Abstract
Thanks to its pharmaceutical properties, the Schiff group of isatin has recently had a wide range of uses. In this study, seven new Schiff bases of isatin and its derivatives were prepared from thiocarbohydrazide, isatin and substituted aldehydes in the presence of ethanol under reflux. The chemical structures of the products were confirmed by 1H NMR, 13C NMR, IR and elemental analysis. The in vitro antioxidant features of all the compounds were evaluated by 1,1-diphenyl-2-picrylhydrazyl free radical scavenging method. The antioxidant effect was evaluated separately in two different stages: monosubstituted products synthesized with aldehyde groups and disubstituted products bound with isatin group. Accordingly, the compounds 3 and 4 showed the highest antioxidant activity and the isatin group suppressed the antioxidant effect of the disubstituted Schiff bases products.
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D. Sinha, A.K. Tiwari, S. Singh, G. Shukla, P. Mishra, H. Chandra, A.K. Mishra, Eur. J. Med. Chem. 43, 160 (2008)
S.K. Sridhar, A. Ramesh, Biol. Pharm. Bull. 24, 1149 (2001)
A. Jarrahpour, D. Khalili, E. De Clercq, C. Salmi, J. Brunel, Molecules 12, 1720 (2007)
K. Gangarapu, S. Manda, S. Thota, R. Yerra, S.S. Karki, J. Balzarini, E. De Clercq, H. Tokuda, Lett. Drug Des. Discov 9, 934 (2012)
M.S. Almutairi, A.S. Zakaria, P.P. Ignasius, R.I. Al-Wabli, I.H. Joe, M.I. Attia, J. Mol. Struct. 1153, 333 (2018)
M. Kupinić, M. Medić-Šarić, M. Movrin, D. Maysinger, J. Pharm. Sci. 68, 459 (1979)
D. Sriram, S. Pandeya, G. Nath, E. De Clercq, Arzneimittelforschung 50, 55 (2000)
Z.H. Chohan, H. Pervez, A. Rauf, K.M. Khan, C.T. Supuran, J. Enzyme Inhib. Med. Chem. 19, 417 (2004)
A. Jarrahpour, J. Sheikh, I. El Mounsi, H. Juneja, T.B. Hadda, Med. Chem. Res. 22, 1203 (2013)
M. Verma, S.N. Pandeya, K.N. Singh, J.P. Stables, Acta Pharm. 54, 49 (2004)
S.K. Sridhar, S.N. Pandeya, J.P. Stables, A. Ramesh, Eur. J. Pharm. Sci. 16, 129 (2002)
T.R. Bal, B. Anand, P. Yogeeswari, D. Sriram, Bioorg. Med. Chem. Lett. 15, 4451 (2005)
S. Pandeya, D. Sriram, G. Nath, E. DeClercq, Eur. J. Pharm. Sci. 9, 25 (1999)
M.P. Sathisha, V.K. Revankar, K.S.R. Pai, Met Based Drugs 2008, 1 (2007)
C. Liang, J. Xia, D. Lei, X. Li, Q. Yao, J. Gao, Eur. J. Med. Chem. 74, 742 (2014)
M.T. Gabr, N.S. El-Gohary, E.R. El-Bendary, M.M. El-Kerdawy, N. Ni, Eur. J. Med. Chem. 128, 36 (2017)
K. Meenakshi, N. Gopal, M. Sarangapani, Int. J. Pharm. Sci. 6, 318 (2014)
H. Muğlu, M.S. Çavuş, T. Bakır, H. Yakan, J. Mol. Struct. 1196, 819 (2019)
S.Y. Abbas, A.A. Farag, Y.A. Ammar, A.A. Atrees, A.F. Mohamed, A.A. El-Henawy, Chem. Mon. 144, 1725 (2013)
D. Sriram, T.R. Bal, P. Yogeeswari, Med. Chem. Res. 14, 211 (2005)
L. Matesic, J.M. Locke, J.B. Bremner, S.G. Pyne, D. Skropeta, M. Ranson, K.L. Vine, Bioorg. Med. Chem. 16, 3118 (2008)
W. Droge, Physiol. Rev. 82, 47 (2002)
M. Valko, C. Rhodes, J. Moncol, M. Izakovic, M. Mazur, Chem. Biol. Interact. 160, 1 (2006)
D. Kumar, D.S. Rawat, Bioorg. Med. Chem. Lett. 23, 641 (2013)
Y. Zhang, Y. Fang, H. Liang, H. Wang, K. Hu, X. Liu, X. Yi, Y. Peng, Bioorg. Med. Chem. Lett. 23, 107 (2013)
U.K. Sharma, S. Sood, N. Sharma, P. Rahi, R. Kumar, A.K. Sinha, A. Gulati, Med. Chem. Res. 22, 5129 (2013)
A. El-Faham, W.N. Hozzein, M.A.M. Wadaan, S.N. Khattab, H.A. Ghabbour, H.K. Fun, M.R. Siddiqui, J. Chem. 2015, 1 (2015)
G. Kiran, T. Maneshwar, Y. Rajeshwar, M. Sarangapani, J. Chem. 2013, 1 (2013)
D. Huang, B. Ou, R.L. Prior, J. Agric. Food Chem. 53, 1841 (2005)
S. Mukherjee, N. Pawar, O. Kulkarni, B. Nagarkar, S. Thopte, A. Bhujbal, P. Pawar, BMC Complement. Altern. Med. 11, 38 (2011)
O. Bekircan, H. Bektas, Molecules 13, 2126 (2008)
D. Williams, I. Fleming, RNA Structure and NMR Spectroscopy. Spectroscopic Methods in Organic Chemistry (McGraw-Hill, New York, 1996)
E.N. Frankel, A.S. Meyer, J. Sci. Food Agric. 80, 1925 (2000)
A.R. Božıć, N.R. Fılıpovıć, I.T. Novakovıć, S.K. Bjelogrlıć, J.B. Nıkolıć, S.Z. Drmanıć, A.D. Marınkovıć, J. Serbian Chem. Soc. 82, 495 (2017)
P. Pakravan, S. Kashanian, M.M. Khodaei, F.J. Harding, Pharmacol. Rep. 65, 313 (2013)
N. Naik, H.V. Kumar, P.B. Vidyashree, J. Pharm. Res. 4, 2686 (2011)
G. Kiran, M. Sarangapani, T. Gouthami, A.R. Narsimhareddy, Toxicol. Environ. Chem. 95, 367 (2013)
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We would like to thank Hasan Yakan, Assistant Professor at Ondokuz Mayıs University, for his valuable support.
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Bakır, T.K., Lawag, J.B. Preparation, characterization, antioxidant properties of novel Schiff bases including 5-chloroisatin-thiocarbohydrazone. Res Chem Intermed 46, 2541–2557 (2020). https://doi.org/10.1007/s11164-020-04105-y
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DOI: https://doi.org/10.1007/s11164-020-04105-y