title: Synthesis, X-ray Single Crystal Structure, Molecular Docking and DFT Computations on N-[(1E)-1-(2H-1,3-Benzodioxol-5-yl)-3-(1H-imidazol-1-yl)propylidene]-hydroxylamine: A New Potential Antifungal Agent Precursor.
abstract: Mycoses are serious health problem, especially in immunocompromised individuals. A new imidazole-bearing compound containing an oxime functionality was synthesized and characterized with different spectroscopic techniques to be used for the preparation of new antifungal agents. The stereochemistry of the oxime double bond was unequivocally determined via the single crystal X-ray technique. The title compound4, C13H13N₃O₃·C₃H₈O, crystallizes in the monoclinic space groupP2₁witha= 9.0963(3) Å,b= 14.7244(6) Å,c= 10.7035(4) Å, β = 94.298 (3)°,V= 1429.57(9) Å³,Z= 2. The molecules were packed in the crystal structure by eight intermolecular hydrogen bond interactions. A comprehensive spectral analysis of the title molecule4has been performed based on the scaled quantum mechanical (SQM) force field obtained by density-functional theory (DFT) calculations. A molecular docking study illustrated the binding mode of the title compound4into its target protein. The preliminary antifungal activity of the title compound4was determined using a broth microdilution assay.
authors.affiliation: Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia. ralwabli@KSU.EDU.SA.
authors.forename: Reem I
authors.initials: RI
authors.lastname: Al-Wabli
authors.affiliation: Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia. toto24se@hotmail.com.
authors.forename: Alwah R
authors.initials: AR
authors.lastname: Al-Ghamdi
authors.affiliation: Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia. ghabbourh@yahoo.com.|Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt. ghabbourh@yahoo.com.
authors.forename: Hazem A
authors.initials: HA
authors.lastname: Ghabbour
authors.affiliation: Department of Pharmaceutics, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia. malagamy@ksu.edu.sa.|Microbiology and Immunology Department, Faculty of Pharmacy, Al-Azhar University, Cairo 11884, Egypt. malagamy@ksu.edu.sa.
authors.forename: Mohamed H
authors.initials: MH
authors.lastname: Al-Agamy
authors.affiliation: Muslim Arts College, Thiruvithancode 629174, Tamil Nadu, India. clemymonicka@gmail.com.
authors.forename: James Clemy
authors.initials: JC
authors.lastname: Monicka
authors.affiliation: Centre for Molecular and Biophysics Research, Mar Ivanios College, Thiruvananthapuram 695015, Kerala, India. hubertjoe@gmail.com.
authors.forename: Issac Hubert
authors.initials: IH
authors.lastname: Joe
authors.affiliation: Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia. mattia@ksu.edu.sa.|Medicinal and Pharmaceutical Chemistry Department, Pharmaceutical and Drug Industries Research Division, National Research Centre (ID: 60014618), El Bohooth Street, Dokki, Giza 12622, Egypt. mattia@ksu.edu.sa.
authors.forename: Mohamed I
authors.initials: MI
authors.lastname: Attia
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D006898:Hydroxylamines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008958:Models, Molecular; D062105:Molecular Docking Simulation; D011789:Quantum Theory
chemical_list: D000935:Antifungal Agents; D006898:Hydroxylamines; D007093:Imidazoles; C029899:imidazole
keywords: DFT; benzodioxole; crystal structure; imidazole; oxime