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

A series of 17 new phenoxyacetamides has been prepared 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...

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Published inMedChemComm Vol. 9; no. 11; pp. 1933 - 1948
Main Authors Pańczyk, Katarzyna, Żelaszczyk, Dorota, Koczurkiewicz, Paulina, Słoczyńska, Karolina, Pękala, Elżbieta, Żesławska, Ewa, Nitek, Wojciech, Żmudzki, Paweł, Marona, Henryk, Waszkielewicz, Anna
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 01.11.2018
Subjects
Amines
Amino acids
Animal models
Anticonvulsants
Astrocytes
Cell proliferation
Chemical synthesis
Crystallography
Cytotoxicity
Derivatives
Hippocampus
Kindling
Mutagenicity
Neurotoxicity
Organic chemistry
Rats
Rodents
Stability analysis
Toxicity
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Abstract A series of 17 new phenoxyacetamides has been prepared 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 ( MES and rotarod - rats, or , hippocampal kindling - rats, ). 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 ( -(-)-2-(2,6-dimethylphenoxy)- -(1-hydroxypropan-2-yl)acetamide, MES ED = 12.00 mg per kg b.w., rats, ).
AbstractList 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 ED 50 = 12.00 mg per kg b.w., rats, p.o. ).
A series of 17 new phenoxyacetamides has been prepared 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 ( MES and rotarod - rats, or , hippocampal kindling - rats, ). 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 ( -(-)-2-(2,6-dimethylphenoxy)- -(1-hydroxypropan-2-yl)acetamide, MES ED = 12.00 mg per kg b.w., rats, ).
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.).
Author Koczurkiewicz, Paulina
Pękala, Elżbieta
Waszkielewicz, Anna
Żesławska, Ewa
Żmudzki, Paweł
Słoczyńska, Karolina
Marona, Henryk
Żelaszczyk, Dorota
Pańczyk, Katarzyna
Nitek, Wojciech
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  organization: Department of Bioorganic Chemistry , Chair of Organic Chemistry , Faculty of Pharmacy , Jagiellonian University Medical College , Medyczna 9 , 30-688 Cracow , Poland . Email: katarzyna.panczyk@uj.edu.pl
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  surname: Żelaszczyk
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  orcidid: 0000-0003-1946-9370
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  organization: Department of Medicinal Chemistry , Faculty of Pharmacy , Jagiellonian University Medical College , Medyczna 9 , 30-688 Cracow , Poland
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  surname: Marona
  fullname: Marona, Henryk
  email: katarzyna.panczyk@uj.edu.pl
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  orcidid: 0000-0002-2871-9418
  surname: Waszkielewicz
  fullname: Waszkielewicz, Anna
  email: katarzyna.panczyk@uj.edu.pl
  organization: Department of Bioorganic Chemistry , Chair of Organic Chemistry , Faculty of Pharmacy , Jagiellonian University Medical College , Medyczna 9 , 30-688 Cracow , Poland . Email: katarzyna.panczyk@uj.edu.pl
BackLink https://www.ncbi.nlm.nih.gov/pubmed/30568761$$D View this record in MEDLINE/PubMed
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Snippet A series of 17 new phenoxyacetamides has been prepared multistep chemical synthesis as a continuation of the research carried out by our group on di- and...
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...
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...
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StartPage 1933
SubjectTerms Amines
Amino acids
Animal models
Anticonvulsants
Astrocytes
Cell proliferation
Chemical synthesis
Crystallography
Cytotoxicity
Derivatives
Hippocampus
Kindling
Mutagenicity
Neurotoxicity
Organic chemistry
Rats
Rodents
Stability analysis
Toxicity
Title Synthesis and anticonvulsant activity of phenoxyacetyl derivatives of amines, including aminoalkanols and amino acids
URI https://www.ncbi.nlm.nih.gov/pubmed/30568761
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