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Synthesis, characterizations, biological activities and docking studies of novel dihydroxy derivatives of natural phenolic monoterpenoids containing azomethine linkage

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Abstract

In the present work, we report the synthesis of six new azomethine linkage containing dihydroxy derivatives of carvacrol, thymol, and eugenol. All the synthesized derivatives have been characterized by spectroscopic techniques and their structures were confirmed by X-ray single crystallography. Synthesized derivatives were screened for anti-oxidant activity using DPPH radical scavenging assay, and anticancer activity by using SRB assay against pancreatic cancer with MIAPaCa-2 and colon cancer with HCT-15 cell lines. The molecular docking studies of all the synthesized derivatives were performed on cyclooxygenases (COX-2) protein enzyme. In the anti-oxidant test, the values of EC50 indicated that all the compounds show excellent anti-oxidant potency, and similarly the GI50 values in anticancer tests indicated that most of the compounds possess good anticancer efficacy. The overall docking score suggested that all the synthesized compounds exhibit good binding affinity towards cyclooxygenases (COX-2) protein enzyme.

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Acknowledgements

RSB thanks UGC, New Delhi, for SAP (DSA-I) and Jamatsing D. Rajput gratefully thanks UGC, New Delhi, for BSR Fellowship of PhD Candidates. We are also grateful to Prof. T. N. Guru Row, IISC, Bangalore, for help in solving the crystal structures. Finally, we are grateful to Dr. Davinder Tuli for the molecular docking studies.

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Authors and Affiliations

  1. School of Chemical Sciences, North Maharashtra University, Jalgaon, Maharashtra, 425001, India

    Jamatsing D. Rajput, Suresh D. Bagul, Manohar M. Patil & Ratnamala S. Bendre

  2. Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, 560 012, India

    Amar A. Hosamani

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  1. Jamatsing D. Rajput
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Correspondence to Ratnamala S. Bendre.

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Rajput, J.D., Bagul, S.D., Hosamani, A.A. et al. Synthesis, characterizations, biological activities and docking studies of novel dihydroxy derivatives of natural phenolic monoterpenoids containing azomethine linkage. Res Chem Intermed 43, 5377–5393 (2017). https://doi.org/10.1007/s11164-017-2933-4

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