Microwave-assisted synthesis of triazole derivatives conjugated with piperidine as new anti-enzymatic agents

Naeem A. Virk, Aziz ur Rehman, Muhammad A. Abbasi, Sabahat Z. Siddiqui, Javed Iqbal, Shahid Rasool, Shafi U. Khan, Thet T. Htar, Hira Khalid, Sabina J. Laulloo, Syed A. Ali Shah

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    Abstract

    The current study was aimed for the study of piperidine-based triazole compounds for their biological potential against various enzymes. A novel library of compounds, 9a-r, having piperidine, 1,2,4-triazole, and propanamides was synthesized through consecutive steps including the formation of sulfonamide, hydrazide, 1,2,4-triazole, and thio-ether. Initially, 4-methoxybenzenesulfonyl chloride (1) and ethyl isonipecotate (2) were utilized to develop ethyl 1-(4-methoxyphenylsulfonyl)-4-piperidinecarboxylate (3). The product 3 was converted into respective hydrazide (4) which was further cyclized into 1,2,4-triazole (5) nucleus. A series of propanamides, 8a-r, were synthesized from different amines, 6a-r. These electrophiles, 8a-r, were reacted with compound 5 under conventional and microwave-assisted protocols to acquire the library of hybrids, 9a-r. The structural confirmations were availed by 1H-NMR, 13C-NMR, and IR techniques. The whole series was evaluated for biological potential against acetylcholinesterase (AChE) and α-glucosidase enzymes. The biological evaluation ranges low to high in potential for different compounds based on the structural variations of synthesized compounds. Almost all the compounds remained active against both the enzymes except a few ones. The bovine serum albumin (BSA) binding study demonstrated the flow of drug in the body, and the docking study explained the interactions responsible for active behavior of synthesized compounds.

    Original languageEnglish
    Pages (from-to)1387-1402
    Number of pages16
    JournalJournal of Heterocyclic Chemistry
    Volume57
    Issue number3
    DOIs
    Publication statusPublished - Mar 2020

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