Synthesis and Antibacterial Activity of Oxalates and Acetamides of {2-[2-Sopropyltetrahydropyran-4-yl-4-(4-Fluorophenyl)]Ethyl}Arylamines

Arutyunyan, N. S.; Akopyan, L. A.; Nazaryan, Robert; Gevorgyan, G. A.; Stepanyan, G. M.; Paronikyan, R. V.; Panosyan, G. A.

doi:10.1007/s11094-013-0987-1

Cited by 7 publications

(2 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[2][3][4][5][6] The acetamides are singled out from the rest of the derivatives of amides by the diversity of their pharmacological properties. It has been found that some derivatives of acetamides are used as antiprotozoics 7,8 , as bactericides 9 , in agriculture as insecticides 10 , herbicides 11 and fungicides. 12 It is not unknown that many of them are applied as analgesics 13 , anticonvulsants 14 and antioxidants.…”

Section: Introductionmentioning

confidence: 99%

Thin-Layer Chromatography on Reversed Phase in the Characterization of Retention Behaviour, Lipophilicity, and Pharmacokinetics of Cyanoacetamide Derivatives

Apostolov

Vastag

Matijević

et al. 2020

J. Chil. Chem. Soc.

View full text Add to dashboard Cite

Biological activity of a molecule is closely related to its lipophilicity. This significant parameter was determined for a group of potentially bioactive N-(4-phenylmonosubstituted)-2-cyanoacetamides applying thin-layer chromatography on reversed phase (RP-TLC) in mixtures of water and two organic modifiers separately, i-propanol and dioxane. The effect of the chemical structure of derivatives and the influence of the applied organic modifier on their retention were studied. The determined chromatographic retention constants, RM 0 , and the chromatographic parameter, m, of compounds were correlated with software calculated partition coefficients, log P as the standard measure of lipophilicity and with different pharmacokinetic predictors applying classical linear and multiple regression analysis. By classical linear regression analysis in both water-modifier systems only RM 0-log P and m-log P correlations were established (average r, 0.909 and 0.826). All studied relationships were enhanced by molecular descriptors that fulfilled the modified Lipinski's rule of five. Thereby, the performed multiple regression analysis gave better correlations (for RM 0-log P and m-log P average r 2 , 0.994 and 0.993; for RM 0-pharmacokinetic parameters and m-pharmacokinetic parameters average r 2 0.978 and 0.980). The obtained results indicate that the chromatographic parameters, RM 0 and m determined by RP-TLC at given conditions could be used successfully for the description of lipophilicity and the evaluation of pharmacokinetic properties of N-(4-phenylmonosubstituted)-2-cyanoacetamides as potential bioactive molecules.

show abstract

Section: Introductionmentioning

confidence: 99%

Thin-Layer Chromatography on Reversed Phase in the Characterization of Retention Behaviour, Lipophilicity, and Pharmacokinetics of Cyanoacetamide Derivatives

Apostolov

Vastag

Matijević

et al. 2020

J. Chil. Chem. Soc.

View full text Add to dashboard Cite

show abstract

“…Derivatives of amides are a very attractive group of compounds due to a broad spectrum of different activities as bactericides , fungicides , insecticides , anthelmintics , antipyretics , analgesics anticonvulsants , antidepressants , and cytostatics . Generally, as is well known, the type and intensity of an activity of a molecule, what also relates to derivatives of cyanoacetamides significantly depends on its interactions with the environment, respectively, on possibility to form a range of chemical bonds (ionic bonds and hydrogen bonds) with the corresponding groups present in the receptor cavities.…”

Section: Introductionmentioning

confidence: 99%

Structure‐interaction relationship study of N‐(4‐phenylsubstituted) cyanoacetamides by multivariate methods

Vastag

Apostolov

Matijević

et al. 2015

Journal of Chemometrics

View full text Add to dashboard Cite

Derivatives of amides belong to a very attractive group of compounds due to a broad spectrum of different biological activities. The type of molecule activity significantly depends on its interactions with the environment, which on the other hand largely depends on the nature of the substituent attached to the basic molecule as well as of solvents properties. In this work, the influence of the mentioned parameters on the interaction ability of the group of N-(4-phenylsubstituted) cyanoacetamides is investigated by using multivariate methods, based on the results obtained by reverse-phase thin-layer chromatography and ultraviolet absorption spectroscopy. Results obtained by the used chemometrics methods are very similar, within which the principal component analysis has provided the most detailed information. The obtained results suggest that the interactions of the investigated compounds are dominantly regulated by the polarity of the used solvents and their proton donor ability inside the chromatographic measurements, while in the case of the spectrophotometric data, the solvent's hydrogen bond ability has the greatest impact on the future interaction capability of the investigated cyanoacetamides. In the case of the substituent effect which is attached to the benzene ring, the greatest impact on the future interaction ability of the investigated cyanoacetamides is the orientation effect of ring substituent. Based on all the obtained results, it can be noticed that the used multivariate methods are able to detect effects of the substituent and solvent properties on the future interaction ability of the investigated derivatives.

show abstract

Synthesis of 3-(4-fluorophenyl)-3-(4-methoxyphenyl)-1-propanarylamines and their antibacterial activity

Arutyunyan

Akopyan

et al. 2017

Russ J Gen Chem

View full text Add to dashboard Cite

Synthesis and Antibacterial Activity of Oxalates and Acetamides of {2-[2-Sopropyltetrahydropyran-4-yl-4-(4-Fluorophenyl)]Ethyl}Arylamines

Cited by 7 publications

References 0 publications

Thin-Layer Chromatography on Reversed Phase in the Characterization of Retention Behaviour, Lipophilicity, and Pharmacokinetics of Cyanoacetamide Derivatives

Thin-Layer Chromatography on Reversed Phase in the Characterization of Retention Behaviour, Lipophilicity, and Pharmacokinetics of Cyanoacetamide Derivatives

Structure‐interaction relationship study of N‐(4‐phenylsubstituted) cyanoacetamides by multivariate methods

Synthesis of 3-(4-fluorophenyl)-3-(4-methoxyphenyl)-1-propanarylamines and their antibacterial activity

Contact Info

Product

Resources

About