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Novel (Thio)Barbituric-Phenoxy-N-Phenylacetamide Derivatives As Potent Urease Inhibitors: Synthesis, in Vitro Urease Inhibition, and in Silico Evaluations Publisher



Sedaghati S1 ; Azizian H2 ; Montazer MN1 ; Mohammadikhanaposhtani M3 ; Asadi M1 ; Moradkhani F1 ; Ardestani MS4 ; Asgari MS5 ; Yahyameymandi A6 ; Biglar M7 ; Larijani B7 ; Sadatebrahimi SE1 ; Foroumadi A1 ; Amanlou M1 Show All Authors
Authors
  1. Sedaghati S1
  2. Azizian H2
  3. Montazer MN1
  4. Mohammadikhanaposhtani M3
  5. Asadi M1
  6. Moradkhani F1
  7. Ardestani MS4
  8. Asgari MS5
  9. Yahyameymandi A6
  10. Biglar M7
  11. Larijani B7
  12. Sadatebrahimi SE1
  13. Foroumadi A1
  14. Amanlou M1
  15. Mahdavi M7
Show Affiliations
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. Department of Medicinal Chemistry, School of Pharmacy-International Campus, Iran University of Medical Sciences, Tehran, Iran
  3. 3. Cellular and Molecular Biology Research Center, Health Research Institute, Babol University of Medical Sciences, Babol, Iran
  4. 4. Department of Radiopharmacy and Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  5. 5. School of Chemistry, College of Science, University of Tehran, Tehran, Iran
  6. 6. Department of Chemistry, Faculty of Science, University of Birjand, Birjand, Iran
  7. 7. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran

Source: Structural Chemistry Published:2021


Abstract

A novel series of (thio)barbituric-phenoxy-N-phenylacetamide derivatives 7a-l was synthesized and evaluated against Helicobacter pylori urease. The latter assay revealed that all the synthesized compounds 7a-l (IC50 = 0.69 ± 0.33–2.47 ± 0.23 μM) were significantly more potent than two used standard inhibitors, thiourea (IC50 = 23 ± 0.73 μM) and hydroxyurea (IC50 = 100 ± 1.7 μM). Docking study of the synthesized compounds demonstrated that these compounds as well fitted in the urease active site. Moreover, molecular dynamic study of the most potent compound 7d showed that this compound created important interactions with the active site flap residues, Cys592 and His593. Furthermore, in silico pharmacokinetic study predicted that all the synthesized compounds are drug-like. © 2020, Springer Science+Business Media, LLC, part of Springer Nature.
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