Substituted 2-[2-(pyridin-3-yl) phenyl] acetamides and ureas: design, synthesis, and anticonvulsant screening in mice

Shindikar, A. V.; Viswanathan, C. L.

doi:10.1007/s00044-011-9717-y

Cited by 3 publications

(2 citation statements)

References 16 publications

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“…This reaction is applied for direct synthesis of 1-substituted 3,4-dihydroisoquinolines [4], 1-substituted 3,4-dihydroβ-carbolines [5], quinazolinones [6], isochromanes [7], etc. Besides their use as synthetic scaffolds, ketoamides are also known for their anticonvulsant [8], antidepressant [9], and antiproliferative [10] activities. In the past two decades, coronaviruses have appeared on a large pandemic scale displayed by the appearance of the severe acute respiratory syndrome virus (SARS-CoV) followed by another type of coronavirus (MERS-CoV).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of N-[1-(2-Acetyl-4,5-dimethoxyphenyl)propan-2-yl]benzamide and Its Copper(II) Complex

2023

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This paper represents a convenient method for the synthesis of N- [1-(2-acetyl-4,5-dimethoxyphenyl)propan-2-yl]benzamide and its Cu(II) complex. In silico analysis predicted spasmolytic activity for the compound. Based on the in silico calculations, the importance of the predicted ketoamide, and our previous experiments, we synthesized the ketoamide via ortho-acylation of N- [1-(3,4-dimethoxyphenyl)propan-2-yl]benzamide with acetic anhydride in polyphosphoric acid. We applied the title ketoamide in reaction with Cu(II) varying the solvents. We found that the reaction leads to the formation of a coordination compound when the ligand dissolved in DMSO reacts with a water solution of CuCl 2 in an alkaline environment in a molar ratio M : L : OH -= 1 : 2 : 2. The structures of the new compounds are discussed based on their melting points, IR, 1 H, 13 C NMR and Raman spectral data.

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Section: Introductionmentioning

confidence: 99%

Synthesis of N-[1-(2-Acetyl-4,5-dimethoxyphenyl)propan-2-yl]benzamide and Its Copper(II) Complex

2023

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“…Besides their use as synthetic scaffolds, 2-phenylacetamides are also known for their application in medicinal chemistry as they possess a variety of biological activities depending on the structural features of the substituents. Their anticonvulsant [2], antidepressant [3] and antiproliferative [4] activities are only a few to mention. Herein, we report the crystal structure of N-(2-benzoyl-4,5-dimethoxyphenethyl)-2-phenylacetamide obtained by singlecrystal X-ray diffraction analysis.…”

Section: Introductionmentioning

confidence: 99%

N-(2-Benzoyl-4,5-dimethoxyphenethyl)-2-phenylacetamide

Marinova

Nikolova

Dołęga

et al. 2022

Molbank

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The crystal structure of N-(2-benzoyl-4,5-dimethoxyphenethyl)-2-phenylacetamide indicates that the compound crystallizes in the monoclinic C2/c space group with eight molecules in the unit cell. The heteroatoms from the amide group form a chain of intermolecular N-H ··· O hydrogen bonds propagating along the b axis. The carbonyl group from the benzoyl substituent participates in short contacts with two H-atoms from the ethyl or phenyl groups.

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Establishing Dependences between Different Lipophilic Parameters of New Potentially Biologically Active N-Substituted-2-Phenylacetamide Derivatives by Applying Multivariate Methods

Vastag

Apostolov

Matijević

et al. 2014

Journal of Chromatographic Science

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Lipophilicity, a very important parameter in the potential biological activities of molecules, was investigated for newly synthesized N-substituted-2-phenylacetamide derivatives. The determination was carried out in two ways: first experimentally, by applying thin-layer chromatography (TLC) on reversed-phase TLC (RPTLC) RP18F254s in the presence of one protic (methanol) and one aprotic solvent (acetonitrile) and then mathematically, by using different software packages. The intercept of the linear dependence between volume fractions of the organic solvent and the retention parameters obtained by TLC is known as the retention chromatographic constant, R(M)(0), while the slope represents the m value. In order to establish the dependences between the partition coefficient, log P as the standard measure of lipophilicity and the alternative lipophilic parameters obtained experimentally by TLC, R(M)(0) and m values, linear regression analysis and multivariate methods, cluster analysis (CA) and principal component analysis (PCA), were used. All applied methods gave approximately similar results. Although there is a linear dependence between the two chromatographic parameters, the retention constant, R(M)(0), and the m values, only R(M)(0) shows suitable similarity with the standard measure of lipophilicity of the investigated N-substituted-2-phenylacetamide derivatives at the given conditions. The existence of this resemblance proves that the chromatographic retention constant, R(M)(0), obtained by RPTLC could be successfully used for the description of lipophilicity of investigated compounds. On the other hand, the results confirmed that the applied linear regression analysis and the multivariate analysis (CA and PCA) have the ability to compare lipophilic parameters of the investigated phenylacetamide derivatives obtained in different ways.

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Substituted 2-[2-(pyridin-3-yl) phenyl] acetamides and ureas: design, synthesis, and anticonvulsant screening in mice

Cited by 3 publications

References 16 publications

Synthesis of N-[1-(2-Acetyl-4,5-dimethoxyphenyl)propan-2-yl]benzamide and Its Copper(II) Complex

Synthesis of N-[1-(2-Acetyl-4,5-dimethoxyphenyl)propan-2-yl]benzamide and Its Copper(II) Complex

N-(2-Benzoyl-4,5-dimethoxyphenethyl)-2-phenylacetamide

Establishing Dependences between Different Lipophilic Parameters of New Potentially Biologically Active N-Substituted-2-Phenylacetamide Derivatives by Applying Multivariate Methods

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