New tetrahydropyrimidone derivatives with structural modifications of anti-cancer drug, monastrol, were synthesized, and molecular docking study of the interaction with epidermal growth factor ...receptor tyrosine kinase (EGFR-TK) was performed. The substituted aromatic part was derived from benzaldehyde derivatives having hydroxy, methoxy and fluoro substituents at 3,4,5 positions. Structural modifications in monastrol with conversion of methyl group to trifluoromethyl fraction and the sulphur atom in place of oxygen atom are the core of synthesis in this paper. Structural and bonding features of newly synthesized compounds are reported along with molecular docking study with EGFR-TK in comparison to monastrol. Target compounds were synthesized using
p-
toluenesulfonic acid as catalyst. Synthesized compounds show improved binding affinity as compared to monastrol in docking study. ADMET study of all the compounds shows high GI absorption. Single-crystal X-ray study of four derivatives with superposition of the crystal structures is also reported in the study.
A series of novel isoxazol derivatives was synthesized by green route in aqueous phase at room temperature by the reaction of 3-methyl-4H-isoxazol-5-one with 3-(substituted ...phenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde by one-pot Knoevenagel condensation method using sodium benzoate as a catalyst. Compounds were characterized on the basis of IR, 1H NMR, mass spectroscopy and melting point determination. Crystal structures of five compounds were determined by X-ray diffraction. The compounds formed were screened for antibacterial and antifungal activity. Some compounds showed activity close to ampicillin against E. coli, S. aureus, and S. pyogenus. Two compounds showed antifungal activity against C. albicans close to standard greseofulvin.
•Series of novel isoxazole derivatives is synthesized by green route in aqueous phase.•Effect of the catalyst was monitored.•5 new crystal structures are reported with hydrogen bonding and π-π interactions.•Hydrogen bonding diversity was observed in 3-hydroxy and 4-hydroxy derivatives.•Antibacterial and antifungal studies are carried out for all compounds.
Manganese(II) bis(4,4,4-trifluoro-1-phenylbutane-1,3-dionate) complexes with pyridin-4-one (pyon), 3-hydroxypyridin-2-one (hpyon), 1-fluoropyridine (pyF) and methanol were prepared and the ...solid-state structures were determined by single-crystal X-ray analysis. The coordination of the metal center in all complexes was found to be octahedral. In compounds Mn(tfpb)2(pyon)2 (1) and Mn(tfpb)2(hpyon)2 (2) extended hydrogen bonding is present facilitating the formation of a three-dimensional supramolecular structure in 1 and a layered structure in 2 through N–H···O hydrogen bonding enhanced by C–H···O interactions as well as C–F···π interactions. In Mn(tfpb)2(pyF)2 (3) a layered structure is formed through C–H···O and C–H···F interactions as well as π···π and C–F···π interactions. In Mn(tfpb)2(MeOH)2 (4) a layered structure is formed through a combination of O–H···O and C–F···π interactions.
The interaction with erythrocytes of four VVO2L2− complexes, with L = picolinate (pic), 5-cyanopicolinate (picCN), 3-aminopyrazine-2-carboxylate (przNH2), and ...1,2-dimethyl-3-hydroxy-4(1H)-pyridinonate (dhp), was studied. The thermodynamic stability at physiological pH is: VVO2(dhp)2− > VVO2(przNH2)2− > VVO2(pic)2− > VVO2(picCN)2−. With picCN and pic, V exists at physiological pH as H2VVO4 –, with przNH2 as a mixture of H2VVO4 – and VVO2(przNH2)2− and with dhp as VVO2(dhp)2−. In the systems with pic and picCN, H2VVO4 – and the ligands cross the erythrocyte membrane independently, with dhp the uptake occurs by diffusion, whereas with przNH2 both the mechanisms are active. Inside erythrocytes stable VIVOL2 complexes are formed, indicating that there is no relationship with the stability and redox state of the administered compounds and that, if the metal ion changes its oxidation state in the cytosol as V does, unstable complexes in the extracellular medium could become stable inside the cells and contribute to the pharmacological action.
A series of hexa(heteroaryl)benzenes were synthesized by the Ru(II)–carboxylate-catalyzed multiple C–H activation of benzenes carrying pyridyl, pyrimidyl, or pyrazolyl directing groups using ...N-heteroaryl bromides as coupling partners. The reactions proceeded with high selectivity under microwave irradiation in water. Iterative penta-arylation could be implemented via activation of C–H bonds of generated intermediates by cascade chelation assistance of in situ installed pyridyl groups. This strategy provides multidentate ligands for selective complexation of transition metals and potential building of photoredox systems.
This article analyzes the treatment of chemical elements in six general monolingual explanatory dictionaries. Two approaches are observed with respect to the formation of headword lists: either a ...complete set of chemical elements is included or only a selection according to the frequency in general language usage. The inventory of hypernyms used as genus words and the degree of systematicity in their usage are presented. Chemical elements represent a reasonable number of lexical units of the same semantic group, therefore a high degree of systematicity of definitions in dictionaries is expected; however, we can only partially confirm this. The use of terminological labels varies greatly from one dictionary to another: in some dictionaries they are not used at all, in others they are used only partially, and in some they are always used. In the case of polysemic entries, one dictionary uses sense indicators.
In this paper, the microwave (MW)-assisted catalyst-free and mostly solvent-free Kabachnik-Fields reaction of amino alcohols, paraformaldehyde, and various >P(O)H reagents (dialkyl phosphites, ethyl ...phenyl-
-phosphinate, and secondary phosphine oxides) is reported. The synthesis of
-2-hydroxyethyl-α-aminophosphonate derivatives was optimized in respect of the temperature, the reaction time, and the molar ratio of the starting materials. A few by-products were also identified.
,
-Bis(phosphinoylmethyl)amines containing a hydroxyethyl group were also prepared by the double Kabachnik-Fields reaction of ethanolamine with an excess of paraformaldehyde and secondary phosphine oxides. The crystal structure of a 2-hydroxyethyl-α-aminophosphine oxide and a bis(phosphinoylmethyl)ethanolamine was studied by X-ray analysis.
Self-assembly of AgOTf and AgF with the hexatopic ligands hexakis(pyridin-2-yl)benzene (2) and 2,4,6-tris(pyridin-2-yl)-1,3,5-tris(quinolin-2-yl)benzene (3) affords the discrete sandwich-shaped ...complexes Ag4F(2)2(OTf)3, Ag4F(3)2(OTf)3, and Ag5F(2)2(OTf)4. The solid-state structures of the complexes were characterized by single-crystal X-ray diffraction analysis, which revealed that the fluoride anion is coordinated in the center of the Ag4-square or Ag5-pentagon units which are positioned between two molecules of the hexakis(azaheteroaryl)benzene. The generation of complexes is dictated by a unique cooperation of ligand coordination, argentophilicity, and fluoride anion inclusion. All three complexes adopt highly symmetrical structures in solution, as evidenced by appearance of one set of proton resonances for the two ligands arranged face to face.
Dear readers of Acta Chimica Slovenica, In this year Acta Chimica Slovenica, the journal published by Slovenian Chemical Society, is celebrating 70th anniversary.
Silver(I) complexes with aza-oxa macrocyclic Schiff bases L (L = 1,5-diaza-2,4:7,8:16,17-tribenzo-9,15-dioxa-cyclooctadeca-1,5-dien) were prepared by the reaction of the corresponding macrocycle with ...four different silver salts (AgX; X = ClO4, PF6, SbF6 and BF4). In all four compounds, silver ions are exo-coordinated by two neighboring ligand molecules in linear and T-shaped geometries. Such a coordination mode results in the formation of infinite 1D polymeric chains. Compounds AgLClO4 and AgLBF4 are isostructural, and polymeric chains display 1D zigzag topology. In AgLPF6 there are three symmetrically unique Ag ions in the asymmetric unit of the compound. Two silver ions are linearly coordinated with two neighboring ligand molecules and are part of a discrete polymer chain. The third silver ion is coordinated with two ligand molecules and a methanol molecule in a T-shaped geometry. Such coordination geometry results in the formation of two discrete infinite polymer chains in the crystal structure. In the AgLSbF6 compound, the chain topology is a linear zigzag chain, but in this compound, there is a difference in the orientation of the Ag-N bond. The Ag-N-Ag bonds are in the trans position relative to the plane calculated through the ligand molecule, while the Ag-N bonds are in the cis position in all other compounds. Due to the presence of a bulky SbF6 anion, the ligand molecule is planar compared to other compounds. Considering intermolecular interactions, there is a huge variety of different interactions, mostly depending on the type of anion. A general supramolecular motif in all compounds is best described as 2D sheets of ligand–metal polymers with anions and solvent molecules sandwiched between them. In addition, the obtained compounds were characterized by IR spectroscopy and thermal analysis. The TG analysis indicates a rather surprising and considerable thermal stability of the prepared compounds, with some compounds thermally stable over 300 °C.
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