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Vol. 30 No. 2 (2018): Vol 30 Issue 2

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Synthesis and Structural Analysis of Persuasive Antibacterial Agents and Enzyme Inhibitors Derived from 5-(1-(4-Tosyl)piperidin-4-yl)-1,3,4-oxadiazol-2-thiol

https://doi.org/10.14233/ajchem.2018.20871
Aziz-ur-Rehman
Department of Chemistry, Government College University, Lahore-54000, Pakistan
Almas Sattar
Department of Chemistry, Government College University, Lahore-54000, Pakistan
Muhammad Athar Abbasi
Department of Chemistry, Government College University, Lahore-54000, Pakistan
Sabahat Z. Siddiqui
Department of Chemistry, Government College University, Lahore-54000, Pakistan
M. Arslan Raza
Department of Chemistry, Government College University, Lahore-54000, Pakistan
Muhammad Ashraf
Department of Biochemistry and Biotechnology, The Islamia University of Bahawalpur, Bahawalpur-63100, Pakistan
Munibaanum Nazir
Department of Biochemistry and Biotechnology, The Islamia University of Bahawalpur, Bahawalpur-63100, Pakistan
Syed Adnan Ali Shah
Faculty of Pharmacy and Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor Darul Ehsan, Malaysia

Corresponding Author(s) : Aziz-ur-Rehman

azizryk@yahoo.com

Asian Journal of Chemistry, Vol. 30 No. 2 (2018): Vol 30 Issue 2

Abstract

Due to outstanding biological activities of 1,3,4-oxadiazole, a series of S-substituted derivatives of 5-[1-(4-tosyl)piperidin-4-yl]-1,3,4-oxadiazol-2-thiol (5a-f) was synthesized. The reaction of p-toluene sulfonyl chloride (a) with ethyl isonepacotate (b) produced ethyl 1-(4-tosyl)piperidin-4-carboxylate (1) which was successively converted to 1-(4-tosyl)piperidin-4-carbohydrazide (2) by hydrazine and 5-[1-(4-tosyl)piperidin-4-yl]-1,3,4-oxadiazol-2-thiol (3) by CS2 in the presence of KOH. The aimed compounds (5a-f) were synthesized by the reaction of compound 3 with different electrophiles in DMF using lithium hydride as catalyst. The structural confirmation was done by IR, 1H NMR & EI-MS spectral analysis. The synthesized compounds were screened against a-glucosidase enzyme and five Gram bacterial strains.

Keywords

1,3,4-Oxadiazole a-Glucosidase Antibacterial activity Ethyl isonipecotate Toluenesulfonylchloride
Aziz-ur-Rehman, ., Sattar, A., Abbasi, M. A., Siddiqui, S. Z., Raza, M. A., Ashraf, M., … Ali Shah, S. A. (2017). Synthesis and Structural Analysis of Persuasive Antibacterial Agents and Enzyme Inhibitors Derived from 5-(1-(4-Tosyl)piperidin-4-yl)-1,3,4-oxadiazol-2-thiol. Asian Journal of Chemistry, 30(2), 260–264. https://doi.org/10.14233/ajchem.2018.20871
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