title: Substituted N-benzylpyrazine-2-carboxamides: synthesis and biological evaluation.
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 &#181;g/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 &#181;mol/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, IC(50) = 7.4 &#181;mol/L) and 5-tert-butyl-6-chloro-N-(4-chlorobenzyl)pyrazine-2-carboxamide (11, IC(50) = 13.4 &#181;mol/L), only moderate or weak photosynthesis-inhibiting activity in spinach chloroplasts (Spinacia oleracea L.) was detected.
authors.affiliation: Department of Pharmaceutical Chemistry and Drug Control, Faculty of Pharmacy, Charles University in Prague, Heyrovského 1203, 500 05 Hradec Králové, Czech Republic. barbora.servusova@faf.cuni.cz
authors.forename: Barbora
authors.initials: B
authors.lastname: Servusová
authors.forename: Drahomíra
authors.initials: D
authors.lastname: Eibinová
authors.forename: Martin
authors.initials: M
authors.lastname: Doležal
authors.forename: Vladimír
authors.initials: V
authors.lastname: Kubíček
authors.forename: Pavla
authors.initials: P
authors.lastname: Paterová
authors.forename: Matúš
authors.initials: M
authors.lastname: Peško
authors.forename: Katarína
authors.initials: K
authors.lastname: Kráľová
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000494:pharmacology; D000904:Antibiotics, Antitubercular / Q000138:chemical synthesis* / Q000494:pharmacology; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002736:Chloroplasts / Q000187:drug effects / Q000378:metabolism; D006540:Herbicides / Q000138:chemical synthesis / Q000494:pharmacology; D057927:Hydrophobic and Hydrophilic Interactions; D008826:Microbial Sensitivity Tests; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D010788:Photosynthesis / Q000187:drug effects; D011719:Pyrazines / Q000138:chemical synthesis* / Q000494:pharmacology; D018724:Spinacia oleracea / Q000187:drug effects / Q000378:metabolism; D014249:Trichophyton / Q000187:drug effects
chemical_list: D000577:Amides; D000904:Antibiotics, Antitubercular; D000935:Antifungal Agents; D006540:Herbicides; D011719:Pyrazines