Preparation of 2- And 4-(2-alkylcarbamoyl-1-methylvinyl)-7-alkyloxybenzo[b]furans having potent antagonistic activity against human leukotriene B4 BLT1 and/or BLT2 receptors

Organic and Biomolecular Chemistry

Volumn 2, Issue 23, 2004, Pages 3427-3431

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

^a MUKOGAWA WOMEN'S UNIVERSITY   (Japan)

^b KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

^c UNIVERSITY OF TOKYO   (Japan)

^d Japan Science and Technology Agency   (Japan)

^e JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL ANALYSIS; CHEMICAL BONDS; COMPOSITION; CONCENTRATION (PROCESS); ENZYME INHIBITION; HUMAN ENGINEERING; ISOMERS; MOLECULAR BIOLOGY;

ANTAGONISTIC ACTIVITY; CHEMICAL COMPLEXES; HUMAN LEUKOTRIENE; RECEPTORS;

ORGANIC COMPOUNDS;

2 (2 MORPHOLINOCARBO 1 METHYLVINYL) 7 ETHOXYCARBOPROPOXYBENZO(B)FURAN; 2 ACETYL 4 (2 DIETHYLCARBAMOYL 1 METHYLVINYL) 7 (1 PHENYLETHOXY)BENZO(B)FURAN; 2-(2-MORPHOLINOCARBO-1-METHYLVINYL)-7-ETHOXYCARBOPROPOXYBENZO(B)FURAN; 2-ACETYL-4-(2-DIETHYLCARBAMOYL-1-METHYLVINYL)-7-(1-PHENYLETHOXY)BENZO(B)FURAN; BENZOFURAN DERIVATIVE; CALCIUM; CARBAMIC ACID DERIVATIVE; LEUKOTRIENE B4 RECEPTOR; LTB4R PROTEIN, HUMAN; LTB4R2 PROTEIN, HUMAN; MORPHOLINE DERIVATIVE; PURINE P2 RECEPTOR;

ANIMAL; ARTICLE; CALCIUM SIGNALING; CHEMICAL STRUCTURE; CHEMISTRY; CHO CELL; CONFORMATION; DRUG ANTAGONISM; DRUG EFFECT; GENE EXPRESSION; GENETICS; HAMSTER; HUMAN; IC 50; METABOLISM; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ANIMALS; BENZOFURANS; CALCIUM; CALCIUM SIGNALING; CARBAMATES; CHO CELLS; CRICETINAE; CRYSTALLOGRAPHY, X-RAY; GENE EXPRESSION; HUMANS; INHIBITORY CONCENTRATION 50; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; MORPHOLINES; RECEPTORS, LEUKOTRIENE B4; RECEPTORS, PURINERGIC P2;

EID: 10644266977     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b411286e     Document Type: Article

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27. 4 antagonist were reported previously as follows. (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) ;; (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);; (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);; (d) T. S. Shoupe, S. M. Coutts, D. C. Baker, E. S. Hand, Can. Pat. Appl., 1991 63pp. CPXXEB CA 2013960, AA 19910319, CAN 115:158949, AN 1991: 558949 (PF 10042, dibenzofuran derivative); (e) C. D. Wright, P. J. Kuipers, M. D. Hoffman, D. O. Thueson and M. C. Conroy, Biochem. Biophys. Res. Commun., 1990, 167, 828-834(Cl 949, indole derivative); (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); (g) C. Can, M. G. Cinar, S. Ulker, A. Evinc and S. Kosay, Eur. J. Pharmacol., 1998, 350, 223-228.
28. 4 antagonist were reported previously as follows. (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) ;; (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);; (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);; (d) T. S. Shoupe, S. M. Coutts, D. C. Baker, E. S. Hand, Can. Pat. Appl., 1991 63pp. CPXXEB CA 2013960, AA 19910319, CAN 115:158949, AN 1991: 558949 (PF 10042, dibenzofuran derivative); (e) C. D. Wright, P. J. Kuipers, M. D. Hoffman, D. O. Thueson and M. C. Conroy, Biochem. Biophys. Res. Commun., 1990, 167, 828-834(Cl 949, indole derivative); (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); (g) C. Can, M. G. Cinar, S. Ulker, A. Evinc and S. Kosay, Eur. J. Pharmacol., 1998, 350, 223-228.
29. 4 antagonist were reported previously as follows. (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) ;; (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);; (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);; (d) T. S. Shoupe, S. M. Coutts, D. C. Baker, E. S. Hand, Can. Pat. Appl., 1991 63pp. CPXXEB CA 2013960, AA 19910319, CAN 115:158949, AN 1991: 558949 (PF 10042, dibenzofuran derivative); (e) C. D. Wright, P. J. Kuipers, M. D. Hoffman, D. O. Thueson and M. C. Conroy, Biochem. Biophys. Res. Commun., 1990, 167, 828-834(Cl 949, indole derivative); (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); (g) C. Can, M. G. Cinar, S. Ulker, A. Evinc and S. Kosay, Eur. J. Pharmacol., 1998, 350, 223-228.
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51. 4 antagonist in the following literature. (a) S. W. Djuric, P. W. Collins, P. H. Jones, R. L. Shone, B. S. Tosai, D. J. Fretland, G. M. Butchko, D. Villani-Prince, R. H. Keith, J. M. Zemaitis, L. Metcalf and R. F. Bauer, J. Med. Chem, 1989, 32, 1147-1156; (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, R. Breslow, M. J. Conklyn, M. A. Smith, B. C. Hackman, N. S. Doherty, E. Salter, C. A. Farrell and G. Schulte, J. Med. Chem, 1989, 37, 3197-3199; (c) J.-M. Poudrel, P. Hullot, 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.
52. 4 antagonist in the following literature. (a) S. W. Djuric, P. W. Collins, P. H. Jones, R. L. Shone, B. S. Tosai, D. J. Fretland, G. M. Butchko, D. Villani-Prince, R. H. Keith, J. M. Zemaitis, L. Metcalf and R. F. Bauer, J. Med. Chem, 1989, 32, 1147-1156; (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, R. Breslow, M. J. Conklyn, M. A. Smith, B. C. Hackman, N. S. Doherty, E. Salter, C. A. Farrell and G. Schulte, J. Med. Chem, 1989, 37, 3197-3199; (c) J.-M. Poudrel, P. Hullot, 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.
53. 50 values.
54. 1 (Fig. 6). We also have confirmed that the inhibition by these compounds was not due to their cytotoxicity because they did not affect ATP-dependent calcium mobilization through intrinsic ATP receptors in CHO cells at the concentrations of BLT inhibition (data not shown).
55. H.-P. Nothacker, Z. Wang, Y. Zhu, R. K. Reinscheid, S. H. S. Lin and O. Civelli, Mol. Pharmacol., 2000, 58, 1601-1608.
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