An efficient reduction of double bonds conjugated with nitrile groups and acid or base sensitive furan rings with 2-phenylbenzimidazoline generated in situ has been successfully accomplished with high yields and excellent selectivity. The employed reducing agent was prepared in one step from ordinary chemicals. The other advantages of the presented method include mild and convenient reaction conditions, a benign and cost effective reagent, simple work-up and separation of the products. As this process does neither affect cyano and nitro groups nor furan rings, it is a valuable alternative when metal-catalyzed hydrogenations or borohydride reductions have failed.

• MeSH
• furany chemická syntéza   chemie   MeSH
• nitrily chemie   MeSH
• oxidace-redukce MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• furan MeSH Prohlížeč
• furany MeSH
• nitrily MeSH

Fatty acid (FA) composition was analyzed in muscle and gonad tissues of marketed common carp (Cyprinus carpio). The extracted lipids were separated into four fractions: polar lipids (PL), diacylglycerols, free fatty acids and triacylglycerols (TAG) using thin layer chromatography. FA content within the lipid fractions was determined by gas chromatography with flame ionization detector (GC/FID). The muscle lipids consisted primarily of TAG (96.9% of total FA), while PL were the major component of both male (67.6%) and female gonad (58.6%) lipids. Polyunsaturated fatty acids predominated in PL of all tissues (52.2-55.8% of total FA); monounsaturated fatty acids were the most abundant FA group in TAG of muscle (51.8%) and female gonads (47.8%) whereas high proportion of furan fatty acids (F-acids) (38.2%) was detected in TAG of male gonads. Eight F-acids were identified by gas chromatography-mass spectrometry (GC/MS) in male gonad samples, including less common 12,15-epoxy-13,14-dimethylnonadeca-12,14-dienoic acid with even-numbered alkyl moiety.

• Klíčová slova
• Common carp, Cyprinus carpio, Fatty acids, Furan fatty acids, Lipids, Milt, Muscle, Roe,
• MeSH
• chromatografie plynová MeSH
• furany analýza   chemie   MeSH
• kapři krev   MeSH
• lipidy analýza   chemie   MeSH
• mastné kyseliny analýza   chemie   MeSH
• ryby MeSH
• zvířata MeSH
• Check Tag
• zvířata MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• furany MeSH
• lipidy MeSH
• mastné kyseliny MeSH

Two novel coordination compounds containing heterocyclic bidentate N,N-donor ligand 2-(furan-2-yl)-5-(pyridin-2-yl)-1,3,4-oxadiazole (fpo) were synthesized. A general formula for compounds originating from perchlorates of iron, cobalt, and fpo can be written as: [M(fpo)2(H2O)2](ClO4)2 (M = Fe(II) for (1) Co(II) for (2)). The characterization of compounds was performed by general physico-chemical methods-elemental analysis (EA), Fourier transform infrared spectroscopy (FT-IR), nuclear magnetic resonance (NMR) in case of organics, and single crystal X-ray diffraction (sXRD). Moreover, magneto-chemical properties were studied employing measurements in static field (DC) for 1 and X-band EPR (Electron paramagnetic resonance), direct current (DC), and alternating current (AC) magnetic measurements in case of 2. The analysis of DC magnetic properties revealed a high spin arrangement in 1, significant rhombicity for both complexes, and large magnetic anisotropy in 2 (D = -21.2 cm-1). Moreover, 2 showed field-induced slow relaxation of the magnetization (Ueff = 65.3 K). EPR spectroscopy and ab initio calculations (CASSCF/NEVPT2) confirmed the presence of easy axis anisotropy and the importance of the second coordination sphere.

• Klíčová slova
• 1,3,4-oxadiazole, second coordination sphere, single-molecule magnet,
• MeSH
• anizotropie MeSH
• elektronová paramagnetická rezonance MeSH
• furany chemie   MeSH
• kobalt chemie   MeSH
• komplexní sloučeniny chemie   MeSH
• krystalografie rentgenová MeSH
• magnetická rezonanční spektroskopie MeSH
• molekulární modely MeSH
• oxadiazoly chemie   MeSH
• spektroskopie infračervená s Fourierovou transformací MeSH
• spektroskopie Mossbauerova MeSH
• železnaté sloučeniny chemie   MeSH
• železo chemie   MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• 1,3,4-oxadiazole MeSH Prohlížeč
• furan MeSH Prohlížeč
• furany MeSH
• kobalt MeSH
• komplexní sloučeniny MeSH
• oxadiazoly MeSH
• železnaté sloučeniny MeSH
• železo MeSH

BACKGROUND: The aim of the current work was to determine thermo dynamical properties of 5(2-nitro phenyl)-furan-2-carbaldehyde, 5(3-nitro phenyl)-furan-2-carbaldehyde and 5(4-nitro phenyl)-furan-2-carbaldehyde. RESULTS: The temperature dependence of saturated vapor pressure of 5(2-nitro phenyl)-furan-2-carbaldehyde, 5(3-nitro phenyl)-furan-2-carbaldehyde and 5(4-nitro phenyl)-furan-2-carbaldehyde was determined by Knudsen's effusion method. The results are presented by the Clapeyron-Clausius equation in linear form, and via this form, the standard enthalpies, entropies and Gibbs energies of sublimation and evaporation of compounds were calculated at 298.15 K. The standard molar formation enthalpies of compounds in crystalline state at 298.15 K were determined indirectly by the corresponding standard molar combustion enthalpy, obtained using bomb calorimetry combustion. CONCLUSIONS: Determination of the thermodynamic properties for these compounds may contribute to solving practical problems pertaining optimization processes of their synthesis, purification and application and it will also provide a more thorough insight regarding the theoretical knowledge of their nature.Graphical abstract:Generalized structural formula of investigated compounds and their formation enthalpy determination scheme in the gaseous state.

• Klíčová slova
• 5(2-Nitrophenyl)-furan-2-carbaldehydes, Combustion enthalpy, Formation enthalpy, Isomerisation enthalpy, Sublimation enthalpy, Vapor pressure, Vaporization enthalpy,
• Publikační typ
• časopisecké články MeSH

3-(Substituted phenyl)-5-acyloxymethyl-2H,5H-furan-2-ones related to the natural product (-)incrustoporine were synthesized and their in vitro antifungal activity evaluated. The compounds with halogen substituents on the phenyl ring displayed much higher antifungal effect against Aspergillus fumigatus than selected representatives of azole antifungal drugs. In particular, the activity (1.34 microg/mL) of the most promising derivative, 3-(3,4-dichlorophenyl)-5-pivaloyloxymethyl-2H,5H-furan-2-one, was comparable to that of amphotericin B (0.5 microg/mL). Preliminary evaluation of the toxicity of the compound was carried out as well. Considering the size and properties of these molecules in comparison with those of amphotericin B, further development of this novel group of antifungals may lead to substances with better pharmacological profiles than that of the standard anti-Aspergillus drug.

• MeSH
• amfotericin B farmakologie   MeSH
• antifungální látky chemická syntéza   chemie   farmakologie   MeSH
• furany chemická syntéza   chemie   farmakologie   MeSH
• gama-butyrolakton analogy a deriváty   chemická syntéza   chemie   farmakologie   MeSH
• houby účinky léků   MeSH
• lidé MeSH
• mikrobiální testy citlivosti MeSH
• stereoizomerie MeSH
• vztahy mezi strukturou a aktivitou MeSH
• Check Tag
• lidé MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• srovnávací studie MeSH
• Názvy látek
• 3-(3,4-dichlorophenyl)-5-pivaloylmethyl-2H,5H-furan-2-one MeSH Prohlížeč
• amfotericin B MeSH
• antifungální látky MeSH
• furany MeSH
• gama-butyrolakton MeSH

• Klíčová slova
• FUNGI/effect of drugs on *, FURAN DERIVATIVES/effects *,
• MeSH
• furany farmakologie   MeSH
• houby účinky léků   MeSH
• kyseliny * MeSH
• Publikační typ
• časopisecké články MeSH
• Názvy látek
• furan MeSH Prohlížeč
• furany MeSH
• kyseliny * MeSH

Two silver(I) complexes with biologically relevant heterocyclic ligands, pyrrole and furan-2- carboxylic acid, were synthesized and their composition was confirmed using elemental, spectral, thermal and structural analyses. The {[Ag(Py2c)]}n (AgPy2c, Py2c = pyrrole-2-carboxylate) and {[Ag(Fu2c)]}n (AgFu2c, Fu2c = furan-2-carboxylate) solubility and stability in biological test stock solution were confirmed by 1H NMR spectroscopy. The X-ray analysis has enabled us to determine typical argentophilic interactions and bridging carboxylate coordination mode of both ligands. Potentiometric data analysis by BSTAC program resulted in the determination of the stability constant of only one species, i.e., the ML (M = Ag+, L = Fu2c-), log βML = 0.59 ± 0.04. Antimicrobial and anticancer tests were performed against selected microorganisms and cell lines with new silver(I) complexes and compared with AgSD (silver(I) sulfadiazine) and cisplatin. From their microbial toxicity point of view, selectivity was determined against lactobacilli (AgPy2c is 8× more effective against S. aureus and E. coli and AgFu2c is 8× more effective against E. coli and 4× against S. aureus). AgFu2c significant anticancer activity was determined against Jurkat cell lines (IC50 = 8.00 μM) and was similar to cisPt (IC50 = 6.3 μM) similarly to its selectivity (SI (AgFu2c) = 7.3, SI (cisPt) = 6.4, SI = selectivity index). In addition, cell cycle arrest was observed already in the Sub-G0 phase during a flow cytometry experiment. To evaluate the AgPy2c and AgFu2c bioavailability we also discuss their Lipinski's Rule of Five.

• Klíčová slova
• Anticancer, Antimicrobial, Cell cycle, Crystallography, Lipophilicity, Potentiometry, Selectivity, Silver(I) complexes, Stability,
• MeSH
• antibakteriální látky farmakologie   chemie   MeSH
• antiinfekční látky * farmakologie   chemie   MeSH
• Escherichia coli MeSH
• furany farmakologie   MeSH
• komplexní sloučeniny * farmakologie   chemie   MeSH
• ligandy MeSH
• mikrobiální testy citlivosti MeSH
• Staphylococcus aureus MeSH
• stříbro farmakologie   chemie   MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• 2-furoic acid MeSH Prohlížeč
• antibakteriální látky MeSH
• antiinfekční látky * MeSH
• furany MeSH
• komplexní sloučeniny * MeSH
• ligandy MeSH
• stříbro MeSH

We report a dissociative electron attachment study to 2-furoic acid (C5H4O3) isolated in a gas phase, which is a model molecule consisting of a carboxylic group and a furan ring. Dissociation of furan by low energy electrons is accessible only via electronic excited Feshbach resonances at energies of incident electrons above 5 eV. On the other hand, carboxylic acids are well-known to dissociate via attachment of electrons at subexcitation energies. Here we elucidate how the electron and proton transfer reactions induced by carboxylation influence stability of the furan ring. Overlap of the furan and carboxyl π orbitals results in transformation of the nondissociative π2 resonance of the furan ring to a dissociative resonance. The interpretation of hydrogen transfer reactions is supported by experimental studies of 3-methyl-2-furoic and 5-methyl-2-furoic acids (C6H6O3) and density functional theory (DFT) calculations.

• Publikační typ
• časopisecké články MeSH

A series of racemic 3-phenyl-5-methyl-2H,5H-furan-2-ones related to a natural product, (-)incrustoporine, was synthesized, and their antifungal activity evaluated. The key structural feature, furanone ring, was closed via H2SO4-mediated cyclization of 2-phenylpent-4-enoic acids. The compounds displayed antifungal activity, especially against filamentous fungi. Expressed as the minimum inhibition concentration (MIC) in micromol/L, the activity of the most promising derivative against Absidia corymbifera matched that of ketoconazole (31.25 micromol/L). In terms of microg/mL, the substance was more active (7.6 microg/mL) than this standard antifungal drug (16.6 microg/mL).

• MeSH
• antifungální látky chemická syntéza   chemie   farmakologie   MeSH
• chlorbenzeny chemická syntéza   chemie   farmakologie   MeSH
• cyklizace MeSH
• gama-butyrolakton analogy a deriváty   chemická syntéza   chemie   farmakologie   MeSH
• houby účinky léků   MeSH
• ketokonazol farmakologie   MeSH
• lidé MeSH
• molekulární struktura MeSH
• racionální návrh léčiv MeSH
• Check Tag
• lidé MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• Názvy látek
• 3-(3,4-dichlorophenyl)-5-methyl-2H,5H-furan-2-one MeSH Prohlížeč
• antifungální látky MeSH
• chlorbenzeny MeSH
• gama-butyrolakton MeSH
• incrustoporin MeSH Prohlížeč
• ketokonazol MeSH

On model examples, we compare the performance of the vibrational self-consistent field, variational, and four perturbational schemes used for computations of vibrational energies of semi-rigid molecules, with emphasis on the numerical stability. Although the accuracy of the energies is primarily dependent on the quality of the potential energy surface, approximate approaches to the anharmonic vibrational problem often do not converge to the same results due to the approximations involved. For furan, the sensitivity to variations of the anharmonic potential was systematically investigated by adding random noise to the cubic and quartic constants. The self-consistent field methods proved to be the most resistant to the potential variations. The second order perturbational techniques are sensitive to random degeneracies and provided the least stable results. However, their stability could be significantly improved by a simple generalization of the perturbational formula. The variational configuration interaction is practically limited by the size of the matrix that can be diagonalized for larger molecules; however, relatively fewer states need to be involved than for smaller ones, in favor of the computing.

• MeSH
• algoritmy * MeSH
• formaldehyd chemie   MeSH
• furany chemie   MeSH
• počítačová simulace * MeSH
• spektrální analýza MeSH
• velikost částic MeSH
• vibrace * MeSH
• Publikační typ
• časopisecké články MeSH
• práce podpořená grantem MeSH
• srovnávací studie MeSH
• Názvy látek
• formaldehyd MeSH
• furan MeSH Prohlížeč
• furany MeSH