Synthesis and evaluation of a classical 2,4-diamino-5-substituted-furo[2,3-d]pyrimidine and a 2-amino-4-oxo-6-substituted-pyrrolo[2,3-d]pyrimidine as antifolates

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 24, 2006, Pages 8590-8598

  Gangjee, Aleem ^a   Yang, Jie ^a   McGuire, John J ^b   Kisliuk, Roy L ^c  

^a DUQUESNE UNIVERSITY   (United States)

^b ROSWELL PARK CANCER INSTITUTE   (United States)

^c TUFTS UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Antifolates; Dihydrofolate reductase; Pyrrolo 2,3 d pyrimidines

Indexed keywords

CARBON; DIHYDROFOLATE REDUCTASE INHIBITOR; FOLIC ACID ANTAGONIST; FOLYLPOLYGLUTAMATE SYNTHASE; GLUTAMIC ACID DIETHYL ESTER; KETONE DERIVATIVE; N [4 [(2 AMINO 4 OXO 4,7 DIHYDRO 3H PYRROLO[2,3 D]PYRIMIDIN 6 YL)METHYL]BENZOYL]GLUTAMIC ACID; N [4 [(2,4 DIAMINOFURO[2,3 D]PYRIMIDIN 5 YL)METHYL]BENZOYL]GLUTAMIC ACID; PTEROPTIN; PYRIMIDINE DERIVATIVE; THYMIDYLATE SYNTHASE; UNCLASSIFIED DRUG;

ARTICLE; CELL CULTURE; DRUG HYDROLYSIS; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LEUKEMIA CELL; SAPONIFICATION;

ANTIMETABOLITES, ANTINEOPLASTIC; DRUG RESISTANCE, NEOPLASM; ENZYME INHIBITORS; FOLIC ACID ANTAGONISTS; HUMANS; LEUKEMIA, LYMPHOCYTIC; METHOTREXATE; PEPTIDE SYNTHASES; PYRIMIDINES; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAHYDROFOLATE DEHYDROGENASE; THYMIDYLATE SYNTHASE; TUMOR CELLS, CULTURED;

EID: 33750530573     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.08.029     Document Type: Article

References (35)

1. Presented in part in the 12th International Symposium on Pteridine and Folates, National Institutes of Health, Bethesda, Maryland, June 17-22, 2001.
2. Gangjee A., Elzein E., Kothare M., and Vasudevan A. Curr. Pharm. Des. 2 (1996) 263
3. Berman E.F., and Werbel L.M. J. Med. Chem. 34 (1991) 479
4. Jackson, R. C. In Antifolate Drugs in Cancer Therapy, Jackman, A.L., Ed.; Humana Press: Totowa, NJ, 1999; pp. 1-12.
5. Schnell J.R., Dyson H.J., and Wright P.E. Annu. Rev. Biophys. Biomol. Struct. 33 (2004) 119
6. Carreras C.W., and Santi D.V. Annu. Rev. Biochem. 64 (1975) 721
7. Jones T.R., Calvert H., Jackman A.L., Brown S.J., and Harrap K.R. Eur. J. Med. Chem. 17 (1981) 11
8. Walling J. Investig. New Drugs 24 (2006) 37
9. Kisliuk R.L., Gaumont Y., Powers J.F., Thorndike J., Nair M.G., and Piper J.R. Synergistic growth inhibition by combinations of antifolates. In: Picciano M.F., Stokstad E.L.R., and Gregory III J.F. (Eds). Evaluation of Folate Metabolism in Health and Disease (1990), Alan R. Liss, New York 79-89
10. Taylor E.C., Kuhnt D., Shih C., Rinzel S.M., Grindey G.B., Barredo J., Lannatipour M., and Moran R.A. J. Med. Chem. 35 (1992) 4450
11. Miwa T., Hitaka T., Akimoto H., and Nomura H. J. Med. Chem. 34 (1991) 555
12. Gangjee A., Devraj R., McGuire J.J., and Kisliuk R.L. J. Med. Chem. 38 (1995) 3798
13. Gangjee A., Devraj R., McGuire J., Kisliuk R.L., Queener S.F., and Barrows L.R. J. Med. Chem. 37 (1994) 1169
14. Gangjee A., Zeng Y., McGuire J.J., and Kisliuk R.L. J. Med. Chem. 43 (2000) 3125
15. Takimoto C.H. Semin. Oncol. 24 (1997) S18
16. Rosowsky A. Prog. Med. Chem. 26 (1989) 1
17. Gangjee A., Yu J., McGuire J.J., Cody V., Galitsky N., Kisliuk R.L., and Queener S.F. J. Med. Chem. 43 (2000) 3837
18. Barredo J., and Moran R.G. Mol. Pharmacol. 42 (1992) 687
19. Aso K., Imai Y., Yakishige K., Ootsu K., and Akimoto H. Chem. Pharm. Bull. Jpn. 49 (2001) 1280
20. Gangjee A., Devraj R., McGuire J.J., and Kisliuk R.L. J. Med. Chem. 38 (1995) 4495
21. Secrist III J.A., and Liu P.S. J. Org. Chem. 43 (1978) 3937
22. Gangjee A., Yang J., Ihnat M.A., and Kamat S. Bioorg. Med. Chem. 11 (2003) 5155
23. Grell W., Hurnaus R., Griss G., Sauter R., Rupprecht E., Mark M., Luger P., Nar H., Wittneben H., and Mueller P. J. Med. Chem. 41 (1998) 5219
24. Giroux A., Nadeau C., and Han Y. Tetrahedron Lett. 41 (2000) 7601
25. Banztti C., Carfagna N., Commisso R., Heidempergher F., Pegrassi L., and Melloni P. J. Med. Chem. 31 (1988) 1466
26. Danhesier R.L., Brisbois R.G., Kowalczyk J.J., and Miller R.F. J. Am. Chem. Soc. 112 (1990) 3093
27. DeGraw J.I., Tsakotellis P., Kisliuk R.L., and Gaumont Y. J. Heterocycl. Chem. 10 (1971) 105
28. Gangjee A., Mavandadi F., and Queener S.F. J. Med. Chem. 40 (1997) 1173
29. Mini E., Srimatkandada S., Medina W.D., Moroson B.A., Carman M.D., and Bertino J.R. Cancer Res. 45 (1985) 317
30. Rosowsky A., Lazarus H., Yuan G.C., Beltz W.R., Mangini L., Abelson H.T., Modest E.J., and Frei III E. Biochem. Pharmacol. 29 (1980) 648
31. McCloskey D.E., McGuire J.J., Russell C.A., Rowan B.G., Bertino J.R., Pizzorno G., and Mini E. J. Biol. Chem. 266 (1991) 6181
32. Blakley R.L. The Biochemistry of Folic Acid and Related Pteridines (1969), Elsevier, Amsterdam p. 569
33. Foley G.F., Lazarus H., Farber S., Uzman B.G., Boone B.A., and McCarthy R.E. Cancer 18 (1965) 522
34. McGuire J.J., Magee K.J., Russell C.A., and Canestrari J.M. Oncol. Res. 9 (1997) 139
35. Gangjee A., Yu J., Kisliuk R.L., Haile W.H., Sobrero G., and McGuire J.J. J. Med. Chem. 46 (2003) 591