Synthesis and adrenolytic activity of 1-(1H-indol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol and its enantiomers. Part 1

European Journal of Medicinal Chemistry

Volumn 44, Issue 2, 2009, Pages 809-817

  Groszek, Grazyna ^a   Bednarski, Marek ^b   Dybała, Małgorzata ^b   Filipek, Barbara ^b  

^a RZESZOW UNIVERSITY OF TECHNOLOGY   (Poland)

^b JAGIELLONIAN UNIVERSITY MEDICAL COLLEGE   (Poland)

Author keywords

1 , 2 , 1 Adrenoceptor antagonist; Antiarrhythmic, hypotensive and spasmolytic activities; Synthesis

Indexed keywords

1 (1H INDOL 4 YLOXY) 3 [[2 (2 METHOXYPHENOXY)ETHYL]AMINO]PROPAN 2 OL; ADRENERGIC RECEPTOR BLOCKING AGENT; ALPHA 1 ADRENERGIC RECEPTOR; ALPHA 2 ADRENERGIC RECEPTOR; BETA 1 ADRENERGIC RECEPTOR; SPASMOLYTIC AGENT; UNCLASSIFIED DRUG;

ADRENERGIC RECEPTOR BLOCKING; ANIMAL EXPERIMENT; ANTIARRHYTHMIC ACTIVITY; ANTIHYPERTENSIVE ACTIVITY; ARTICLE; CONTROLLED STUDY; DIASTOLIC BLOOD PRESSURE; DRUG RECEPTOR BINDING; ELECTROCARDIOGRAM; MALE; NONHUMAN; RAT; RECEPTOR AFFINITY; SYSTOLIC BLOOD PRESSURE;

2-PROPANOL; ADRENERGIC ANTAGONISTS; ANIMALS; ANTI-ARRHYTHMIA AGENTS; ARRHYTHMIAS, CARDIAC; ELECTROCARDIOGRAPHY; HYPOTENSION; PARASYMPATHOLYTICS; PROPANOLS; RABBITS; RATS; RECEPTORS, ADRENERGIC; RECEPTORS, ADRENERGIC, ALPHA-1; RECEPTORS, ADRENERGIC, BETA-1; SPASM; STEREOISOMERISM;

EID: 60149100618     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2008.05.019     Document Type: Article

References (35)

1. Gomer B. Hosp. Pharm. 14 (2007) 119-125
2. F. Wiedemann, W. Kampe, M. Thiel, G. Sponer, E. Roesch, K. Dietmann, Patent DE 2 815 926, 1978; US Patent 4 503 067, 1985.
3. Hirohashi M., Takasuna K., Takamura K., Yamaguchi K., Moekawa K., Yamada M., Iwasaki S., Yoshida M., Nomura M., Taguchi K., and Suzuki Y. Drug Res. 40 7 (1990) 735-746
4. 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
5. Pönicke K., Heinroth-Hoffmann I., and Brodde O. J. Pharmacol. Exp. Ther. 301 (2002) 71-76
6. Matsuda Y., Akita H., Terashima M., Shiga N., Kenzawa K., and Yokoyama M. Am. Heart J. 140 5 (2000) 753-758
7. M. Bednarski, B. Filipek, G. Groszek, D. Macia{ogonek}g, Patent PL 195413, 2002.
8. Marvel C.S., and Tanenbaum A.L. J. Am. Chem. Soc. 44 (1922) 2647
9. Organic Synthesis coll. vol. I (1956), John Wiley and Sons, Inc., New York, NY p. 435
10. Gibson M.S., and Bradshaw R.W. Angew. Chem., Int. Ed. 7 12 (1968) 919-930
11. Ma{ogonek}kosza M., Danikiewicz W., and Wojciechowski K. Liebigs Ann. Chem. (1988) 203-208
12. Tejani-Butt S.M., and Brunswick D.J. J. Med. Chem. (1986) 1524-1527
13. Cahn R.S., Ingold C.K., and Prelog V. Angew. Chem., Int. Ed. Engl. 5 (1966) 385
14. ChemIDplus - .
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. Litchfield J.T., and Wilcoxon F. J. Pharmacol. Exp. Ther. 96 (1949) 99-113
17. Huang H., Shan J., Pan X.H., Wang H.P., Qian L.B., and Xia Q. Diabetes Res. Clin. Pract. 75 (2007) 7-13
18. Reiter M. Prog. Cardiovasc. Dis. 47 (2004) 11-33
19. Kim Y.S., Kim M.S., Ha H., Park J., Kim H.J., and Park K. Surg. Today 32 (2002) 230-235
20. Poole-Wilson P.A., Swedberg K., and Cleland J.G. Lancet 362 (2003) 7-13
21. Brodde O.E., and Michel M.C. Pharmacol. Rev. 51 (1999) 651-689
22. Dulin B., and Abraham W.T. Pharmacol. Carvedilol Am. J. Cardiol. 93 (2004) 3B-6B
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. Cheng J., Niwa R., Kamiya K., Toyama J., and Kodama I. Eur. J. Pharmacol. 376 (1999) 189-201
25. 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
26. Kikuta J., Ishii M., Kishimoto K., and Kurachi Y. Eur. J. Pharmacol. 529 (2006) 47-54
27. Grochowski E., and Eckstein Z. Bull. Acad. Pol. Sci. Ser. Sci. Chim. 11 (1963) 443-446
28. Augstein J., Austin W.C., Boscott R.J., Green S.M., and Worthing C.R. J. Med. Chem. 8 (1965) 356-367
29. Rashidbaigi A., and Ruoho A.E. J. Pharm. Sci. 71 (1982) 305
30. Cheng Y.C., and Prusoff W.H. Biochem. Pharmacol. 22 (1973) 3099
31. Cambridge G.W., Parsons J.F., and Stafford R. In: Budden R., Detweiler D.K., and Zbinden G. (Eds). The Rat Electrocardiogram in Pharmacology and Toxicology (1981), Pergamon Press, Oxford, New York, Toronto 135-138
32. Szekeres L., and Papp G. In: Schmier J., and Eichler O. (Eds). Handbook of Experimental Pharmacology (1975), Springer-Verlag, Berlin, Heidelberg, New York
33. 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
34. Magnus R. Versuche am überlebenden Dünnalarm von Säugetieren. Pflügers Arch. 102 (1904) 123-151
35. Orisadipe A., Amos S., Adesomoju A., Binda L., Emeje M., Okogun J., Wamebe C., and Gamaniel K. Biol. Pharm. Bull. 24 (2001) 364-367