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Synthesis and Structure-Activity Relationship of 1-(2-Furoyl)Piperazine Bearing Benzamides as Butyrylcholinesterase Inhibitors

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Pharmaceutical Chemistry Journal Aims and scope

Four benzamide derivatives (5a, 5b, 8a, 8b) bearing heterocyclic furan and piperazine ring have been synthesized and evaluated for enzyme inhibition and hemolytic activity. Initial 4-(chloromethyl)benzoyl chloride (1) and 3-(chloromethyl)benzoyl chloride (6) were stirred with benzyl amine (2a) and cyclohexyl amine (2b), respectively, in aqueous medium at pH 9 – 10 maintained by aqueous sodium carbonate. The resulting benzamides (3a, 3b, 7a, 7b) were refluxed with 1-(2-furoyl)piperazine (4) in the presence of K2CO3 and CH3CN to acquire target compounds (5a, 5b, 8a, 8b). The spectroscopic techniques including 13C NMR, 1H NMR, IR and EI-MS corroborated the proposed molecular structures of final compounds. Among these, two compounds (5b, 8b) proved to be considerable inhibitors of butyrylcholinesterase enzyme. Study of the hemolytic activity potential revealed low toxicity level of compound 5b.

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Acknowledgements

The Higher Education Commission (HEC) of Pakistan is highly acknowledged by the authors for fiscal aid to conduct spectral analysis. 602 M. A. Abbasi et al. Fig. 5. Structure – activity relationship of compounds 8a and 8b.

CONFLICT OF INTEREST

The authors declare that they have no conflict of interest.

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Authors and Affiliations

  1. Department of Chemistry, Government College University, Lahore, -54000, Pakistan

    M. A. Abbasi,  Aziz-ur-Rehman, S. Z. Siddiqui & H. M. Junaid

  2. Division of Science and Technology, University of Education, Township Campus, Lahore, -54770, Pakistan

    M. Irshad

  3. Faculty of Pharmacy & Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), Level 9, FF3, Universiti Teknologi MARA, Puncak Alam Campus, 42300, Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia

    S. A. A. Shah

  4. Department of Chemistry, The Islamia University of Bahawalpur, -63100, Bahawalpur, Pakistan

    M. Ashraf

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  1. M. A. Abbasi
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Correspondence to M. A. Abbasi.

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Abbasi, M.A., Irshad, M., Aziz-ur-Rehman et al. Synthesis and Structure-Activity Relationship of 1-(2-Furoyl)Piperazine Bearing Benzamides as Butyrylcholinesterase Inhibitors. Pharm Chem J 54, 596–603 (2020). https://doi.org/10.1007/s11094-020-02247-2

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  • DOI: https://doi.org/10.1007/s11094-020-02247-2

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