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Synthesis, Characterization and Assessment of Local Anesthetic Activity of Some Benzohydroxamic Acids
Corresponding Author(s) : Tilal Elsaman
Asian Journal of Chemistry,
Vol. 31 No. 1 (2019): Vol 31 Issue 1
Abstract
In the present investigation, 6 compounds (E1-E6) were synthesized by reaction of ethyl esters of p-substituted benzoic acid with hydroxylamine. The chemical structures of the synthesized hydroxamic acids were verified on the basis of spectral analysis (IR, 1H NMR, 13C NMR and mass spectra). The benzohydroxamic acids were examined for potential local anesthetic activity using foot withdrawal reflex of the frog and benzocaine was used as standard drug. Compounds were tested at two different solvents; 5 % DMSO and 0.65 % NaOH, each solution was tested at three different concentration levels (40, 100 and 200 μg/mL). Local anesthetic activity of the compounds differed according to the concentration level and selected solvent. Compounds E4 and E5 were found to be the most active and were comparable to the standard drug in tested solvents at all investigated concentrations. All compounds displayed an enhanced activity in the the aqueous basic solutions.
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- D.E. Becker and K.L. Reed, Anesth. Prog., 53, 98 (2006); https://doi.org/10.2344/0003-3006(2006)53[98:EOLAP]2.0.CO;2.
- M.W. Hollmann, S. Herroeder, K.S. Kurz, C.W. Hoenemann, D. Struemper, K. Hahnenkamp and M.E. Durieux, Am. Soc. Anesthesiol., 100, 852 (2004); https://doi.org/10.1097/00000542-200404000-00015.
- J.E. Heavner, Curr. Opin. Anaesthesiol., 20, 336 (2007); https://doi.org/10.1097/ACO.0b013e3281c10a08.
- M.A. Magdi, M.E.M. Mahmoud and A. A. Abdalla, Int. J. Pharm. Res. Bio-Sci., 3, 132 (2014).
- S.J. Gorzynski, Organic Chemistry, McGraw-Hill: New York (2011).
- F.A. Carey and R.J. Sundberg. Advanced Organic Chemistry, Springer Science+Business Media: New York, p. 721 (2007).
- R.C. Hauser and W.B. Renfrow, Org. Synth., 19, 15 (1939); https://doi.org/10.15227/orgsyn.019.0015.
- D.L. Pavia, G.M. Lampman, G.S. Kriz and J.R. Vyvyan, Introduction to Spectroscopy, Cengage Learning: Belmont, Canada, p. 52 (2008).
- H. Agarwal, O.P. Agarwal, R. Karnawat, K.I. Sharma and P.S. Verma, Int. J. Appl. Biol. Pharm. Technol., 1, 1293 (2010).
- R.M. Robe, J.C. Gilberf, L.B. Rodewald and A.S. Wingrove, Modern Experimental Organic Chemistry, Saunders College: Philadelphia, USA, p. 621 (1979).
- J. McMurry. Organic chemistry, Cengage Learning: Belmont, Canada, p. 424 (2012).
References
D.E. Becker and K.L. Reed, Anesth. Prog., 53, 98 (2006); https://doi.org/10.2344/0003-3006(2006)53[98:EOLAP]2.0.CO;2.
M.W. Hollmann, S. Herroeder, K.S. Kurz, C.W. Hoenemann, D. Struemper, K. Hahnenkamp and M.E. Durieux, Am. Soc. Anesthesiol., 100, 852 (2004); https://doi.org/10.1097/00000542-200404000-00015.
J.E. Heavner, Curr. Opin. Anaesthesiol., 20, 336 (2007); https://doi.org/10.1097/ACO.0b013e3281c10a08.
M.A. Magdi, M.E.M. Mahmoud and A. A. Abdalla, Int. J. Pharm. Res. Bio-Sci., 3, 132 (2014).
S.J. Gorzynski, Organic Chemistry, McGraw-Hill: New York (2011).
F.A. Carey and R.J. Sundberg. Advanced Organic Chemistry, Springer Science+Business Media: New York, p. 721 (2007).
R.C. Hauser and W.B. Renfrow, Org. Synth., 19, 15 (1939); https://doi.org/10.15227/orgsyn.019.0015.
D.L. Pavia, G.M. Lampman, G.S. Kriz and J.R. Vyvyan, Introduction to Spectroscopy, Cengage Learning: Belmont, Canada, p. 52 (2008).
H. Agarwal, O.P. Agarwal, R. Karnawat, K.I. Sharma and P.S. Verma, Int. J. Appl. Biol. Pharm. Technol., 1, 1293 (2010).
R.M. Robe, J.C. Gilberf, L.B. Rodewald and A.S. Wingrove, Modern Experimental Organic Chemistry, Saunders College: Philadelphia, USA, p. 621 (1979).
J. McMurry. Organic chemistry, Cengage Learning: Belmont, Canada, p. 424 (2012).