Synthesis and biological evaluation of N-{4-[5-(2,4-diamino-6-oxo-1,6- dihydropyrimidin-5-yl)-2-(2,2,2-trifluoroacetyl)pentyl]benzoyl}-L-glutamic acid as a potential inhibitor of GAR Tfase and the de novo purine biosynthetic pathway

Bioorganic and Medicinal Chemistry

Volumn 13, Issue 10, 2005, Pages 3593-3599

  Cheng, Heng ^a   Hwang, Inkyu ^a   Chong, Youhoon ^a   Tavassoli, Ali ^b   Webb, Michael E ^b   Zhang, Yan ^a   Wilson, Ian A ^a   Benkovic, Stephen J ^b   Boger, Dale L ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 CHLORO 3 IODOPROPANE; 4 (4,4,4 TRIFLUORO 3 DIMETHYLHYDRAZONOBUTYL)BENZOATE; 4 [5 (2,4 DIAMINO 6 OXO 1,6 DIHYDROPYRIMIDIN 5 YL) 2 (2,2,2 TRIFLUOROACETYL)PENTYL]BENZOATE; BENZOIC ACID DERIVATIVE; DI TERT BUTYL N [4 [5 (2,4 DIAMINO 6 OXO 1,6 DIHYDROPYRIMIDIN 5 YL) 2 (2,2,2 TRIFLUORO 1 DIMETHYLHYDRAZONOETHYL)PENTYL]BENZOYL]GLUTAMIC ACID; DI TERT BUTYL N [4 [5 (2,4 DIAMINO 6 OXO 1,6 DIHYDROPYRIMIDIN 5 YL) 2 (2,2,2 TRIFLUOROACETYL)PENTYL]BENZOYL]GLUTAMIC ACID; ENZYME INHIBITOR; FLUORINE DERIVATIVE; GLUTAMIC ACID DERIVATIVE; METHYL 4 [5 (2,4 DIAMINO 6 OXO 1,6 DIHYDROPYRIMIDIN 5 YL) 2 (2,2,2 TRIFLUORO 1 DIMETHYLHYDRAZONOETHYL)PENTYL]BENZOATE; N [4 [5 (2,4 DIAMINO 6 OXO 1,6 DIHYDROPYRIMIDIN 5 YL) 2 (2,2,2 TRIFLUOROACETYL)PENTYL]BENZOYL]GLUTAMIC ACID; PHOSPHORIBOSYLAMINOIMIDAZOLECARBOXAMIDE FORMYLTRANSFERASE; PHOSPHORIBOSYLGLYCINAMIDE FORMYLTRANSFERASE; PROPANE; PYRIMIDINONE DERIVATIVE; RECOMBINANT ENZYME; RECOMBINANT PHOSPHORIBOSYLGLYCINAMIDE FORMYLTRANSFERASE; UNCLASSIFIED DRUG; [4 [5 (2,4 DIAMINO 6 OXO 1,6 DIHYDROPYRIMIDIN 5 YL) 2 (2,2,2 TRIFLUORO 1 DIMETHYLHYDRAZONOETHYL)PENTYL]BENZOYL]GLUTAMIC ACID;

ALKYLATION; ARTICLE; CANCER CELL CULTURE; CANCER INHIBITION; CONTROLLED STUDY; DRUG SYNTHESIS; ESCHERICHIA COLI; HUMAN; HUMAN CELL; IC 50; PURINE SYNTHESIS;

TRIFLUORO;

EID: 17444418621     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.11.049     Document Type: Article

References (30)

1. L. Warren, and J.M. Buchanan J. Biol. Chem. 229 1957 613
2. J.M. Buchanan, and S.C. Hartman Adv. Enzymol. 21 1959 199
3. M.S. Warren, K.M. Mattia, A.E. Marolewski, and S.J. Benkovic Pure Appl. Chem. 68 1996 2029
4. Review: R.I. Christopherson, S.D. Lyons, and P.K. Wilson Acc. Chem. Res. 35 2002 961
5. G.P. Beardsley, B.A. Moroson, E.C. Taylor, and R.G. Moran J. Biol. Chem. 264 1989 328
6. For related analogues and studies, see: E.C. Taylor, J.M. Hamby, C. Shih, G.B. Grindey, S.M. Rinzel, G.P. Beardsley, and R.G. Moran J. Med. Chem. 32 1989 1517
7. R.G. Moran, S.W. Baldwin, E.C. Taylor, and C. Shih J. Biol. Chem. 264 1989 21047
8. E.C. Bigham, S.J. Hodson, W.R. Mallory, D. Wilson, D.S. Duch, G.K. Smith, and R. Ferone J. Med. Chem. 35 1992 1399
9. E.C. Taylor, D. Kuhnt, C. Shih, S.M. Rinzel, G.B. Grindey, J. Barredo, M. Jannatipour, and R.G. Moran J. Med. Chem. 35 1992 4450
10. C. Shih, L.S. Gossett, J.F. Worzalla, S.M. Rinzel, G.B. Grindey, P.M. Harrington, and E.C. Taylor J. Med. Chem. 35 1992 1109
11. C. Shih, L.L. Habeck, L.G. Mendelsohn, V.J. Chen, and R.M. Schultz Adv. Enzyme Regul. 38 1998 135
12. T.H. Marsilje, M.P. Hedrick, J. Desharnais, A. Tavassoli, J. Ramcharan, Y. Zhang, I.A. Wilson, S.J. Benkovic, and D.L. Boger Bioorg. Med. Chem. 11 2003 4487
13. S.E. Greasley, T.H. Marsilje, H. Cai, S. Baker, S.J. Benkovic, D.L. Boger, and I.A. Wilson Biochemistry 40 2001 13538
14. D.L. Boger, N.-E. Haynes, P.A. Kitos, M.S. Warren, J. Ramcharan, A.E. Marolewski, and S.J. Benkovic Bioorg. Med. Chem. 5 1997 1817
15. D.L. Boger, N.-E. Haynes, M.S. Warren, L.T. Gooljarsingh, J. Ramcharan, P.A. Kitos, A.E. Marolewski, and S.J. Benkovic Bioorg. Med. Chem. 5 1997 1831
16. D.L. Boger, N.-E. Haynes, M.S. Warren, J. Ramcharan, P.A. Kitos, and S.J. Benkovic Bioorg. Med. Chem. 5 1997 1839
17. D.L. Boger, N.-E. Haynes, M.S. Warren, J. Ramcharan, A.E. Marolewski, P.A. Kitos, and S.J. Benkovic Bioorg. Med. Chem. 5 1997 1847
18. D.L. Boger, N.-E. Haynes, M.S. Warren, J. Ramcharan, P.A. Kitos, and S.J. Benkovic Bioorg. Med. Chem. 5 1997 1853
19. D.L. Boger, M.J. Kochanny, H. Cai, D. Wyatt, P.A. Kitos, M.S. Warren, L.T. Ramcharan, L.T. Gooljarsingh, and S.J. Benkovic Bioorg. Med. Chem. 6 1998 643
20. D.L. Boger, M.A. Labroli, T.H. Marsilje, Q. Jin, M.P. Hedrick, S.J. Baker, J.H. Shim, and S.J. Benkovic Bioorg. Med. Chem. 8 2000 1075
21. D.L. Boger, T.H. Marsilje, R.A. Castro, M.P. Hedrick, Q. Jin, S.J. Baker, J.H. Shim, and S.J. Benkovic Bioorg. Med. Chem. Lett. 10 2000 1471
22. T.H. Marsilje, M.P. Hedrick, J. Desharnais, K. Capps, A. Tavassoli, Y. Zhang, I.A. Wilson, S.J. Benkovic, and D.L. Boger Bioorg. Med. Chem. 11 2003 4503
23. T.H. Marsilje, M.A. Labroli, M.P. Hedrick, Q. Jin, J. Desharnais, S.J. Baker, L.T. Gooljarsingh, J. Ramcharan, A. Tavassoli, Y. Zhang, I.A. Wilson, G.P. Beardsley, S.J. Benkovic, and D.L. Boger Bioorg. Med. Chem. 10 2002 2739
24. J. Desharnais, I. Hwang, Y. Zhang, A. Tavassoli, J. Baboval, S.J. Benkovic, I.A. Wilson, and D.L. Boger Bioorg. Med. Chem. 11 2003 4511
25. Y. Zhang, J. Desharnais, T.H. Marsilje, C. Li, M.P. Hedrick, L.T. Gooljarsingh, A. Tavassoli, S.J. Benkovic, A.J. Olson, D.L. Boger, and I.A. Wilson Biochemistry 42 2003 6043
26. S.E. Greasley, M.M. Yamashita, H. Cai, S.J. Benkovic, D.L. Boger, and I.A. Wilson Biochemistry 38 1999 16783
27. E.C. Taylor, W.B. Young, R. Chaudhari, and H.H. Patel Heterocycles 36 1993 1897
28. J. Biovin, L. El Kaim, and S.Z. Zard Tetrahedron Lett. 33 1992 1285
29. J. Biovin, L. El Kaim, and S.Z. Zard Tetrahedron 51 1995 2573
30. L.L. Habeck, T.A. Leitner, K.A. Shackelford, L.S. Gossett, R.M. Schultz, S.L. Andis, C. Shih, G.B. Grindey, and L.G. Mendelsohn Cancer Res. 54 1994 1021