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Synthesis, molecular docking and biological evaluation of new thiazolopyrimidine carboxylates as potential antidiabetic and antibacterial agents

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Abstract

A series of new thiazolopyrimidine analogues were conveniently synthesized by one-pot multicomponent condensation reaction of ethyl acetoacetate, 2-aminothiazole and benzaldehyde substituted with different electron-donating and electron-withdrawing groups, in order to find some more potent antidiabetic and antibacterial drugs. The structures of the synthesized compounds were assigned based on elemental analyses and spectral data. An in vitro effect on total serum concentration of glucose, cholesterol and triglycerides was evaluated in adult male BALB/c mice, compared to two standard drugs “alloxan” and “glibenclamide,” and good results were observed with the presence of –Cl and –Br groups at the para position of the phenyl ring. The antibacterial activities were tested against five bacterial strains, Micrococcus luteus, Salmonella typhimurium, Bacillus subtilis, Bordetella bronchiseptica and Escherichia coli. Most of the compounds showed good to excellent bacterial zone inhibition compared to the reference drug “kanamycin.” An in silico molecular docking was also performed on synthesized compounds to support the experimental findings, which were in good agreement with computational results. The current study is expected to provide useful insights into the design of antidiabetic and antibacterial drugs, and understanding the mechanism by which such drugs interact with RNA and diabetes targets and exert their biochemical action.

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Abbreviations

CVD:

Cardiovascular diseases

CHD:

Comprising coronary heart

T2DM:

Type 2 diabetes mellitus

MI:

Myocardial infarction

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Acknowledgments

I.B. gratefully acknowledges a research scholarship from HEC Islamabad under the HEC Indigenous Ph.D. Scholarship 5000 Scheme.

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Authors and Affiliations

  1. Department of Chemistry, Quaid-i-Azam University, Islamabad, 45320, Pakistan

    Iram Batool, Aamer Saeed & Saima Kalsoom

  2. Department of Animal Science, Quaid-i-Azam University, Islamabad, 45320, Pakistan

    Irfan Zia Qureshi & Ayesha Razzaq

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  1. Iram Batool
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Batool, I., Saeed, A., Qureshi, I.Z. et al. Synthesis, molecular docking and biological evaluation of new thiazolopyrimidine carboxylates as potential antidiabetic and antibacterial agents. Res Chem Intermed 42, 1139–1163 (2016). https://doi.org/10.1007/s11164-015-2078-2

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