title: New Diethyl Ammonium Salt of Thiobarbituric Acid Derivative: Synthesis, Molecular Structure Investigations and Docking Studies.
abstract: The synthesis of the new diethyl ammonium salt of diethylammonium(E)-5-(1,5-bis(4-fluorophenyl)-3-oxopent-4-en-1-yl)-1,3-diethyl-4,6-dioxo-2-thioxohexaydropyrimidin-5-ide 3 via a regioselective Michael addition of N,N-diethylthiobarbituric acid 1 to dienone 2 is described. In 3, the carboanion of the thiobarbituric moiety is stabilized by the strong intramolecular electron delocalization with the adjacent carbonyl groups and so the reaction proceeds without any cyclization. The molecular structure investigations of 3 were determined by single-crystal X-ray diffraction as well as DFT computations. The theoretically calculated (DFT/B3LYP) geometry agrees well with the crystallographic data. The effect of fluorine replacement by chlorine atoms on the molecular structure aspects were investigated using DFT methods. Calculated electronic spectra showed a bathochromic shift of the π-π* transition when fluorine is replaced by chlorine. Charge decomposition analyses were performed to study possible interaction between the different fragments in the studied systems. Molecular docking simulations examining the inhibitory nature of the compound show an anti-diabetic activity with Pa (probability of activity) value of 0.229.
authors.affiliation: Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia. ambarakat@ksu.edu.sa.|Department of Chemistry, Faculty of Science, Alexandria University, P. O. Box 426, Ibrahimia, Alexandria 21321, Egypt. ambarakat@ksu.edu.sa.
authors.forename: Assem
authors.initials: A
authors.lastname: Barakat
authors.affiliation: Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia. amajid@ksu.edu.sa.
authors.forename: Abdullah Mohammed
authors.initials: AM
authors.lastname: Al-Majid
authors.affiliation: Department of Chemistry, College of Science &amp; Arts, King Abdulaziz University, P. O. Box 344,Rabigh 21911, Saudi Arabia. saied1soliman@yahoo.com.|Department of Chemistry, Faculty of Science, Alexandria University, P. O. Box 426, Ibrahimia, Alexandria 21321, Egypt. saied1soliman@yahoo.com.
authors.forename: Saied M
authors.initials: SM
authors.lastname: Soliman
authors.affiliation: Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, Egypt. lotfygehad@yahoo.com.
authors.forename: Gehad
authors.initials: G
authors.lastname: Lotfy
authors.affiliation: Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P. O. Box 2457, Riyadh 11451, Saudi Arabia. ghabbourh@yahoo.com.
authors.forename: Hazem A
authors.initials: HA
authors.lastname: Ghabbour
authors.affiliation: Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P. O. Box 2457, Riyadh 11451, Saudi Arabia. hfun.c@ksu.edu.sa.|X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, Penang 11800, Malaysia. hfun.c@ksu.edu.sa.
authors.forename: Hoong-Kun
authors.initials: HK
authors.lastname: Fun
authors.affiliation: Department of Biochemistry, Abdul Wali Khan University, Mardan-23200, Pakistan. awadood@awkum.edu.pk.
authors.forename: Abdul
authors.initials: A
authors.lastname: Wadood
authors.affiliation: Department of Chemistry, Science College, Al-Najah National University, P. O. Box 7, Nablus 0097, Palestine. warad@najah.edu.
authors.forename: Ismail
authors.initials: I
authors.lastname: Warad
authors.affiliation: School of Science and Technology, Georgia Gwinnett College, 1000 University Center Lane, Lawrenceville, GA 30043, USA. jsloop@ggc.edu.
authors.forename: Joseph C
authors.initials: JC
authors.lastname: Sloop
mesh_terms: D064751:Ammonium Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008958:Models, Molecular; D062105:Molecular Docking Simulation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012492:Salts / Q000138:chemical synthesis / Q000737:chemistry*; D013858:Thiobarbiturates / Q000737:chemistry*
chemical_list: D064751:Ammonium Compounds; D012492:Salts; D013858:Thiobarbiturates; C029684:thiobarbituric acid
keywords: DFT; barbituric acid; fluorine compound; molecular docking simulations