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N-(5-Methyl-1,3-Thiazol-2-yl)-2-{[5-((Un)Substituted- Phenyl)1,3,4-Oxadiazol-2-yl]Sulfanyl}acetamides. Unique Biheterocycles as Promising Therapeutic Agents

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Abstract

An electrophile, 2-bromo-N-(5-methyl-1,3-thiazol-2-yl)acetamide, was synthesized by the reaction of 5-methyl-1,3-thiazol-2-amine and bromoacetyl bromide in an aqueous medium. In a parallel scheme, a series of (un)substituted benzoic acids was converted sequentially into respective esters, acid hydrazides, and then into 1,3,4-oxadiazole heterocyclic cores. The electrophile was coupled with the aforementioned 1,3,4-oxadiazoles to obtain the targeted bi-heterocyles. Structural analysis of the synthesized compounds was performed by IR, EI-MS, 1H NMR, and 13C NMR. The enzyme inhibition study of these molecules was carried out against four enzymes, namely, acetylcholinesterase, butyrylcholinesterase, α-glucosidase, and urease. The interactions of these compounds with respective enzymes were recognized by their in silico study. Moreover, their cytotoxicity was also determined to find out their utility as possible therapeutic agents.

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Abbreviations

AChE:

acetylcholinesterase

AGIs:

α-glucosidase inhibitors

BChE:

butyrylcholinesterase

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Authors and Affiliations

  1. College of Natural Science, Department of Biological Sciences, Kongju National University, Gongju, 32588, South Korea

    M. A. Abbasi, M. Hassan & S.-Y. Seo

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

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

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

    S. A. A. Shah

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

    S. A. A. Shah

  5. Department of Chemistry, Islamia University of Bahawalpur, Bahawalpur, 63100, Pakistan

    M. Ashraf

  6. Department of Biochemistry, Quaid-i-Azam University, Islamabad, 45320, Pakistan

    B. Mirza & H. Ismail

Authors
  1. M. A. Abbasi
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  2. M. S. Ramzan
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  3. Aziz-ur-Rehman
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  4. S. Z. Siddiqui
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  5. S. A. A. Shah
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  6. M. Hassan
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  7. S.-Y. Seo
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  8. M. Ashraf
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  9. B. Mirza
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  10. H. Ismail
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Correspondence to M. A. Abbasi.

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Abbasi, M.A., Ramzan, M.S., Aziz-ur-Rehman et al. N-(5-Methyl-1,3-Thiazol-2-yl)-2-{[5-((Un)Substituted- Phenyl)1,3,4-Oxadiazol-2-yl]Sulfanyl}acetamides. Unique Biheterocycles as Promising Therapeutic Agents. Russ J Bioorg Chem 44, 801–811 (2018). https://doi.org/10.1134/S106816201806002X

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  • DOI: https://doi.org/10.1134/S106816201806002X

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