In vitro anti-Candida activity and single crystal X-ray structure of ({(1E)-[3-(1H-imidazol-1-yl)-1-phenylpropylidene]amino}oxy)(4-nitrophenyl)methanone

  • Mohamed I. Attia Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia; and Medicinal and Pharmaceutical Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, 12622, Dokki, Giza, Egypt
  • Hazem A. Ghabbour Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh
  • Azza S. Zakaria Department of Pharmaceutics, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia Riyadh 11451, Saudi Arabia; and Department of Microbiology, Faculty of Pharmacy, Alexandria University, Alexandria, Egypt.
  • Hoong-Kun Fun Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh
Keywords: Anti-Candida, Azoles, X-ray

Abstract

Synthesis, characterization, and anti-Candida activity of ({(E)-[3-(1H-imidazol-1-yl)-1-phenylpropylidene]amino}oxy)(4-nitrophenyl)methanone (4) are reported. Compound 4 showed anti-Candida albicans activity (MIC = 0.6862 µmol/mL) being nearly 5-fold more potent than the gold standard antifungal drug, fluconazole (MIC ˃ 3.265 µmol/mL), on the clinical isolates of Candida albicans. Single crystal X-ray structure of the title compound 4 confirmed its assigned (E)-configuration. The compound crystallizes in the triclinic, P-1 (no. 2), a = 6.4633 (1) Å, b = 11.1063 (2) Å, c = 12.9872 (2) Å, α = 67.650 (1)°, β = 86.415 (1)°, γ = 86.776 (1)°, V = 860.01 (3)Å3, Z = 2, R(F) = 0.046, wR(F2) = 0.139, T = 296 K. The crystal structure is stabilized by weak intermolecular C—H•••O hydrogen interactions.

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Published
2014-01-27
How to Cite
Attia, M., H. Ghabbour, A. Zakaria, and H.-K. Fun. “In Vitro Anti-Candida Activity and Single Crystal X-Ray Structure of ({(1E)-[3-(1H-Imidazol-1-Yl)-1-Phenylpropylidene]amino}oxy)(4-Nitrophenyl)methanone”. Bangladesh Journal of Pharmacology, Vol. 9, no. 1, Jan. 2014, pp. 43-48, doi:10.3329/bjp.v9i1.16990.
Section
Research Articles