Synthesis and vasorelaxant activity of 2-fluoromethylbenzopyran potassium channel openers

Bioorganic and Medicinal Chemistry

Volumn 6, Issue 3, 1998, Pages 323-337

  Takahashi, Tadakatsu ^a   Koga, Hiroshi ^a   Sato, Haruhiko ^a   Ishizawa, Takenori ^a   Taka, Naoki ^a   Imagawa, Jun Ichi ^a  

^a CHUGAI PHARMACEUTICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 (6 CYANO 2,2 DIMETHYL 2H 1 BENZOPYRAN 4 YL)PYRIDINE 1 OXIDE; APRIKALIM; BENZOPYRAN DERIVATIVE; BIMAKALIM; CROMAKALIM; FLUORINE; FLUOROFORM; METHYL GROUP; PINACIDIL; POTASSIUM CHANNEL; POTASSIUM CHANNEL STIMULATING AGENT; TETRAHYDROFURAN;

ANIMAL TISSUE; ANTIHYPERTENSIVE ACTIVITY; AORTA; ARTICLE; CHANNEL GATING; CONTROLLED STUDY; DRUG ACTIVITY; DRUG POTENCY; DRUG SYNTHESIS; ISOLATED ARTERY; NONHUMAN; RAT; SMOOTH MUSCLE RELAXATION; VASODILATATION;

ANIMALS; AORTA, THORACIC; BENZOPYRANS; HYDROCARBONS, FLUORINATED; MALE; MUSCLE, SMOOTH, VASCULAR; POTASSIUM CHANNELS; RATS; RATS, SPRAGUE-DAWLEY; STRUCTURE-ACTIVITY RELATIONSHIP; VASODILATOR AGENTS;

ANIMALIA;

EID: 0031891088     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(97)10035-9     Document Type: Article

References (39)

1. (a) Potassium Channels: Structure, Classification, Function, and Therapeutic Potential; Cook, N.S.; ed. Chicheter:Ellis Horwood Limited, 1990.
2. (b) Robertson, D. W.; Steinberg, M. I. J. Med. Chem. 1990, 33, 1529.
3. (c) Edward, G.; Weston, A. H. Trends Pharmacol. Sci. 1990, 11, 417.
4. (d) Evans, J. M.; Longman, S. D. Ann. Rep. Med. Chem. 1991, 26, 73.
5. (e) Bray, K. M.; Quast, U. J. Biol. Chem. 1992, 267, 11689.
6. For selected papers, see: (a) Peterson, H. J.; Nielsen, C. K.; Arrigoni-Martelli, E. J. Med. Chem. 1978, 21, 773.
7. (b) Ashwood, V. A.; Buckingham, R. E.; Cassidy, F.; Evans, J. M.; Faruk, E. A.; Hamilton, T. C.; Nash, D. J.; Stemp, G.; Willcocks, K. J. Med. Chem. 1986, 29, 2194.
8. (c) Jacobsen, E. N.; Zhang, W.; Muci, A. R.; Ecker, J. R.; Deng, L. J. Am. Chem. Soc. 1991, 113, 7063.
9. (d) Attwood, M. R.; Churcher, I.; Dundoson, R. M.; Hurst, D. N.; Jones, P. N. Tetrahedron Lett. 1991, 32, 811.
10. (e) Buckle, D. R.; Eggleston, D. S.; Pinto, I. L.; Smith, D. G.; Tedder, J. M. Bioorg. Med. Chem. Lett. 1992, 2, 1161.
11. (f) Brown, T. J.; Chapman, R. F.; Cook, D. C.; Hart, T. W.; McLag, I. M.; Jordan, R.; Mason, J. S.; Palfreyman, M. N.; Walsh, R. J. A.; Withnall, M. T.; Aloup, J-C.; Cavero, I.; Farge, D.; James, C.; Mondot, S. J. Med. Chem. 1992, 35, 3613.
12. (g) Hart, T. W.; Guillochon, D.; Perrier, G.; Sharp, B. W.; Vacher, B. Tetrahedron Lett 1992, 33, 5117.
13. (h) Hart, T. W.; Guillochon, D.; Perrier, G.; Sharp, B. W.; Toft, M. P.; Vacher, B.; Walsh, R. J. A. ibid 1992, 33, 7211.
14. (i) Hart, T. W.; Smith, D. G. ibid 1992, 33, 7215.
15. (j) Pint, I. L.; Buckle, D. R.; Rami, H. K.; Smith, D. G.; ibid 1992, 33, 7597.
16. (k) Gogfrey, J. D.; Mueller, R. H.; Sedergran, T. C.; Soundararajan, N.; Colandrea, V. J. ibid. 1994, 35, 6405.
17. For preliminary reports, see; (a) Taka, N.; Koga, H.; Sato, H.; Ishizawa, T.; Takahashi, T.; Imagawa, I. Bioorg. Med. Chem. Lett. 1994, 4, 2893.
18. (b) Taka, N.; Koga, H.; Sato, H.; Ishizawa, T.; Takahashi, T.; Imagawa, I. ibid. 1995, 5, 529.
19. Attwood, M. R.; Jones, P. S.; Kay, P. B.; Paciorek, P. M.; Redshaw, S. Life Sci. 1991, 48, 803.
20. (a) Koga, H.; Ohta, M.; Sato, H.; Ishizawa, T.; Nabata, H. Bioorg. Med. Chem. Lett. 1993, 3, 625.
21. (b) Koga, H.; Sato, H.; Ishizawa, T.; Kuromaru, K.; Nabata, H.; Imagawa, J.; Yoshida, S.; Sugo, I. ibid. 1993, 3, 1111.
22. (c) Koga, H.; Sato, H.; Kuromaru, K.; Ishizawa, T.; Makino, T.; Taka, N.; Takahashi, T.; Sato, T.; Nabata, H. ibid. 1993, 3, 1115.
23. (d) Ishizawa, T.; Koga, H.; Ohta, M.; Sato, H.; Makino, T.; Kuromaru, K.; Taka, N.; Takahashi, T.; Sato, T.; Nabata, H. ibid. 1993, 3, 1659.
24. (e) Sato, H.; Koga, H.; Ishizawa, T.; Makino, T.; Kuromaru, K.; Taka, N.; Takahashi, T.; Sato, T.; Nabata, H. ibid 1993, 3, 2627.
25. (f) Koga, H.; Sato, H.; Imagawa, J.; Ishizawa, T.; Yoshida, S.; Sugo, I.; Taka, N.; Takahashi, T.; Nabata, H. ibid 1993, 3, 2005.
26. (g) Ishizawa, T.; Koga, H.; Sato, H.; Makino, T.; Taka, N.; Takahashi, T.; Sato, T.; Nabata, H. ibid 1994, 4, 1995.
27. (h) Ohta, M.; Koga, H.; Sato, H.; Ishizawa, T. ibid. 19944: 2903.
28. Fenwick, A.E. Tetrahedron Lett. 1993, 34, 1815.
29. Freskos, J. N. Synth. Commun. 1988, 18, 965.
30. Yoo, S.; Suh, J. H.; Lee, S. J.; Jeong, N. Bioorg. Med. Chem. Lett. 1992, 2, 381.
31. The benzopyran-4-one 15a was prepared by a procedure similar to that previously reported f.
32. (a) Sato, H.; Koga, H.; Ishizawa, T.; Makino, T.; Taka, N.; Takahashi, T.; Nabata, H. Bioorg. Med. Chem. Lett. 1995, 5, 233.
33. (b) Koga, H.; Sato, H.; Ishizawa, T.; Taka, N.; Takahashi, T. Tetrahedron Lett. 1995, 36, 87.
34. Bergmann, R.; Gericke, R. J. Med. Chem. 1990, 33, 492.
35. For recent reviews, see: (a) Ritter, K. Synthesis 1993, 735.
36. (b) Kalinin, V. N. ibid. 1992, 413.
37. Takahashi, T.; Koga, H.; Sato, H.; Ishizawa, T.; Taka, N. Heterocycles 1995, 41, 2405.
38. Aloup, J. C.; Farge, D.; James, C.; Mondot, S.; Cavero, I. Drugs Fut. 1990, 15, 1097.
39. Nabata, H.; Imagawa, J. unpublished results.