Synthesis and biological evaluation of 5-arylfuro[2,3-d]pyrimidines as novel dihydrofolate reductase inhibitors

Chemical and Pharmaceutical Bulletin

Volumn 47, Issue 2, 1999, Pages 156-164

  Wahid, Farid ^a   Monneret, Claude ^a   Dauzonne, Daniel ^a  

^a INSTITUT CURIE   (France)

Author keywords

Antibacterial; Antifolate; Antimalarial; Dihydrofolate reductase inhibition; Furo 2,3 d pyrimidine; Trimethoprim analogue

Indexed keywords

ANTIINFECTIVE AGENT; ANTIMALARIAL AGENT; DIHYDROFOLATE REDUCTASE INHIBITOR; FURO[2,3 D]PYRIMIDINE DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ANTIMALARIAL ACTIVITY; ARTICLE; DRUG SYNTHESIS; ENTEROCOCCUS; ENZYME INHIBITION; ESCHERICHIA COLI; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PLASMODIUM FALCIPARUM; PNEUMOCYSTIS CARINII; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS EPIDERMIDIS;

EID: 0032913096     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.47.156     Document Type: Article

References (65)

1. a) Kisliuk R. L., "Folates Antagonists as Therapeutic Agents," Vol. 1, ed. by Sirotnak F. M., Burchall J. J., Ensminger W. B., Montgomery J. A. , Academic Press, Orlando FL, 1984, pp. 1-68;
2. b) Freisheim J. H., Matthews D. A., ibid., pp. 69-131;
3. c) Blakley R. L., "Folates and Pterins, Vol. 1., Chemistry and Biochemistry of Folates," ed. by Blakley R., Benkovic S. J., John Wiley & Sons, New York, 1984, pp. 191-253;
4. d) Kraut J., Matthews D. A., "Biological Macromolecules and Assemblies," Vol. 3, ed. by Jurnak F. A., McPherson A., John Wiley & Sons, New York, 1987, pp. 1-72;
5. e) Young D. W., Chem. Soc. Rev., 119-128 (1994).
6. a) Roth B., Cheng C. C., Prog. Med. Chem., 19, 269-331 (1982);
7. b) Palmer D. C., Skotnicki J. S., Taylor E. C., ibid., 25, 85-231 (1988);
8. c) Rosowski A., ibid., 26, 1-252 (1989);
9. d) Hitchings G. H., Jr., In Vitro Cell Dev. Biol., 25, 303-310 (1989);
10. e) Christopherson R. O., Lyons S. D., Med. Res. Rev., 10, 505-548 (1990);
11. f) Schweitzer B. I., Dicker, A. P., Bertino J. R., FASEB J., 4, 2441-2452 (1990);
12. g) Taylor E. C., J. Heterocyclic Chem., 27, 1-12 (1990);
13. h) Berman E. M., Werbel L. M., J. Med. Chem., 34, 479-485 (1991);
14. i) Taylor E. C., Adv. Exp. Med. Biol., 338, 387-408 (1993);
15. j) Roche V. F., Am. J. Pharm. Educ., 58, 196-203 (1994).
16. a) Chen A. P., Grem J. L., Curr. Opin. Oncol., 4, 1089-1098 (1992);
17. b) Huennekens F. M., Adv. Enzyme Regul., 34, 397-419 (1994);
18. c) Gorlick R., Goker E., Trippett T., Waltham M., Banerjee D., Bertino J. R., N. Engl. J. Med., 335, 1041-1048 (1996);
19. d) Kamen B., Semin. Oncol., 24, Supp.1. 18, S18-30-S18-39 (1997).
20. a) Leoung G. S., Mills J., Hopewell P. C., Hughes W., Wofsy C., Ann. Intern. Med., 105, 45-48 (1986);
21. b) Allegra C. J., Chabner B. A., Tuazon C. U., Ogata-Arakaki D., Baird B., Drake J. C., Simmons J. T., Lack E. E., Shelhamer J. H., Balis F., Walker R., Kovacs J. A., Lane H., Masur H., N. Engl. J. Med., 317, 978-985 (1987);
22. c) Queener S. F., Bartlett M. S., Jay M. A., Durkin M. M., Smith J. W., Antimicrob. Agents Chemother., 31, 1323-1327 (1987);
23. d) Allegra C. J., Kovacs J. A., Drake J. C., Swan J. C., Chabner B. A., Masur H., J. Clin. Invest., 79, 478-482 (1987);
24. e) Kovacs J. A., Allegra C. J., Chabner B. A., Swan J. C., Drake J., Lunde M., Parillo J. E., Masur H., J. Infect. Dis., 155, 1027-1032 (1987);
25. f) Allegra C. J., Kovacs J. A., Drake J. C., Swan J. C., Chabner B. A., Masur H., J. Exp. Med., 165, 926-931 (1987);
26. g) Kovacs J. A., Masur H., J. Infect. Dis., 158, 254-259 (1988);
27. h) Fischl M. A., Dickinson G. M., La Voie L., J. Am. Med. Assoc., 259, 1185-1189 (1988);
28. i) Leport C., Raffi F., Matheron S., Katlama C., Regnier B., Saimot A. G., Marche C., Vedrenne C., Vilde J. L., Am. J. Med., 84, 94-100 (1988);
29. j) Kovacs J. A., Allegra C. J., Swan J. C., Drake J. C., Parillo J. E., Chabner B. A., Masur H., Antimicrob. Agents Chemother., 32, 430-433 (1988);
30. k) Kovacs J. A., Allegra C. J., Kennedy S., Swan J. C., Drake J. C., Parillo J. E., Chabner B. A., Masur H., Am. J. Trop. Med. Hyg., 39, 491-496 (1988);
31. l) Falloon J., Allegra C. J., Kovacs J., O'Neill D., Ogata-Arakaki D., Feuerstein I., Polis M., Davey R., Lane H. C., LaFon S., Rogers M., Zunich K., Zurlo J., Tuazon C., Parenti D., Simon G., Masur H., Clin. Res., 38, 361A (1990);
32. m) de Gans J., Portegies P., Reiss P., Troost D., van Gool T., Lange J. M., J. Acquired Immune Defic. Syndr., 9, 137-142 (1992);
33. n) Schnapp, L. M., Geaghan S. M., Campagna A., Fahy J., Steiger D., Ng V., Hadley W. K., Hopewell, P. C., Stansell J. D., Arch. Intern. Med., 152, 1073-1077 (1992);
34. o) Masur H., Polis M. A., Tuazon C. U., Ogata-Arakaki D., Kovacs J. A., Katz D., Hilt D. Simmons T., Feuerstein I., Lundgren B., Lane H. C., Chabner B.A., Allegra C. J., J. Infect. Dis., 167, 1422-1426 (1993);
35. p) Devita V. T., Hellman S., Rosenberg S. A. (eds.), "Infectious Complications of HIV in AIDS, Etiology, Diagnosis, Treatment and Prevention," 3rd ed., Lippincot & Co., Philadelphia, 1992;
36. q) Queener S. F., J. Med. Chem., 38, 4739-4759 (1995).
37. Dauzonne D., Adam-Launay A., Tetrahedron, 48, 3069-3080 (1992).
38. a) Kotake Y., Iijima A., Yoshimatsu K., Tamai N., Ozawa Y., Koyanagi N., Kitoh K., Nomura H., J. Med. Chem., 37, 1616-1624 (1994);
39. b) McGuire J. J., Bergoltz V. V., Heitzman K. J., Haile W. H., Russell C. A., Bolanowska E. E., Kotake Y., Haneda T., Nomura H., Cancer Res., 54, 2673-2679 (1994);
40. c) Kotake Y., Okauchi T., Iijima A., Yoshimatsu K., Nomura H., Chem. Pharm. Bull., 43, 829-841 (1995);
41. d) Rosowsky A., Papoulis A. T., Queener S. F., J. Med. Chem., 41, 913-918 (1998).
42. a) Miwa T., Hitaka T., Akimoto H., Nomura H., J. Med. Chem., 34, 555-560 (1991);
43. b) Miwa T., Hitaka T., Akimoto H., J. Org. Chem., 58, 1696-1701 (1993);
44. c) Shih C., Gossett L. S., Heterocycles, 35, 825-841 (1993);
45. d) Taylor E. C., Patel H. H., Jun J. G., J. Org. Chem., 60, 6684-6687 (1995);
46. e) Aso K., Hitaka T., Yukishige K., Ootsu K., Akimoto H., Chem. Pharm. Bull., 43, 256-261 (1995);
47. f) Gangjee A., Mavandadi F., Queener S. F., J. Med. Chem., 38, 2158-2165 (1995);
48. g) Taylor E. C., Mao Z., J. Org. Chem., 61, 7973-7974 (1996);
49. h) Gangjee A., Mavandadi F., Kisliuk R. L., McGuire J. J., Queener, S. F., J. Med. Chem., 39, 4563-4568 (1996);
50. i) Itoh F., Yoshioka Y., Yukishige K., Yoshida S., Wajima M., Ootsu K., Akimoto H., Chem. Pharm. Bull., 44, 1498-1509 (1996);
51. j) Taylor E. C., Jennings L. D., Mao Z., Hu B., Jun J.-G., Zhou P., J. Org. Chem., 62, 5392-5403 (1997).
52. Taylor E. C., Young W. B., J. Org. Chem., 60, 7947-7952 (1995).
53. a) Rosowski A., Mota C. E., Wright J., Freisheim J. E., Heusner J. J., McCormack J. J., Queener S. F., J. Med. Chem., 36, 3103-3112 (1993);
54. b) Rosowski A., Mota C. E., Queener S. F., J. Heterocyclic Chem., 33, 1959-1966 (1996);
55. c) Rosowski A., Papoulis A. T., Queener S. F., J. Med. Chem., 40, 3694-3699 (1997).
56. Gangjee A., Vasudevan A., Queener S. F., J. Med. Chem., 40, 3032-3039 (1997).
57. a) Gangjee A., Devraj R., Queener S. F. Kisliuk R. L., "Chemistry and Biology of Pteridines and Folates," ed. by Ayling J. E., Nair M. G., Baugh C. M., Plenum Press, New York, 1993, pp. 445-448;
58. b) Gangjee A., Devraj R., McGuire J. J., Kisliuk R. L., Queener S. F., Barrows L. R., J. Med. Chem., 37, 1169-1176 (1994);
59. c) Gangjee A., Devraj R., McGuire J. J., Kisliuk R. L., ibid., 38, 3798-3805 (1995);
60. d) Gangjee A., Guo, X., Queener S. F., Cody V., Galitsky N., Luft J. R., Pangborn W., Barrows L. R., ibid., 41, 1263-1271 (1998);
61. e) Gangjee A., Elzein E., Queener S. F., McGuire J. J., ibid., 41, 1409-1416 (1998).
62. Dauzonne D., Demerseman P., Synthesis, 1990, 66-70.
63. Dauzonne D., Folléas B., Martinez L., Chabot G.G., Eur. J. Med. Chem., 32, 71-82 (1997).
64. Angehrn P., Hohl P., Hubschwerlen C., Page M., Then R., Antimicrob. Agents Chemother., 36, 2825-2834 (1992).
65. Desjardins R. E., Canfield C. J., Haynes J. D., Chulay J. D., Antimicrob. Agents Chemother., 16, 710-718 (1979).