Synthesis, characterization and antioxidant activity of new dibasic tridentate ligands: X-ray crystal structures of DMSO adducts of 1,3-dimethyl-5-acetyl-barbituric acid o-hydroxybenzoyl hydrazone copper(II) complex

Giziroglu, Emrah; Aygün, Muhıttın; Sarıkürkçü, Cengiz; Kazar, Didem; Orhan, Nil; Fırıncı, Erkan; Söyleyici, Hakan Can; Gokcen, Ceren

doi:10.1016/j.inoche.2013.09.013

Cited by 28 publications

(18 citation statements)

References 44 publications

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“…The 13 C NMR for compound 4 also confirmed the enol form 4C rather than the keto form or the enol form 4B, where 13 C NMR showed peaks at 24.8 (CH 3 ), two peaks at 27.9 and 28.1 for the 2 N-CH 3 , 95.9 (C4=C-OH), 150.5 (C1), 161.0 (C5), 169.5 (acetyl C=O), and 196.2 (C=C3-OH) (Supporting Information Figure S7 in Supplementary Material). This observation is in agreement with the reported data by Sharma et al [38] and Giziroglu et al [39].…”

Section: Resultssupporting

confidence: 94%

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Synthesis, Characterization, and Tautomerism of 1,3-Dimethyl Pyrimidine-2,4,6-Trione s-Triazinyl Hydrazine/Hydrazone Derivatives

Sharma

Jad

Siddiqui

et al. 2017

Journal of Chemistry

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1,3,5-Triazines and pyrimidine-2,4,6-triones belong to that class of compounds which are well known in literature for possessing wide range of biological activities. Here, we report a new family of compounds that encompasses these two structures. The union of both heterocycles was carried out through a hydrazone moiety incorporated into an acetyl group at the position 5 of 1,3-dimethyl pyrimidine derivative. The synthetic strategy adopted allowed the preparation of the target compounds with excellent yields and good purities. The synthesized compounds were well characterized by NMR (1H and 13C), HRMS, and elemental analysis. Furthermore, the tautomerism of enhydrazine versus hydrazone has also been studied.

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Section: Resultssupporting

confidence: 94%

“…In addition, the hydrogen bond in the enhydrazine form stabilizes the structure 5b-B more than the hydrazone isomer 5b-A as shown in Figure 3. This is also in agreement with the reported data for aroylhydrazine derivatives reported by Giziroglu et al [39].…”

Section: Resultssupporting

confidence: 94%

Synthesis, Characterization, and Tautomerism of 1,3-Dimethyl Pyrimidine-2,4,6-Trione s-Triazinyl Hydrazine/Hydrazone Derivatives

Sharma

Jad

Siddiqui

et al. 2017

Journal of Chemistry

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“…The 13 C NMR ( Figure S6, Supplementary Materials) showed peaks at δ = 9.8 and 28.1 for the ethyl group (CH 3 -CH 2 ) and one peak at δ 30.1 for the two methyl (N-CH 3 ), the peak at δ = 95.4 for the C=C-OH, one peak at δ = 150.5 for C1 (C-CO-C), The spectral data did not change except that the peaks at 17.6 became broader. This mean that the enol form is stabilized by strong H-bond, and the obtained results agreed with the reported data for the aroylhydrazone derivatives of 1,3-dimethyl-5-acetylbarbituric acid reported by DaSilva and others [19,20]. Finally, the NMR data obtained explain that this type of compound exists in solution in the enol form and the structure of the enol depends on the type and polarity of the solvent use as it is stabilized by presence of strong intra-molecular hydrogen bond which was further confirmed by X-ray spectroscopy.…”

Section: Nmr Studiessupporting

confidence: 92%

“…Recently, DaSilva et al [19] and Giziroglu et al [20] reported that the acetyl derivative (R = CH 3 ) exist in three tautomeric structures, as indicated in Figure 1. To select the right tautomer for the title compound, 1 H NMR in CDCl 3 , DMSO-d 6 and acetone-d 6 was checked.…”

Section: Nmr Studiesmentioning

confidence: 98%

Synthesis, Crystal Structure and DFT Studies of 1,3-Dimethyl-5-propionylpyrimidine-2,4,6(1H,3H,5H)-trione

et al. 2017

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Novel 1,3-Dimethyl-5-propionylpyrimidine-2,4,6(1H,3H,5H)-trione was synthesized and recrystallized from ethanol. The compound was characterized by 1 H NMR, 13 C NMR in CDCl 3 , DMSO-d 6 and acetone-d 6 , elemental analysis and X-ray diffraction. The NMR data observed that the title compound exists in the enol tautomer rather than keto, and it stabilized by strong H-bond as observed form the NMR data at different temperatures. Theoretical calculations (DFT) were carried out using Gaussian09 program package and B3LYP correlation function. Full geometry optimization of the keto and enol forms were carried out using 6-311G++(d,p) basis set. The structure and energy of the transition state between these two tautomers were calculated. The frontier orbital energy and atomic net atomic charges of the tautomers were presented. The experimental results of the title compound have been compared with the theoretical results and it was found that the experimental data are in a good agreement with the calculated values. The transition state calculations also support the stability of enol form compared to keto form at room temperature.

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“…Since barbituric acid is associated with a number of biological activities and do make a part of anticonvulsant, 12 anti-seizures, 13 anticancer, 14,10d anti-inflammatory, 15 antioxidants, 16 antidiabetic and antibacterial agents; 17 here, we planned to replace pyrazole and indolinone moieties of compounds 1 and 2 with barbituric acid for the design of compound 3. and (S)-10 were screened for the inhibition of COX-1, COX-2 and 5-LOX enzymes. All the enzyme immunoassays were performed as per the kit manufacturer's protocol.…”

Section: Resultsmentioning

confidence: 99%

Triblock Conjugates: Identification of a Highly Potent Antiinflammatory Agent

et al. 2015

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Rationally designed conjugates of chrysin, indole, and barbituric acid were synthesized and screened for their antiinflammatory activities through in vitro and in vivo experiments. Improved over the previously reported chrysin-indole-pyrazole conjugates and also in comparison to the chrysin, indole, and barbituric acid based COX-2 inhibitors, the new compounds have displayed significantly better IC50 for COX-2 and some of them also exhibited inhibition of 5-LOX enzyme. For one of the test compounds, IC50 for COX-2 and 5-LOX was 1 and 1.5 nM, respectively. Investigations of Swiss Albino mice through capsaicin induced paw lickings and dextran induced inflammation showed that these compounds possess appreciable analgesic and antiinflammatory activities. Ki, Ka, and ΔG for the enzyme-compound interaction were calculated and found to be in agreement with the biological data. The experimental results were supported by the molecular docking studies of the compounds in the active site of COX-2 and 5-LOX. Overall, a highly promising antiinflammatory agent was identified.

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Synthesis, characterization and antioxidant activity of new dibasic tridentate ligands: X-ray crystal structures of DMSO adducts of 1,3-dimethyl-5-acetyl-barbituric acid o-hydroxybenzoyl hydrazone copper(II) complex

Cited by 28 publications

References 44 publications

Synthesis, Characterization, and Tautomerism of 1,3-Dimethyl Pyrimidine-2,4,6-Trione s-Triazinyl Hydrazine/Hydrazone Derivatives

Synthesis, Characterization, and Tautomerism of 1,3-Dimethyl Pyrimidine-2,4,6-Trione s-Triazinyl Hydrazine/Hydrazone Derivatives

Synthesis, Crystal Structure and DFT Studies of 1,3-Dimethyl-5-propionylpyrimidine-2,4,6(1H,3H,5H)-trione

Triblock Conjugates: Identification of a Highly Potent Antiinflammatory Agent

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