Synthesis of N-[4-[1-ethyl-2-(2,4-diaminofuro[2,3-d] pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid as an antifolate1

Journal of Medicinal Chemistry

Volumn 45, Issue 9, 2002, Pages 1942-1948

  Gangjee, Aleem ^a   Zeng, Yibin ^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

[No Author keywords available]

Indexed keywords

2,4 DIAMINO 5 (CHLOROMETHYL)FURO[2,3 D]PYRIMIDINE; 4 PROPIONYLPHENOL; DIHYDROFOLATE REDUCTASE; FOLIC ACID ANTAGONIST; FOLYLPOLYGLUTAMATE SYNTHASE; GLUTAMIC ACID DERIVATIVE; GLUTAMIC ACID DIETHYL ESTER; METHOTREXATE; METHYL GROUP; N [4 [1 ETHYL 2 (2,4 DIAMINOFURO[2,3 D]PYRIMIDIN 5 YL)ETHYL]BENZOYL] LEVO GLUTAMIC ACID; PALLADIUM; PHENOL DERIVATIVE; PYRIMIDINE DERIVATIVE; THYMIDYLATE SYNTHASE; UNCLASSIFIED DRUG;

ALKYLATION; ANTINEOPLASTIC ACTIVITY; ARTICLE; CATALYSIS; CONTROLLED STUDY; CYTOTOXICITY; DRUG DESIGN; DRUG EFFICACY; DRUG POTENCY; DRUG SYNTHESIS; ENZYME INHIBITION; GROWTH INHIBITION; HUMAN; HUMAN CELL; HYDROGENATION; HYDROLYSIS; METABOLITE;

ANTINEOPLASTIC AGENTS; DRUG RESISTANCE, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME INHIBITORS; FOLIC ACID ANTAGONISTS; GLUTAMIC ACID; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; PYRIMIDINES; STRUCTURE-ACTIVITY RELATIONSHIP; THYMIDYLATE SYNTHASE; TUMOR CELLS, CULTURED;

EID: 0037171724     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm010575m     Document Type: Article

References (37)

1. The renewed potential for folate antagonists in contemporary cancer chemotherapy
2. Chemistry and biological activity of antifolates
3. Classical and nonclassical antifolates as potential antitumor, antipneumocystis and antitoxoplasma agents
4. Effect of c9-methyl substitution and C8-C9 conformational restriction on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines
5. Effect of bridge region variation on antifolate and antitumor activity of classical 5-substituted 2,4-diaminofuro[2,3-d]pyrimidines
6. Structural design, biochemical properties, and evidence for improved therapeutic activity of 5-alkyl derivatives of 5-deazaaminopterin and 5-deazamethotrexate compared to methotrexate in murine tumor models
7. Synthesis and antitumor activity of 10-alkyl-10-deazaaminopterin. A convenient synthesis of 10-deazaaminopterin
8. Synthesis and biological activity of resolved C-10 diastereomers of 10-methyl and 10-ethyl-10-deazaaminopterin
9. Synthesis and antifolate properties of 5,10-ethano-5,10-dideazaminopterin
10. Synthesis and antifolate properties of 10-alkyl-5,10-dideaza analogues of methotrexate and tetrahydrofolic acid
11. The effect of polyglutamylation on the inhibitory activity of folate analogues
12. Antifolate polyglutamylation in preclinical and clinical antifolate resistance
13. Differing specificities for 4-aminofolate analogues of folylpolyglutamyl synthetase from tumors and proliferative intestinal epithelium of the mouse with significance for selective antitumor action
14. The catalytic mechanism and structure of thymidylate synthase
15. Synthesis of benzoic and tetralone carboxylic acid esters from phenols by palladium catalyzed alkoxy/aryloxy carbonylation
16. Studies directed toward a total synthesis of Nucleoside Q. The Annulation of 2,6-diaminopyrimidin-4-one with α-halo carbonyls to form pyrrolo[2,3-d]-pyrimidines and furo[2,3-d]pyrimidines
17. Continuous culture of lymphoblasts from peripheral blood of a child with acute leukemia
18. Molecular and karyological analysis of methotrexate-resistant and -sensitive human leukemic CCRF-CEM cells
19. Effects of methotrexate esters and other lipophilic antifoflates on methotrexate-resistant human leukemic lymphoblasts
20. Decreased folylpolyglutamate synthetase activity as a mechanism of methotrexate resistance in CCRF-CEM human leukemia sublines
21. Inherent resistance of human squamous cell lines to methotrexate as a result of decreased polyglutamylation of this drug
22. Pteroylpolyglutamates: Biosynthesis, degradation, and function
23. Biochemical and biological studies on 2-desamino-2-methylaminopterin, an antifolate the polyglutumates of which are more potent than the monoglutamate against three key enzymes of folate metabolism
24. Inhibition of human dihydrofolate reductase by antifolyl polyglutamates
25. Synthesis and antifolate properties of 9-alkyl-10-deazaminopterins
26. δ-hemiphthaloyl-L-ornithine (PT523) with modifications in the side chain, p-aminobenzoyl moiety, or 9,10-bridge: Synthesis and in vitro antitumor activity
27. Diastereoisomers of 5, 10-methylene-5,6,7,8-tetrahydropteroyl-D-glutamic acid
28. The enzymatic synthesis of thymidylate. Early step in the purification of thymidylate synthetase of escherichia coli
29. Expression of human thymidylate synthase in escherichia coli