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Antioxidant activities and transition metal ion chelating studies of some hydroxyl Schiff base derivatives

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Abstract

Several hydroxyl Schiff base (HSB) compounds (1–10) with good radical scavenging activity (RSA) were designed. Compounds 6, 7, and 10 showed better RSAs than the common synthetic antioxidant 2,6-diter-butyl-4-methylphenol (BHT) in DPPH• and ABTS• assays. To probe whether these HSB compounds may exert their antioxidant effect through transition metal ion chelation, the copper and ferrous chelating abilities of them were investigated. It was found by fluorescence quenching spectra that the binding constants K a were in the range of 0.85×103–7.30×104 M−1. Further study was carried out by the complexation of a representative compound 5 with ferrous ion in mass spectrum. A 2:1 5-ferrous complex was readily formed in a methanol–water solution (v:v, 8:2), which confirmed that the chelation happened when the HSB compounds were treated with transition metal ions. The above results indicated that the transition metal ion chelation play an important role in their antioxidant abilities.

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Acknowledgments

This study was supported by the National Natural Science Foundation of China (No. 20762001), the Project of the Key Laboratory of Medicinal Chemical Resources and Molecular Engineering, Guangxi Normal University, China (No.0630006-5D09), and the Guangxi Department of Education research project (No. 200807MS075, 200807MS076, 200911MS281, 200911MS282).

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, South Central University, Hunan, 410083, People’s Republic of China

    Ye Zhang

  2. Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources, College of Chemistry & Chemical Engineering, Guangxi Normal University, Guilin, 541004, People’s Republic of China

    Ye Zhang, Biqun Zou, Yingming Pan, Hong Liang & Hengshan Wang

  3. Department of Chemistry and Engineering Technology, Guilin Normal College, Guilin, 541001, People’s Republic of China

    Ye Zhang, Kai Wang & Xianghui Yi

Authors
  1. Ye Zhang
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  2. Biqun Zou
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  3. Kai Wang
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  4. Yingming Pan
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  5. Hong Liang
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  6. Xianghui Yi
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  7. Hengshan Wang
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Corresponding authors

Correspondence to Hong Liang, Xianghui Yi or Hengshan Wang.

Appendix: synthesis of the derivatives

Appendix: synthesis of the derivatives

Synthesis

General procedure for the preparation of 1–10: the mixture of aminophenol (5 mmol), aromatic aldehydes (6 mmol), ethanol (10 ml), and triethylamine (0.1 mmol) was refluxed at 90°C for 2 h and then filtered to give crystal or powder of HSB derivatives.

Spectra data for compounds 1–10

Compound 1: 1H NMR (DMSO, 500HZ) δ: 9.50 (s, 1H, OH), 8.62 (s, 1H, N=CH), 7.90 (d, J = 7.67 Hz, 2H, Ar-H), 7.49–7.51 (m, 3H, Ar-H), 7.21 (d, J = 8.57 Hz, 2H, Ar-H), 6.82 (d, J = 8.57 Hz, 2H, Ar-H). EMS: m/z: 198 [M + H]+.

Compound 2: 1H NMR (DMSO, 500HZ) δ: 8.29 (d, J = 7.20 Hz, 1H, N=CH), 7.90 (d, J = 8.50 Hz, 1H, Ar-H), 7.68 (dd, J = 8.79 Hz, 5.5 Hz, 2H, Ar-H), 7.62 (t, J = 7.26 Hz, 1H, OH), 7.51 (d, J = 7.38 Hz, 1H, Ar-H), 7.37 (d, J = 7.27 Hz, 1H, Ar-H), 7.29 (s, 2H, Ar-H), 6.83 (t, J = 7.30 Hz, 1H, Ar-H), 6.65 (t, J = 7.57 Hz, 1H, Ar-H), 6.18 (d, J =  7.5 Hz, 1H, Ar-H). EMS: m/z: 198 [M + H]+

Compound 3: 1H NMR (DMSO,500HZ) δ: 13.12 (s, 1H, OH), 9.64 (s, 1H, OH), 8.91 (s, 1H, N=CH), 7.67 (d, J = 7.53 Hz, 1H, Ar-H), 7.42 (d, J = 7.75 Hz, 1H, Ar-H), 7.25 (d, J = 7.86 Hz, 1H, Ar-H), 6.96 (d, J = 7.47 Hz, 2H, Ar-H), 6.84 (d, J = 7.65 Hz, 1H, Ar-H), 6.78–6.74 (m, 2H, Ar-H). EMS: m/z: 214 [M+H]+.

Compound 4: 1H NMR (DMSO,500HZ) δ: 13.41 (s, 1H, OH), 9.67 (s, 1H, OH), 8.91 (s, 1H, N=CH), 7.60 (d, J = 8.11 Hz, 1H, Ar-H), 7.32-7.39 (m, 3H, Ar-H), 6.93-6.98 (m, 2H, Ar-H), 6.85 (d, J = 8.6 Hz, 2H, Ar-H). EMS: m/z: 214 [M + H]+.

Compound 5: 1H NMR (DMSO,500HZ) δ: 13.76 (s, 1H, OH), 9.71 (s, 1H, OH), 8.97 (s, 1H, N=CH), 7.62 (d, J = 7.50 Hz, 1H, Ar-H), 7.36-7.41 (m, 2H, Ar-H), 7.14 (t, J = 7.50 Hz, 1H, Ar-H), 6.87–6.98 (m, 4H, Ar-H). EMS: m/z: 214 [M + H]+.

Compound 6: 1H NMR (DMSO,500HZ) δ: 9.42 (1s, 1H, OH), 8.58 (s, 1H, N=CH), 7.82 (d, 2H, J = 8.84Hz, Ar-H), 7.28 (d, J = 7.87Hz, 1H, Ar-H), 7.14 (d, J = 7.94Hz, 1H, Ar-H), 7.01 (d, J = 8.16Hz, 1H, Ar-H), 6.91 (d, J = 7.5Hz, 1H, Ar-H), 6.78 (d, J = 8.9Hz, 2H, Ar-H), 3.01 (s, 6H, CH3). EMS: m/z: 241 [M + H]+

Compound 7: 1H NMR (DMSO, 500HZ) δ: 9.31 (1s, 1H, OH), 8.39 (s, 1H, N=CH), 7.70 (d, J = 8.67 Hz, 2H, Ar-H), 7.10 (d, J = 8.56 Hz, 2H, Ar-H), 6.77 (m, 4H, Ar-H), 3.00 (s, 6H, CH3). EMS: m/z: 241 [M + H]+.

Compound 8: 1H NMR (DMSO,500HZ) δ: 9.48 (s, 1H, OH), 8.38 (d, J = 8.78 Hz, 1H, N=CH), 7.63 (d, J = 7.39 Hz, 2H, Ar-H), 7.33-7.42 (3H, m, Ar-H), 7.26 (d, J = 15.96 Hz, 1H, Ar-H), 7.07-7.12 (m, 3H, Ar-H), 6.76 (d, 2H, J = 7.76 Hz, =CH). EMS: m/z: 224 [M + H]+.

Compound 9: 1H NMR (DMSO,500HZ) δ: 9.77 (s, 1H, OH), 8.39 (d, J = 8.78 Hz, 1H, N=CH), 7.77 (d, J = 7.39 Hz, 2H, Ar-H), 7.35–7.44 (3H, m, Ar-H), 7.28 (d, J = 15.96 Hz, 1H, Ar-H), 7.09–7.14 (m, 3H, Ar-H), 6.73 (d, 2H, J = 7.76 Hz, =CH). EMS: m/z: 224 [M + H]+.

Compound 10: 1H NMR (DMSO, 500 Hz) δ: 9.90 (s, 1H, OH), 8.41 (s, 1H, N=CH), 7.83 (d, J = 7.37 Hz, 1H), 7.20 (d, J = 8.73 Hz, 2H), 7.07 (t, J = 11.62 Hz, 1H), 6.80 (d, J = 8.32, 2H), 6.67 (d, J = 7.47 Hz, 1H), 6.53-6.46 (m, 1H). EMS: m/z:188 [M + H]+.

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Zhang, Y., Zou, B., Wang, K. et al. Antioxidant activities and transition metal ion chelating studies of some hydroxyl Schiff base derivatives. Med Chem Res 21, 1341–1346 (2012). https://doi.org/10.1007/s00044-011-9648-7

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  • DOI: https://doi.org/10.1007/s00044-011-9648-7

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