Synthesis and anticonvulsant activity of some alkanamide derivatives

Tarikogullari, Ayse H.; Fatma, Sultan Kilic; Erol, Kevser; Pabuççuoğlu, Varol

doi:10.1055/s-0031-1296331

Cited by 6 publications

(7 citation statements)

References 16 publications

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“…The organic phases were combined and dried over anhydrous na 2 So 4 and evaporated under reduced pressure. The product was purified by crystallization from water (15). The synthetic pathway is given in Scheme 1.…”

Section: General Procedures For the Synthesis Of The Compounds 1-12mentioning

confidence: 99%

“…Donepezil, rivastigmine and galanthamine also carry heterocyclic rings and according to literature survey, most of the compounds that have exhibited Ache inhibition consists of heterocyclic ring systems including pyrazole and 1,2,4-triazole (5)(6)(7)(8)(9)(10)(11)(12)(13)(14). Besides Ache inhibitory activity, pyrazole and 1,2,4-triazole containing systems have a wide spectrum of biological activities such as antibacterial, antifungal, analgesic, antipyretic, antiinflammatory, antiviral, anticancer, antituberculosis, antiparasitic, antihyperglycemic, antidepression, antihypertensive, vasodilatory, anticonvulsant activity (5,9,10,(14)(15)(16).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and cholinesterase inhibitory activity of some phenylacetamide derivatives bearing 1H-pyrazole and 1H-1,2,4-triazole

Tarikogullari¹,

Cizmecioglu²,

Saylam³

et al. 2015

Marmara Pharm J

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A group of N-phenylacetamide derivatives bearing five membered heterocyclic rings, pyrazole or 1,2,4-triazole, were synthesized to investigate their cholinesterase inhibitory activities. Acetylcholinesterase (Ache) and butyrylcholinesterase (Buche) inhibitory activities were evaluated by using ellman's spectroscopic method. results indicated that all of the compounds displayed moderate and selective Ache inhibitory activity and the most active compound was 2-(1H-1,2,4-triazole-1-yl)-N-(3-methoxyphenyl)acetamide with an ıc 50 value of 6.68 mM. Docking studies were also carried out for the most active compound.

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Section: General Procedures For the Synthesis Of The Compounds 1-12mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and cholinesterase inhibitory activity of some phenylacetamide derivatives bearing 1H-pyrazole and 1H-1,2,4-triazole

Tarikogullari¹,

Cizmecioglu²,

Saylam³

et al. 2015

Marmara Pharm J

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“…Moreover, recently particular attention was given to numerous derivatives of acetamides by the researchers as these molecules exhibit different biological activity such as antibacterial and antifungal (Ertan et al, 2007, Jamkhandi and Disouza, 2012, Hamad et al, 2017, antiinflammatory (de Castro Barbosa et al, 2009), antilieshmania (Pacheco et al, 2013), antituberculosis (Yadav et al, 2018), insecticide (Kalyanasundaram and Mathew, 2006), anthelmintic (Sawant and Kawade, 2011), antioxidant and anticancer (Özkay et al, 2010, Chen et al, 2013, Pawar et al, 2017, anticonvulsant and antidepressant (Soyer et al, 2004, Tarikogullari et al, 2010, Guan et al, 2016. In this study, various NSAIDs 2a-f were attached to N-(2,6-dimethyl phenyl) acetamide 1 to decrease the gastric irritation by masking the acidic carboxylic group through ester linkage as shown in Scheme 1.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Antibacterial Activity of Novel Mutual Non-Steroidal Anti-inflammatory Prodrugs

hamadameen

Ameen

2019

ZJPAS

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Non steroidal anti-inflammatory drugs (NSAIDs) are among the most used analgesic and anti-inflammatory drugs. However inhibition of cyclooxygenase1 and acidic groups such as carboxylic groups in most NSAIDs cause gastrointestinal (GI) side effects. Therefore masking the acidic groups till it pass through the GI tract will decrease the direct GI side effects and because N-(2,6-dimethylphenyl)-acetamide 1 also has anti-inflammatory activity so the synthesized ester prodrugs might act as mutual prodrugs. Moreover, because of emerging of new strains of bacteria and resistance of bacteria to the available antibacterial agents, new antibacterial agents are needed. The NSAIDs have antibacterial activity and N-(2,6-dimethylphenyl) acetamide 1 also has antibacterial activity so binding of these molecules with each other might give more potent antibacterial agent. 2-Chloro-N-(2,6dimethyl phenyl) acetamide 1 was utilized to synthesize ester prodrug of various NSAIDs 2a-f. The 2-Chloro-N-(2,6dimethylphenyl)-acetamide 1 undergo substitution reaction at α position with various sodium carboxylate of NSAIDs 2a-f in DMSO. The constitution of the newly synthesized ester prodrugs of NSAIDs 3a-f had been confirmed on the basis of their IR, ¹H and ¹³C-NMR spectral data. All the synthesized ester prodrugs 3a-f were screened for their in vitro antibacterial activities against Staphylococcus aureus ATCC 25923 and Escherichia coli ATCC 25922 however, their antibacterial activity decreased compared with their starting 1 and 2a-f.

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“…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

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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.

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Synthesis and anticonvulsant activity of some alkanamide derivatives

Cited by 6 publications

References 16 publications

Synthesis and cholinesterase inhibitory activity of some phenylacetamide derivatives bearing 1H-pyrazole and 1H-1,2,4-triazole

Synthesis and cholinesterase inhibitory activity of some phenylacetamide derivatives bearing 1H-pyrazole and 1H-1,2,4-triazole

Synthesis, Characterization, and Antibacterial Activity of Novel Mutual Non-Steroidal Anti-inflammatory Prodrugs

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

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