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Synthesis and evaluation of urea and thiourea derivatives of lopinavir intermediate as potent antimicrobial, antioxidant agents and molecular docking studies against Staphopain

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Abstract

A series of new urea and thiourea derivatives of lopinavir intermediate 7a–k was designed and synthesized from lopinavir intermediate by treating various biopotent isocyanates and isothiocyanates in the presence of base, 1,4-dimethyl piperazine, and their biological activity was evaluated . The bio-assay revealed that the compounds exhibited moderate to good antimicrobial and antioxidant activities; particularly, 7k showed high activity against Staphylococcus aureus. Further, to know the binding interactions of the title products with protease enzyme, molecular studies were performed, which revealed that 7j exhibited high binding affinity towards the enzyme cysteine protease from Staphylococcus aureus. The results from in vitro studies revealed that they can be used as effective antimicrobial and antioxidant agents. Furthermore, molecular docking studies shown very good interaction.

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Acknowledgments

The author Hasti Sudhamani is very thankful to the DST INSPIRE (Department of Science and Technology) for awarding JRF.

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Authors and Affiliations

  1. Department of Chemistry, Sri Venkateswara University, Tirupati, Andhra Pradesh, India

    H. Sudhamani, S. K. Thaslim Basha & C. Naga Raju

  2. Nanotechnology Laboratory, Institute of Frontier Technology, Regional Agricultural Research Station (RARS), Tirupati, Andhra Pradesh, 517 502, India

    S. Adam

  3. Department of Bioinformatics, Sri Venkateswara University, Tirupati, Andhra Pradesh, India

    S. Madhusudhana & A. Usha Rani

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  1. H. Sudhamani
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Correspondence to C. Naga Raju.

Electronic supplementary material

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11164_2016_2609_MOESM1_ESM.docx

Experimental part of antimicrobial and antioxidant (DPPH and FRAP methods) activities, molecular docking studies of the title compounds and scanned spectra of 1H, 13C and HRMS reports of 7d and 7h compounds are given in the supplemental information. (DOCX 688 kb)

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Sudhamani, H., Thaslim Basha, S.K., Adam, S. et al. Synthesis and evaluation of urea and thiourea derivatives of lopinavir intermediate as potent antimicrobial, antioxidant agents and molecular docking studies against Staphopain. Res Chem Intermed 43, 103–120 (2017). https://doi.org/10.1007/s11164-016-2609-5

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  • DOI: https://doi.org/10.1007/s11164-016-2609-5

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