Design, synthesis, and biological evaluation of simplified α-Keto heterocycle, trifluoromethyl ketone, and formyl substituted folate analogues as potential inhibitors of GAR transformylase and AICAR transformylase

作者: Thomas H Marsilje , Michael P Hedrick , Joel Desharnais , Ali Tavassoli , Yan Zhang

DOI: 10.1016/S0968-0896(03)00456-5

关键词:

摘要: A series of simplified alpha-keto heterocycle, trifluoromethyl ketone, and formyl substituted folate analogues lacking the benzoylglutamate subunit were prepared examined as potential inhibitors glycinamide ribonucleotide transformylase (GAR Tfase) aminoimidazole carboxamide (AICAR Tfase).

参考文章(90)
Leonard Warren, John M. Buchanan, Biosynthesis of the purines. XIX. 2-Amino-N-ribosylacetamide 5'-phosphate (glycinamide ribotide) transformylase. Journal of Biological Chemistry. ,vol. 229, pp. 613- 626 ,(1957) , 10.1016/S0021-9258(19)63669-0
Marilyn Jansen, Michael Dykstra, Jacqueline I. Lee, Jeremy Stables, Peter Topley, Vincent C. Knick, Robert J. Mullin, David S. Duch, Gary K. Smith, Effect of purine synthesis inhibition on WiDr spheroids in vitro or on WiDr or colon 38 tumors in vivo: Complete growth inhibition but not regression Biochemical Pharmacology. ,vol. 47, pp. 1067- 1078 ,(1994) , 10.1016/0006-2952(94)90419-7
B A Moroson, G P Beardsley, R G Moran, E C Taylor, A new folate antimetabolite, 5,10-dideaza-5,6,7,8-tetrahydrofolate is a potent inhibitor of de novo purine synthesis. Journal of Biological Chemistry. ,vol. 264, pp. 328- 333 ,(1989) , 10.1016/S0021-9258(17)31261-9
Katherine A. Shackelford, Lillian L. Habeck, Lynn S. Gossett, Richard M. Schultz, Laurane G. Mendelsohn, Sherri L. Andis, Gerald B. Grindey, Tracy A. Leitner, Chuan Shih, A Novel Class of Monoglutamated Antifolates Exhibits Tight-binding Inhibition of Human Glycinamide Ribonucleotide Formyltransferase and Potent Activity against Solid Tumors Cancer Research. ,vol. 54, pp. 1021- 1026 ,(1994)
Sudsawat Laohavinij, Stephen R. Wedge, Micheal J. Lind, Nigel Bailey, Alison Humphreys, Madeleine Proctor, Fiona Chapman, Dorothy Simmons, Avril Oakley, Lesley Robson, Lyndsey Gumbrell, Gordon A. Taylor, Huw D. Thomas, Alan V. Boddy, David R. Newell, A. Hilary Calvert, A Phase I clinical study of the antipurine antifolate lometrexol (DDATHF) given with oral folic acid Investigational New Drugs. ,vol. 14, pp. 325- 335 ,(1996) , 10.1007/BF00194536
Carol A. Caperelli, N10-substituted 5,8-dideazafolate inhibitors of glycinamide ribonucleotide transformylase. Journal of Medicinal Chemistry. ,vol. 30, pp. 1254- 1256 ,(1987) , 10.1021/JM00390A024
Nancy K. Harn, Christine J. Gramer, Benjamin A. Anderson, Acylation of oxazoles by the copper-mediated reaction of oxazol-2-ylzinc chloride derivatives Tetrahedron Letters. ,vol. 36, pp. 9453- 9456 ,(1995) , 10.1016/0040-4039(95)02051-9
Edward C. Taylor, James M. Hamby, Chuan Shih, Gerald B. Grindey, Sharon M. Rinzel, G. Peter Beardsley, Richard G. Moran, Synthesis and antitumor activity of 5-deaza-5,6,7,8-tetrahydrofolic acid and its N10-substituted analogues. Journal of Medicinal Chemistry. ,vol. 32, pp. 1517- 1522 ,(1989) , 10.1021/JM00127A019
John D. Roberts, Elizabeth A. Poplin, Mary Beth Tombes, Brenda Kyle, Darcy V. Spicer, Steven Grant, Timothy Synold, Richard Moran, Weekly lometrexol with daily oral folic acid is appropriate for phase II evaluation. Cancer Chemotherapy and Pharmacology. ,vol. 45, pp. 103- 110 ,(2000) , 10.1007/S002800050017