286 FRANCISZEK S•CZEWSKI et al.not be classified as hypertensive agents. This studyhas widened the scope of developing imidazolinederivatives as promising antihypertensive agents.AcknowledgmentsPart of this research (A.L. Hudson, M.Ferdousi) was funded by a grant from NationalSciences and Engineering Council of Canada (No,371863). F. Sπczewski and A. Wasilewska acknowledgefinancial support of this work by MedicalUniversity of GdaÒsk (Research Project ST-38).REFERENCES1. Benedict C.R.: Curr. Hypertens. Rep. 1999,305.2. Van Zweiten P.A.: J. Hypertension 15 (Suppl.1), S3 (1997).3. Guyent P.G.: Am. J. Physiol. 273, R1580(1997).4. Khan Z.P., Ferguson C.N., Jones R.M.:Anaesthesia 54, 146 (1999).5. Kobinger W., Pichler L.: Centrally ActingDrugs (Clonidine, Methyldopa, Guanfacine), inHandbook of Experimental Pharmacology.Pharmacology of Antihypertensive Therapeutics.Ganten D. and Murlow P.J. Eds., vol. 93,p. 227, Springer-Verlag, Berlin 1990.6. Ma D., Rajakumaraswamy N., Maze M.: Br.Med. Bull. 71, 77 (2005).7. Mantz J.: Bailliereís Clinical Anaesthesiology14, 433, (2000).8. Rodriguez F., Rozas I., Ortega J.E., Meana J.J.,Callado L.F.: J. Med. Chem. 50, 4516 (2007).9. Rodriguez F., Rozas I., Ortega J.E., ErdozianA.M., Meana J.J., Callado L.F.: J. Med. Chem.52, 601 (2009).10. Ruffolo Jr., R.R., Nichols A.J., Stadel J.M.,Hieble J.P.: Annu. Rev. Pharmacol. Toxicol. 33,243 (1993).11. Sanders R.D., Maze M.: Curr. Opinion Invest.Drugs 8, 25 (2007).12. Dardonville C., Goya P., Rozas I., Alsasua A.,Martin M.I., Borrego M.J.: Bioorg. Med. Chem.8, 1567 (2000).13. Docherty J.R.: Cell. Mol. Life Sci. 67, 405(2010).14. Garcia-Sainz J.A., Villalobos-Molina R.: Eur. J.Pharmacol. 500, 113 (2004).15. Hague Ch., Chen Z., Uberti M., MinnemannK.P.: Life Sci. 74, 411 (2003).16. Piascik M.T., Perez D.M.: J. Pharmacol. Exp.Ther. 298, 403 (2001).17. Struyker Boudier H., Smeets G., Brouwer G,van Rossum J.: Life Sci. 15, 887 (1974).18. Sπczewski F., Kornicka A., RybczyÒska P.,Hudson A.L., Miao S.S., Gdaniec M., BoblewskiA., Lehmann A.: J. Med. Chem. 51, 3599 (2008).19. Sπczewski F., Kornicka A., Hudson A.L., LairdS., Scheinin M., Laurila J.M., RybczyÒska A. etal.: Bioorg. Med. Chem. 19, 321 (2011).20. Sπczewski J., Hudson A.L., RybczyÒska A.,Boblewski K., Lehmann A., Ma D., Maze M. etal.: Arch. Pharm. Life Sci. 345, 33 (2012).21. Sπczewski J., Hudson A.L., Scheinin M.,RybczyÒska A., Ma D, Sπczewski F., Laird S. etal.: Bioorg. Med. Chem. 20, 108 (2012).22. WrÛblewska M., Kasprzyk J., Sπczewski F.,Kornicka A., Boblewski K., Lehmann A.,RybczyÒska A.: Pharmacol. Rep. 85, 1025 (2013).23. a) Bormann G., Berthold R.: 1-Aminoindolines,process for their production and pharmaceuticalcomposition containing them. EP 0 000 151 A1(1979); b) Bormann G, Berthold R: 1-Aminosubstituted indoline derivatives as vasoconstrictingagents. Canadian Patent 1094556 (1981).24. Bormann G., Berthold R.: N-substituted cyclicamines, their production and pharmaceuticalcomposition containing them. UK Patent Appl.2031427 (1980).25. Pigini M., Quaglia W., Gentili F., Marucci G.,Cantalamessa F., Franchini S., Sorbi C., BrasiliL.: Bioorg. Med. Chem. 8, 883 (2000).26. Cho H., Toeroek F., Toeroek B.: Org. Biomol.Chem. 11, 1209 (2013).27. Florvall L., Kumar Y., Ask A.L., Fagervall I.,Renyi L., Ross S.B.: J. Med. Chem. 29, 1406(1986).28. Kost A.N., Yudin L.G., Berlin Yu.A., TerentíevA.P.: Zhur. Obshchei Khim. 29, 2820 (1959).29. Trani A., Belasio E.: J. Heterocycl. Chem. 11,257 (1974).30. Mundla S.R., Wilson L.J., Klopfstein S.R.,Seibel W.L., Nikolaides N.N.: TetrahedronLett. 41, 6563 (2000).31. Lione L.A., Nutt D.J., Hudson A.L.: Eur. J.Pharmacol. 763, 123 (1998).32. Ernsberger P., Graves M.E., Graff L.M., ZakiehN., Nguyen P., Collins L.A., Westbrooks K.L.,Johnson G.G.: Ann. N.Y. Acad. Sci. 763, 22(1995).33. Hudson A.L., Chapleo C.B., Lewis J.W.,Husbands S., Grivas K., Mallard N.J., Nutt D.J.:Neurochem. Int. 30, 47 (1997).34. Nutt D.J., French N., Handley S., Hudson A.L.,Husbands S., Jackson H., Jordan S. et al.: Ann.N.Y. Acad. Sci. 763, 125 (1995).
1-[(Imidazolin-2-yl)amino]indoline and 1-[(imidazolin-2-yl)amino]1,2,3,4-tetrahydroquinoline... 28735. Cheng Y.C., Prusoff W.H.: Biochem.Pharmacol. 22, 3099 (1973).36. RybczyÒska A., Boblewski K., Lehmann A.,Orlewska C., Foks H., Drewnowska K., HoppeA.: Am. J. Hypertens. 18, 364 (2005).37. Woodcock E.A., Du Xj., Reichelt M.E.,Graham R.M.: Cardiovas. Res. 77, 452 (2008).38. Shannon R., Chaudhry M.: Am. Heart J. 152,842 (2006).39. O-Uchi J., Komukai K., Kusakari Y., MorimotoS., Kawai M., Jhun B.S., Hurst S. et al.:Biochem. Biophys. Res. Commun. 433, 183(2013).40. Jensen B.C., Swigart P.M., De Marco T.,Hoopes C., Simpson P.C.: Circ. Heart Fail. 2,654 (2009).41. Shi T., Moravec C.S., Perez D.M.: J. Recept.Signal Transduct. Res. 33, 96 (2013).42. Lˆffelholz K., Pappano A.J.: Pharmacol. Rev.37, 1 (1985).43. Boblewski K., Lehmann A., Sπczewski F.,Kornicka A., RybczyÒska A.: Pharmacol. Rep.66, 874 (2014).44. Philipp M., Brede M., Hein L.: Am. J. Physiol.Regul. Integr. Comp. Physiol. 283, R287(2002).45. Philipp M., Hein L.: Pharmacol. Ther. 101, 65(2004).Received: 28. 01. 2014