Substituted N-Benzylpyrazine-2-carboxamides: Synthesis and Biological Evaluation
A series of twelve amides was synthesized via aminolysis of substituted pyrazinecarboxylic acid chlorides with substituted benzylamines. Compounds were characterized with analytical data and assayed in vitro for their antimycobacterial, antifungal, antibacterial and photosynthesis-inhibiting activit...
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MDPI AG
2012-11-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/17/11/13183 |
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| author | Katarína Kráľová Pavla Paterová Matúš Peško Vladimír Kubíček Martin Doležal Drahomíra Eibinová Barbora Servusová |
| author_facet | Katarína Kráľová Pavla Paterová Matúš Peško Vladimír Kubíček Martin Doležal Drahomíra Eibinová Barbora Servusová |
| author_sort | Katarína Kráľová |
| collection | DOAJ |
| description | A series of twelve amides was synthesized via aminolysis of substituted pyrazinecarboxylic acid chlorides with substituted benzylamines. Compounds were characterized with analytical data and assayed in vitro for their antimycobacterial, antifungal, antibacterial and photosynthesis-inhibiting activity. 5-tert-Butyl-6-chloro-N-(4-methoxybenzyl)pyrazine-2-carboxamide (12) has shown the highest antimycobacterial activity against Mycobacterium tuberculosis (MIC = 6.25 µg/mL), as well as against other mycobacterial strains. The highest antifungal activity against Trichophyton mentagrophytes, the most susceptible fungal strain tested, was found for 5-chloro-N-(3-trifluoromethylbenzyl)-pyrazine-2-carboxamide (2, MIC = 15.62 µmol/L). None of the studied compounds exhibited any activity against the tested bacterial strains. Except for 5-tert-butyl-6-chloro-N-benzylpyrazine-2-carboxamide (9, IC50 = 7.4 µmol/L) and 5-tert-butyl-6-chloro-N-(4-chlorobenzyl)pyrazine-2-carboxamide (11, IC50 = 13.4 µmol/L), only moderate or weak photosynthesis-inhibiting activity in spinach chloroplasts (Spinacia oleracea L.) was detected. |
| first_indexed | 2024-12-23T03:22:53Z |
| format | Article |
| id | doaj.art-5d32dfb1035847108d7bc4d3575a9fda |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-23T03:22:53Z |
| publishDate | 2012-11-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-5d32dfb1035847108d7bc4d3575a9fda2022-12-21T18:01:57ZengMDPI AGMolecules1420-30492012-11-011711131831319810.3390/molecules171113183Substituted N-Benzylpyrazine-2-carboxamides: Synthesis and Biological EvaluationKatarína KráľováPavla PaterováMatúš PeškoVladimír KubíčekMartin DoležalDrahomíra EibinováBarbora ServusováA series of twelve amides was synthesized via aminolysis of substituted pyrazinecarboxylic acid chlorides with substituted benzylamines. Compounds were characterized with analytical data and assayed in vitro for their antimycobacterial, antifungal, antibacterial and photosynthesis-inhibiting activity. 5-tert-Butyl-6-chloro-N-(4-methoxybenzyl)pyrazine-2-carboxamide (12) has shown the highest antimycobacterial activity against Mycobacterium tuberculosis (MIC = 6.25 µg/mL), as well as against other mycobacterial strains. The highest antifungal activity against Trichophyton mentagrophytes, the most susceptible fungal strain tested, was found for 5-chloro-N-(3-trifluoromethylbenzyl)-pyrazine-2-carboxamide (2, MIC = 15.62 µmol/L). None of the studied compounds exhibited any activity against the tested bacterial strains. Except for 5-tert-butyl-6-chloro-N-benzylpyrazine-2-carboxamide (9, IC50 = 7.4 µmol/L) and 5-tert-butyl-6-chloro-N-(4-chlorobenzyl)pyrazine-2-carboxamide (11, IC50 = 13.4 µmol/L), only moderate or weak photosynthesis-inhibiting activity in spinach chloroplasts (Spinacia oleracea L.) was detected.http://www.mdpi.com/1420-3049/17/11/13183pyrazinamide analogueslipophilicity determinationin vitro antimycobacterialantifungal and photosynthesis inhibitory activity |
| spellingShingle | Katarína Kráľová Pavla Paterová Matúš Peško Vladimír Kubíček Martin Doležal Drahomíra Eibinová Barbora Servusová Substituted N-Benzylpyrazine-2-carboxamides: Synthesis and Biological Evaluation Molecules pyrazinamide analogues lipophilicity determination in vitro antimycobacterial antifungal and photosynthesis inhibitory activity |
| title | Substituted N-Benzylpyrazine-2-carboxamides: Synthesis and Biological Evaluation |
| title_full | Substituted N-Benzylpyrazine-2-carboxamides: Synthesis and Biological Evaluation |
| title_fullStr | Substituted N-Benzylpyrazine-2-carboxamides: Synthesis and Biological Evaluation |
| title_full_unstemmed | Substituted N-Benzylpyrazine-2-carboxamides: Synthesis and Biological Evaluation |
| title_short | Substituted N-Benzylpyrazine-2-carboxamides: Synthesis and Biological Evaluation |
| title_sort | substituted n benzylpyrazine 2 carboxamides synthesis and biological evaluation |
| topic | pyrazinamide analogues lipophilicity determination in vitro antimycobacterial antifungal and photosynthesis inhibitory activity |
| url | http://www.mdpi.com/1420-3049/17/11/13183 |
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