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Synthesis, in vitro urease inhibitory activity, and molecular docking studies of (perfluorophenyl)hydrazone derivatives

  • Momin KhanEmail author
  • Ghulam Ahad
  • Abdul Manaf
  • Reshma Naz
  • Syed Roohul Hussain
  • Farah Deeba
  • Sana Shah
  • Ajmal Khan
  • Majid Ali
  • Khair Zaman
  • Salman Zafar
  • Uzma Salar
  • Abdul Hameed
  • Khalid Mohammed Khan
Original Research
  • 11 Downloads

Abstract

A series of (perfluorophenyl)hydrazone derivatives 127 were synthesized by the condensation reaction of (perfluorophenyl)hydrazine with a variety of benzaldehydes. Compounds were structurally characterized by various spectroscopic techniques. All compounds were screened for their urease inhibitory activity which revealed that most of the analogs exhibited significant urease inhibitory activity in the range of IC50 = 14.09 ± 0.23–78.69 ± 1.56 µM as compare to the standard thiourea (IC50 = 21.10 ± 0.31 µM). Amongst active compounds, derivatives 2 (IC50 = 14.23 ± 0.21 µM), 5 (IC50 = 16.78 ± 0.33 µM), 7 (IC50 = 15.59 ± 0.60 µM), 9 (IC50 = 20.18 ± 0.78 µM), 10 (IC50 = 16.13 ± 0.93 µM), and 11 (IC50 = 14.09 ± 0.23 µM) showed potent inhibitory activity better than the standard thiourea. A limited structure-activity relationship (SAR) was established by rationalized the effect of different groups on the inhibitory potential. Molecular docking study was performed to understand the binding modes of active analogs into the active site of urease enzyme.

Keywords

Synthesis (Perfluorophenyl)hydrazones Schiff bases Urease inhibition Structure-activity relationship Molecular docking 

Notes

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Momin Khan
    • 1
    Email author
  • Ghulam Ahad
    • 1
  • Abdul Manaf
    • 1
  • Reshma Naz
    • 1
  • Syed Roohul Hussain
    • 1
  • Farah Deeba
    • 1
  • Sana Shah
    • 1
  • Ajmal Khan
    • 2
  • Majid Ali
    • 2
  • Khair Zaman
    • 1
  • Salman Zafar
    • 3
  • Uzma Salar
    • 4
  • Abdul Hameed
    • 4
  • Khalid Mohammed Khan
    • 4
    • 5
  1. 1.Department of ChemistryAbdul Wali Khan UniversityMardanPakistan
  2. 2.UoN Chair of Oman’s Medicinal Plants and Marine Natural ProductsUniversity of NizwaNizwaOman
  3. 3.Institute of Chemical SciencesUniversity of PeshawarPeshawarPakistan
  4. 4.H. E. J. Research Institute of Chemistry, International Centre for Chemical and Biological ScienceUniversity of KarachiKarachiPakistan
  5. 5.Department of Clinical Pharmacy, Institute for Research and Medical Consultations (IRMC)Imam Abdulrahman Bin Faisal UniversityDammamSaudi Arabia

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