Traceless solid-phase synthesis of nitrogen-containing heterocycles and their biological evaluations as inhibitors of neuronal sodium channels

Journal of Combinatorial Chemistry

Volumn 6, Issue 6, 2004, Pages 928-933

  Kong, Kah Hoe ^a   Chen, Yu ^a   Ma, Xiang ^a   Wai, Keung Chui ^a   Lam, Yulin ^a  

^a NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

2 (4 METHOXYPHENYL) 4 PHENYL 2,3 DIHYDRO 1H BENZO[B][1,4]DIAZEPINE; 2 PYRIMIDINETHIONE DERIVATIVE; 2,4 DIPHENYL 2,3 DIHYDRO 1H BENZO[B][1,4]DIAZEPINE; 2,4,6 TRIPHENYLPYRIMIDINE; 3,4 DIMETHYL 2 PHENYL 2,3 DIHYDRO 1H BENZO[B][1,4]DIAZEPINE; 3,6 DIMETHYL 4 PHENYL 3,4 DIHYDRO 1H PYRIMIDIN 2 ONE; 4 (4 BROMOPHENYL) 2,6 DIPHENYLPYRIMIDINE; 4 (4 BROMOPHENYL) 3 METHYL 6 PHENYL 3,4 DIHYDRO 1H PYRIMIDINE 2 THIONE; 4 (4 BROMOPHENYL) 3,6 DIMETHYL 3,4 DIHYDRO 1H PYRIMIDINE 2 THIONE; 4 (4 BROMOPHENYL) 6 METHYLPYRIMIDIN 2 YLAMINE; 4 (4 BROMOPHENYL) 6 PHENYLPYRIMIDIN 2 YLAMINE; 4 (4 METHOXYPHENYL) 2,6 DIPHENYLPYRIMIDINE; 4 (4 METHOXYPHENYL) 3 METHYL 6 PHENYL 3,4 DIHYDRO 1H PYRIMIDINE 2 ONE; 4 (4 METHOXYPHENYL) 3 METHYL 6 PHENYL 3,4 DIHYDRO 1H PYRIMIDINE 2 THIONE; 4 (4 METHOXYPHENYL) 5,6 DIMETHYL 2 PHENYLPYRIMIDINE; 4 (4 METHOXYPHENYL) 5,6 DIMETHYL 3,4 DIHYDRO 1H PYRIMIDINE 2 THIONE; 4 (4 METHOXYPHENYL) 5,6 DIPHENYLPYRIMIDIN 2 YLAMINE; 4 (4 METHOXYPHENYL) 6 DIPHENYLPYRIMIDIN 2 YLAMINE; 4 (4 METHOXYPHENYL) 6 PHENYL 3,4 DIHYDRO 1H PYRIMIDINE 2 THIONE; 4 METHYL 2 PHENYL 2,3 DIHYDRO 1H BENZO[B][1,4]DIAZEPINE; 4 METHYL 6 PHENYLPYRIMIDIN 2 YLAMINE; 4,5 DIMETHYL 2,6 DIPHENYLPYRIMIDINE; 4,6 DIPHENYL 3,4 DIHYDRO 1H PYRIMIDINE 2 THIONE; 4,6 PHENYLPYRIMIDIN 2 YLAMINE; DIAZEPINE DERIVATIVE; NITROGEN; PYRIMIDINE DERIVATIVE; SODIUM CHANNEL BLOCKING AGENT; SULFONE DERIVATIVE; THIOUREA; UNCLASSIFIED DRUG;

ALKYLATION; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BINDING ASSAY; CHEMICAL COMPOSITION; CYCLIZATION; DRUG SCREENING; DRUG SYNTHESIS; ELIMINATION REACTION; NONHUMAN; OXIDATION; RADIOASSAY; RAT; SODIUM CHANNEL; SOLID;

ANIMALS; BENZODIAZEPINES; COMBINATORIAL CHEMISTRY TECHNIQUES; HETEROCYCLIC COMPOUNDS; NEURONS; NITROGEN; PYRIMIDINES; RATS; SODIUM CHANNEL BLOCKERS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 9344270469     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc049910t     Document Type: Article

References (27)

1. Gilchrist, T. L. Heterocyclic Chemistry; Addison-Wesley Longman Ltd.: England, 1998.
2. (a) Gelen, E.; Koot, W. J.; Menge, W. M. P. B.; Ottenheijm, H. C. J.; Timmerman, H. Comb. Chem. High Throughput Screening 2003, 6, 79-99.
3. (b) Krchnák, V.; Holladay, M. V Chem. Rev. 2002, 102, 61-91.
4. (c) Phoon, C. W.; Sim, M. M. Cur. Org. Chem. 2002, 5, 937-964.
5. (d) Franzén, R. G. J. Comb. Chem. 2000, 2, 195-214.
6. Simpkins, N. S. Sulfones in Organic Synthesis; Pergamon Press: Oxford, 1993.
7. (a) Cheng, W. C.; Kurth, M. J. J. Org. Chem. 2002, 67, 4387-4391.
8. (b) Cheng, W. C.; Wong, M.; Olmstead, M. M.; Kurth, M. J. Org. Lett. 2002, 4, 741-744.
9. (c) Cheng, W. C.; Lin, C. C.; Kurth, M. J. Tetrahedron Lett. 2002, 43, 2967-2970.
10. (d) Cheng, W. C.; Olmstead, M. M.; Kurth, M. J. J. Org. Chem. 2001, 66, 5528-5533.
11. (e) Cheng, W. C.; Halm, C.; Evarts, J. B.; Olmstead, M. M.; Kurth, M. J. J. Org. Chem. 1999, 64, 8557-8562.
12. (f) Halm, C.; Evarts, J.; Kurth, M. J. Tetrahedron Lett. 1997, 38, 7709-7712.
13. (a) Huang, W.; Cheng, S.; Sun, W. Tetrahedron Lett. 2001, 42, 1973-1974.
14. (b) Fyles, T. M.; Leznoff, C. C. Can. J. Chem. 1976, 54, 935-942.
15. (c) Fyles, T. M.; Leznoff, C. C. Can. J. Chem. 1978, 56, 1031-1041.
16. (a) Chen, Y.; Lam, Y. L.; Lai, Y. H. Org. Lett. 2003, 5, 1067-1069.
17. (b) Chen, Y.; Lam, Y. L.; Lai, Y. H. Org. Lett. 2002, 4, 3935-3937.
18. (c) Chen, Y.; Lam, Y. L.; Lee, S. Y. Chem. Lett. 2001, 3, 274-275.
19. (a) Kappe, C. O. Eur. J. Med. Chem. 2000, 35, 1043.
20. (b) McCombie, S. W.; Tagat, J. R.; Vice, S. F.; Lin, S. I.; Steensma, R.; Endres, M.; Cox, K.; Dan, N.; Chou, C. C. Bioorg. Med. Chem. Lett. 2003, 13, 567.
21. (c) Schutz, H. Benzodiazepines; Springer: Heidelberg, 1982.
22. (d) In The Pyrimidines; Taylor, E. C., Weissberger, A., Eds.; Wiley: New York, 1994.
23. (a) Claremon, D. A.; Rosenthal, S. A. Synthesis 1986, 664.
24. (b) Chimirri, A.; Grasso, S.; Ottana, R.; Romeo, G.; Zappala, M. J. Heterocycl. Chem. 1990, 27, 371.
25. (c) Aversa, M. C.; Ferlazzo, A.; Giannetto, P.; Kohnke, F. H. Synthesis 1986, 230.
26. Nefzi, A.; Ostresh, J. M.; Houghten, R. A. Chem. Rev. 1997, 97, 449-472.
27. Brown, M. L.; Zha, C. C.; Van Dyke, C. C.; Brown, G. B.; Brouillette, W. J. J. Med. Chem. 1999, 75, 1537-1545.