3,4-Dimethoxybenzohydrazide derivatives as antiulcer

Molecular modeling and density functional studies

Muhammad Taha, Nor Hadiani Ismail, Hamizah Mohd Zaki, Abdul Wadood, El Hassane Anouar, Syahrul Imran, Bohari Mohd. Yamin, Fazal Rahim, Muhammad Ali, Khalid Mohammed Khan

Research output: Contribution to journalArticle

4 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)235-241
Number of pages7
JournalBioorganic Chemistry
Volume75
DOIs
Publication statusPublished - 1 Dec 2017

Fingerprint

Molecular modeling
Urease
Inhibitory Concentration 50
Derivatives
Thiourea
X ray crystallography
X Ray Crystallography
Cytotoxicity
Catalytic Domain
Nuclear magnetic resonance
Enzymes
8-1 compound
Proton Magnetic Resonance Spectroscopy

Keywords

  • 3,4-Dimethoxybenzohydrazide
  • Cytotoxicity
  • DFT
  • Docking study
  • Synthesis
  • Urease inhibition
  • X-rays analysis

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Organic Chemistry

Cite this

Taha, M., Ismail, N. H., Zaki, H. M., Wadood, A., Anouar, E. H., Imran, S., ... Khan, K. M. (2017). 3,4-Dimethoxybenzohydrazide derivatives as antiulcer: Molecular modeling and density functional studies. Bioorganic Chemistry, 75, 235-241. https://doi.org/10.1016/j.bioorg.2017.10.004

3,4-Dimethoxybenzohydrazide derivatives as antiulcer : Molecular modeling and density functional studies. / Taha, Muhammad; Ismail, Nor Hadiani; Zaki, Hamizah Mohd; Wadood, Abdul; Anouar, El Hassane; Imran, Syahrul; Mohd. Yamin, Bohari; Rahim, Fazal; Ali, Muhammad; Khan, Khalid Mohammed.

In: Bioorganic Chemistry, Vol. 75, 01.12.2017, p. 235-241.

Research output: Contribution to journalArticle

Taha, M, Ismail, NH, Zaki, HM, Wadood, A, Anouar, EH, Imran, S, Mohd. Yamin, B, Rahim, F, Ali, M & Khan, KM 2017, '3,4-Dimethoxybenzohydrazide derivatives as antiulcer: Molecular modeling and density functional studies', Bioorganic Chemistry, vol. 75, pp. 235-241. https://doi.org/10.1016/j.bioorg.2017.10.004
Taha, Muhammad ; Ismail, Nor Hadiani ; Zaki, Hamizah Mohd ; Wadood, Abdul ; Anouar, El Hassane ; Imran, Syahrul ; Mohd. Yamin, Bohari ; Rahim, Fazal ; Ali, Muhammad ; Khan, Khalid Mohammed. / 3,4-Dimethoxybenzohydrazide derivatives as antiulcer : Molecular modeling and density functional studies. In: Bioorganic Chemistry. 2017 ; Vol. 75. pp. 235-241.
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