Synthesis and structure of new 1-cyanoacetyl-4-arylsemicarbazide derivatives with potential anticancer activity

Pitucha, Monika; Sobótka-Polska, Karolina; Pachuta‐Stec, Anna; Mendyk, Ewaryst; Kaczor, Agnieszka A.

doi:10.1016/j.molstruc.2015.09.025

Cited by 6 publications

(2 citation statements)

References 28 publications

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“…NCI maps of ligand-receptor interactions were computed with NCIPlot v. 3.0 [60] at the distance below 4 Å from the ligand and visualized with VMD v. 1.9.1, [61] as reported earlier. [62] 4.4 | In vivo behavioral tests…”

Section: Molecular Dockingmentioning

confidence: 99%

Synthesis, docking studies, and pharmacological evaluation of 2‐hydroxypropyl‐4‐arylpiperazine derivatives as serotoninergic ligands

Magli

Kędzierska

Kaczor

et al. 2021

Archiv der Pharmazie

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A new series of norbornene and exo-N-hydroxy-7-oxabicyclo[2.2.1]hept-5-ene-2,3dicarboximide derivatives was prepared, and their affinities to the 5-HT 1A , 5-HT 2A , and 5-HT 2C receptors were evaluated and compared with a previously synthesized series of derivatives characterized by the same nuclei, to identify selective ligands for the subtype receptors. Arylpiperazines represent one of the most important classes of 5-HT 1A R ligands, and the research of new derivatives has been focused on the modification of one or more portions of this pharmacophore. The combination of structural elements (heterocyclic nucleus, hydroxyalkyl chain, and 4-substituted piperazine), known to be critical for the affinity to 5-HT 1A receptors, and the proper selection of substituents resulted in compounds with high specificity and affinity toward serotoninergic receptors. The most active compounds were selected for further in vivo assays to determine their functional activity. Finally, to rationalize the obtained results, molecular docking studies were performed. The results of the pharmacological studies showed that 3e, 4j, and 4n were the most active and promising derivatives for the serotonin receptor considered in this study.

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Section: Molecular Dockingmentioning

confidence: 99%

Synthesis, docking studies, and pharmacological evaluation of 2‐hydroxypropyl‐4‐arylpiperazine derivatives as serotoninergic ligands

Magli

Kędzierska

Kaczor

et al. 2021

Archiv der Pharmazie

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“…The computed IR spectra were corrected using the scaling factor of 0.962 as recommended for this level of theory [24]. Moreover, the computed vibrational frequencies have been unambiguously assigned by means of the potential energy distribution (PED) analysis of all the fundamental vibration modes by using VEDA 4 program [25,26] as described previously [27][28][29][30].…”

Section: Computational Studiesmentioning

confidence: 99%

Thermal and spectroscopic studies of 2,3,5-trisubstituted and 1,2,3,5-tetrasubstituted indoles as non-competitive antagonists of GluK1/GluK2 receptors

Bartyzel

Kaczor

Głuchowska

et al. 2018

J Therm Anal Calorim

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This paper reports the thermal stability and thermal degradation of six derivatives of indole by means of TG-DSC (in air) and TG-FTIR (in nitrogen) techniques. The compounds were also characterized by infrared spectroscopy. In addition, IR spectra were calculated and compared with the experimental data. In particular, the potential energy distribution analysis was performed to assign IR signals. The studied compounds are characterized by good thermal stability in oxidizing and inert atmospheres which is important for potential medical application. Thermogravimetric measurements in air atmosphere showed that the decomposition of compounds proceeds in two or three main stages. The thermal degradation of compounds is preceded by the melting process. The pyrolysis of samples is a one-step process. Together with the analyses performed in nitrogen, the FTIR spectra of the evolved gas phase products were recorded. On the FTIR spectra of gaseous products, only the bands of water, carbon dioxide and carbon oxide molecules are present. In the case of indole derivatives containing the p-chlorobenzyl substituent in position 1, the bands of anisole, p-chlorotoluene and chlorobenzene also appear.

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Experimental and computational studies of tautomerism pyridine carbonyl thiosemicarbazide derivatives

et al. 2023

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Tautomerism is one of the most important phenomena to consider when designing biologically active molecules. In this work, we use NMR spectroscopy, IR, and X-ray analysis as well as quantum-chemical calculations in the gas phase and in a solvent to study tautomerism of 1- (2-, 3- and 4-pyridinecarbonyl)-4-substituted thiosemicarbazide derivatives. The tautomer containing both carbonyl and thione groups turned out to be the most stable. The results of the calculations are consistent with the experimental data obtained from NMR and IR spectroscopy and with the crystalline forms from the X-ray studies. The obtained results broaden the knowledge in the field of structural studies of the thiosemicarbazide scaffold, which will translate into an understanding of the interactions of compounds with a potential molecular target.

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Synthesis and structure of new 1-cyanoacetyl-4-arylsemicarbazide derivatives with potential anticancer activity

Cited by 6 publications

References 28 publications

Synthesis, docking studies, and pharmacological evaluation of 2‐hydroxypropyl‐4‐arylpiperazine derivatives as serotoninergic ligands

Synthesis, docking studies, and pharmacological evaluation of 2‐hydroxypropyl‐4‐arylpiperazine derivatives as serotoninergic ligands

Thermal and spectroscopic studies of 2,3,5-trisubstituted and 1,2,3,5-tetrasubstituted indoles as non-competitive antagonists of GluK1/GluK2 receptors

Experimental and computational studies of tautomerism pyridine carbonyl thiosemicarbazide derivatives

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