3,4-Dimethoxybenzohydrazide derivatives as antiulcer: Molecular modeling and density functional studies

Taha M 1 , Ismail NH 2 , Zaki HM 2 , Wadood A 3 , Anouar EH 4 , Imran S 2 Show all authors , Yamin BM 5 , Rahim F 6 , Ali M 7 , Khan KM 8

Affiliations 

  • 1 Department of Clinical Pharmacy, Institute for Research and Medical Consultations (IRMC), University of Dammam, Dammam 31441, Saudi Arabia. Electronic address: mtaha@uod.edu.sa
  • 2 Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor, Malaysia; Faculty of Applied Science, UiTM, 40450 Shah Alam, Selangor, Malaysia
  • 3 Department of Biochemistry, Abdul Wali Khan University, Mardan, Khyber Pukhtunkhwa, Pakistan
  • 4 Department of Chemistry, College of Sciences and Humanities, Prince Sattam bin Abdulaziz University, P.O. Box 83, Al-Kharij 11942, Saudi Arabia
  • 5 Universiti Kebangsaan Malaysia, School of Chemical Sciences and Food Technology, Bangi, Malaysia
  • 6 Department of Chemistry, Hazara University, Mansehra 21300, Khyber Pukhtunkhwa, Pakistan
  • 7 Department of Chemistry, COMSATS Institute of Information Technology, University Road, Abbottabad 22060, KPK, Pakistan
  • 8 H. E. J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
Bioorg Chem, 2017 12;75:235-241.
PMID: 29031169 DOI: 10.1016/j.bioorg.2017.10.004

Abstract

3,4-Dimethoxybenzohydrazide derivatives (1-25) have been synthesized and evaluated for their urease inhibitory potential. Among the series, compounds 2, 3, 4 and 5 with IC50 values 12.61 ± 0.07, 18.24 ± 0.14, 19.22 ± 0.21, and 8.40 ± 0.05 µM, respectively, showed excellent urease inhibitory potentials when compared with standard thiourea (IC50 value 21.40 ± 0.21 µM). Compounds 1, 6, 8, 18, 19 and 20 also showed good to moderate inhibition, while the remaining compounds were found to be completely inactive. The structures of compounds 6 and 25 were confirmed through X-ray crystallography while the structures of remaining compounds were confirmed through ESI-MS and 1H NMR. Molecular docking studies were performed understand the binding interactions with enzyme active site. The synthesized compounds were evaluated for cytotoxicity and found to be nontoxic.

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