Tropical Journal of Pharmaceutical Research

Original Research Article | OPEN ACCESS

X-ray molecular structure of ({[(1E)-3-(1H-Imidazol-1-yl)-1-phenylpropylidene]amino} oxy)(3,4,5-trimethoxyphenyl)methanone: A potential anti-candida agent

Maha S Almutairi¹, Hazem A Ghabbour^1,2, Soraya W Ghoneim¹, Hoong-Kun Fun^1,3, Mohamed I Attia^1,4

¹Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia; ²Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt; ³X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, Penang 11800, Malaysia,; ⁴Medicinal and Pharmaceutical Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre, Dokki, Giza 12622, Egypt.

For correspondence:- Mohamed Attia Email: mattia@ksu.edu.sa Tel:+966114677337

Received: 13 June 2015 Accepted: 25 September 2015 Published: 29 November 2015

Citation: Almutairi MS, Ghabbour HA, Ghoneim SW, Fun H, Attia MI. X-ray molecular structure of ({[(1E)-3-(1H-Imidazol-1-yl)-1-phenylpropylidene]amino} oxy)(3,4,5-trimethoxyphenyl)methanone: A potential anti-candida agent. Trop J Pharm Res 2015; 14(11):2041-2046 doi: 10.4314/tjpr.v14i10.13

© 2015 The authors.
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Abstract

Purpose: To elucidate the solid-state conformation as well as the imine double bond configuration of a potential anti-Candida agent ({[(1E)-3-(1H-imidazol-1-yl)-1-phenylpropylidene]amino}oxy)(3,4,5-trimethoxyphenyl)methanone.

Methods: Acetophenone was used as a starting material to prepare the target oximino ester in a four-step reaction sequence. Nuclear magnetic resonance (¹H-NMR and ¹³C-NMR) and mass spectrometry were used to confirm the chemical structure of the synthesized compounds. Thereafter, x-ray crystallography was performed on single crystals of the target compound. The solid-state conformation of the target molecule and the (E)-configuration of its imine double bond were determined via the investigation of its single crystal x-ray molecular structure.

Results: The titled compound crystallized in the triclinic space group P-1 with a = 11.0719 (7) Å, b = 14.6602 (9) Å, c = 14.8530 (9) Å, α = 67.205 (4)°, β = 80.388 (5)º, γ = 70.100 (5)°, V = 2088.2 (2) Å³, and Z = 4. Individual molecules were packed in the crystal by three weak non-classical intermolecular hydrogen interactions, including C9A—H9AA•••O3A, C9B—H9BA•••O3B, C18B—H18C•••O2A and C20B—H20B•••O4B.

Conclusion:The results of the single crystal x-ray molecular structure of the titled anti-Candida agent unequivocally confirmed its (E)-configuration.

Keywords: Molecular structure, X-ray crystallography, Synthesis, Azole, Anti-Candida