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Synthesis, crystal structures, spectroscopic characterization and in vitro antidiabetic studies of new Schiff base Copper(II) complexes

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Abstract

Two new Schiff base copper(II) complexes, [CuL1(tmen)] (1) and [Cu\(_{\mathrm {2}}\mathrm {L}_{\text {2}}^{\text {2}}\) (tmen)] (2) {where, H\(_{\mathrm {2}}\textit {L}^{\mathrm {1}}=\) N-(salicylidene)-L-valine, H\(_{\mathrm {2}}\textit {L}^{\mathrm {2}}=\) N-(3,5-dichlorosalicylidene)-L-valine and tmen = N,N,N\(^{\prime }\),N\(^{\prime }\)-tetramethylethylene-1,2-diamine} have been synthesized and characterized by molar conductance, elemental analyses, VSM-RT, UV-Vis, FTIR, EPR, and CD spectra. Both the complexes were structurally characterized by single crystal XRD. The crystal structure of complex 1 displays a distorted square pyramidal geometry in which Schiff base is coordinated to the Cu(II) ion via ONO-donor in the axial mode, whereas, the chelating diamine displays axial and equatorial mode of binding via NN-donor atoms. The crystal structure of the complex 2 reveals a syn-anti mode of carboxylate bridged dinuclear complex, in which, the coordination geometry around Cu(1) is square pyramid and distorted square planar around Cu(2). The target complexes were screened for in vitro antidiabetic activity. Both the complexes showed good inhibitory activity for α-amylase and α-glucosidase.

Two new Schiff base copper(II) complexes, [CuL1(tmen)] (1) and [Cu2 \(L_{2}^{2}\) (tmen)] (2) {where, H2L1 = N-(salicylidene)-L-valine, H2L2 = N-(3, 5-dichlorosalicylidene)-L-valine and tmen = N, N, N’, N’-tetramethylethylene-1, 2-diamine} have been synthesized and characterized by molar conductance, elemental analyses, VSM-RT, UV-Vis, FTIR, EPR, and CD spectra. Both the complexes were structurally characterized by single crystal XRD. Both the complexes showed good inhibitory activity for α-amylase and α-glucosidase.

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Acknowledgements

The authors express their gratitude to D.K.M. College for Women and Muthurangam Govt. Arts College, Vellore. S. S. L. thanks Dr. K. Gunasekaran, Department of Crystallography and Biophysics, University of Madras and Dr. Sivasankar Chinnappan, Department of Chemistry, Pondicherry University for single crystal XRD studies; VIT, Vellore, for antidiabetic studies; and Mr. J. Jayamani, CSIR-Senior Research Fellow, Bioorganic Chemistry Laboratory, CSIR-CLRI, Chennai, for his help in UV-Vis. and CD measurements.

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Authors and Affiliations

  1. Department of Chemistry, D K M College for Women, Vellore, Tamil Nadu, 632 001, India

    SUNDARAMURTHY SANTHA LAKSHMI

  2. Department of Chemistry, Muthurangam Govt. Arts College, Vellore, Tamil Nadu, 632 002, India

    KANNAPPAN GEETHA

  3. Department of Biotechnology, School of Bio-Sciences and Technology, VIT University, Vellore, Tamil Nadu, 632 014, India

    M GAYATHRI

  4. Bioorganic Chemistry Laboratory, CSIR-Central Leather Research Institute, Adyar, Chennai, Tamil Nadu, 600 020, India

    GANESH SHANMUGAM

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  1. SUNDARAMURTHY SANTHA LAKSHMI
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  2. KANNAPPAN GEETHA
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  3. M GAYATHRI
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  4. GANESH SHANMUGAM
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Correspondence to KANNAPPAN GEETHA.

Additional information

Supplementary Information (SI)

CCDC 933779 (for complex 1) and 919273 (for complex 2) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html. Crystal data and structure refinement for the copper(II) complexes 1 and 2 (table S1), Selected bond lengths (Å) and angles (deg) for complexes 1 and 2 (table S2), Diffusion of glucose through dialysis membrane to the external solution concentration of glucose (mg/dL) (table S3), Relative movement of glucose through dialysis membrane over 180 minutes (table S4), Inhibitory activity of complexes at varying concentrations on α-amylase and α-glucosidase compaed with standard drug acarbose table S5), FTIR (figures S1, S2), ESR (figures S3, S4) and electronic absorption spectra (figures S5, S6) of the complexes 1 and 2 are given in Supplementary Information, available at www.ias.ac.in/chemsci.

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LAKSHMI, S.S., GEETHA, K., GAYATHRI, M. et al. Synthesis, crystal structures, spectroscopic characterization and in vitro antidiabetic studies of new Schiff base Copper(II) complexes. J Chem Sci 128, 1095–1102 (2016). https://doi.org/10.1007/s12039-016-1099-8

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  • DOI: https://doi.org/10.1007/s12039-016-1099-8

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