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Stannous chloride catalyzed synthesis of Schiff bases from hydroxybenzaldehydes and determination of their antioxidant activity by ABTS and DPPH assay

  • Gyanashree Bora
  • Dipankoj Gogoi
  • Subhasmita Saikia
  • Archana Pareek
  • Jyotirekha G HandiqueEmail author
Regular Article
  • 87 Downloads

Abstract

Phenolic compounds play a very important role in human life because of their antioxidant activity which can prevent harmful diseases caused by free radicals. In the present work, we have synthesized some Schiff bases by the reaction of different hydroxybenzaldehydes and primary aromatic diamines using Stannous Chloride (\(\hbox {SnCl}_{2}{\cdot }2\hbox {H}_{2}\hbox {O}\)) as the catalyst. The products were characterized by FT-IR spectroscopy, GCMS and NMR spectroscopy. Furthermore, the antioxidant activity of the Schiff bases were determined by using DPPH assay and ABTS assay and the results were compared with a standard compound, trolox as well as with the parent aldehydes. The synthesized compounds were found to have better antioxidant activity than their corresponding parent aldehydes.

Graphic abstract

Phenolic Schiff bases were synthesized by the reaction of different hydroxybenzaldehydes and primary aromatic diamines using \(\hbox {SnCl}_{2}\cdot 2\hbox {H}_{2}\hbox {O}\) as the catalyst and dichloromethane as the solvent. Antioxidant activity of the synthesized compounds were determined by DPPH assay and ABTS assay and results were compared to the parent aldehydes as well as Trolox.

Keywords

Phenolic compounds Schiff bases antioxidant activity ABTS assay DPPH assay 

Notes

Acknowledgements

The authors gratefully acknowledge the University Grant Commission’s Basic Scientific Research programme for providing Research Fellowship for Meritorious Students (UGC-BSR-RFSMS fellowship) to GB and UGC-SAP-DRS and DST-FIST for financial support.

Supplementary material

12039_2019_1645_MOESM1_ESM.pdf (2.3 mb)
Supplementary material 1 (pdf 2380 KB)

References

  1. 1.
    Valko M, Leibfritz D, Moncol J, Cronin M T, Mazur M and Telser J 2007 Free radicals and antioxidants in normal physiological functions and human disease Int. J. Biochem. Cell Biol. 39 44CrossRefGoogle Scholar
  2. 2.
    Shubakara K, Umesha K B, Srikantamurthy N and Chethan J 2014 Antioxidant and DNA damage inhibition activities of 4-Aryl-N-(4-arylthiazol- 2-yl)-5,6-dihydro-4H-1,3,4-oxadiazine-2-carboxamides J. Chem. Sci. 126 1913CrossRefGoogle Scholar
  3. 3.
    Saundan A R, Yarlakatti M, Walmik P and Katkar V 2012 Synthesis, antioxidant and antimicrobial evaluation of thiazolidinone, azetidinone encompassing indolylthienopyrimidines J. Chem. Sci. 124 469CrossRefGoogle Scholar
  4. 4.
    Kathrotiya H G and Patel M P 2013 An efficient synthesis of 3-indolyl substituted pyrido[1,2-\(a\)]benzimidazoles as potential antimicrobial and antioxidant agents J. Chem. Sci. 125 993CrossRefGoogle Scholar
  5. 5.
    Herrera M B, Sayago A and Beltrán R 2017 Exploring antioxidant reactivity and molecular structure of phenols by means of two coupled assays using fluorescence probe (2,3-diazabicyclo[2.2.2]oct-2-ene, DBO) and free radical (2,2-diphenyl-1-picrylhydrazyl, DPPH) J. Chem. Sci. 129 1381CrossRefGoogle Scholar
  6. 6.
    Cimerman Z, Miljanic S and Galic N 2000 Schiff bases derived from aminopyridines as spectrofluorimetric analytical reagents Croat. Chem. Acta 73 81Google Scholar
  7. 7.
    Chandramouli C, Shivanand M R, Nayanbhai T B, Bheemachari B and Udupi R H 2012 Synthesis and biological screening of certain new triazole schiff’s bases and their derivatives bearing substituted benzothiazole moiety J. Chem. Pharm. Res. 4 1151Google Scholar
  8. 8.
    Chinnasamy R P, Sundararajan R and Govindaraj S 2010 Synthesis, characterization, and analgesic activity of novel schiff base of isatin derivatives J. Adv. Pharm. Technol. Res. 1 342CrossRefGoogle Scholar
  9. 9.
    Venkatesh P 2011 Synthesis, characterization and antimicrobial activity of various schiff bases complexes of Zn(II) and Cu(II) ions Asian. J. Pharm. Health. Sci. 1 8Google Scholar
  10. 10.
    Chaubey A and Pandeya S N 2012 Synthesis and anticonvulsant activity (Chemo Shock) of Schiff and Mannich bases of Isatin derivatives with 2-Amino pyridine (mechanism of action) Int. J. Pharmtech. Res. 4 590Google Scholar
  11. 11.
    Aboul-Fadl T, Mohammed F A and Hassan E A 2003 Synthesis, antitubercular activity and pharmacokinetic studies of some Schiff bases derived from 1-alkylisatin and isonicotinic acid hydrazide Arch. Pharm. Res. 26 778CrossRefGoogle Scholar
  12. 12.
    Ali S M, Azad M A, Jesmin M, Ahsan S, Rahman M M, Khanam J A, Islam M N and Shahriar S M 2012 In vivo anticancer activity of vanillin semicarbazone Asian. Pac. J. Trop. Biomed. 2 438CrossRefGoogle Scholar
  13. 13.
    Wei D, Li N, Lu G and Yao K 2006 Synthesis, catalytic and biological activity of novel dinuclear copper complex with Schiff base Sci. China Ser. B 49 225CrossRefGoogle Scholar
  14. 14.
    Avaji P G, Vinod Kumar C H, Patil S A, Shivananda K N and Nagaraju C 2009 Synthesis, spectral characterization, in-vitro microbiological evaluation and cytotoxic activities of novel macrocyclic bishydrazone Eur. J. Med. Chem. 44 3552CrossRefGoogle Scholar
  15. 15.
    Venugopala K N and Jayashree B S 2003 Synthesis of carboxamides of 2\(\prime \)-amino-4\(\prime \)-(6-bromo-3-coumarinyl) thiazole as analgesic and antiinflammatory agents Indian J. Heterocycl. Chem. 12 307Google Scholar
  16. 16.
    Vashi K and Naik H B 2004 Synthesis of novel Schiff base and azetidinone derivatives and their antibacterial activity Eur. J. Chem. 1 272Google Scholar
  17. 17.
    Dhar D N and Taploo C L 1982 Schiff bases and their applications J. Sci. Ind. Res. 41 501Google Scholar
  18. 18.
    Li S, Chen S, Lei S, Ma H, Yu R and Liu D 1999 Investigation on some Schiff bases as HCl corrosion inhibitors for copper Corros. Sci. 41 1273CrossRefGoogle Scholar
  19. 19.
    Xavier A and Srividhya N 2014 Synthesis and study of Schiff base ligands IOSR J. Appl. Chem. 7 06CrossRefGoogle Scholar
  20. 20.
    Worku D, Negussie M, Raju V J T, Negussie R, Solomon T, Jönsson J A and Negussie R 2003 Studies on transition metal complexes of herbicidal compounds II: Transition metal complexes of derivatized 2-chloro-4-ethylamino-6-isopropylamino-\(s\)-triazine (atrazine) Bull. Chem. Soc. Ethiop. 17 35Google Scholar
  21. 21.
    Williams W B, Cuvelier M E and Berset C 1995 Use of a free radical method to evaluate antioxidant activity Lebensm.-Wiss.-Technol. 28 25CrossRefGoogle Scholar
  22. 22.
    Arnao M B, Cano A and Acosta M 2001 The hydrophilic and lipophilic contribution to total antioxidant activity Food Chem. 73 239CrossRefGoogle Scholar

Copyright information

© Indian Academy of Sciences 2019

Authors and Affiliations

  1. 1.Department of ChemistryDibrugarh UniversityAssamIndia

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