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New potentially active pyrazinamide derivatives synthesized under microwave conditions
O. Jandourek, M. Dolezal, J. Kunes, V. Kubicek, P. Paterova, M. Pesko, V. Buchta, K. Kralova, J. Zitko,
Language English Country Switzerland
Document type Journal Article, Research Support, Non-U.S. Gov't
Grant support
NT13346
MZ0
CEP Register
Digital library NLK
Full text - Article
Source
NLK
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- MeSH
- Antifungal Agents chemical synthesis pharmacology MeSH
- Antitubercular Agents chemical synthesis pharmacology MeSH
- Candida albicans drug effects MeSH
- Chloroplasts drug effects metabolism MeSH
- Photosynthesis drug effects MeSH
- Herbicides chemical synthesis pharmacology MeSH
- Hydrophobic and Hydrophilic Interactions MeSH
- Inhibitory Concentration 50 MeSH
- Microbial Sensitivity Tests MeSH
- Microwaves MeSH
- Mycobacterium tuberculosis drug effects MeSH
- Pyrazinamide analogs & derivatives chemical synthesis pharmacology MeSH
- Spinacia oleracea drug effects metabolism MeSH
- Staphylococcus epidermidis drug effects MeSH
- Electron Transport drug effects MeSH
- Structure-Activity Relationship MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
A series of 18 N-alkyl substituted 3-aminopyrazine-2-carboxamides was prepared in this work according to previously experimentally set and proven conditions using microwave assisted synthesis methodology. This approach for the aminodehalogenation reaction was chosen due to higher yields and shorter reaction times compared to organic reactions with conventional heating. Antimycobacterial, antibacterial, antifungal and photosynthetic electron transport (PET) inhibiting in vitro activities of these compounds were investigated. Experiments for the determination of lipophilicity were also performed. Only a small number of substances with alicyclic side chain showed activity against fungi which was the same or higher than standards and the biological efficacy of the compounds increased with rising lipophilicity. Nine pyrazinamide derivatives also inhibited PET in spinach chloroplasts and the IC50 values of these compounds varied in the range from 14.3 to 1590.0 μmol/L. The inhibitory activity was connected not only with the lipophilicity, but also with the presence of secondary amine fragment bounded to the pyrazine ring. Structure-activity relationships are discussed as well.
References provided by Crossref.org
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- $a Janďourek, Ondřej. $u Department of Medicinal Chemistry and Drug Analysis, Faculty of Pharmacy, Charles University in Prague, Heyrovskeho 1203, Hradec Kralove 50005, Czech Republic. jando6aa@faf.cuni.cz. $7 xx0230412
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- $a New potentially active pyrazinamide derivatives synthesized under microwave conditions / $c O. Jandourek, M. Dolezal, J. Kunes, V. Kubicek, P. Paterova, M. Pesko, V. Buchta, K. Kralova, J. Zitko,
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- $a A series of 18 N-alkyl substituted 3-aminopyrazine-2-carboxamides was prepared in this work according to previously experimentally set and proven conditions using microwave assisted synthesis methodology. This approach for the aminodehalogenation reaction was chosen due to higher yields and shorter reaction times compared to organic reactions with conventional heating. Antimycobacterial, antibacterial, antifungal and photosynthetic electron transport (PET) inhibiting in vitro activities of these compounds were investigated. Experiments for the determination of lipophilicity were also performed. Only a small number of substances with alicyclic side chain showed activity against fungi which was the same or higher than standards and the biological efficacy of the compounds increased with rising lipophilicity. Nine pyrazinamide derivatives also inhibited PET in spinach chloroplasts and the IC50 values of these compounds varied in the range from 14.3 to 1590.0 μmol/L. The inhibitory activity was connected not only with the lipophilicity, but also with the presence of secondary amine fragment bounded to the pyrazine ring. Structure-activity relationships are discussed as well.
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