5-Propyl-6-(p-tolylsulfanyl)pyrimidine-2,4(1H,3H)-dione

Al-Omary, Fatmah A. M.; Ghabbour, Hazem A.; El-Emam, Ali A.; Kumar, C. S. Chidan; Fun, Hoong‐Kun

doi:10.1107/s1600536814000749

Cited by 4 publications

(5 citation statements)

References 15 publications

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“…The heterocycle containing the structural unit CON 2 H 2 CO forms a dihedral of 77.81 (10)° with the adjacent benzene ring. Bond lengths and angles in (I) show normal values (Allen et al, 1987) and are comparable with those in related structures (Al-Omary et al, 2014;El-Brollosy et al, 2011;Wang et al, 2006) (Table 1) hydrogen bonds link the two adjacent molecules into centrosymmetric inversion related dimers incorparating R 2 1 (9) and R 2 2 (8) loops (Fig. 2, Bernstein et al, 1995).…”

Section: Data Collectionsupporting

confidence: 70%

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

et al. 2014

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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.

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Section: Data Collectionsupporting

confidence: 70%

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

et al. 2014

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“…The result suggests that crystals 1 and 2 show a 2D supramolecular construct (SC; the layer of molecules match) among these three molecules (Figure S4, Supporting Information). Crystals 1 and 2 also share 0D SC (dimer with N3–H3···O4 hydrogen bond) with the closely related structure 6-((4-methylphenyl)sulfanyl)-5-propylpyrimidine-2,4(1 H ,3 H )-dione …”

Section: Resultsmentioning

confidence: 95%

“…This compound packed in a columnar manner with a herringbone feature when projected onto the crystallographic a axis, and the other two compounds display a columnar packing. However, the relative geometric conformation and positions of molecules in the solid state show invariant and variable 80 Lattice Energies and Energy Frameworks. The total lattice energies (E tot ) for crystals 1−3 were calculated using the PIXELC code.…”

Section: ■ Introductionmentioning

confidence: 99%

Invariant and Variable Supramolecular Self-Assembly in 6-Substituted Uracil Derivatives: Insights from X-ray Structures and Quantum Chemical Study

Al-Wahaibi

Bysani

Tawfik

et al. 2021

Crystal Growth & Design

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In this study, three new 6-(arylthio)uracil derivatives, namely, 6-(phenylthio)pyrimidine-2,4(1H,3H)-dione (1), C 10 H 8 N 2 O 2 S; 6-(p-tolylthio)pyrimidine-2,4(1H,3H)-dione (2), C 11 H 10 N 2 O 2 S; and 6-(3,5-dimethylphenylthio)pyrimidine-2,4-(1H,3H)-dione (3), C 12 H 12 N 2 O 2 S, have been synthesized. Singlecrystal structures of these compounds reveal an invariant molecular tape contains alternate R 2 2 (8) synthons formed by N−H•••O hydrogen bonds in 1 and 3. This alternate hydrogen-bonded pattern disappeared in 2; instead, a new synthon is generated. The lattice energy calculation suggests that the methyl-substituted derivatives (2 and 3) have high stabilization energy than compound 1. The electrostatic potential map reveals the difference in the accepting tendency of the carbonyl oxygen. The Hirshfeld surface and 2D-fingerprint plots analyses demonstrate that the major intermolecular interactions come from H•••O contacts in 1, and these contacts were reduced due to the presence of methyl substitutions in 2 and 3. This reduction is compensated by the increase of the same amount of H•••H contacts in these structures. Further, the PIXEL energy and DFT calculations at the M06-2X-D3/cc-pVTZ level of theory were used to characterize the dimeric topology formed in structures of 1−3. The intermolecular interaction energies of dimers calculated by the PIXEL method were compared with the B97D3/def2-TZVP level of approximation. Although these molecules' crystal packing is somewhat different, the energy frameworks show similarities on the respective crystal structure's shortest axis. Furthermore, the nature and strength of various noncovalent interactions such as N−H•••O, C−H•••O/S/π, π•••π, and a chalcogen bond of type C−S•••OC were evaluated using the Bader's quantum theory of atoms-in-molecules framework.

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“…In addition, potent anticancer [7][8][9][10] and antimicrobial activities [11,12] was observed for several pyrimidine-2,4-diones. In continuation to our interest in the chemical and pharmacological properties of pyrimidine and uracil derivatives [13][14][15][16] we synthesized the title compound as potential chemotherapeutic agent. X-ray crystallography is a decisive analytical tool which can confirm the configuration of compounds.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of 6-(phenylsulfanyl)-5-propylpyrimidine-2,4(1H,3H)- dione, C13H14N2O2S

Al-Omary

Ghabbour

Attia

et al. 2015

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialA mixture of 6-chloro-5-propyluracil (943 mg, 5 mmol), thiophenol (551 mg, 5 mmol) and potassium hydroxide (281 mg, 5 mmol), in ethanol (10 mL), was heated under reflux for three hours. DiscussionPyrimidine-2,4(1H,3H)-dione (uracil) is an important pharmacophore found in many chemotherapeutic agents. The chemotherapeutic efficacy of uracil and pyrimidine derivatives is related to their ability to inhibit vital enzymes responsible for DNA biosynthesis such as dihydrofolate reductase (DHFR), thymidylate synthetase (TSase), thymidine phosphorylase (TPase) and reverse transcriptase (RTase). Pyrimidine-2,4-diones and their related derivatives have long been known for their diverse chemotherapeutic activities including antiviral activity against HIV [1][2][3][4][5] and HSV viruses [6]. In addition, potent anticancer [7-10] and antimicrobial activities [11,12] was observed for several pyrimidine-2,4-diones. In continuation to our interest in the chemical and pharmacological properties of pyrimidine and uracil derivatives [13][14][15][16] we synthesized the title compound as potential chemotherapeutic agent. X-ray crystallography is a decisive analytical tool which can confirm the configuration of compounds. Fortunately, we have succeeded to get single crystals of the title compound which were suitable for X-ray crystallography. The crystal structure of title compound contains two crystallographic independant molecules in the asymmetric unit. The two sixmembered rings in both molecules are nearly planar. The dihedral angles between the six-membered rings are 67.36(10)°and 83.57(11)°for the second molecule in the unit cell. The molecules are twisted about the C pyrimidine-S bond, with a C6-S1-C7-N2 torsion angle of 22.23(16)°and C6A-S1A-C7A-N2A torsion angle of -59.23(15)°in the second molecule. The molecules packing in the crystal structure is stabilized by three intermolecular hydrogen bonds, of which O1A, O1 and O2 work as hydrogen bond acceptors and N1A, N1 and C5 work as hydrogen bond donors. The distance of the interactions between N1A-H1AB×××O1A is 2.11(1) Å, N1-H1B×××O1 is 2.00(1) Å and C5-H5A×××O2 is 2.49(1) Å and the angles are 164°, 172°, 140°, respectively.

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5-Propyl-6-(p-tolylsulfanyl)pyrimidine-2,4(1H,3H)-dione

Cited by 4 publications

References 15 publications

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

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

Invariant and Variable Supramolecular Self-Assembly in 6-Substituted Uracil Derivatives: Insights from X-ray Structures and Quantum Chemical Study

Crystal structure of 6-(phenylsulfanyl)-5-propylpyrimidine-2,4(1H,3H)- dione, C13H14N2O2S

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