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Issue 11, 2018
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Synthesis and anticonvulsant activity of phenoxyacetyl derivatives of amines, including aminoalkanols and amino acids

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Abstract

A series of 17 new phenoxyacetamides has been prepared via multistep chemical synthesis as a continuation of the research carried out by our group on di- and tri-substituted phenoxyalkyl and phenoxyacetyl derivatives of amines. The obtained compounds vary in an amide component, for example aminoalkanol or (un)modified amino acid moieties were introduced. The structures of selected products were confirmed by means of crystallographic methods. All 17 compounds were the subject of preliminary screening for potential anticonvulsant activity (MES, 6 Hz and/or scMET tests) and neurotoxicity (rotarod) in mice after intraperitoneal administration, while several active compounds were subsequently examined in additional models (e.g. MES and rotarod – rats, p.o. or i.p., hippocampal kindling – rats, i.p.). Finally, safety studies (cytotoxicity and cell proliferation assays on astrocytes, metabolic stability assessment, mutagenicity evaluation) were performed for several active compounds, including the most promising one (R-(−)-2-(2,6-dimethylphenoxy)-N-(1-hydroxypropan-2-yl)acetamide, MES ED50 = 12.00 mg per kg b.w., rats, p.o.).

Graphical abstract: Synthesis and anticonvulsant activity of phenoxyacetyl derivatives of amines, including aminoalkanols and amino acids

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Publication details

The article was received on 29 Aug 2018, accepted on 20 Sep 2018 and first published on 19 Oct 2018


Article type: Research Article
DOI: 10.1039/C8MD00430G
Citation: Med. Chem. Commun., 2018,9, 1933-1948
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    Synthesis and anticonvulsant activity of phenoxyacetyl derivatives of amines, including aminoalkanols and amino acids

    K. Pańczyk, D. Żelaszczyk, P. Koczurkiewicz, K. Słoczyńska, E. Pękala, E. Żesławska, W. Nitek, P. Żmudzki, H. Marona and A. Waszkielewicz, Med. Chem. Commun., 2018, 9, 1933
    DOI: 10.1039/C8MD00430G

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