Substituted N-Phenylpyrazine-2-carboxamides: Synthesis and Antimycobacterial Evaluation
The condensation of chlorides of substituted pyrazinecarboxylic acids with ringsubstituted anilines yielded twelve substituted pyrazinecarboxylic acid amides. The synthetic approach, analytical, and lipophilicity data of the newly synthesized compounds are presented. Two antituberculosis assays were...
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| Format: | Article |
| Language: | English |
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MDPI AG
2009-10-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/14/10/4180/ |
| _version_ | 1818827019186601984 |
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| author | Michaela Svobodová Jiří Kuneš Martin Doležal Diana Kešetovičová Jan Zitko |
| author_facet | Michaela Svobodová Jiří Kuneš Martin Doležal Diana Kešetovičová Jan Zitko |
| author_sort | Michaela Svobodová |
| collection | DOAJ |
| description | The condensation of chlorides of substituted pyrazinecarboxylic acids with ringsubstituted anilines yielded twelve substituted pyrazinecarboxylic acid amides. The synthetic approach, analytical, and lipophilicity data of the newly synthesized compounds are presented. Two antituberculosis assays were used. Firstly, the antimycobacterial activity against four different Mycobacterium strains in a series of pyrazine derivatives was investigated. Secondly, the antimycobacterial evaluation was performed at the Tuberculosis Antimicrobial Acquisition and Coordinating Facility (TAACF) program. Interesting in vitro antimycobacterial activity was found, N-(3-iodo-4-methylphenyl) pyrazine-2-carboxamide (9) was most active derivative compound against M. tuberculosis (MIC < 2.0 μmol/L), while another iodo derivative 5-tert-butyl-6-chloro-N-(3-iodo-4-methyl-phenyl)pyrazine-2-carboxamide (12) was the most active compound in the TAACF antituberculosis screening program (IC90 = 0.819 μg/mL). |
| first_indexed | 2024-12-19T00:36:54Z |
| format | Article |
| id | doaj.art-e538ec9583b048fcb361631e45962cfd |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-19T00:36:54Z |
| publishDate | 2009-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-e538ec9583b048fcb361631e45962cfd2022-12-21T20:44:46ZengMDPI AGMolecules1420-30492009-10-0114104180418910.3390/molecules14104180Substituted N-Phenylpyrazine-2-carboxamides: Synthesis and Antimycobacterial EvaluationMichaela SvobodováJiří KunešMartin DoležalDiana KešetovičováJan ZitkoThe condensation of chlorides of substituted pyrazinecarboxylic acids with ringsubstituted anilines yielded twelve substituted pyrazinecarboxylic acid amides. The synthetic approach, analytical, and lipophilicity data of the newly synthesized compounds are presented. Two antituberculosis assays were used. Firstly, the antimycobacterial activity against four different Mycobacterium strains in a series of pyrazine derivatives was investigated. Secondly, the antimycobacterial evaluation was performed at the Tuberculosis Antimicrobial Acquisition and Coordinating Facility (TAACF) program. Interesting in vitro antimycobacterial activity was found, N-(3-iodo-4-methylphenyl) pyrazine-2-carboxamide (9) was most active derivative compound against M. tuberculosis (MIC < 2.0 μmol/L), while another iodo derivative 5-tert-butyl-6-chloro-N-(3-iodo-4-methyl-phenyl)pyrazine-2-carboxamide (12) was the most active compound in the TAACF antituberculosis screening program (IC90 = 0.819 μg/mL).http://www.mdpi.com/1420-3049/14/10/4180/pyrazinecarboxamide synthesisin vitro antimycobacterial screeninglipophilicitySAR |
| spellingShingle | Michaela Svobodová Jiří Kuneš Martin Doležal Diana Kešetovičová Jan Zitko Substituted N-Phenylpyrazine-2-carboxamides: Synthesis and Antimycobacterial Evaluation Molecules pyrazinecarboxamide synthesis in vitro antimycobacterial screening lipophilicity SAR |
| title | Substituted N-Phenylpyrazine-2-carboxamides: Synthesis and Antimycobacterial Evaluation |
| title_full | Substituted N-Phenylpyrazine-2-carboxamides: Synthesis and Antimycobacterial Evaluation |
| title_fullStr | Substituted N-Phenylpyrazine-2-carboxamides: Synthesis and Antimycobacterial Evaluation |
| title_full_unstemmed | Substituted N-Phenylpyrazine-2-carboxamides: Synthesis and Antimycobacterial Evaluation |
| title_short | Substituted N-Phenylpyrazine-2-carboxamides: Synthesis and Antimycobacterial Evaluation |
| title_sort | substituted n phenylpyrazine 2 carboxamides synthesis and antimycobacterial evaluation |
| topic | pyrazinecarboxamide synthesis in vitro antimycobacterial screening lipophilicity SAR |
| url | http://www.mdpi.com/1420-3049/14/10/4180/ |
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