Synthesis and adrenolytic activity of 1-(1H-indol-4-yloxy)-3-(2-(2-methoxy phenoxy)ethylamino)propan-2-ol analogs and its enantiomers. Part 2

European Journal of Medicinal Chemistry

Volumn 44, Issue 12, 2009, Pages 5103-5111

  Groszek, Grazyna ^a   Nowak Król, Agnieszka ^a   Wdowik, Tomasz ^a   Świerczyński, Dariusz ^b   Bednarski, Marek ^c   Otto, Monika ^c   Walczak, Maria ^c   Filipek, Barbara ^c  

^a RZESZOW UNIVERSITY OF TECHNOLOGY   (Poland)

^b INSTITUTE OF PHYSICAL CHEMISTRY   (Poland)

^c JAGIELLONIAN UNIVERSITY MEDICAL COLLEGE   (Poland)

Author keywords

1 , 2 and 1 Adrenoceptor antagonists; Cardiovascular and spasmolytic activities; Enantiomers; Synthesis

Indexed keywords

1 (1H INDOL 4 YLOXY) 3 [2 (2 METHOXYPHENOXY)ETHYLAMINO]PROPAN 2 OL; 1 (5 METHOXY 1H INDOL 4 YLOXY) 3 [2 (2 METHOXYPHENOXY)ETHYLAMINO]PROPAN 2 OL; 1 (7 METHOXY 1H INDOL 4 YLOXY) 3 [2 (2 METHOXYPHENOXY)ETHYLAMINO]PROPAN 2 OL; ADRENERGIC RECEPTOR BLOCKING AGENT; ALPHA 1 ADRENERGIC RECEPTOR STIMULATING AGENT; ALPHA 2 ADRENERGIC RECEPTOR STIMULATING AGENT; ANTIARRHYTHMIC AGENT; ANTIHYPERTENSIVE AGENT; BETA 1 ADRENERGIC RECEPTOR; CARVEDILOL; PROPRANOLOL; SPASMOLYTIC AGENT; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIARRHYTHMIC ACTIVITY; ANTIHYPERTENSIVE ACTIVITY; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG ACTIVITY; DRUG EFFECT; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROGRAPHY; ENANTIOMER; HEART ARRHYTHMIA; HYPOTENSION; ILEUS; MALE; NONHUMAN; RAT;

2-PROPANOL; ADRENERGIC ANTAGONISTS; ANIMALS; ANTIHYPERTENSIVE AGENTS; CARBAZOLES; ILEUM; MALE; MOLECULAR STRUCTURE; PROPANOLAMINES; RABBITS; RATS; RATS, WISTAR; STEREOISOMERISM;

EID: 70449657722     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.07.012     Document Type: Article

References (39)

1. Panjrath G.S., and Messerli F.H. Prog. Cardiovasc. Dis. 49 (2006) 76-87
2. Thamer M., Ray N.F., and Taylor T. Clin. Ther. 21 (1999) 1387-1400
3. Toda N. Pharmacol. Ther. 100 (2003) 215-234
4. Marona H., Szkaradek N., Kubacka M., Bednarski M., Filipek B., Cegła M., and Szneler E. Arch. Pharm. (Weinheim) 341 (2008) 90-98
5. McTavish D., Campoli-Richards D., and Sorkin E.M. Drugs 45 (1993) 232-258
6. Dunn C.J., Lea A.P., and Wagstaff A.J. Drugs 54 (1997) 161-185
7. Sica D.A. Am. J. Cardiol. 98 (2006) 1-4
8. CAPRICORN Investigators. Lancet 357 (2001) 1358-1390
9. Brunvand H., Liu G., Ma X.L., Yue T.L., Ruffolo R.R., and Feuerstein G.Z. Eur. J. Pharmacol. 356 (1998) 193-198
10. Han-Chieh L., Yi-Tsau H., Hung-Chi W., Ying-Ying Y., Tzung-Yan L., Ying-Wen W., Ming-Chih H., and Shou-Dong L. J. Gastroenterol. 41 (2006) 361-368
11. Kikuta J., Ishii M., Kishimoto K., and Kurachi Y. Eur. J. Pharmacol. 529 (2006) 47-54
12. Groszek G., Bednarski M., Dybała M., and Filipek B. Eur. J. Med. Chem. 44 (2008) 809-817
13. Fukuyama Y., Iwatsuki Ch., Kodama M., Ochi M., Kataoka K., and Shibata K. Tetrahedron 54 (1998) 10007-10016
14. Pönicke K., Heinroth-Hoffmann I., and Brodde O. J. Pharmacol. Exp. Ther. 301 (2002) 71-76
15. Siemieniuk A., Szałkowska-Pa{ogonek}gowska H., Lochyński S., Pia{ogonek}tkowski K., Filipek B., Krupińska J., Czarnecki R., Librowski T., and Biała S. Pol. J. Pharmacol. Pharm. 44 (1992) 557-593
16. Huang H., Shan J., Pan X.H., Wang H.P., Qian L.B., and Xia Q. Diabetes Res. Clin. Pract. 75 (2007) 7-13
17. Kopecky S.L. Am. J. Cardiol. 98 (2006) 1115-1119
18. Reiter M. Prog. Cardiovasc. Dis. 47 (2004) 11-33
19. Poole-Wilson P.A., Swedberg K., and Cleland J.G. Lancet 362 (2003) 7-13
20. Kim Y.S., Kim M.S., Ha H., Park J., Kim H.J., and Park K. Surg. Today 32 (2002) 230-235
21. Dulin B., and Abraham W.T. Am. J. Cardiol. 93 (2004) 3B-6B
22. Brodde O.E., and Michel M.C. Pharmacol. Rev. 51 (1999) 651-689
23. Ruffolo R.R., Gellai M., Hieble J.P., Willette R.N., and Nichols A.J. Eur. J. Clin. Pharmacol. 38 (1990) 82-88
24. Deng B., Yu X., Kuang S., Zhang W., Zhou Z., Zhang K., Qian W., Shan Z., Yang M., Wu S., and Lin S. Life Sci. 80 (2007) 665-671
25. Karle C., Kreye V., Zhang W., Thomas D., Ro{combining double acute accent}cki K., Katho{combining double acute accent}fer S., and Kiehn J. Cardiovasc. Res. 49 (2001) 361-370
26. Cheng J., Niwa R., Kamiya K., Toyama J., and Kodama I. Eur. J. Pharmacol. 376 (1999) 189-201
27. Gibson M.S., and Bradshaw R.W. Angew. Chem. Int. Ed. 7 12 (1968) 919-930
28. Cotelle P., and Catteau J.P. Synth. Commun. 22 14 (1992) 2071-2076
29. Howe C.A., Howe A., Hamel C.R., Gibson H.W., and Flynn R.R. J. Chem. Soc. (1965) 795-797
30. Press J.B., Deegan E.G., McNally J.J., and Roberts J.R. J. Heterocycl. Chem. 23 (1986) 1821-1828
31. Kato S., and Morie T. J. Heterocycl. Chem. 33 (1996) 1171-1178
32. Julia M., Manoury P., and Voillaume M.C. Bull. Soc. Chim. Fr. (1965) 1417-1423
33. Tejani-Butt S.M., and Brunswick D.J. J. Med. Chem. (1986) 1524-1527
34. Cheng Y.C., and Prudoff W.H. Biochem. Pharmacol. 22 (1973) 3099-3108
35. Cambridge G.W., Parsons J.F., and Stafford R. In: inBudden R., Detweiler D.K., and Zbinden G. (Eds). The Rat Electrocardiogram in Pharmacology and Toxicology (1981), Pergamon Press, Oxford, New York, Toronto 135-138
36. Szekeres L., and Papp G. In: Schmier J., and Eichler O. (Eds). Handbook of Experimental Pharmacology (1975), Springer-Verlag, Berlin, Heidelberg, New York
37. Walker M.J., Curtis M.J., Hearse D.J., Campbell R.W., Janse M.J., Yellon D.M., Cobbe S.M., Coker S.J., Harness J.B., Harron D.W., Higgins A.J., Julian D.G., Lab M.J., Manning A.S., Northover B.J., Parratt J.R., Riemersma R.A., Riva E., Russel D.C., Sheridan D.J., Winslow E., and Woodward B. Cardiovasc. Res. 22 (1988) 447-455
38. Magnus R. Versuche am überlebenden Dünnalarm von Säugetieren. Pflügers Arch. 102 (1904) 123-151
39. Orisadipe A., Amos S., Adesomoju A., Binda L., Emeje M., Okogun J., Wamebe C., and Gamaniel K. Biol. Pharm. Bull. 24 (2001) 364-367