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Synthesis of azomethines derived from cinnamaldehyde and vanillin: in vitro aetylcholinesterase inhibitory, antioxidant and insilico molecular docking studies

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Abstract

In the present study, we report the synthesis of azomethines derived from cinnamaldehyde (C1–C3) and vanillin (V1–V3) using ethanol as a green solvent in the presence of triethyl amine. The synthesized compounds were characterized and investigated for their free radical scavenging activity and anti-Alzheimer properties by DPPH and acetylcholinesterase (AChE) inhibition assays. The anti-Alzheimer properties of the compounds were determined by molecular docking and ADME predictions. Compounds, C1 and V1 were found to be potential with IC50 values of 0.01 ± 0.09 µM and 0.31 ± 0.03 µM respectively. The antioxidant activity of C1 in terms of DPPH and ABTS was found to be 16.22 ± 0.02 µM and 17.2 ± 0.02 µM, whereas V1 showed antioxidant activities at 14.07 ± 0.02 µM and 15.06 ± 0.03 µM respectively. In silico studies based on molecular docking and ADME predictions revealed the significance of azomethine derivatives as the potent anti-Alzheimer agents.

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Acknowledgements

The authors are thankful to AIMST University, Malaysia for providing laboratory facilities. These authors are indebted to the Ministry of Higher Education (MOHE), Putrajaya, Malaysia for funding the computational part (software and workstation) through the Translational Research Grant Scheme (TRGS) 600-RMI/TRGS 5/3 (1/2014) -3 to Universiti Teknologi MARA (UiTM).

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Authors and Affiliations

  1. Faculty of Pharmacy, AIMST University, Semeling, 08100, Bedong, Kedah, Malaysia

    Sridevi Chigurupati & Shaikh S. Akhtar

  2. Integrative Pharmacogenomics Institute (iPROMISE), Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia

    Manikandan Selvaraj, Lay K. Teh & Mohd Z. Salleh

  3. Department of Pharmacology and Toxicology, College of Pharmacy, Qassim University, Buraidah, 51452, Saudi Arabia

    Vasudevan Mani

  4. Department of Pharmacology, Faculty of Medicine, Cyberjaya University College of Medical Sciences, CUCMS, Cyberjaya, 63000, Malaysia

    Jahidul I. Mohammad

  5. Department of Pharmacology and Toxicology, College of Pharmacy, University of Hail, Hail, 2440, Saudi Arabia

    Kesavanarayanan K. Selvarajan, Lay K. Teh & Mohd Z. Salleh

  6. School of Pharmacy, International Medical University, 57000, Kuala Lumpur, Malaysia

    Maharajan Marikannan

  7. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Teegala Ram Reddy College of Pharmacy, Hyderabad, 500097, India

    Suthakaran Raj

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  1. Sridevi Chigurupati
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  2. Manikandan Selvaraj
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  3. Vasudevan Mani
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  4. Jahidul I. Mohammad
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  5. Kesavanarayanan K. Selvarajan
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  8. Suthakaran Raj
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  9. Lay K. Teh
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  10. Mohd Z. Salleh
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Correspondence to Sridevi Chigurupati or Manikandan Selvaraj.

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Chigurupati, S., Selvaraj, M., Mani, V. et al. Synthesis of azomethines derived from cinnamaldehyde and vanillin: in vitro aetylcholinesterase inhibitory, antioxidant and insilico molecular docking studies. Med Chem Res 27, 807–816 (2018). https://doi.org/10.1007/s00044-017-2104-6

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