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Synthesis and in Vitro Urease Inhibitory Activity of 5-Nitrofuran-2-Yl-Thiadiazole Linked to Different Cyclohexyl-2-(Phenylamino)Acetamides, in Silico and Kinetic Studies Publisher Pubmed



Asadi M1 ; Iraji A2, 3, 7 ; Sherafati M4 ; Nazari Montazer M4 ; Ansari S5, 6 ; Mohammadi Khanaposhtani M5 ; Tanideh N2 ; Dianatpour M2 ; Biglar M6 ; Larijani B6 ; Foroumadi A4 ; Azizian H6 ; Amanlou M4 ; Mahdavi M6
Authors
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Authors Affiliations
  1. 1. Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran
  2. 2. Stem Cells Technology Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
  3. 3. Central Research Laboratory, Shiraz University of Medical Sciences, Shiraz, Iran
  4. 4. Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  5. 5. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran
  6. 6. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
  7. 7. Liosa Pharmed Parseh Company, Shiraz, Iran

Source: Bioorganic Chemistry Published:2022


Abstract

A series of 5-nitrofuran-2-yl-thiadiazole linked to different cyclohexyl-2-(phenylamino)acetamides were rationally designed and synthesized. All synthetic compounds were evaluated for their urease inhibitory activity and exhibited good inhibitory potential against urease with IC50 values in the range of 0.94 – 6.78 μM as compared to the standard thiourea (IC50 = 22.50 μM). Compound 8g (IC50 = 0.94 μM) with a thiophene substituent at the R2 position was found to be the most active member of the series. Kinetic studies exhibited that the compound 8g was a non-competitive inhibitor. In silico study showed the critical interactions of potent inhibitors with the active site of the enzyme. These newly identified inhibitors of the urease enzyme can serve as leads for further research and development. © 2021
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