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Synthesis and pharmacological screening: Sulfa derivatives of 2-pipecoline-bearing 1,3,4-oxadiazole core

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Abstract

An electrophile, 1-(4-(bromomethylbenzenesulfonyl)-2-methylpiperidine, was synthesized by the reaction of 2-methylpiperidine (2-pipecoline) and 4-bromomethylbenzenesulfonyl chloride in a weak basic medium under pH control. A series of nucleophiles, 5-aryl/aralkyl-1,3,4-oxadiazol-2-thiols, were synthesized from corresponding carboxylic acids in three steps. The title molecules were synthesized by coupling the electrophile to nucleophiles in an aprotic medium using LiH as an activator. The structures of all synthesized compounds were corroborated through IR, 1H NMR, and EI-MS techniques. All the compounds were screened for their pharmacological behavior, particularly, antibacterial and enzyme inhibitory activities. Notably efficient results were obtained against both gram-positive and gram-negative bacterial strains. Regarding enzyme inhibition, compounds were efficient against acetylcholinesterase and butyrylcholinesterase.

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Authors and Affiliations

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

    Aziz-ur-Rehman, A. Arif, M. A. Abbasi, S. Z. Siddiqui & S. Rasool

  2. Faculty of Pharmacy, University of Technology MARA, Puncak Alam Campus, Bandar Puncak Alam, Selangor Darul Ehsan, 42300, Malaysia

    S. A. A. Shah

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

    S. A. A. Shah

Authors
  1. Aziz-ur-Rehman
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  2. A. Arif
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  3. M. A. Abbasi
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  4. S. Z. Siddiqui
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  5. S. Rasool
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  6. S. A. A. Shah
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Correspondence to Aziz-ur-Rehman.

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Aziz-ur-Rehman, Arif, A., Abbasi, M.A. et al. Synthesis and pharmacological screening: Sulfa derivatives of 2-pipecoline-bearing 1,3,4-oxadiazole core. Russ J Bioorg Chem 43, 328–339 (2017). https://doi.org/10.1134/S1068162017030025

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  • DOI: https://doi.org/10.1134/S1068162017030025

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