S.M., Zon G., Egan W., Todhunter J.A., and Dickerson R. J. Med. Chem. 24 (1981) 1404
12. Borch R.F., and Canute G.W. J. Med. Chem. 34 (1991) 3044
13. Ludeman S.M., and Zon G. J. Med. Chem. 18 (1975) 1251
14. Li Z., Han J., Jiang Y., Browne P., Knox R.J., and Hu L. Bioorg. Med. Chem. 11 (2003) 4171
15. Borch R.F., and Valente R.R. J. Med. Chem. 34 (1991) 3052
16. Tietze L.F., Neumann M., Fischer R., et al. Ger. Offen DE3819634 (1989)
17. Firestone A., Mulcahy R.T., and Borch R.F. J. Med. Chem. 34 (1991) 2933
18. Borch R.F., Liu J., Schmidt J.P., Marakovits J.T., and Joswig C. J. Med. Chem. 43 (2000) 2258
19. Borch R.F., Liu J., Joswig C., Baggs R.B., Dexter D.L., and Mangold G.L. J. Med. Chem. 44 (2001) 74
20. Steinberg G., and Borch R.F. J. Med. Chem. 44 (2001) 69
21. Flader C., Liu J., and Borch R.F. J. Med. Chem. 43 (2000) 3157
22. Hernick M., Flader C., and Borch R.F. J. Med. Chem. 45 (2002) 3540
23. Jain M., Fan J., Baturay N.Z., and Kwon C.H. J. Med. Chem. 47 (2004) 3843
24. Safonova T.S., Chernov V.A., and Minakova S.M. Khim. Farm. Zh. 17 (1983) 626
25. Nicolas C., Verny M., Giraud I., Ollier M., Rapp M., Maurizis J.C., and Madelmont J.C. J. Med. Chem. 42 (1999) 5235
26. Giraud I., Rapp M., Maurizis J.C., and Madelmont J.C. J. Med. Chem. 45 (2002) 2116
27. Li R.T., Chen H.C., and Yang J.Z. Yaoxue Xuebao (Acta Pharm. Sinica) 30 (1995) 69
28. Li R.T., Chen H.C., and Yang J.Z. Yaoxue Xuebao (Acta Pharm. Sinica) 30 (1995) 144
29. Dong J.C., Wang X., Li R.T., Zhang H.M., Cheng T.M., and Li C.L. Bioorg. Med. Chem. Lett. 13 (2003) 4327
30. Liu H., Cheng T.M., Zhang H.M., and Li R.T. Arch. Pharm. Pharm. Med. Chem. 336 (2003) 510
31. Wang X., Gao F.L., Piao H.B., Cheng T.M., and Li R.T. Bioorg. Med. Chem. Lett. 13 (2003) 1729
32. Gao F.L., Wang X., Zhang H.M., Cheng T.M., and Li R.T. Bioorg. Med. Chem. Lett. 13 (2003) 1535
33. Li, R. T.; Sun, Q.; Ge, Z. M.; Cui, J. R.; Cheng, T. M. Preparation of quaternary ammonium salt of cyclophosphamide and its derivatives as antitumor agents. Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), Patent written in Chinese, p 24.
34. Li R.T., Chen H.C., and Yang J.Z. Huaxue tongbao 6 (1993) 29