18957-56-7Relevant academic research and scientific papers
Close insight into the nature of intermolecular interactions in dihydropyrimidine-2(1H)-thione derivatives
Saeed, Aamer,Fl?rke, Ulrich,Fantoni, Adolfo,Khurshid, Asma,Pérez, Hiram,Erben, Mauricio F.
, p. 1495 - 1508 (2017)
The crystal structures of four 1-(R-phenyl)-4,4,6-trimethyl-3,4-dihydropyrimidine-2(1H)-thione derivatives [R = 2-chloro (1), 2,3-di-chloro (2), 2,4-di-methyl (3), and 4-methoxy (4)] were determined and analysis of their molecular conformations was carried out. A comparative study of the intermolecular interactions—including eight closely related structures from CSD—was performed and the degree of isostructurality was quantified. The intermolecular interactions were characterized in terms of the periodic system electron density and the topological analysis highlighted the role of N-H?S=C hydrogen bonds in the stabilization of the different supramolecular architectures. PIXEL lattice energy calculations revealed that the dispersion component was the major contributor, together with the important role of the Coulombic term to the total energy. The interaction energies for molecular pairs involving N-H?S=C hydrogen bonds indicated a dominant contribution to packing stabilization coming from the Coulombic components. Hirshfeld surfaces and fingerprint plots allowed us to visualize different intermolecular contacts and their relative contributions to the total surface for each compound. Analysis of the electrostatic potentials (ESP) correlated well with the computed energies, thus characterizing the strengths of the different interactions.
New Substituted 1-Aryl-4,4,6-Trimethyl-3,4-Dihydropyrimidine-2-(1H)Thiones; A Metal-Free and Solvent-Free Synthesis, Characterization, and Lymphoid Tyrosine Phosphatase Inhibition Studies
Khurshid, Asma,Saeed, Aamer
, p. 224 - 230 (2017/02/23)
A series of fourteen 3,4-dihydropyrimidine-2-thiones (3a–n) were synthesized by a green protocol, and their structures were characterized by spectroanalytical data. The compounds were obtained in high yields by efficient annulation of mesityl oxide (4-methylpent-3-en-2-one) with anilines in the presence of potassium thiocyanate. The reaction is essentially metal-catalyst- and solvent-free, as mesityl oxide itself is the solvent as well as the reactant. The compounds were tested for their ability to inhibit the lymphoid tyrosine phosphatase PTPN22, and 5 of the 14 compounds exhibited IC50 values in the mid-micromolar range, with the most potent hit being the compound 3d, having a methoxy substituent at the 2-position of the phenyl ring with an IC50 = 18 ± 1 μM, and second most potent compound (3c) with an IC50 value of 45 ± 3 μM, having methyl substituents at both 2- and 4-position of the phenyl ring.
