Kinetics and mechanism investigation of electro-oxidation of mesalazine drug in the presence of arylsulfinic acid

Document Type : Original Article

Authors

1 Department of Chemistry, Payame Noor niversity (PNU), 19395-4697 Tehran, I. R. of Iran

2 Chemistry Dept. Faculty of science, Persian Gulf University, Booshehr, Iran

3 1-Pharmaceutics Research Center, Kerman University of Medical Sciences, Kerman, Iran. Postal code: 7616911319 2- Plant Protection Research Department, Kerman Agricultural and Natural Resources, AREEO, Kerman, Iran

Abstract

In this research, the electrochemical oxidation of mesalazine was investigated in presence and absence of benzenesulfinic acid and 4-toluenesulfinic acid as a nucleophile using cyclic voltammetry and controlled-potential coulometry. The results indicate that quinoneimine generated by oxidation of mesalazine, participates in reaction with arylsulfinic acids via Michael addition reaction in a ECC electrochemical mechanism pattern. To approve the proposed ECC mechanism, electrochemical synthesis of oxidation of mesalazine was also performed in the presence of benzenesulfinic acid and the obtained product, was identified by of FT-IR and mass spectrometry spectra. Homogenous rate constants (kobs) of Michael addition reaction for quinoneimine generated by oxidation of mezalasine with arylsulfinic acids, were estimated by cyclic voltamogram digital simulation method.

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References

[1] R. Plasmeier and D. Radzik C, Pharmaceutical Research, 9 (1992) 933.
[2] M. Mohadjerani and Kh. Pakzad, Journal of Applied Chemistry, 7 (2013) 45.
[3] J.P. Uetrecht and W. Trager, Drug metabolism: chemical and enzymatic aspects, United States, CRC Press, (2007) 115.
[4] R. Karagozian and R. Burakoff, Ther Clin Risk Manag., 3 (2007) 893.
[5] E. Tammari and Sh. Lotfi, Journal of Electroanalytical Chemistry, 766 (2016) 162.
[6] D. Nematollahi and R. Rahchamani, Tetrahedron, 43 (2002) 147.
[7] A. K. Timmbbla, CD. Souza, C. Soldi, MG. Pizzolatti and A. Spinelli, Journal of Applied Chemistry, 37 (2007) 617.
[8] E. Tammari, M. Kazemi and A. Amani, Journal of the Electrochemical Society, 161 (2014) G69.
[9] A. J. Bard and L. R. Faulkner, Electrochemical Methods. 2nd ed. New York, Wiley, (2001) 1.
[10] H. Biuck, A. Zahra, R. Jalal, J. Of Applied Chemistry, 46 (1397) 9, in Persian.
[11] D. Nematollahi and A. Maleki, Electrochemistry Communications, 11 (2009) 488.
[12] E. Tammari and D. Nematollahi, Electroanalysis, 23 (2011) 784.
[13] E. Tammari, A. Amani, D. Nematollahi, R. Jalili and M. Kazemi, Mechanism and Kinetics Evaluation. Res. J. Chem. Environ, 17 (2013) 41.
[14] B. Nigovic and B. Simunic, Journal of Pharmaceutical and Biomedical Analysis, 31 (2003) 169.
[15] E. Beckett, N. Lawrence, R. Evans, J. Davis and R. Compton, Talanta, 54 (2001) 871.
[16] B. Nigovic, Z. Mandic, B.  Simunic and I. Fistric, Journal of Pharmaceutical and Biomedical Analysis, 26 (2001) 978.
[17] E. Tammari, A. Nezhadali, Sh. Lotfi and MR. Mohammadizadeh, Anal. Bioanal. Chem. Res., 4 (2017) 319.
Applied Chemistry Today
Volume 14, Issue 51
July 2019
Pages 177-192

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