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
- Authors: Abbasi M.A.1,2, Ramzan M.S.2, Aziz-ur-Rehman 2, Siddiqui S.Z.2, Shah S.A.3,4, Hassan M.1, Seo S.1, Ashraf M.2, Mirza B.5, Ismail H.5
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Affiliations:
- College of Natural Science, Department of Biological Sciences
- Department of Chemistry
- Faculty of Pharmacy, University Technology MARA, Puncak Alam Campus
- Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), University Technology MARA, Puncak Alam Campus
- Department of Biochemistry
- Issue: Vol 44, No 6 (2018)
- Pages: 801-811
- Section: Article
- URL: https://journals.rcsi.science/1068-1620/article/view/229078
- DOI: https://doi.org/10.1134/S106816201806002X
- ID: 229078
Cite item
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.
About the authors
M. A. Abbasi
College of Natural Science, Department of Biological Sciences; Department of Chemistry
Author for correspondence.
Email: abbasi@gcu.edu.pk
Korea, Republic of, Gongju, 32588; Lahore, 54000
M. S. Ramzan
Department of Chemistry
Email: abbasi@gcu.edu.pk
Pakistan, Lahore, 54000
Aziz-ur-Rehman
Department of Chemistry
Email: abbasi@gcu.edu.pk
Pakistan, Lahore, 54000
S. Z. Siddiqui
Department of Chemistry
Email: abbasi@gcu.edu.pk
Pakistan, Lahore, 54000
S. A. A. Shah
Faculty of Pharmacy, University Technology MARA, Puncak Alam Campus; Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), University Technology MARA, Puncak Alam Campus
Email: abbasi@gcu.edu.pk
Malaysia, Selangor Darul Ehsan, 42300; Selangor Darul Ehsan, 42300
M. Hassan
College of Natural Science, Department of Biological Sciences
Email: abbasi@gcu.edu.pk
Korea, Republic of, Gongju, 32588
S.-Y. Seo
College of Natural Science, Department of Biological Sciences
Email: abbasi@gcu.edu.pk
Korea, Republic of, Gongju, 32588
M. Ashraf
Department of Chemistry
Email: abbasi@gcu.edu.pk
Pakistan, Bahawalpur, 63100
B. Mirza
Department of Biochemistry
Email: abbasi@gcu.edu.pk
Pakistan, Islamabad, 45320
H. Ismail
Department of Biochemistry
Email: abbasi@gcu.edu.pk
Pakistan, Islamabad, 45320