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Design and Synthesis of Novel Nitrothiazolacetamide Conjugated to Different Thioquinazolinone Derivatives As Anti-Urease Agents Publisher Pubmed



Sohrabi M1 ; Nazari Montazer M2 ; Farid SM1 ; Tanideh N3 ; Dianatpour M3 ; Moazzam A1 ; Zomorodian K4 ; Yazdanpanah S4 ; Asadi M1 ; Hosseini S5 ; Biglar M1 ; Larijani B1 ; Amanlou M2, 6 ; Barazandeh Tehrani M2 Show All Authors
Authors
  1. Sohrabi M1
  2. Nazari Montazer M2
  3. Farid SM1
  4. Tanideh N3
  5. Dianatpour M3
  6. Moazzam A1
  7. Zomorodian K4
  8. Yazdanpanah S4
  9. Asadi M1
  10. Hosseini S5
  11. Biglar M1
  12. Larijani B1
  13. Amanlou M2, 6
  14. Barazandeh Tehrani M2
  15. Iraji A3, 7, 8
  16. Mahdavi M1
Show Affiliations
Authors Affiliations
  1. 1. Endocrinology and Metabolism Research Center, Endocrinology and Metabolism Clinical Sciences Institute, Tehran University of Medical Sciences, Tehran, Iran
  2. 2. Department of Medicinal Chemistry, Faculty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medical Sciences, Tehran, Iran
  3. 3. Stem Cells Technology Research Center, Shiraz University of Medical Sciences, Shiraz, Iran
  4. 4. Department of Medical Mycology and Parasitology, School of Medicine, Shiraz University of Medical Sciences, Shiraz, Iran
  5. 5. Department of Pharmaceutical Chemistry, School of Pharmacy, Shahid Beheshti University of Medical Sciences, Tehran, Iran
  6. 6. Department of Medicinal Chemistry, Faculty of Pharmacy, Tehran University of Medical Sciences, Tehran, Iran
  7. 7. Central Research Laboratory, Shiraz University of Medical Sciences, Shiraz, Iran
  8. 8. Liosa Pharmed Parseh Company, Shiraz, Iran

Source: Scientific Reports Published:2022


Abstract

The present article describes the design, synthesis, in vitro urease inhibition, and in silico molecular docking studies of a novel series of nitrothiazolacetamide conjugated to different thioquinazolinones. Fourteen nitrothiazolacetamide bearing thioquinazolinones derivatives (8a-n) were synthesized through the reaction of isatoic anhydride with different amine, followed by reaction with carbon disulfide and KOH in ethanol. The intermediates were then converted into final products by treating them with 2-chloro-N-(5-nitrothiazol-2-yl)acetamide in DMF. All derivatives were then characterized through different spectroscopic techniques (1H, 13C-NMR, MS, and FTIR). In vitro screening of these molecules against urease demonstrated the potent urease inhibitory potential of derivatives with IC50 values ranging between 2.22 ± 0.09 and 8.43 ± 0.61 μM when compared with the standard thiourea (IC50 = 22.50 ± 0.44 μM). Compound 8h as the most potent derivative exhibited an uncompetitive inhibition pattern against urease in the kinetic study. The high anti-ureolytic activity of 8h was confirmed against two urease-positive microorganisms. According to molecular docking study, 8h exhibited several hydrophobic interactions with Lys10, Leu11, Met44, Ala47, Ala85, Phe87, and Pro88 residues plus two hydrogen bound interactions with Thr86. According to the in silico assessment, the ADME-Toxicity and drug-likeness profile of synthesized compounds were in the acceptable range. © 2022, The Author(s).
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