Crystal structure of propylthiouracil determined using high-resolution synchrotron X-ray powder diffraction

Ferreira, Fábio Furlan; Trindade, Antonio Carlos; Antônio, Selma Gutierrez; Paiva‐Santos, Carlos de Oliveira

doi:10.1039/c1ce05362k

Cited by 31 publications

(26 citation statements)

References 26 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Ni(II) complexes, containing benzoylthiourea ligands, have shown cytotoxicity against T47D cell [15] and according to the investigations water soluble platinum(II) benzoylthiourea complexes have shown considerable antimalarial activity [23,24]. Very recently, there have been many studies on noncovalent interactions acting on the crystal structure and packing of sulfur-containing compounds [25]. Hydrogen bonds are generally dominant in the crystal packing of acyl thiourea compounds, mostly determined to be both, N-H⋯O=C and N-H⋯S=C interactions [26,27].…”

Section: N-(alkyl/aryl)-n'-acylthiourea and N-di(alkyl/aryl)-n´-mentioning

confidence: 99%

N-(Dibenzylcarbamothioyl)-3-methylbutanamide: Crystal structure, Hirshfeld surfaces and antimicrobial activity

et al. 2017

View full text Add to dashboard Cite

The compound N-(dibenzylcarbamothioyl)-3-methylbutanamide as a thiourea derivative was synthesized and structurally characterized by NMR and FT-IR spectroscopic techniques. The molecular structure of compound was also characterized by single crystal X-ray diffraction method. Crystal data for title compound C20H24N2OS: monoclinic, space group C2/c (no. 15), a = 19.6882(9) Å, b = 9.4045(4) Å, c = 19.5012(8) Å, β = 98.433(2)°, V = 3571.8(3) Å3, Z = 8, μ(CuKα) = 1.665 mm-1, 25057 reflections measured (9.168° ≤ 2Θ ≤ 144.196°), 3500 unique (Rint = 0.0322, Rsigma = 0.0200) which were used in all calculations. The final R1 was 0.0363 (I>2σ(I)) and wR2 was 0.0910 (all data). Intermolecular contacts obtained from X-ray single crystal diffraction study were also explored using both Hirshfeld surfaces and fingerprint plots. Hirshfeld surface analysis showed the occurrence of S···H, O···H and H···H contacts that display an important role to crystal packing stabilization of the thiourea derivative compound. In addition, the compound was evaluated for both their in-vitro antibacterial and antifungal activity.

show abstract

Section: N-(alkyl/aryl)-n'-acylthiourea and N-di(alkyl/aryl)-n´-mentioning

confidence: 99%

N-(Dibenzylcarbamothioyl)-3-methylbutanamide: Crystal structure, Hirshfeld surfaces and antimicrobial activity

et al. 2017

View full text Add to dashboard Cite

show abstract

“…[64][65][66][67] The hydrogen atoms were introduced into calculated positions considering the orbital geometry using the Mercury soware program 68 and their B iso values were constrained to be 1.2 times the value of the respective atoms to which they are connected. [64][65][66][67] The hydrogen atoms were introduced into calculated positions considering the orbital geometry using the Mercury soware program 68 and their B iso values were constrained to be 1.2 times the value of the respective atoms to which they are connected.…”

Section: Resultsmentioning

confidence: 99%

Structural feature evolution – from fluids to the solid phase – and crystal morphology study of LASSBio 1601: a cyclohexyl-N-acylhydrazone derivative

Costa

Silva

et al. 2015

RSC Adv.

Self Cite

View full text Add to dashboard Cite

LASSBio-1601, a cyclohexyl-N-acylhydrazone derivative, was synthesized as part of a research program to develop a series of anti-inflammatory and analgesic compounds. A complete knowledge of the structure, including stereochemistry, is essential to lead optimization in drug discovery. In this work different techniques were used to obtain detailed information on the evolution of the structural characteristics of this compound from fluids to the solid state, in order to shed some light on the conformation of the molecule in different physical states. By quoting the aforementioned structural analysis, a crystal morphology prediction, compared with the experimentally inferred SEM images, has been performed to analyze potentially alternative routes useful for pharmaceutical tableting.

show abstract

“…The self-association takes place via a pair of N-HÁ Á ÁO hydrogen bonds and forms an R 2 2 (8) motif which involves the pyrimidine ring N1/N3 atom and the carbonyl/thiocarbonyl O2 or S2/O4/O6 atom of the derivatives of nucleobases (T/U/BA/TBA). (Liu et al, 2004;Freisinger et al, 2001;Ferreira et al, 2011), where the motif involves N3-H and C O4 atoms of the pyrimidine residue in the self-association. In addition, compound (I) also forms a type IV motif as in the reported TBA structures (Chierotti et al, 2010) by utilizing its N1-H and C O6 atoms to form its self-associated pairs.…”

Section: Comparative Analysismentioning

confidence: 99%

Hydrogen bonding patterns in salts of derivatives of aminopyrimidine and thiobarbituric acid

Gomathi

Nirmalram

Muthiah

2015

Acta Crystallogr Sect B

View full text Add to dashboard Cite

Three salts, namely 2-amino-4,6-dimethylpyrimidin-1-ium thiobarbiturate trihydrate (I), 2-amino-4,6-dimethoxypyrimidin-1-ium thiobarbiturate dihydrate (II) and 2,4-diamino-5-(3',4',5'-trimethoxybenzyl)pyrimidin-1-ium thiobarbiturate (III), were synthesized and characterized by IR and X-ray diffraction techniques. The primary interaction between the acid and base happens via N-H...O hydrogen bonds in (II) and (III), and via water-mediated N-H...OW and OW-HW...S in (I). The water molecules present in compound (I) form a (H2O)12 water cluster via water-water interactions. In all three compounds (I)-(III), thiobarbiturate anions form self-complementary pairs with a robust R2(2)(8) motif via a pair of N-H...O/N-H...S hydrogen bonds. They mimic the nucleobase base pairs by utilizing the same groups (thymine/uracil uses N3-H and C4=O8 groups during the formation of Watson-Crick and Hoogsteen base pairs with adenine). Compound (I) forms a water-mediated base pair through N-H...OW hydrogen bonds and forms an R4(2)(12) motif. The formation of N-H...S hydrogen bonds, water-mediated base pairs and water-water interactions in these crystal systems offers scope for these systems to be considered as a model in the study of hydration of nucleobases and water-mediated nucleobase base pairs in macromolecules.

show abstract

Crystal structure of propylthiouracil determined using high-resolution synchrotron X-ray powder diffraction

Cited by 31 publications

References 26 publications

N-(Dibenzylcarbamothioyl)-3-methylbutanamide: Crystal structure, Hirshfeld surfaces and antimicrobial activity

N-(Dibenzylcarbamothioyl)-3-methylbutanamide: Crystal structure, Hirshfeld surfaces and antimicrobial activity

Structural feature evolution – from fluids to the solid phase – and crystal morphology study of LASSBio 1601: a cyclohexyl-N-acylhydrazone derivative

Hydrogen bonding patterns in salts of derivatives of aminopyrimidine and thiobarbituric acid

Contact Info

Product

Resources

About