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Molecules 2012, 17(11), 13183-13198; doi:10.3390/molecules171113183
Article

Substituted N-Benzylpyrazine-2-carboxamides: Synthesis and Biological Evaluation

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Received: 22 October 2012; in revised form: 31 October 2012 / Accepted: 2 November 2012 / Published: 6 November 2012
(This article belongs to the Section Medicinal Chemistry)
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Abstract: 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.
Keywords: pyrazinamide analogues; lipophilicity determination; in vitro antimycobacterial; antifungal and photosynthesis inhibitory activity pyrazinamide analogues; lipophilicity determination; in vitro antimycobacterial; antifungal and photosynthesis inhibitory activity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Servusová, B.; Eibinová, D.; Doležal, M.; Kubíček, V.; Paterová, P.; Peško, M.; Kráľová, K. Substituted N-Benzylpyrazine-2-carboxamides: Synthesis and Biological Evaluation. Molecules 2012, 17, 13183-13198.

AMA Style

Servusová B, Eibinová D, Doležal M, Kubíček V, Paterová P, Peško M, Kráľová K. Substituted N-Benzylpyrazine-2-carboxamides: Synthesis and Biological Evaluation. Molecules. 2012; 17(11):13183-13198.

Chicago/Turabian Style

Servusová, Barbora; Eibinová, Drahomíra; Doležal, Martin; Kubíček, Vladimír; Paterová, Pavla; Peško, Matúš; Kráľová, Katarína. 2012. "Substituted N-Benzylpyrazine-2-carboxamides: Synthesis and Biological Evaluation." Molecules 17, no. 11: 13183-13198.



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