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...
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MDPI AG
2015-05-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/20/5/8687 |
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| author | Lucia Semelkova Klara Konecna Pavla Paterova Vladimir Kubicek Jiri Kunes Lucie Novakova Jan Marek Lieve Naesens Matus Pesko Katarina Kralova Martin Dolezal Jan Zitko |
| author_facet | Lucia Semelkova Klara Konecna Pavla Paterova Vladimir Kubicek Jiri Kunes Lucie Novakova Jan Marek Lieve Naesens Matus Pesko Katarina Kralova Martin Dolezal Jan Zitko |
| author_sort | Lucia Semelkova |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-04-11T23:50:39Z |
| format | Article |
| id | doaj.art-3653008a8d034514ae0939014f3aae09 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-11T23:50:39Z |
| publishDate | 2015-05-01 |
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| record_format | Article |
| series | Molecules |
| spelling | doaj.art-3653008a8d034514ae0939014f3aae092022-12-22T03:56:30ZengMDPI AGMolecules1420-30492015-05-012058687871110.3390/molecules20058687molecules20058687Synthesis and Biological Evaluation of N-Alkyl-3-(alkylamino)-pyrazine-2-carboxamidesLucia Semelkova0Klara Konecna1Pavla Paterova2Vladimir Kubicek3Jiri Kunes4Lucie Novakova5Jan Marek6Lieve Naesens7Matus Pesko8Katarina Kralova9Martin Dolezal10Jan Zitko11Faculty of Pharmacy, Charles University in Prague, Heyrovskeho 1203, Hradec Kralove 50005, Czech RepublicFaculty of Pharmacy, Charles University in Prague, Heyrovskeho 1203, Hradec Kralove 50005, Czech RepublicFaculty of Pharmacy, Charles University in Prague, Heyrovskeho 1203, Hradec Kralove 50005, Czech RepublicFaculty of Pharmacy, Charles University in Prague, Heyrovskeho 1203, Hradec Kralove 50005, Czech RepublicFaculty of Pharmacy, Charles University in Prague, Heyrovskeho 1203, Hradec Kralove 50005, Czech RepublicFaculty of Pharmacy, Charles University in Prague, Heyrovskeho 1203, Hradec Kralove 50005, Czech RepublicFaculty of Pharmacy, Charles University in Prague, Heyrovskeho 1203, Hradec Kralove 50005, Czech RepublicLaboratory of Virology and Chemotherapy, Rega Institute KU Leuven, Minderbroedersstraat 10, Leuven B-3000, BelgiumDepartment of Environmental Ecology, Faculty of Natural Sciences, Comenius University, Mlynska Dolina CH-2, Bratislava 84215, SlovakiaInstitute of Chemistry, Faculty of Natural Sciences, Comenius University, Mlynska Dolina CH-2, Bratislava 84215, SlovakiaFaculty of Pharmacy, Charles University in Prague, Heyrovskeho 1203, Hradec Kralove 50005, Czech RepublicFaculty of Pharmacy, Charles University in Prague, Heyrovskeho 1203, Hradec Kralove 50005, Czech RepublicA 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.http://www.mdpi.com/1420-3049/20/5/8687pyrazinamidepyrazinealkylationaminodehalogenationantimycobacterial activityinhibition of photosynthetic electron transportstructure-activity relationships |
| spellingShingle | Lucia Semelkova Klara Konecna Pavla Paterova Vladimir Kubicek Jiri Kunes Lucie Novakova Jan Marek Lieve Naesens Matus Pesko Katarina Kralova Martin Dolezal Jan Zitko Synthesis and Biological Evaluation of N-Alkyl-3-(alkylamino)-pyrazine-2-carboxamides Molecules pyrazinamide pyrazine alkylation aminodehalogenation antimycobacterial activity inhibition of photosynthetic electron transport structure-activity relationships |
| 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 | pyrazinamide pyrazine alkylation aminodehalogenation antimycobacterial activity inhibition of photosynthetic electron transport structure-activity relationships |
| url | http://www.mdpi.com/1420-3049/20/5/8687 |
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