Two novel thiosemicarbazones and eight novel 2-{[1-(5-alkyl/arylalkylpyrazin-2-yl)ethylidene]hydrazono}-1,3-thiazolidin-4-ones were prepared and tested against a panel of eight fungal strains-Candida albicans ATCC 44859, Candida tropicalis 156, Candida krusei E 28, Candida glabrata 20/I, Trichosporon asahii 1188, Aspergillus fumigatus 231, Lichtheimia corymbifera 272, and Trichophyton interdigitale 445. 1,3-Thiazolidin-4-ones exhibited activity against all strains, the most potent derivative was 2-{[1-(5-butylpyrazin-2-yl)ethylidene]hydrazono}e-1,3-thiazolidin-4-one. Susceptibility of C. glabrata to the studied 1,3-thiazolidin-4-ones (minimum inhibitory concentrations (MICs) were in the range 0.57 to 2.78 mg/L) is of great interest as this opportunistic pathogen is poorly susceptible to azoles and becomes resistant to echinocandins. Antifungal potency of thiosemicarbazones was slightly lower than that of 1,3-thiazolidin-4-ones.

• Klíčová slova
• 1,3-thiazolidin-4-ones, Candida glabrata, acetylpyrazine, antifungal, thiosemicarbazones,
• MeSH
• antifungální látky chemická syntéza   chemie   farmakologie   MeSH
• Aspergillus účinky léků   MeSH
• Candida účinky léků   MeSH
• mikrobiální testy citlivosti MeSH
• molekulární struktura MeSH
• Mucorales účinky léků   MeSH
• thiazolidindiony chemická syntéza   chemie   farmakologie   MeSH
• thiosemikarbazony chemická syntéza   chemie   farmakologie   MeSH
• Trichophyton účinky léků   MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• antifungální látky MeSH
• thiazolidindiony MeSH
• thiosemikarbazony MeSH

A series of N-alkyl-3-(alkylamino)pyrazine-2-carboxamides and their N-alkyl-3-chloropyrazine-2-carboxamide precursors were prepared. All compounds were characterized by analytical methods and tested for antimicrobial and antiviral activity. The antimycobacterial MIC values against Mycobacterium tuberculosis H37Rv of the most effective compounds, 3-(hexylamino)-, 3-(heptylamino)- and 3-(octylamino)-N-methyl-pyrazine-2-carboxamides 14‒16, was 25 μg/mL. The compounds inhibited photosystem 2 photosynthetic electron transport (PET) in spinach chloroplasts. This activity was strongly connected with the lipophilicity of the compounds. For effective PET inhibition longer alkyl chains in the 3-(alkylamino) substituent in the N-alkyl-3-(alkylamino)pyrazine-2-carboxamide molecule were more favourable than two shorter alkyl chains.

• Klíčová slova
• alkylation, aminodehalogenation, antimycobacterial activity, inhibition of photosynthetic electron transport, pyrazinamide, pyrazine, structure-activity relationships,
• MeSH
• antituberkulotika chemická syntéza   farmakologie   MeSH
• bakteriální proteiny antagonisté a inhibitory   metabolismus   MeSH
• chloroplasty metabolismus   MeSH
• mikrobiální testy citlivosti MeSH
• Mycobacterium tuberculosis účinky léků   metabolismus   MeSH
• pyrazinamid chemická syntéza   chemie   farmakologie   MeSH
• pyraziny chemická syntéza   farmakologie   MeSH
• Spinacia oleracea metabolismus   MeSH
• syntázy mastných kyselin antagonisté a inhibitory   metabolismus   MeSH
• transport elektronů účinky léků   MeSH
• vztahy mezi strukturou a aktivitou MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• antituberkulotika MeSH
• bakteriální proteiny MeSH
• fatty acid synthase I, mycobacteria MeSH Prohlížeč
• pyrazinamid MeSH
• pyraziny MeSH
• syntázy mastných kyselin MeSH