6-[(2-Methylphenyl)sulfanyl]-5-propylpyrimidine-2,4(1H,3H)-dione

Abstract

In the title pyrimidine-2,4-dione derivative, C14H16N2O2S, the dihedral angle between the six-membered rings is 77.81 (10)°. The mol­ecule is twisted about the Cp—S (p = pyrimidine) bond, with a C—S—C—N torsion angle of −59.01 (17)°. An intramolecular C—H⋯S hydrogen bond generates an S(5) ring motif. In the crystal, bifurcated acceptor N—H⋯O and C—H⋯O hydrogen bonds generate inversion-related dimers incorporating R 2 1(9) and R 2 2(8) loops. These dimers are connected into a chain extending along the a-axis direction by a second pair of inversion-related N—H⋯O hydrogen bonds, forming another R 2 2(8) loop. The crystal structure is further stabilized by weak inter­molecular C—H⋯π inter­actions, generating a three-dimensional network.

Molecular structure, vibrational spectra, NBO, Fukui function, HOMO-LUMO analysis and molecular docking study of 6-[(2-methylphenyl)sulfanyl]-5-propylpyrimidine-2,4(1H,3H)-dione

“…: 210-212 °C. The structure of the title compound was established by 1 H NMR, 13 C NMR and single crystal X-ray diffraction [36]. 1 H NMR (DMSO-d 6 , 500.13 MHz):  0.84 (t, 3H, CH 2 CH 3 , J = 7.0 Hz), 1.37-1.40 (m, 2H, CH 2 CH 3 ), 2.33 (s, 3H, Ar-CH 3 ), 2.43 (t, 2H, CH 2 CH 2 CH 3 , J = 7.0 Hz), 6.92-7.02 (m, 3H, Ar-H), 7.26-7.28 (m, 1H, Ar-H), 10.91 (s, 1H, NH), 11.24 (s, 1H, NH).…”

“…The optimized molecular geometry of the title compound was obtained from the Gaussian 03W program with the atom numbering scheme shown in Figure 1. The comparative optimized structural parameters such as bond length, bond angle along with its experimental data [36] are presented in Table 1. The most optimized geometry is performed at the B3LYP /6-311++G(d, P) basis set of the title molecule.…”

“…1-[(2-Hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) and its related analogues [26][27][28][29] were discovered as potent and selectively active agents against HIV-1 infections. In continuation of our ongoing interest in the pharmacological and structural properties of pyrimidine and uracil derivatives [3,4,17,18,[30][31][32][33][34][35], we synthesized the title compound as the more lipophilic 5-propyl HEPT analog for evaluation as a potential chemotherapeutic agent [36].…”

Crystal structure of 6-chloro-5-isopropylpyrimidine-2,4(1H,3H)-dione

“…For the use of 5-alkyl-6chloropyrimidine-2,4(1H,3H)-diones in synthesis, see: El-Emam et al (2004). For related pyrimidine-2,4-dione structures, see: El-Brollosy et al (2011); Al-Omary et al (2014); Haress et al (2014). For the synthesis of the title compound, see: Al-Turkistani et al (2011); Koroniak et al (1993).…”

“…In addition, potent anticancer activity was observed for several pyrimidine-2,4-diones (Klein et al, 2001;Nencka et al, 2006). In a continuation of our interest in the chemical and pharmacological properties of pyrimidine and uracil derivatives (Al-Omary et al, 2014;Haress et al, 2014, El-Brollosy et al, 2009, we have synthesized the title compound (I) as a precursor to the synthesis of a potential chemotherapeutic agent (Al-Turkistani et al, 2011).…”