Synthesis of novel quinazoline-based antifolates with modified glutamate side chains as potential inhibitors of thymidylate synthase and antitumour agents

Tetrahedron

Volumn 53, Issue 39, 1997, Pages 13383-13396

  Bavetsias, Vassilios ^a   Bisset, Graham M F ^a   Kimbell, Rosemary ^a   Boyle, F Thomas ^b   Jackman, Ann L ^a  

^a INSTITUTE OF CANCER RESEARCH   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; FOLIC ACID ANTAGONIST; QUINAZOLINE DERIVATIVE; THYMIDYLATE SYNTHASE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL; CHEMICAL MODIFICATION; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LEUKEMIA L 1210; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030758895     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00851-X     Document Type: Article

References (26)

1. Friedkin, M. Adv. Enzymol. 1973, 38, 235-287
2. Bisset, G. M. F.; Bavetsias, V.; Thornton, T. J.; Pawelczack, K.; Calvert, A. H.; Hughes, L. R.; Jackman, A. L. J. Med. Chem. 1994, 37, 3294-3302.
3. Bavetsias, V.; Jackman, A. L.; Kimbell, R.; Gibson, W.; Boyle, F. T.; Bisset, G. M. F. J. Med. Chem. 1996, 39, 73-85.
4. Bavetsias, V.; Jackman, A. L.; Kimbell, R.; Boyle, F. T.; Bisset, G. M. F. Bioorg. Med. Chem. Lett. 1996, 6, 631-636.
5. Jodrell, D. I.; Gibson, W.; Bisset, G. M. F.; Boyle, F. T.; Judson, I. R.; Jackman, A. L. Biochem. Pharmacol. 1993, 46, 2229-2234.
6. For an excellent review on amide bond isosteres see: Spatola, A. F. in Chemistry and Biochemistry of Amino Acids, Peptides and Proteins, Weinstein, B. Ed; Dekker: New York, 1983; 7, Chapter 5.
7. Sherman, D. B.; Spatola, A. F. J. Am. Chem. Soc. 1990, 112, 433-441.
8. Meienhover, J. in The Peptides, Analysis, Synthesis, Biology; Gross, E. and Meienhover, J. Eds; Academic Press, New York: 1979; 1, pp 264-309.
9. Cava, M. P.; Levinson, M. I. Tetrahedron 1985, 41, 5061-5087.
10. For nomenclature and symbolism of amide bond isosteres see: IUPAC-IUB Joint Commission on Biochemical Nomenclature, Nomenclature and Symbolism for Amino Acids and Peptides, Recommendations 1983, Eur. J. Biochem, 1984, 138, 9.
11. Rosowsky, A.; Forsch, R.; Uren, J.; Wick, M. J. Med. Chem. 1981, 24, 1450-1455.
12. Lott, R. S.; Chauhan, V. S.; Stammer, C. H. J. Chem. Soc., Chem. Commun. 1979, 495-496.
13. Subhas Bose, D.; Thurston, D. E. Tetrahedron Lett. 1990, 31, 6903-6906.
14. Roeske, R. W.; Weitl, F. L.; Prasad, K. U.; Thompson, R. M. J. Org. Chem. 1976, 41, 1260-1261.
15. Kokotos, G. Synthesis 1990, 299-301.
16. Hann, M. H.; Sammes, P. G.; Kennewell, P. D.; Taylor, J. B. J. Chem. Soc., Perkin Transactions I 1982, 307-314.
17. Marshall, G. R.; Humblet, C.; Van Opdenbosch, N.; Zabrocki, J. in Peptides: Synthesis-Structure-Function. Proceedings of the Seventh American Peptide Symposium; Rich, D. H. and Gross, E. Eds; Pierce Chemical, Rockford: Illinois; 1981; pp 669-672.
18. Boyle, F. T.; Crook, J. W.; Matusiak, Z. S. UK Pat. GB2272217A1 1994 (Chem. Absrt. 1995, 122, 160665).
19. Zabrocki, J.; Dunbar, J. B.; Marshall, K. W.; Toth, M. V.; Marshall, G. R. J. Org. Chem. 1992, 57, 202-209.
20. (a) Jackman, A. L.; Alison, D. L.; Calvert, A. H.; Harrap, K. R. Cancer Res. 1986, 46, 2810-2815.
21. (b) Sikora, E.; Jackman, A. L.; Newell, D. R.; Calvert, A. H. Biochem. Pharmacol. 1988, 37, 4047-4054.
22. Jackman, A. L.; Taylor, G. A.; O'Connor, B. M.; Bishop, J. A.; Moran, R. G.; Calvert, A. H. Cancer Res. 1990, 50, 5212-5218.
23. Jackman, A. L.; Kimbell, R.; Brown, M.; Brunton, L.; Boyle, F.T. Anti-Cancer Drug Des. 1995, 10, 555-572.
24. Rolski, S; Paruszewski, R. Rocz. Chem. 1967, 41, 341-349.
25. Kolasa, T.; Miller, M. J. J. Org. Chem. 1990, 55, 1711-1721.
26. Prepared in 0.05 mol scale as described in Fieser & Fieser Reagents for Organic Synthesis; John Wiley and Sons, Inc: New York, 1967; pp 446, and used without titration.