Regioselectivity and Tautomerism of Novel Five-Membered Ring Nitrogen Heterocycles Formed via Cyclocondensation of Acylthiosemicarbazides

Tomascikova, Jana; Imrich, Ján; Danihel, Ivan; Böhm, Stanislav; Kristián, Pavol; Pisarčíková, Jana; Sabol, Marián; Klika, Karel D.

doi:10.3390/molecules13030501

Cited by 21 publications

(6 citation statements)

References 34 publications

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“…The process of proton transfer might be as follows: The NH group in the keto form was ionized by forming strong intermolecular hydrogen bonds with some polar solvent (such as CH 3 COOH), and then the proton was transferred to the carbonyl in the same ring, forming an enol form. Similar exchangeable NH protons have been reported in some acridinyl derivatives [ 37 ].…”

Section: Resultssupporting

confidence: 85%

A New Coumarin-Acridone Compound as a Fluorescence Probe for Fe3+ and Its Application in Living Cells and Zebrafish

et al. 2021

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A new coumarin-acridone fluorescent probe S was designed and synthesized, and the structure was confirmed with 1H/13C NMR spectrometry, single-crystal X-ray diffraction, and high-resolution mass spectrometry. This probe has high sensitivity and selectivity for Fe3+ over other testing metal ions at 420 or 436 nm in acetonitrile–MOPS (3-Morpholinopropanesulfonic Acid) buffer solution (20.0 μM, pH = 6.9, 8:2 (v/v)). Under physiological conditions, the probe displayed satisfying time stability with a detection limit of 1.77 µM. In addition, probe S was successfully used to detect intracellular iron changes through a fluorescence-off mode, and the imaging results of cells and zebrafish confirmed their low cytotoxicity and satisfactory cell membrane permeability, as well as their potential biological applications.

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Section: Resultssupporting

confidence: 85%

A New Coumarin-Acridone Compound as a Fluorescence Probe for Fe3+ and Its Application in Living Cells and Zebrafish

et al. 2021

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“…Jana et al 46 calculated 13 C NMR chemical shifts of 4-(acridin-9-yl)-5-methyl-2,4-dihydro 1,2,4 triazole-3-thione in the gas phase by the B3LYP/6-311++G(2d,2p) method, and the calculated results correlated with the experimental values.…”

Section: And 1 H Nmr Studiesmentioning

confidence: 50%

The spectroscopic NMR analysis of 2-dicyanovinyl-5-phenylthiophene by the density functional method

LiXiao-Hong

ZhangXian-Zhou

2013

Can. J. Chem.

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Quantum chemistry calculations have been performed by using the Gaussian03 program to compute the optimized geometry and harmonic vibrational frequency of 2-dicyanovinyl-5-phenylthiophene (C 14 H 8 N 2 S) in the ground state. Atomic charges at B3LYP/6-311++G(d,p) level are also calculated. Potential energy distributions (PEDs) using MOLVIB program are also used to interpret the theoretical vibrational spectra of the title compound. A detailed interpretation of the infrared spectra of the title compound is reported. The theoretical spectrograms for the IR spectra of the title compound have been constructed. The crystal structure obtained by molecular mechanics belongs to the P2 1 space group, with lattice parameters Z = 2, a = 6.6745 Å, b = 14.7672 Å, c = 11.0986 Å, = 0.921 g cm -3 . In addition, the 13 C and 1 H NMR are further investigated by the B3LYP/6-311++G(d,p) and B3LYP/6-311++G(2d,2p) methods. Résumé :On a procédé à des calculs de chimie quantique à l'aide du programme Gaussian03 pour déterminer les fréquences de vibration harmoniques pour une géométrie optimisée du 2-dicyanovinyl-5-phénylthiophène (C 14 H 8 N 2 S) à l'état fondamental. On a également calculé les charges atomiques au niveau B3LYP/6-311++G(d,p). Les distributions des énergies potentielles (PED) obtenues à l'aide du programme MOLVIB sont aussi utilisées pour interpréter les spectres vibrationnels théoriques du composé susmentionné. On présente une interprétation détaillée des spectres infrarouges de ce composé. On a construit les spectrogrammes théoriques de ces spectres infrarouges. La structure cristalline obtenue par la mécanique moléculaire appartient au groupe d'espace P2 1 ayant les paramètres de réseau Z = 2, a = 6,6745 Å, b = 14,7672 Å, c = 11,0986 Å, = 0,921 g cm -3 . En outre, on a étudié la RMN du 13 C et du 1 H par les méthodes B3LYP/6-311++G(d,p) et B3LYP/6-311++G(2d,2p). [Traduit par la Rédaction] Mots-clés : 2-dicyanovinyl-5-phénylthiophène, spectre vibrationnel, DFT, analyse RMN, charges de Mulliken.

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“…It is then followed by a nucleophilic addition reaction of an aliphatic amine of 3 to the DMAD 4 leading to the formation of the target compound. [27] Compound 6 was previously reported as a product of reaction c. [28] But, based on the determined structure of the target compound which was resolved by single-crystal X-ray diffraction analysis, we conclude that the presence of an electron-withdrawing group influenced the formation of a thiazole ring that includes nitrogen adjacent to the para-nitro substituted ring instead of the nitrogen atom that is part of the hydrazone group reported in the previous works. [29] The structure of the compound was elucidated based on spectral data such as FT-IR, 1 H-NMR, 13 C-NMR, HRMS, UVspectroscopy and single-crystal X-ray analysis.…”

Section: Chemistrymentioning

confidence: 53%

Synthesis, Molecular Docking and Antiproliferative Activity Studies of a Thiazole‐Based Compound Linked to Hydrazone Moiety

et al. 2022

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(A new 4‐oxothiazolidin‐2‐ylidene derivative bearing hydrazone moiety was synthesized via Michael addition between the reaction of 4‐(4‐nitrophenyl)‐3‐thiosemicarbazide and dimethyl acetylenedicarboxylate (DMAD). The structure of synthesized compound was elucidated using various spectral techniques such as FTIR, UV‐spec, 1H NMR and 13C NMR. The structure of the related compound was confirmed by single‐crystal X‐ray analysis. Antiproliferative activity of the synthesized compound was evaluated in two human cancer cell lines, HepG2 (liver hepatocellular carcinoma cell line) and DLD‐1 (human colon cancer cell line). In addition, molecular docking of synthesized compound was investigated to give an insight of its activity against Epidermal Growth Factor Receptor tyrosine kinase domain proteins (EGFR) (lung cancer) (PDB ID: 1 M17), deleted in Liver Cancer 2 proteins (DLC2) (liver cancer) (PDB ID: 2H80), and MLK4 kinase proteins (colon cancer) (PDB ID: 4UYA) were investigated. Furthermore, the ability of the molecule to be a drug was examined by ADME/T analysis.)

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Regioselectivity and Tautomerism of Novel Five-Membered Ring Nitrogen Heterocycles Formed via Cyclocondensation of Acylthiosemicarbazides

Cited by 21 publications

References 34 publications

A New Coumarin-Acridone Compound as a Fluorescence Probe for Fe3+ and Its Application in Living Cells and Zebrafish

A New Coumarin-Acridone Compound as a Fluorescence Probe for Fe3+ and Its Application in Living Cells and Zebrafish

The spectroscopic NMR analysis of 2-dicyanovinyl-5-phenylthiophene by the density functional method

Synthesis, Molecular Docking and Antiproliferative Activity Studies of a Thiazole‐Based Compound Linked to Hydrazone Moiety

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