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Synthesis, biological evaluation and molecular docking studies of novel 2-(2-cyanophenyl)-N-phenylacetamide derivatives

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Abstract

A series of novel 2-(2-cyanophenyl)-N-phenylacetamide derivatives 3(a-u) were designed and synthesized via selective amidation of methyl-2-(2-cyanophenyl)acetates over amidine formation by using AlMe3 as catalyst in good yields. All the newly synthesized derivatives were well characterized by 1H NMR, 13C NMR, FTIR and HRMS spectral techniques. All the synthesized title compounds were evaluated for their in vitro anticancer activity against three cancer cell lines. Among all compounds, 3i (IC50 = 1.20 μM, IC50 = 1.10 μM), 3j (IC50 = 0.11 μM, IC50 = 0.18 μM), 3o (IC50 = 0.98 μM, IC50 = 2.76 μM) showed excellent inhibitory activity than the standard Etoposide (IC50 = 2.11 μM, IC50 = 3.08 μM) against MCF-7 and A-549 cell lines, respectively. Docking analysis of all the compounds with the human topoisomerase II revealed that the compound 3j fitted well in the active site pocket, showing the best docking score of 158.072 kcal/mol.

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Acknowledgements

The authors express their profound thanks to the management of GVK Biosciences Private Limited for financial support. We thank Dr. Sudhir Kumar Singh and Dr. Somesh Sharma and Dr. Krishna Reddy Valluru for their invaluable support and motivation.

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Authors and Affiliations

  1. GVK Biosciences Private Limited, Medicinal Chemistry Laboratory, Hyderabad, 500076, India

    Lakshmi Narayana Sharma Konidena, Suresh Kumar Chettu, Kumaraswamy Sorra & Praveena Mukkavilli

  2. Andhra University, Department of Engineering Chemistry, Andhra University College of Engineering (A), Visakhapatnam, 530003, India

    Lakshmi Narayana Sharma Konidena, Suresh Kumar Chettu & Raghu Babu Korupolu

  3. Department of Chemistry, Osmania University, Tarnaka, Hyderabad, 500007, India

    Sathish Kumar Boda & P. V. Anantha Lakshmi

  4. Department of Bioinformatics, Averin Biotech Pvt. Ltd, Windsorplaza, Nallakunta, Hyderabad, 500044, India

    Sreenivas Enaganti

  5. Koneru Lakshmaiah Education Foundation, Deemed to be University, Vaddeswaram, Guntur, 522502, India

    N. S. Kameswara Rao

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  1. Lakshmi Narayana Sharma Konidena
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  2. Sathish Kumar Boda
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Correspondence to Lakshmi Narayana Sharma Konidena or Raghu Babu Korupolu.

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Konidena, L.N.S., Boda, S.K., Chettu, S.K. et al. Synthesis, biological evaluation and molecular docking studies of novel 2-(2-cyanophenyl)-N-phenylacetamide derivatives. Res Chem Intermed 44, 5467–5481 (2018). https://doi.org/10.1007/s11164-018-3434-9

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