Synthesis of 4-thiazolidinone analogs as potent in vitro anti-urease agents

Rahim F 1 , Zaman K 2 , Ullah H 2 , Taha M 3 , Wadood A 4 , Javed MT 2 Show all authors , Rehman W 2 , Ashraf M 5 , Uddin R 6 , Uddin I 2 , Asghar H 5 , Khan AA 2 , Khan KM 6

Affiliations 

  • 1 Department of Chemistry, Hazara University, Mansehra 21120, Pakistan. Electronic address: fazalstar@gmail.com
  • 2 Department of Chemistry, Hazara University, Mansehra 21120, Pakistan
  • 3 Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor D.E., Malaysia; Faculty of Applied Science, Universiti Teknologi MARA, 40450 Shah Alam, Malaysia
  • 4 Department of Biochemistry, Abdul Wali Khan University Mardan, Mardan 23200, Pakistan
  • 5 Department of Biochemistry and Biotechnology, The Islamia University of Bahawalpur, Bahawalpur 63100, Pakistan
  • 6 HEJ, Research Institute of Chemistry, ICCBS, University of Karachi, Karachi 75270, Pakistan
Bioorg Chem, 2015 Dec;63:123-31.
PMID: 26520885 DOI: 10.1016/j.bioorg.2015.10.005

Abstract

4-Thiazolidinone analogs 1-20 were synthesized, characterized by (1)H NMR and EI-MS and investigated for urease inhibitory activity. All twenty (20) analogs exhibited varied degree of urease inhibitory potential with IC50 values 1.73-69.65μM, if compared with standard thiourea having IC50 value of 21.25±0.15μM. Among the series, eight derivatives 3, 6, 8, 10, 15, 17, 19, and 20 showed outstanding urease inhibitory potential with IC50 values of 9.34±0.02, 14.62±0.03, 8.43±0.01, 7.3±0.04, 2.31±0.002, 5.75±0.003, 8.81±0.005, and 1.73±0.001μM, respectively, which is better than the standard thiourea. The remaining analogs showed good to excellent urease inhibition. The binding interactions of these compounds were confirmed through molecular docking studies.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.

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