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The Scientific World Journal
Volume 2013 (2013), Article ID 274570, 13 pages
http://dx.doi.org/10.1155/2013/274570
Research Article

Synthesis and Biological Evaluation of 2-Hydroxy-3-[(2-aryloxyethyl)amino]propyl 4-[(Alkoxycarbonyl)amino]benzoates

1Department of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackého 1/3, 612 42 Brno, Czech Republic
2Medis International a.s., Průmyslová 16, 747 23 Bolatice, Czech Republic
3Department of Environmental Ecology, Faculty of Natural Sciences, Comenius University, Mlynska dolina Ch-2, 842 15 Bratislava, Slovakia
4Department of Biological Sciences, Cork Institute of Technology, Bishopstown, Cork, Ireland
5Department of Human Pharmacology and Toxicology, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences, Palackého 1/3, 612 42 Brno, Czech Republic
6Institute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynská dolina CH-2, 842 15 Bratislava, Slovakia

Received 29 June 2013; Accepted 7 August 2013

Academic Editors: A. Concheiro and M. Ozyazici

Copyright © 2013 Jan Tengler et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. S. Morais, E. Dias, and M. de Lourdes Pereira, “Carbamates: human exposure and health effects,” in The Impact of Pesticides, M. Jokanovic, Ed., pp. 21–38, Academy Publish, Cheyenne, Wyoming, 2012. View at Google Scholar
  2. D. Zhi, S. Zhang, F. Qureshi et al., “Synthesis and biological activity of carbamate-linked cationic lipids for gene delivery in vitro,” Bioorganic and Medicinal Chemistry Letters, vol. 22, pp. 3837–3841, 2012. View at Publisher · View at Google Scholar · View at Scopus
  3. V. Végh, J. Čižmárik, and K. Hahnenkamp, “Is there a place for local anesthetics structurally different from classical amid or ester local anesthetics?” Current Opinion in Anesthesiology, vol. 19, pp. 509–515, 2006. View at Google Scholar
  4. E. Račanská, J. Csöllei, and P. Švec, “Pharmacological evaluation of new alkylesters of 4-[(2-hydroxy-3-alkylamino)propoxy]phenylcarbamic acids with beta-adrenolytic properties,” Pharmazie, vol. 45, no. 11, pp. 851–853, 1990. View at Google Scholar · View at Scopus
  5. P. Mokrý, M. Zemanová, J. Csöllei, E. Račanská, and I. Tůmová, “Synthesis and pharmacological evaluation of novel potential ultrashort-acting beta-blockers,” Pharmazie, vol. 58, pp. 18–21, 2003. View at Google Scholar
  6. Y. L. Janin, “Antituberculosis drugs: ten years of research,” Bioorganic and Medicinal Chemistry, vol. 15, no. 7, pp. 2479–2513, 2007. View at Publisher · View at Google Scholar · View at Scopus
  7. Q. Meng, H. Luo, Y. Liu, W. Li, W. Zhang, and Q. Yao, “Synthesis and evaluation of carbamate prodrugs of SQ109 as antituberculosis agents,” Bioorganic and Medicinal Chemistry Letters, vol. 19, no. 10, pp. 2808–2810, 2009. View at Publisher · View at Google Scholar · View at Scopus
  8. A. Imramovský, J. Vinšová, J. M. Férriz et al., “New antituberculotics originated from salicylanilides with promising in vitro activity against atypical mycobacterial strains,” Bioorganic and Medicinal Chemistry, vol. 17, pp. 3572–3579, 2009. View at Google Scholar
  9. A. Imramovský, J. Vinšová, J. M. Férriz, V. Buchta, and J. Jampílek, “Salicylanilide esters of N-protected amino acids as novel antimicrobial agents,” Bioorganic and Medicinal Chemistry Letters, vol. 19, pp. 348–351, 2009. View at Google Scholar
  10. J. Otevřel, Z. Mandelová, M. Peško et al., “Investigating the spectrum of biological activity of ring-substituted salicylanilides and carbamoylphenylcarbamates,” Molecules, vol. 15, pp. 8122–8142, 2010. View at Google Scholar
  11. A. Blaser, B. D. Palmer, H. S. Sutherland et al., “Structure-activity relationships for amide-, carbamate-, and urea-linked analogues of the tuberculosis drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl] oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824),” Journal of Medicinal Chemistry, vol. 55, no. 1, pp. 312–326, 2012. View at Publisher · View at Google Scholar · View at Scopus
  12. J. Čižmárik, M. Švejnochová, and E. Schwartz, “Tuberculostatic activity of the piperidinoethylester of the alkoxyphenylcarbamide acid in vitro,” Pharmazie, vol. 41, pp. 744–745, 1986. View at Google Scholar
  13. K. Waisser, J. Čižmárik, K. Dražková, and J. Kaustová, “Antimycobacterial effects of pyrrolidinoethylester alkoxysubstituted phenylcarbamic acids,” Česká a Slovenská Farmacie, vol. 51, pp. 140–144, 2002. View at Google Scholar
  14. K. Waisser, K. Dražková, J. Čižmárik, and J. Kaustová, “Antimycobacterial activity of basic ethyl esters of alkoxy-substituted phenylcarbamic acids,” Folia Microbiologica, vol. 48, pp. 45–50, 2003. View at Google Scholar
  15. K. Waisser, K. Dražková, J. Čižmárik, and J. Kaustová, “A new group of potential antituberculotics: Hydrochlorides of piperidinylalkyl esters of alkoxy-substituted phenylcarbamic acids,” Folia Microbiologica, vol. 49, no. 3, pp. 265–268, 2004. View at Google Scholar · View at Scopus
  16. K. Waisser and J. Čižmárik, “Derivatives of phenylcarbamic acid as potential antituberculotics,” Česká a Slovenská Farmacie, vol. 61, pp. 17–20, 2012. View at Google Scholar
  17. S. Kečkésová, E. Sedlárová, J. Čižmárik et al., “Antimycobacterial activity of novel derivatives of arylcarbonyloxyaminopropanols,” Česká a Slovenská Farmacie, vol. 58, pp. 203–207, 2009. View at Google Scholar
  18. V. Račanský, E. Béderová, and P. Balgavý, “Decrease of gel-liquid crystal transition temperature in dipalmitoylphosphatidylcholine model membrane in the presence of local anesthetics,” Studia Biophysica, vol. 103, pp. 231–241, 1984. View at Google Scholar
  19. K. Ondriáš, L. I. Horváth, P. Balgavý, and S. Štolc, “Effects of tertiary amine local anaesthetics on the phase behaviour of the dipalmitoylphosphatidylcholine model membrane. Electron spin resonance tetrametylpiperidinyloxyl partition study,” Physiologia Bohemoslovaca, vol. 33, pp. 489–494, 1984. View at Google Scholar
  20. J. Gallová, J. Bágel'ová, P. Balgavý, and J. Čižmárik, “Interaction of [2-(alkyloxy)-phenyl]-2-(l-piperidinyl)ethyl esters of carbamic acid with dipalmitoylphosphatidylglycerol model membranes: A calorimetric study,” General Physiology and Biophysics, vol. 12, pp. 357–370, 1993. View at Google Scholar
  21. J. Gallová, D. Uhríková, and P. Balgavý, “Biphasic effect of local anaesthetic carbisocaine on fluidity of phosphatidylcholine bilayer,” Pharmazie, vol. 47, pp. 444–448, 1992. View at Google Scholar
  22. J. Gallová, J. Čižmárik, and P. Balgavý, “Biphasic effect of local anesthetic and β-blocker heptacaine on fluidity of phosphatidylcholine bilayers as detected by ESR spin probe method,” Pharmazie, vol. 50, no. 7, pp. 486–488, 1995. View at Google Scholar · View at Scopus
  23. D. Mlynarčík, S. P. Denyer, and W. B. Hugo, “A study of the action of bisquaternary ammonium salt, an amine oxide and an alkoxy phenylcarbamic acid ester on some metabolic functions in Staphylococcus aureus,” Microbios, vol. 30, no. 119, pp. 27–35, 1981. View at Google Scholar · View at Scopus
  24. F. Andriamainty, J. Filípek, F. Devínsky, and P. Balgavý, “Effect of N, N-dimethylalkylamine N-oxides on the activity of purified sarcoplasmic reticulum (Ca-Mg)ATPase,” Pharmazie, vol. 52, pp. 240–242, 1997. View at Google Scholar
  25. B. K. Semin, M. N. Tschudinovskih, and I. I. Ivanov, “Local anaestheics-induced inhibition of chloroplast electron transport,” General Physiology and Biophysics, vol. 8, pp. 233–244, 1989. View at Google Scholar
  26. S. Izawa and N. E. Good, “Hill reaction rates and chloroplast fragment size,” Biophysics Including Photosynthesis, vol. 109, no. 2, pp. 372–381, 1965. View at Google Scholar · View at Scopus
  27. E. I. Apostolova, “Effect of detergent treatment and glutaraldehyde modification on the photochemical activity of chloroplasts,” Comptes Rendus de l'Academie Bulgare des Sciences, vol. 41, pp. 117–120, 1988. View at Google Scholar
  28. S. Mona, P. Ravanel, and X. de Cherade, “Uncoupling activity of some N-phenylcarbamates,” Pesticide Biochemistry and Physiology, vol. 27, no. 3, pp. 261–266, 1987. View at Google Scholar · View at Scopus
  29. J. Sikkema, J. A. M. de Bont, and B. Poolman, “Interactions of cyclic hydrocarbons with biological membranes,” Journal of Biological Chemistry, vol. 269, no. 11, pp. 8022–8028, 1994. View at Google Scholar · View at Scopus
  30. A. Aksmann, T. Shutova, G. Samuelsson, and Z. Tukaj, “The mechanism of anthracene interaction with photosynthetic apparatus: a study using intact cells, thylakoid membranes and PS II complexes isolated from Chlamydomonas reinhardtii,” Aquatic Toxicology, vol. 104, no. 3-4, pp. 205–210, 2011. View at Publisher · View at Google Scholar · View at Scopus
  31. J. Augstein, W. C. Austin, R. J. Boscott, S. M. Green, and C. R. Worthing, “Some cardiovascular effects of a series of aryloxyalkylamines. I,” Journal of Medicinal Chemistry, vol. 8, no. 3, pp. 356–367, 1965. View at Google Scholar · View at Scopus
  32. V. S. Reznik, V. D. Akamsin, and I. V. Galyametdinova, “Two-fragment α-adrenolytics 4. Synthesis of phosphorylated derivatives of 2-aryloxyethylamines and N-phenylpiperazine,” Russian Chemical Bulletin, vol. 50, no. 1, pp. 125–129, 2001. View at Publisher · View at Google Scholar · View at Scopus
  33. P. Wiczling, M. J. Markuszewski, and R. Kaliszan, “Determination of pKa by pH gradient reversed-phase HPLC,” Analytical Chemistry, vol. 76, no. 11, pp. 3069–3077, 2004. View at Publisher · View at Google Scholar · View at Scopus
  34. M. Gumustas, S. Şanli, N. Şanli, and S. A. Ozkan, “Determination of pKa values of some antihypertensive drugs by liquid chromatography and simultaneous assay of lercanidipine and enalapril in their binary mixtures,” Talanta, vol. 82, no. 4, pp. 1528–1537, 2010. View at Publisher · View at Google Scholar · View at Scopus
  35. F. Rouessac, A. Rouessac, and D. Cruche, Chemical Analysis: Modern Instrumentation Methods and Techniques, John Wiley & Sons, Chichester, UK, 2007.
  36. I. Canals, F. Z. Oumada, M. Rosés, and E. Bosch, “Retention of ionizable compounds on HPLC. 6. pH measurements with the glass electrode in methanol-water mixtures,” Journal of Chromatography A, vol. 911, no. 2, pp. 191–202, 2001. View at Publisher · View at Google Scholar · View at Scopus
  37. F. Rived, I. Canals, E. Bosch, and M. Rosés, “Acidity in methanol-water,” Analytica Chimica Acta, vol. 439, no. 2, pp. 315–333, 2001. View at Publisher · View at Google Scholar · View at Scopus
  38. E. Masarovičová and K. Král'ová, “Approaches to measuring plant photosynthesis activity,” in Handbook of Photosynthesis, M. Pessarakli, Ed., pp. 617–656, Taylor and Francis Group, Boca Raton, Fla, USA, 2nd edition, 2005. View at Google Scholar
  39. K. Král'ová, F. Šeršeň, and E. Sidóová, “Photosynthesis inhibition produced by 2-alkylthio-6-R-benzothiazoles,” Chemical Papers, vol. 46, pp. 348–350, 1992. View at Google Scholar
  40. P. Kollár, T. Bárta, V. Závalová, K. Šmejkal, and A. Hampl, “Geranylated flavanone tomentodiplacone B inhibits proliferation of human monocytic leukaemia (THP-1) cells,” British Journal of Pharmacology, vol. 162, no. 7, pp. 1534–1541, 2011. View at Publisher · View at Google Scholar · View at Scopus
  41. T. Goněc, P. Bobál, J. Šujan et al., “Investigating the spectrum of biological activity of substituted quinoline-2-carboxamides and their isosteres,” Molecules, vol. 17, pp. 613–644, 2012. View at Google Scholar
  42. K. J. Ryan, C. G. Ray, N. Ahmad, W. L. Drew, and J. Plorde, Sherris Medical Microbiology, McGraw Hill, New York, NY, USA, 5th edition, 2010.
  43. J. Koirala, “Mycobacterium avium-intracellulare,” Medscape, 2012, http://emedicine.medscape.com/article/222664-overview.
  44. V. Bocanegra-Garcia, A. Garcia, J. P. Palma-Nicolas, I. Palos, and G. Rivera, “Antitubercular drugs development: recent advances in selected therapeutic targets and rational drug design,” in Drug Development: A Case Study Based Insight Into Modern Strategies, C. Rundfeldt, Ed., pp. 207–242, Rieka, Croatia, 2011. View at Google Scholar
  45. R. E. McCarty, “Delineation of the mechanism of ATP synthesis in chloroplast. Use of uncouplers energy transfer inhibitors and modifiers of CF1,” in Methods in Enzymology, A. San Pietro, Ed., vol. 69, pp. 719–728, Academic Press, New York, NY, USA, 1980. View at Google Scholar
  46. J. Neumann and A. Jagendorf, “Uncoupling photophosphorylation by detergents,” Biophysics Including Photosynthesis, vol. 109, no. 2, pp. 382–389, 1965. View at Google Scholar · View at Scopus
  47. F. Šeršeň and F. Devínsky, “Stimulating effect of quaternary ammonium salts upon the photosynthetic electron transport,” Photosynthetica, vol. 30, pp. 151–154, 1994. View at Google Scholar
  48. F. Šeršeň and I. Lacko, “Stimulation of the photosynthetic electron transport by quaternary ammonium salts,” Photosynthetica, vol. 31, no. 1, pp. 153–156, 1995. View at Google Scholar · View at Scopus
  49. D. Fajkusová, M. Peško, M. Keltošová et al., “Anti-infective and herbicidal activity of N-substituted 2-aminobenzothiazoles,” Bioorganic and Medicinal Chemistry, vol. 20, pp. 7059–7068, 2012. View at Google Scholar