SAR studies of capsazepinoid bronchodilators 3: The thiourea part (coupling region) and the 2-(4-chlorophenyl)ethyl moiety (C-region)

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 5, 2008, Pages 2529-2540

  Berglund, Magnus ^a   Dalence Guzmán, María F ^a,b   Skogvall, Staffan ^c   Sterner, Olov ^a  

^a LUND UNIVERSITY   (Sweden)

^b UNIVERSIDAD MAYOR DE SAN SIMÓN   (Bolivia)

^c Respiratorius AB   (Sweden)

Author keywords

2 (Phenyl)ethyl; Asthma; Bronchodilator; C region; Capsazepine; COPD; Coupling region; SAR; Small human airways; Thiourea

Indexed keywords

2(4 CHLOROPHENYL)ETHYL; AMIDE; BRONCHODILATING AGENT; CAPSAZEPINE; ETHYLENE DERIVATIVE; TETRAHYDROISOQUINOLINE DERIVATIVE; THIOUREA; UNCLASSIFIED DRUG;

ARTICLE; BRONCHODILATING ACTIVITY; DRUG POTENCY; DRUG STRUCTURE; HUMAN; STRUCTURE ACTIVITY RELATION;

BRONCHODILATOR AGENTS; CAPSAICIN; CHLORINE COMPOUNDS; HUMANS; HYDROPHOBICITY; LIPIDS; MOLECULAR STRUCTURE; RESPIRATION; STRUCTURE-ACTIVITY RELATIONSHIP; THIOUREA;

EID: 40749095197     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2007.11.056     Document Type: Article

References (24)

1. Fox A.J. Pulm. Pharmacol. 8 (1995) 207
2. Szolcsanyi J., and Jansco-Gaber A. Arzneimittelforschung 25 (1975) 1877
3. Caterina M.J., Schumacher M.A., Tominaga M., Rosen T.A., Levine J.D., and Julius D. Nature 389 (1997) 81
4. Janusz J.M., Buckwalter B.L., Young P.A., LaHann T.R., Framer R.W., Kasting G.B., Loomans M.E., Kerckaert G.A., Maddin C.S., Berman E.F., Bohne R.L., Cupps T.L., and Milstein J.R. J. Med. Chem. 36 (1993) 2595
5. Wrigglesworth R., Walpole C.S.J., Bevan S.J., Campbell E.A., Dray A., Hughes G.A., James I., Masdin K.J., and Winter J. J. Med. Chem. 39 (1996) 4942
6. Szallasi A., and Blumberg P.M. Pharmacol. Rev. 51 (1999) 159
7. Ellis J.E., and Undem B.J.J. Pharmacol. Exp. Ther. 268 (1994) 85
8. Satoh H., Lou Y.P., and Lundberg J.M. Eur. J. Pharmacol. 236 (1993) 367
9. Skogvall S., Berglund M., Dalence-Guzmán M.F., Svensson K., Jönsson P., Persson C.G.A., and Sterner O. Pulm. Pharmacol. Ther. 20 (2007) 273
10. Skogvall, S.; Dalence-Guzmán, M.F.; Berglund, M.; Svensson, K.; Mesic, A.; Jönsson, P.; Persson C.G. A; and Sterner, O. Pulm. Pharmacol. Ther. in press, doi:10.1016/j.pupt.2007.01.004.
11. Walpole C.S.J., Wrigglesworth R., Bevan S., Campbell E.A., Dray A., James I.F., Perkins M.N., Reid D.J., and Winter J. J. Med. Chem. 36 (1993) 2362
12. Dalence-Guzmán M.F., Berglund M., Skogvall S., and Sterner O. Bioorg. Med. Chem. 18 (2008) 2499
13. Berglund M., Dalence-Guzmán M.F., Skogvall S., and Sterner O. Bioorg. Med. Chem. 18 (2008) 2513
14. Murthy A.R., Sundar N.S., and Rao G.S.R.S. Tetrahedron 38 (1982) 2831
15. Ali F.E.-F., Dandridge P.A., Gleason J.G., Krell R.D., Kruse C.H., Lavanchy P.G., and Snader K.M. J. Med. Chem. 25 (1982) 947
16. Braverman S., Cherkinsky M., Kedrova L., and Reiselman A. Tetrahedron Lett. 40 (1999) 3235
17. Lee J., Lee J., Kang M., Shin M., Kim J.-M., Kang S.-U., Lim J.-O., Choi H.-K., Suh Y.-G., Park H.-G., Oh U., Kim H.-D., Park Y.-H., Ha H.-J., Kim Y.-H., Toth A., Wang Y., Tran R., Pearce L.V., Lundberg D.J., and Blumberg P.M. J. Med. Chem. 46 (2003) 3116
18. Skogvall, S.; Bjork, H.; Berglund, P.M.; Dalence, G.M.F.; Sterner, O. U.S. Pat. Appl. Publ. 2005163712 A1, 2005.
19. Smith D.A., van de Waterband H., and Walker D.K. In: Mannhold R., Kubinyi H., and Timmerman H. (Eds). Pharmacokinetics and Metabolism in Drug Design (2001), Wiley-VCH Verlag, GmbH 1-11
20. Walpole C.S., Bevan S., Bovermann G., Boelsterli J.J., Breckenridge R., Davies J.W., Hughes G.A., James I., Oberer L., and Winter J. J. Med. Chem. 37 (1994) 1942
21. Steiner T. Angew. Chem. Int. Ed. Engl. 41 (2002) 48
22. Sun Q., Tafesse L., Islam K., Zhou X., Victory S.F., Zhang C., Hachicha M., Schmid L.A., Patel A., Rotshteyn Y., Valenzano K.J., and Kyle D.J. Bioorg. Med. Chem. Lett. 13 (2003) 3611
23. Lee J., Kang S.-U., Lim J.-O., Choi H.-K., Jin M.-K., Toth A., Pearce L.V., Tran R., Wang Y., Szabo T., and Blumberg P. Bioorg. Med. Chem. 12 (2004) 371
24. Vierling P., and Greiner J. Curr. Pharm. Des. 9 (2003) 1755