Synthesis of 2-, 4- And 5-(2-alkylcarbamoyl-l-methylvinyl)-7- alkyloxybenzo[b]furans and their leukotriene 64 receptor antagonistic activity

Organic and Biomolecular Chemistry

Volumn 3, Issue 11, 2005, Pages 2129-2139

  Ando, Kumiko ^a   Tsuji, Eriko ^a   Ando, Yuko ^a   Kunitomo, Jun Ichi ^a   Kobayashi, Reina ^b   Yokomizo, Takehiko ^b,c   Shimizu, Takao ^b   Yamashita, Masayuki ^d   Ohta, Shunsaku ^d   Nabe, Takeshi ^d   Kohno, Shigekatsu ^d   Ohishi, Yoshitaka ^a  

^a MUKOGAWA WOMEN'S UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

^c Japan Science and Technology Agency   (Japan)

^d KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CLONING; CONFORMATIONS; DISEASES; ENZYME INHIBITION; ETHERS; FATTY ACIDS; MICROORGANISMS; SYNTHESIS (CHEMICAL); TRANSPLANTATION (SURGICAL);

INHIBITORY ACTIVITY; MOLECULAR CLONING; NEUTROPHILS; RECEPTOR ANTAGONISTS;

AROMATIC COMPOUNDS;

BENZOFURAN DERIVATIVE; LEUKOTRIENE B4 RECEPTOR;

ARTICLE; DRUG ANTAGONISM; ELECTROSPRAY MASS SPECTROMETRY; HUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

BENZOFURANS; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; RECEPTORS, LEUKOTRIENE B4; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 20844461631     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b503615a     Document Type: Article

References (77)

1. Part of this work has been published as a preliminary communication: K. Ando, E. Tsuji, Y. Ando, J. Kunitomo, M. Yamashita, S. Ohta, T. Nabe, S. Kohno, T. Yokomizo, T. Shimizu and Y. Ohishi, Org. Biomol. Chent, 2004, 2, 3427-3431.
2. (a) C. R. Turner, R. Breslow, M. J. Conklyn, C. J. Andresen, D. K. Patterson and A. Lopez-Anaya, J. Clin. Invest., 1996, 97, 381-387;
3. (b) P. Sharon and W. F. Stenson, Gastroenterology, 1984, 86, 453-460;
4. (c) A. Nakao, K.. Nasaka, N. Ohishi, E. Noiri, T. Suzuki and S. Taniguchi, Kidney Int., Suppl., 1997, 63, S236-238;
5. (d) R. J. Griffiths, E. R. Pettipher, K. Kock, C. A. Farrell, R. Breslow and M. Conklyn, Proc. Atal. Acad. Sci USA, 1995, 92, 517-521;
6. (e) R. P. Gladue, L. A. Carroll, A. J. Milici, D. N. Scampoli, H. A. Stukenbrok and E. R. Pettipher, J. Exp. Med., 1996, 183, 1893-1898;
7. (f) T. Yokomizo, K. Kato, K. Terawaki, T. Izumi and T. Shimizu, J. Exp. Med., 2000, 192, 421-431.
8. CP-195543: (a) L. A. Reiter, K. Koch, A. D. Piscopio, H. J. Showell, R. Alpert, M. S. Biggers, R. J. Chambers, M. J. Conklyn, K. Cooper, S. R. Cortina, J. N. Dibrino, B. W. Dominy, C. A. Farrell, G. P. Hingorani, G. J. Martinelli, M. Ramchandani and K. F. Wright, Bioorg. Med. Chem. Lett., 1998, 8, 1781-1786. CP-105696:;
9. (b) K. Koch, L. S. Melvin, Jr., L. A. Reiter, M. S. Biggers, H. J. Showell, R. J. Griffiths, E. R. Pettipher, J. B. Cheng, A. J. Milici and R. Breslow, J. Med. Chem., 1994, 37, 3197-3199. LY-223982:;
10. (c)D. M. Gapinski, B. E. Mallett, L. L. Froelich and W. T. Jackson, J. Med. Chem., 1999, 33, 2807-2813;
11. (d) W. T. Jackson, R. J. Boyd, L. L. Froelich, D. M. Gapinski, B. E. Mallett and J. S. Sawyer, J. Med. Chem., 1993, 36, 1726-1734. LY-255283:;
12. (e) D. K. Herren, T. Goodson, N. G. Bollinger, D. Swanson-Bean, I. G. Wright, G. S. Staten, A. R. Thompson, L. L. Froelich and W. T. Jackson, J. Med. Chem., 1992, 35, 1818-1828;
13. (f) J. S. Sawyer, N. J. Bach, S. R. Baker, R. F. Baldwin, P. S. Borromeo, S. L. Cockerham, J. H. Fleisch, P. Floreancig, L. L. Froelich and W T. Jackson, J. Med. Chem., 1995, 38, 4411-4432. ONO-4057:;
14. (g) K. Kishikawa, S. Nakao, S. Matsumoto, K. Kondo and N. Hamanaka, Adv. Prostaglandin, Thromboxane, Leukotriene Res., 1995, 23, 279-281;
15. (h) K. Kishikawa, N. Tateishi, T. Maruyama, R. Seo, M. Toda and T. Miyamoto, Prostaglandins, 1992, 44, 261-275. ZK-158252:;
16. (i) R. D. Pallavi, K. H. Abdelmadjid, P. Mai, D. S. Wolf-Dieter, M. S. Bruce and W. Walter, J. Biol Chem., 1999, 274, 23341-23348;-sap-
17. (f) M. Matousek, K. Mitsube, M. Mikuni and M. Brannstrom, Mol. Hum. Reprod., 2001, 7, 35-42. 1,3-Disubstituted cyclohexane:;
18. (k) J.-M. Poudrel, P. Hullot, J.-P. Vidal, J.-P. Girard, J.C. Rossi, A. Muller, C. Bonne, V. Bezuglov, I. Serkov, P. Renard and B. Pfeiffer, J. Med. Chem., 1999, 42, 5289-5310. BIIL315:;
19. (l) F. W. Birke, C. J. Meade, R. Anderskewitz, G. A. Speck and H.-M. Jennewein, J. Pharrnacol. Exp. Ther., 2002, 297, 458-466. LY293111:;
20. (m) M. Philip, S. J. Scott, F. L. Larry, M. L. Larry and S. M. Stephen, Biochem. Pharmacol, 1995, 49, 1683-1690.
21. (a) C. Brink, S.-E. Dahlen, J. F. Evans, D. W. P. Hay, S. Nicosia, C. N. Serhan, T. Shimizu and T. Yokomizo, Pharmacol. Rev., 2003, 55, 195-227;
22. (b) A. Toba, T. Yokomizo and T. Shimizu, Prostaglandins & Other Lipid Mediators, 2002, 68-69, 575-585;
23. (c) T. Yokomizo, K. Masuda, K. Toda, T. Izumi and T. Shimizu, Am. J. Respir. Crit. Care Med., 2000, 161, S51-55;
24. (d) T. Yokomizo, T. Izumi and T. Shimizu, Arch. Biochem. Biophys., 2001, 385, 231-241;
25. (e) T. Yokomizo, K. Kato, K. Terawaki, T. Izumi and T. Shimizu, J. Exp. Med., 2000, 192, 421-431.
26. R. J. Aiello, P. A. Bourassa, S. Lindsey, W. Weng, A. Freeman and H. J. Showell, Arterioscler., Thromb., Vasc. Biol, 2002, 22, 443-449;
27. A. Mennander, S. Tiisala, J. Ustinov, A. Räisänen, T. Paavonen and P. Häyry, Arterioscler. Thromb., 1992, 12, 1380-1386.
28. H. Takatsuka, Y. Takemoto, S. Yamada, T. Wakae, A. Mori, M. Okada, N. Iwata and T. Okamoto, Drugs Exp. Clin. Res., 2002, 28, 121-125;
29. M. Tanaka, T. Tamaki, Y. Konoeda, Y. Uchida, T. Kaizu and A. Kawamura, Transplant. Proc., 2000, 32, 2340.
30. L. Iversen, K. Kragballe and V. A. Ziboh, Skin Pharmacol., 1997, 10, 169-177.
31. W.-G. Tong, X.-Z. Ding, R. Hennig, R. C. Witt, J. Standop, P. M. Pour and T. E. Adrian, Clin. Cancer Res., 2002, 8, 3232-3242;
32. M.-H. Yoo, H. Song, C.-H. Woo, H. Kim and J.-H. Kim, Oncogene, 2004, 23, 9259-9268.
33. Y. Kurihara, H. Endo, T. Akahoshi and H. Kondo, Clin. Exp. Immunoi, 2001, 123, 323-330;
34. A. Hashimoto, H. Endo, I. Hayashi, Y. Murakami, H. Kitasato, S. Kono, T. Matsui, S. Tanaka, A. Nishimura, K. Urabe, M. Itoman and H. Kondo, J. Rheumatol., 2003, 30, 1712-1718;
35. Y. Murakami, T. Akahoshi, I. Hayashi, H. Endo, A. Hashimoto, S. Kono, H. Kondo, S. Kawai, M. Inoue and H. Kitasato, Arthritis Rheum., 2003, 48, 2931-2941;
36. R. Alten, E. Gromnica-Ihle, C. Pohl, J. Emmerich, J. Steffgen, R. Röscher, R. Sigmund, B. Schmolke and G Steinmann, Ann. Rheum. Dis., 2004, 63, 170-176.
37. Several heteroaromatic and cyclized aliphatic compounds as an LTB4 antagonist were reported previously: (a) D. Delorme, Y. Ducharme, C. Brideau, C.-C. Chan, N. Chauret, S. Desmarais, D. Dube, J.-P. Falgueyret and R. Relean, J. Med. Chem., 1996, 39, 3951-3970. (L 708780, naphthalene derivative with furan ring);
38. (b) S. W. Djuric, S. H. Docter, S. S. Yu, D. Spangler, B. S. Tsai, C. P. Anglin, T. S. Gaginella, J. F. Kachur and R. H. Keith, Bioorg. Med. Chem. Lett., 1994, 4, 811 -816. (SC-53228, benzopyran derivative);
39. (c) S. W. Djuric, P. W. Collins, P. T. Jones, R. L. Shone, B. S. Tsai, D. J. Fretland, G. M. Butchko, D. Villani-Prince and R. H. Keith, J. Med. Chem., 1989, 32, 1145-1147. (SC 41939, benzopyran derivative);
40. (d) T. S. Shoupe, S. M. Coutts, D. C. Baker and E. S. Hand, Can. Pat. Appl., 1991, 63 pp. CPXXEB CA 2013960, AA 19910319, CAN 115:158949, AN 1991: 558949. (PF 10042, dibenzofuran derivative);
41. (e) C. D. Wright, P. J. Kuipers, M. D. Huffman, D. O. Thueson and M. C. Conroy, Biochem. Biophys. Res. Commun., 1990, 167, 828-834. (CI 949, indole derivative);
42. (f) J. M. Musser, U. R. Chakraborty, S. Sciortino, R. J. Gordon, A. Khandwala, E. S. Neiss, T. P. Pruss, R. V. Inwegen, I. Weinryb and S. M. Coutts, J. Med. Chem., 1997, 30, 96-104. (PF 5901, quinoline derivative);
43. (g) C. Can, M. G. Cinar, S. Ulker, A. Evinc and S. Kosay, Eur. J. Pharmacol., 1998, 350, 223-228. (MK 886, indole derivative);
44. (h) J. M. Poudrel, P. Hullot, J. P. Vidai, J. P. Girard, J. C. Rossi, A. Muller and C. Bonne, Bioorg. Med. Chem. Lett., 1996, 6, 2349-2354.
45. H. Nakai, M. Konno, S. Kosuge, S. Sakuyama, M. Toda, Y. Arai, T. Obata, N. Katsube, T. Miyamoto, T. Okegawa and A. Kawasaki, J. Med. Chem., 1988, 31, 84-91.
46. (a) E. Tsuji, K. Ando, J. Kunitomo, M. Yamashita, S. Ohta, S. Kohno and Y. Ohishi, Org. Biomol. Chem., 2003, 1, 3139-3141;
47. (b) K. Ando, E. Tsuji, Y Ando, N. Kuwata, J. Kunitomo, M. Yamashita, S. Ohta, S. Kohno and Y. Ohishi, Org. Biomol. Chem., 2004, 2, 625-635.
48. P. D. Greenspan, A. J. Main, S. S. Bhagwat, L. I. Barsky, R. A. Doti, A. R. Eagle, L. M. Frey, H. Zhou, K. E. Lipson, M. H. Chin, R. H. Jackson and S. Uziel-Fusi, Bioorg. Med. Chem. Lett., 1997, 7, 949-954;
49. P. D. Greenspan, R. A. Fujimoto, P. J. Marshall, A. Raychaudhuri, K. E. Lipson, H. Zhou, R. A. Doti, D. V. Coppa, L. Zhu, R. Pelletier, S. Uziel-Fusi, R. H. Jackson, M. H. Chin, B. L. Kotyuk and J. J. Fin, J. Med. Chem., 1999, 42, 164-172.
50. Y. Ohishi, T. Mukai, M. Nagahara, M. Yajima and N. Kajikawa, Chem. Pharm. Bull., 1989, 37, 2393-2405.
51. The 3-H signal (7.73 ppm) showed no NOE correlation between other aromatic signals (6.9 ppm, d and 7.4 ppm, d) of Ib. This supported the structure of Ib.
52. M. Watanabe, S. Hisamatsu, H. Hotokezakaand S. Furukawa, Chem. Pharm. Bull., 1986, 34, 2810-2820.
53. (a) J. Boutagy and R. Thomas, Chem. Rev., 1974, 74, 87-99;
54. (b) N. Matsuura, Y. Yashiki, S. Nakashima, M. Maeda and S. Sasaki, Heterocycles, 1999, 51, 975-978;
55. (c) J. K. F. Geirsson, B. O. Gudmundsson and R. Sigurdardottir, Acta Chem. Scand., 1993, 47, 1112-1116.
56. The torsion angle between the 2-(2-alkylcarbamoyl-1-methylvinyl) group and the benzof&Jfuran ring of (E)-isomers ((E)-4c, (E)-4f, (E)-4a) and of (Z)-isomers ((Z)-4c, (Z)-4f, (Z)-4a) was estimated using Cambridge Soft, Chem3D 5.0, MM2. (E)-4c: 0.3°, (E)-4f: 3.5°, (E)4a: 4.4°; (Z)-4c: 28.4°, (Z)-4f: 26.9°, (Z)-4α: 24.9°.
57. X-Ray essential data of (E)-4° and 7i were reported in our previous communication (ref. 1).
58. S. Sano, Yakugaku Zasshi, 2000, 120, 432-444.
59. M. A. Blanchette, W Choy, J. T. Davis, A. P. Essenfeld, S. Masamune, W. R. Roush and T. Sakai, Tetrahedron Lett., 1984, 25, 2183-2186;
60. D. F. Nets and J. L. Seidel, Tetrahedron Lett., 1992, 33, 1957-1958.
61. K. Ando, J. Org. Chem., 1997, 62, 1934-1939;
62. K. Ando, Tetrahedron Lett., 1995, 36, 4105-4108;
63. W. C. Still and C. Gennari, Tetrahedron Lett., 1983, 24, 4405-4408.
64. F. R. Heck, Organic Reactions, John Wiley &. Sons Publishers, New York, 1982, vol. 27, pp. 345-390;
65. 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.
66. R. Adams and M. W. Miller, J. Am. Chem. Soc., 1940, 62, 53-57.
67. W. H. Mills and G. H. Dazeley, J. Chem. Soc., 1936, 460-463.
68. 25
69. The torsion angle between the (E)-4-(2-alkylcarbamoyl-1-methylvinyl) group and the benzo[i]furan ring plane of several (E)-4-_(2-alkylcarbamoyl-l- methylvinyl) compounds (7a, 7c, 7g, 7i, 7j, 7n) was estimated using MM2. 7a: 47.9°, 7c: 39.7°, 7g: 40.2°, 7i: 40.2°, 7j: 38.8° and 7n: 43.4°. The estimated torsion angle (40.2°) of 7i was approximately that (45.7°) found by X ray analysis.
70. C. Paizs, M. Tosa, C. Majdik, P. Moldovan, L. Novak, P. Kolonits, A. Marcovici, F.-D. Irimie and L. Poppe, Tetrahedron: Asymmetry, 2000, 14, 1495-1501;
71. J. P. Bachelet, P. Demerseman, R. Royer, R. Cavier and J. Lemoine, Eur. J. Med. Chem., 1982, 17, 323-325.
72. T. Nabe, H. Yamamura and S. Kohno, Jpn. J. Pharmacol., 1996, 70, 337-345.
73. Several (E)-5-(2-alkylcarbamoyl-l-methylvinyl) compounds previously prepared in our laboratories (ref. 12b) were also evaluated and found to be inactive.
74. T. Yokomizo, T. Izumi, K. Chang, Y. Takuwa and T. Shimizu, Nature, 1997, 387, 620-624.
75. A calcium assay and binding assay for evaluation of cysteinyl leukotriene antagonistic activity were performed according to Nothacker's procedure: H.-P. Nothacker, Z. Wang, Y. Zhu, R. K. Reinscheid, S. H. S. Lin and O. Civelli, Mol. Pharmacol, 2000, 58, 1601-1608.
76. ATP (10 μM)-dependent calcium mobilization through an intrinsic ATP receptor in CHO cells was evaluated at concentrations of 10 nM, 100 nM, 1 μM and 10 (iM of each compound.
77. 2 cell by compounds (4a, 4b′, 4d, 4f, 4y) was not due to its cytotoxicity, because these compounds did not affect calcium mobilization in the CHO-hBLT, cell at 10 μM.