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277 KiB

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Synthesis, Antimycobacterial, Antifungal and Photosynthesis-Inhibiting Activity of Chlorinated N-phenylpyrazine-2-carboxamides ^†

by Martin Dolezal, Jan Zitko, Zdenek Osicka, Jiri Kunes, Marcela Vejsova, Vladimir Buchta, Jiri Dohnal, Josef Jampilek and Katarina Kralova

Molecules 2010, 15(12), 8567-8581; https://doi.org/10.3390/molecules15128567 - 26 Nov 2010

Cited by 39 | Viewed by 7193

Abstract

A series of sixteen pyrazinamide analogues with the -CONH- linker connecting the pyrazine and benzene rings was synthesized by the condensation of chlorides of substituted pyrazinecarboxylic acids with ring-substituted (chlorine) anilines. The prepared compounds were characterized and evaluated for their antimycobacterial and antifungal [...] Read more.

A series of sixteen pyrazinamide analogues with the -CONH- linker connecting the pyrazine and benzene rings was synthesized by the condensation of chlorides of substituted pyrazinecarboxylic acids with ring-substituted (chlorine) anilines. The prepared compounds were characterized and evaluated for their antimycobacterial and antifungal activity, and for their ability to inhibit photosynthetic electron transport (PET). 6-Chloro-N-(4-chlorophenyl)pyrazine-2-carboxamide manifested the highest activity against Mycobacterium tuberculosis strain H37Rv (65% inhibition at 6.25 μg/mL). The highest antifungal effect against Trichophyton mentagrophytes, the most susceptible fungal strain tested, was found for 6-chloro-5-tert-butyl-N-(3,4-dichlorophenyl)pyrazine-2-carboxamide (MIC = 62.5 μmol/L). 6-Chloro-5-tert-butyl-N-(4-chlorophenyl)pyrazine-2-carboxamide showed the highest PET inhibition in spinach chloroplasts (Spinacia oleracea L.) chloroplasts (IC₅₀ = 43.0 μmol/L). For all the compounds, the relationships between the lipophilicity and the chemical structure of the studied compounds as well as their structure-activity relationships are discussed. Full article

(This article belongs to the Special Issue ECSOC-12)

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270 KiB

Open AccessArticle

Rhodanineacetic Acid Derivatives as Potential Drugs: Preparation, Hydrophobic Properties and Antifungal Activity of (5-Arylalkylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)acetic Acids

by Jan Dolezel, Petra Hirsova, Veronika Opletalova, Jiri Dohnal, Vejsova Marcela, Jiri Kunes and Josef Jampilek

Molecules 2009, 14(10), 4197-4212; https://doi.org/10.3390/molecules14104197 - 20 Oct 2009

Cited by 47 | Viewed by 11460

Abstract

Some [(5Z)-(5-arylalkylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)]acetic acids were prepared as potential antifungal compounds. The general synthetic approach to all synthesized compounds is presented. Lipophilicity of all the discussed rhodanine-3-acetic acid derivatives was analyzed using a reversed phase high performance liquid chromatography (RP-HPLC) method. The procedure [...] Read more.

Some [(5Z)-(5-arylalkylidene-4-oxo-2-thioxo-1,3-thiazolidin-3-yl)]acetic acids were prepared as potential antifungal compounds. The general synthetic approach to all synthesized compounds is presented. Lipophilicity of all the discussed rhodanine-3-acetic acid derivatives was analyzed using a reversed phase high performance liquid chromatography (RP-HPLC) method. The procedure was performed under isocratic conditions with methanol as an organic modifier in the mobile phase using an end-capped non-polar C₁₈ stationary RP column. The RP-HPLC retention parameter log k (the logarithm of the capacity factor k) is compared with log P values calculated in silico. All compounds were evaluated for antifungal effects against selected fungal species. Most compounds exhibited no interesting activity, and only {(5Z)-[4-oxo-5-(pyridin-2- ylmethylidene)-2-thioxo-1,3-thiazolidin-3-yl]}acetic acid strongly inhibited the growth of Candida tropicalis 156, Candida krusei E 28, Candida glabrata 20/I and Trichosporon asahii 1188. Full article

(This article belongs to the Special Issue ECSOC-12)

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252 KiB

Open AccessArticle

Examination of Imprinting Process with Molsidomine as a Template

by Piotr Luliński and Dorota Maciejewska

Molecules 2009, 14(6), 2212-2225; https://doi.org/10.3390/molecules14062212 - 17 Jun 2009

Cited by 12 | Viewed by 8464

Abstract

Eight different functional monomers were used with ethylene glycol dimethacrylate as a cross-linker and molsidomine as a template to obtain molecularly imprinted polymers (MIPs). Non-covalent interactions between molsidomine and each functional monomer in DMSO prior to thermal bulk polymerization were utilized. On the [...] Read more.

Eight different functional monomers were used with ethylene glycol dimethacrylate as a cross-linker and molsidomine as a template to obtain molecularly imprinted polymers (MIPs). Non-covalent interactions between molsidomine and each functional monomer in DMSO prior to thermal bulk polymerization were utilized. On the basis of calculated imprinting factors, MIP prepared with N,N’-diallyltartaramide was chosen for further investigations. Examination of interactions in the prepolymerization complex between molsidomine and N,N’-diallyltartaramide was performed using the Job method. The absorbance of isomolar solutions reaching a maximum for the molar ratio of template to monomer equal to 1:4. Scatchard analysis was used for estimation of the dissociation constants and the maximum amounts of binding sites. The polymer based on N,N’-diallyltartaramide has two classes of heterogeneous binding sites characterized by two values of K_d and two B_max: K_d(1) = 1.17 mM^-1 and B_max(1) = 0.8 μmol/mg for the higher affinity binding sites, and K_d(2) = 200 μM^-1 and B_max(2) = 2.05 μmol/mg for the lower affinity binding sites. Furthermore, effects of pH and organic solvent on binding properties of MIP and NIP were investigated, together with release of molsidomine from both MIP and NIP. Full article

(This article belongs to the Special Issue ECSOC-12)

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