Syntheses of 3-acetoacetylaminobenzo[b]furan derivatives having cysteinyl leukotriene 2 receptor antagonistic activity

Organic and Biomolecular Chemistry

Volumn 2, Issue 4, 2004, Pages 625-635

  Ando, Kumiko ^a   Tsuji, Eriko ^a   Ando, Yuko ^a   Kuwata, Noriko ^a   Kunitomo, Jun Ichi ^a   Yamashita, Masayuki ^b   Ohta, Shunsaku ^b   Kohno, Shigekatsu ^b   Ohishi, Yoshitaka ^a  

^a MUKOGAWA WOMEN'S UNIVERSITY   (Japan)

^b KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; ASSAYS; CALCIUM; CELLS; CHEMICAL BONDS; DERIVATIVES; DISEASES; DYES; FLUORESCENCE; HYDROGEN BONDS; ISOMERS; PATHOLOGY; PHYSIOLOGY; PROTEINS;

INFLAMMATORY DISEASES; LEUKOTRIENE RECEPTORS; RING CLOSURE REACTIONS;

AROMATIC COMPOUNDS;

BENZOFURAN DERIVATIVE; CYSTEINYL LEUKOTRIENE RECEPTOR 2; LEUKOTRIENE RECEPTOR;

ANIMAL; ARTICLE; CELL LINE; CHEMICAL STRUCTURE; HAMSTER; HUMAN; METABOLISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANIMALS; BENZOFURANS; CELL LINE; CRICETINAE; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; RECEPTORS, LEUKOTRIENE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 1342281332     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b312682j     Document Type: Article

References (35)

1. Part of this work has been published as a preliminary communication: E. Tsuji, K. Ando, J. Kunikomo, M. Yamashita, S. Ohta, S. Kohno and Y. Ohishi, Org. Biomol. Chem., 2003, 1, 3139-3141.
2. (a) M. Bäck, Life Sciences, 2002, 71, 611-622;
3. (b) J. F. Evans, Prostaglandins & Other Lipid Mediators, 2002, 68-69, 587-597;
4. (c) C. E. Heise, B. F. O'Dowd, D. J. Figueroa, N. Sawyer, T. Nguyen, D.-S. Im, R. Stocco, J. N. Bellefeuille, M. Abramovitz, R. Cheng, D. V. Williams Jr., Z. Zeng, Q. Liu, L. Ma, M. K. Clements, N. Coulombe, Y. Liu, C. P. Austin, S. R. George, G. P. O'Neill, K. M. Metters, K. R. Lynch and J. F. Evans, J. Biol. Chem., 2000, 275, 30531-30536;
5. (d) H.-P. Nothacker, Z. Wang, Y. Zhu. R. K. Reinscheid, S. H. S. Lin and O. Civelli, Mol. Pharmacol., 2000, 58, 1601-1608.
6. W. Laurence, N. Xavier, B. Magnus, G. Lean Pierre, D. Sven-Erik and B. Charies, Br. J. Pharm., 2002, 137, 1339-1345.
7. th International Conference (May 2002, Atlanta) [D38] [Poster F4] Characterization of DUO-LT: A Novel Dual Cysteinyl Receptor Antagonist.
8. I. Fleming, Frontier Orbitals and Organic Chemical Reactions. Wiley, NewYork, 1976, pp. 58.
9. 2 over Pd/C in ethanol easily gave 5-amino-2-ethyl-3(2H)-benzo[b]furanone by treatment with HCl. On the other hand, catalytic reduction of 2-ethyl-3,5-diaminobenzo[b]furan in acetic anhydride gave stable 2-ethyl-3,5-diacetylaminobenzo[b]furan (unpublished data obtained in our laboratory).
10. Y. Ohishi and T. Nakanishi, Chem. Pharm. Bull., 1983, 31, 3418-3423; Y. Ohishi, Y. Doi and T. Nakanishi, Chem. Pharm. Bull., 1984, 32, 4260-4270; Y. Ohishi, Y. Doi and T. Nakanishi, Chem. Pharm. Bull., 1985, 33, 2598-2601; Y. Ohishi, K. Kuriyama, Y. Doi and T. Nakanishi, Chem. Pharm. Bull., 1985, 33, 2854-2861; Y. Ohishi, Y. Doi and T. Nakanishi, Chem. Pharm. Bull., 1988, 36, 1336-1341; Y. Ohishi, T. Mukai, M. Nagahara, M. Yajima and N. Kajikawa, Chem. Pharm. Bull., 1989, 37, 2398-2405.
11. Y. Ohishi and T. Nakanishi, Chem. Pharm. Bull., 1983, 31, 3418-3423; Y. Ohishi, Y. Doi and T. Nakanishi, Chem. Pharm. Bull., 1984, 32, 4260-4270; Y. Ohishi, Y. Doi and T. Nakanishi, Chem. Pharm. Bull., 1985, 33, 2598-2601; Y. Ohishi, K. Kuriyama, Y. Doi and T. Nakanishi, Chem. Pharm. Bull., 1985, 33, 2854-2861; Y. Ohishi, Y. Doi and T. Nakanishi, Chem. Pharm. Bull., 1988, 36, 1336-1341; Y. Ohishi, T. Mukai, M. Nagahara, M. Yajima and N. Kajikawa, Chem. Pharm. Bull., 1989, 37, 2398-2405.
12. Y. Ohishi and T. Nakanishi, Chem. Pharm. Bull., 1983, 31, 3418-3423; Y. Ohishi, Y. Doi and T. Nakanishi, Chem. Pharm. Bull., 1984, 32, 4260-4270; Y. Ohishi, Y. Doi and T. Nakanishi, Chem. Pharm. Bull., 1985, 33, 2598-2601; Y. Ohishi, K. Kuriyama, Y. Doi and T. Nakanishi, Chem. Pharm. Bull., 1985, 33, 2854-2861; Y. Ohishi, Y. Doi and T. Nakanishi, Chem. Pharm. Bull., 1988, 36, 1336-1341; Y. Ohishi, T. Mukai, M. Nagahara, M. Yajima and N. Kajikawa, Chem. Pharm. Bull., 1989, 37, 2398-2405.
13. Y. Ohishi and T. Nakanishi, Chem. Pharm. Bull., 1983, 31, 3418-3423; Y. Ohishi, Y. Doi and T. Nakanishi, Chem. Pharm. Bull., 1984, 32, 4260-4270; Y. Ohishi, Y. Doi and T. Nakanishi, Chem. Pharm. Bull., 1985, 33, 2598-2601; Y. Ohishi, K. Kuriyama, Y. Doi and T. Nakanishi, Chem. Pharm. Bull., 1985, 33, 2854-2861; Y. Ohishi, Y. Doi and T. Nakanishi, Chem. Pharm. Bull., 1988, 36, 1336-1341; Y. Ohishi, T. Mukai, M. Nagahara, M. Yajima and N. Kajikawa, Chem. Pharm. Bull., 1989, 37, 2398-2405.
14. Y. Ohishi and T. Nakanishi, Chem. Pharm. Bull., 1983, 31, 3418-3423; Y. Ohishi, Y. Doi and T. Nakanishi, Chem. Pharm. Bull., 1984, 32, 4260-4270; Y. Ohishi, Y. Doi and T. Nakanishi, Chem. Pharm. Bull., 1985, 33, 2598-2601; Y. Ohishi, K. Kuriyama, Y. Doi and T. Nakanishi, Chem. Pharm. Bull., 1985, 33, 2854-2861; Y. Ohishi, Y. Doi and T. Nakanishi, Chem. Pharm. Bull., 1988, 36, 1336-1341; Y. Ohishi, T. Mukai, M. Nagahara, M. Yajima and N. Kajikawa, Chem. Pharm. Bull., 1989, 37, 2398-2405.
15. Y. Ohishi and T. Nakanishi, Chem. Pharm. Bull., 1983, 31, 3418-3423; Y. Ohishi, Y. Doi and T. Nakanishi, Chem. Pharm. Bull., 1984, 32, 4260-4270; Y. Ohishi, Y. Doi and T. Nakanishi, Chem. Pharm. Bull., 1985, 33, 2598-2601; Y. Ohishi, K. Kuriyama, Y. Doi and T. Nakanishi, Chem. Pharm. Bull., 1985, 33, 2854-2861; Y. Ohishi, Y. Doi and T. Nakanishi, Chem. Pharm. Bull., 1988, 36, 1336-1341; Y. Ohishi, T. Mukai, M. Nagahara, M. Yajima and N. Kajikawa, Chem. Pharm. Bull., 1989, 37, 2398-2405.
16. C. P. Astles, J. T. Brown, F. Halley, M. C. Handscombe, V. N. Harris, N. T. Majid, C. McCarthy, M. I. McLay, A. Morley, B. Porter, G. A. Roach, C. Sargent, C. Smith and J. A. R. Walsh, J. Med. Chem., 2000, 43, 900-910.
17. K. Gewald and H. J. Kaensch, J. Prakt. Chem., 1973, 315, 779-785; V. P. Baidya, S. B. Mahajam and Y. S. Agasimundin, Indian J. Chem., 1981, 20B, 391-393.
18. K. Gewald and H. J. Kaensch, J. Prakt. Chem., 1973, 315, 779-785; V. P. Baidya, S. B. Mahajam and Y. S. Agasimundin, Indian J. Chem., 1981, 20B, 391-393.
19. (a) W. K. R. W. Mederski, M. Osswald, D. Dorsch, M. Christadler, C.-J. Schmitges and C. Wilm, Bioorg. Med. Chem. Lett., 1999, 9, 619-622;
20. (b) S. Rádl, P. Hezký, J. Urbánková, P. Váchal and I. Krejčf, Collect. Czech. Chem. Commun., 2000, 65, 280-297;
21. (c) S. Rádl, P. Hezký, P. Konvička and I. Krejčf, Collect. Czech. Chem. Commun., 2000, 65, 1093-1108.
22. S. S. Sangapure and S. Y. Agasimundin, Indian J. Chem., 1976, 14B, 6886-6891.
23. G. Viti, D. Giannotti, R. Nannicini, R. Ricci and V. Pestellini, J. Heterocycl. Chem., 1990, 27, 1369-1375.
24. G. S. Harwalkar, S. S. Sangapure and Y. S. Agasimundin, Indian J. Heterocycl. Chem., 1995, 4, 235-236.
25. (a) P. D. Greenspan, A. J. Main, S. S. Bhagwat, L. I. Barsky, R. A. Doti, A. R. Engle, L. M. Fery, H. Zhou, K. E. Lipson, M. H. Chin, R. H. Jackson and S. Uziel-Fusi, Bioorg. Med. Chem. Lett., 1997, 7, 949-954;
26. (b) P. D. Greenspan, R. A. Fujimoto, P. J. Marshall, A. Raychaudhuri, K. F. Lipson, H. Zhou, R. A. Doti, D. E. Coppa, L. Zhu, R. Pelletier, S. Uziel-Fusi, R. H. Jackson, M. H. Chin, B. L. Kotyuk and J. J. Fitt, J. Med. Chem., 1999, 42, 164-172.
27. K. Takamura, A. Shioya, T. Yamamoto, S. Takama and Y. Nitta, Chem. Pharm. Bull., 1965, 13, 211-217.
28. F. R. Heck, Organic Reactions, John Wiley & Sons Publishers, New York, 1982, 27, pp 345-390.
29. 5-Methylisoxazole-4-carboxlic acid was prepared starting with ethyl acetoacetate in our laboratory [A. Graul and J. Castañer, Drugs of the Future, 1998, 23, 827-837].
30. E. Kuo, P. Hambleton, D. Kay, P. Evans, S. Matharu, E. Little, C. McDowall, B. Jones, C. Hedgecock, C. Yea, A. Chan, P. Hairsine, I. Ager, W. Tully, R. Williamson and R. Westwood, J. Med. Chem., 1996, 39, 4608-4621.
31. 000 = 1072. CCDC reference numbers 214287 and 222922. See http://www.rsc.org/suppdata/ob/b3/b312682j/ for crystallographic data in .cif or other electronic format.
32. Some of compounds here fluoresced and could not be evaluated for activity.
33. A simple control compound (29) was prepared by cleavage of the isoxazole ring of 28 in our laboratory. M. Herrmann, R. Schleyerbach and B. Kirschbaum, Immunopharmacology, 2000, 47, 273-289; F. C. Breedveid and J.-M. Dayer, Ann. Rheum. Dis., 2000, 59, 841-849.
34. A simple control compound (29) was prepared by cleavage of the isoxazole ring of 28 in our laboratory. M. Herrmann, R. Schleyerbach and B. Kirschbaum, Immunopharmacology, 2000, 47, 273-289; F. C. Breedveid and J.-M. Dayer, Ann. Rheum. Dis., 2000, 59, 841-849.
35. T. Obata, Y. Okada, M. Motoishi, N. Nakagawa, T. Terawaki and H. Aishita, Jpn. J. Pharmacol., 1992, 60, 227-237.