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Ferulic acid amide derivatives as anticancer and antioxidant agents: synthesis, thermal, biological and computational studies

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Abstract

The design and microwave-assisted synthesis of four series (IIIa–IIIo, Va–Vg, VIIa–VIIg and IXa–IXe) of mono and bis-amide derivatives of ferulic acid have been achieved under solvent-free conditions and, subsequently characterized by spectroscopic techniques. During thermal analysis, all the compounds were found stable up to 100 °C and decomposed through single step at higher temperature. The derivatives were screened for their in vitro cytotoxicity and antioxidant activity, respectively and observed that compound Vb was most active against breast (MCF-7; IC50 = 07.49 µM and MDA-MB-231; IC50 = 07.28 µM), Vd against lung (A549; IC50 = 07.11 µM) and liver (HepG2; IC50 = 08.32 µM), and Ve against cervical (HeLa; IC50 = 07.14 µM) cancer cell lines, while compounds IIIf, IIIl, IIIo, VIIe and IXa–IXe were found to exhibit the strong antioxidant activity with respect to their parent molecule. Previous reports for the biological applications of ferulic acid amides also confirmed the importance of work presented here. The 3D-QSAR studies for anticancer and antioxidant activities were also performed by using CoMFA, and the corresponding contour maps of electrostatic and steric fields have been computed. Statistical analysis between experimental and CoMFA-predicted data for pIC50 have been accomplished by curve fitting analysis which showed the significant correlation.

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Acknowledgments

Naresh Kumar gratefully acknowledges CSIR, New Delhi, India, for financial assistance, Indian Institute of Technology Roorkee and NIPER Mohali for instrumentation facility.

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Authors and Affiliations

  1. Department of Biotechnology, Indian Institute of Technology Roorkee, Roorkee, Uttarakhand, 247667, India

    Naresh Kumar, Kumar Nikhil, Partha Roy & Vikas Pruthi

  2. Department of Chemistry, Indian Institute of Technology Roorkee, Roorkee, 247667, India

    Sandeep Kumar & Sham M. Sondhi

  3. Department of Pharmacoinformatics, NIPER, S.A.S. Nagar, Mohali, 160062, India

    Sheenu Abbat

  4. Department of Medicinal Chemistry, NIPER, S.A.S. Nagar, Mohali, 160062, India

    Prasad V. Bharatam

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  1. Naresh Kumar
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  2. Sandeep Kumar
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  3. Sheenu Abbat
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  4. Kumar Nikhil
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Correspondence to Naresh Kumar.

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Kumar, N., Kumar, S., Abbat, S. et al. Ferulic acid amide derivatives as anticancer and antioxidant agents: synthesis, thermal, biological and computational studies. Med Chem Res 25, 1175–1192 (2016). https://doi.org/10.1007/s00044-016-1562-6

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  • DOI: https://doi.org/10.1007/s00044-016-1562-6

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