Synthesis and Biological Evaluation of N-Alkyl-3-(alkylamino)-pyrazine-2-carboxamides

A series of N-alkyl-3-(alkylamino)pyrazine-2-carboxamides and their N-alkyl-3-chloropyrazine-2-carboxamide precursors were prepared. All compounds were characterized by analytical methods and tested for antimicrobial and antiviral activity. The antimycobacterial MIC values against Mycobacterium tube...

Descripción completa

Detalles Bibliográficos
Autores principales: Semelkova, Lucia, Konecna, Klara, Paterova, Pavla, Kubicek, Vladimir, Kunes, Jiri, Novakova, Lucie, Marek, Jan, Naesens, Lieve, Pesko, Matus, Kralova, Katarina, Dolezal, Martin, Zitko, Jan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2015
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272192/
https://www.ncbi.nlm.nih.gov/pubmed/26007174
http://dx.doi.org/10.3390/molecules20058687
_version_ 1783377099571068928
author Semelkova, Lucia
Konecna, Klara
Paterova, Pavla
Kubicek, Vladimir
Kunes, Jiri
Novakova, Lucie
Marek, Jan
Naesens, Lieve
Pesko, Matus
Kralova, Katarina
Dolezal, Martin
Zitko, Jan
author_facet Semelkova, Lucia
Konecna, Klara
Paterova, Pavla
Kubicek, Vladimir
Kunes, Jiri
Novakova, Lucie
Marek, Jan
Naesens, Lieve
Pesko, Matus
Kralova, Katarina
Dolezal, Martin
Zitko, Jan
author_sort Semelkova, Lucia
collection PubMed
description A series of N-alkyl-3-(alkylamino)pyrazine-2-carboxamides and their N-alkyl-3-chloropyrazine-2-carboxamide precursors were prepared. All compounds were characterized by analytical methods and tested for antimicrobial and antiviral activity. The antimycobacterial MIC values against Mycobacterium tuberculosis H37Rv of the most effective compounds, 3-(hexylamino)-, 3-(heptylamino)- and 3-(octylamino)-N-methyl-pyrazine-2-carboxamides 14‒16, was 25 μg/mL. The compounds inhibited photosystem 2 photosynthetic electron transport (PET) in spinach chloroplasts. This activity was strongly connected with the lipophilicity of the compounds. For effective PET inhibition longer alkyl chains in the 3-(alkylamino) substituent in the N-alkyl-3-(alkylamino)pyrazine-2-carboxamide molecule were more favourable than two shorter alkyl chains.
format Online
Article
Text
id pubmed-6272192
institution National Center for Biotechnology Information
language English
publishDate 2015
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-62721922019-01-07 Synthesis and Biological Evaluation of N-Alkyl-3-(alkylamino)-pyrazine-2-carboxamides Semelkova, Lucia Konecna, Klara Paterova, Pavla Kubicek, Vladimir Kunes, Jiri Novakova, Lucie Marek, Jan Naesens, Lieve Pesko, Matus Kralova, Katarina Dolezal, Martin Zitko, Jan Molecules Article A series of N-alkyl-3-(alkylamino)pyrazine-2-carboxamides and their N-alkyl-3-chloropyrazine-2-carboxamide precursors were prepared. All compounds were characterized by analytical methods and tested for antimicrobial and antiviral activity. The antimycobacterial MIC values against Mycobacterium tuberculosis H37Rv of the most effective compounds, 3-(hexylamino)-, 3-(heptylamino)- and 3-(octylamino)-N-methyl-pyrazine-2-carboxamides 14‒16, was 25 μg/mL. The compounds inhibited photosystem 2 photosynthetic electron transport (PET) in spinach chloroplasts. This activity was strongly connected with the lipophilicity of the compounds. For effective PET inhibition longer alkyl chains in the 3-(alkylamino) substituent in the N-alkyl-3-(alkylamino)pyrazine-2-carboxamide molecule were more favourable than two shorter alkyl chains. MDPI 2015-05-14 /pmc/articles/PMC6272192/ /pubmed/26007174 http://dx.doi.org/10.3390/molecules20058687 Text en © 2015 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Semelkova, Lucia
Konecna, Klara
Paterova, Pavla
Kubicek, Vladimir
Kunes, Jiri
Novakova, Lucie
Marek, Jan
Naesens, Lieve
Pesko, Matus
Kralova, Katarina
Dolezal, Martin
Zitko, Jan
Synthesis and Biological Evaluation of N-Alkyl-3-(alkylamino)-pyrazine-2-carboxamides
title Synthesis and Biological Evaluation of N-Alkyl-3-(alkylamino)-pyrazine-2-carboxamides
title_full Synthesis and Biological Evaluation of N-Alkyl-3-(alkylamino)-pyrazine-2-carboxamides
title_fullStr Synthesis and Biological Evaluation of N-Alkyl-3-(alkylamino)-pyrazine-2-carboxamides
title_full_unstemmed Synthesis and Biological Evaluation of N-Alkyl-3-(alkylamino)-pyrazine-2-carboxamides
title_short Synthesis and Biological Evaluation of N-Alkyl-3-(alkylamino)-pyrazine-2-carboxamides
title_sort synthesis and biological evaluation of n-alkyl-3-(alkylamino)-pyrazine-2-carboxamides
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6272192/
https://www.ncbi.nlm.nih.gov/pubmed/26007174
http://dx.doi.org/10.3390/molecules20058687
work_keys_str_mv AT semelkovalucia synthesisandbiologicalevaluationofnalkyl3alkylaminopyrazine2carboxamides
AT konecnaklara synthesisandbiologicalevaluationofnalkyl3alkylaminopyrazine2carboxamides
AT paterovapavla synthesisandbiologicalevaluationofnalkyl3alkylaminopyrazine2carboxamides
AT kubicekvladimir synthesisandbiologicalevaluationofnalkyl3alkylaminopyrazine2carboxamides
AT kunesjiri synthesisandbiologicalevaluationofnalkyl3alkylaminopyrazine2carboxamides
AT novakovalucie synthesisandbiologicalevaluationofnalkyl3alkylaminopyrazine2carboxamides
AT marekjan synthesisandbiologicalevaluationofnalkyl3alkylaminopyrazine2carboxamides
AT naesenslieve synthesisandbiologicalevaluationofnalkyl3alkylaminopyrazine2carboxamides
AT peskomatus synthesisandbiologicalevaluationofnalkyl3alkylaminopyrazine2carboxamides
AT kralovakatarina synthesisandbiologicalevaluationofnalkyl3alkylaminopyrazine2carboxamides
AT dolezalmartin synthesisandbiologicalevaluationofnalkyl3alkylaminopyrazine2carboxamides
AT zitkojan synthesisandbiologicalevaluationofnalkyl3alkylaminopyrazine2carboxamides

Ejemplares similares