Reaction of some 3-(phenylthioaryl)propionic acids with polyphosphoric acid; Formation of 2H-cyclopenta[k,l]thioxanthenes

1979 ◽  
Vol 44 (7) ◽  
pp. 2124-2138 ◽  
Author(s):  
Jiří O. Jílek ◽  
Jiří Holubek ◽  
Emil Svátek ◽  
Miroslav Ryska ◽  
Josef Pomykáček ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Propionic Acid ◽  
Polyphosphoric Acid ◽  
Main Product ◽  
Product Formation ◽  
Acid Formation ◽  
Phenyl Propionic Acid ◽  
Isomeric Acid ◽  
By Products ◽  
Predominant Product

The cyclization of 3-[2-(phenylthio)phenyl]propionic acid (I) with polyphosphoric acid gave equal amounts of 4-(phenylthio)indanone (III) and 2H-cyclopenta[k,l]thioxanthene (VI), accompanied with a small amount of the macrocyclic diketone V. Compound VI was evidently formed via the cation XII and 7-(phenylthio)indanone (X) which was quantitatively dehydrocyclized. Similar cyclization of the isomeric acid XIIIa yielded 5-(phenylthio)indanone (XVIII) as the main product; formation of VI could be detected only chromatographicaly. Cyclization of 3-[2-(chloro-5-(phenylthio)phenyl]propionic acid (XIIIb) gave 3-chloro-2H-cyclopenta[k,l]thioxanthene (VII) as the predominant product. From the by-products formed, only 4-chloro-7-(phenylthio)indanone (XI) could be identified, being the precursor of compound VII. Treatment of thioxanthene-9-acetic acid (XXII) with polyphosphoric acid resulted in a cleavage with thioxanthone (XXIII) and thioxanthene (XXIV) as the main products.

scholarly journals Impact of Fermentable Fibres on the Colonic Microbiota Metabolism of Dietary Polyphenols Rutin and Quercetin

2019 ◽  
Vol 16 (2) ◽  
pp. 292 ◽  
Author(s):  
Bahareh Mansoorian ◽  
Emilie Combet ◽  
Areej Alkhaldy ◽  
Ada L. Garcia ◽  
Christine Ann Edwards
Keyword(s):  
Gas Chromatography ◽  
Acetic Acid ◽  
Propionic Acid ◽  
Phenolic Acids ◽  
Gas Chromatography Mass Spectrometry ◽  
Phenyl Acetic Acid ◽  
Potential Health ◽  
Dietary Polyphenols ◽  
Colonic Microbiota ◽  
Phenyl Propionic Acid

Dietary fibre and polyphenols are both metabolised to short-chain fatty acids (SCFAs) and phenolic acids (PA) by the colonic microbiota. These may alter microbiota growth/diversity, but their interaction is not understood. Interactions between rutin and raftiline, ispaghula or pectin were investigated in human faecal batch cultures (healthy participants; 19–33 years, 4 males, 6 females, BMI 18.4–27.4) after a low (poly)phenol diet three days prior to study. Phenolic acids were measured by gas chromatography-mass spectrometry and SCFAs by gas chromatography-flame ionisation after 2, 4, 6, and 24 h. Rutin fermentation produced Phenyl acetic acid (PAA), 4-Hydroxy benzoic acid (4-OHBA), 3-Hydroxy phenyl acetic acid (3-OHPAA), 4-Hydroxy phenyl acetic acid (4-OHPAA), 3,4-Dihydroxy phenyl acetic acid (3,4-diOHPAA), 3-Hydroxy phenyl propionic acid (3-OHPPA), and 4-Hydroxy phenyl propionic acid (4-OHPPA). 3,4-DiOHPAA and 3-OHPAA were predominant at 6 h (1.9 ± 1.8 µg/mL, 2.9 ± 2.5 µg/mL, and 0.05 ± 0.0 µg/mL, respectively) and 24 h (5.5 ± 3.3 µg/mL, 3.1 ± 4.2 µg/mL, and 1.2 ± 1.6 µg/mL). Production of all PA except 3-OHPPA and 4-OHPPA was reduced by at least one fibre. Inhibition of PA was highest for rutin (8-fold, p < 0.01), then pectin (5-fold, p < 0.01), and ispaghula (2-fold, p = 0.03). Neither rutin nor quercetin had a detectable impact on SCFA production. These interactions should be considered when assessing dietary polyphenols and potential health benefits.

Potential metabolites of tricyclic neuroleptics: 2,8-Dihydroxy and 3,8-dihydroxy derivatives of 10-(4-methylpiperazino)-10,11-dihydrodibenzo[b,f]thiepin

1979 ◽  
Vol 44 (10) ◽  
pp. 2987-2996 ◽  
Author(s):  
Miroslav Protiva ◽  
Karel Šindelář ◽  
Zdeněk Šedivý ◽  
Josef Pomykáček
Keyword(s):  
Acetic Acid ◽  
Polyphosphoric Acid ◽  
Substitution Reactions ◽  
Piperazine Derivatives ◽  
Neuroleptic Agent ◽  
Boron Tribromide ◽  
Derivatives Of ◽  
Isomeric Acid ◽  
Central Depressant ◽  
Methoxybenzoic Acid

A synthesis of the title compounds II and III, potential metabolites of the neuroleptic agent perathiepin I, was carried out. A reaction of (2-iodo-5-methoxyphenyl)acetic acid with 4-methoxythiophenol afforded the acid VI. The isomeric acid XI was obtained from 2-iodo-4-methoxybenzoic acid by reaction with 4-methoxythiophenol and via intermediates VIII-X. Both acids (VI,XI) were cyclized with polyphosphoric acid to dimethoxydibenzo[b,f]thiepin-10(11H)-onesXIIab which were transformed via the alcohols XIIIab to the chloro compounds XIVab. Substitution reactions with 1-methylpiperazine gave the piperazine derivatives IV and V and dimethoxydibenzo[b,f]thiepins XVab. The dimethoxy compounds IV and V were demethylated with boron tribromide to the diaminodiphenols II and III. The central depressant and cataleptic activity of compounds II-V is lower than that of the unsubstituted substance I.

Fluorinated analogues of the tricyclic neuroleptics; 7-Fluoro and 7-trifluoromethyl derivative of 10-(4-methylpiperazino)-10,11-dihydrodibenzo[b,f]thiepin

1980 ◽  
Vol 45 (4) ◽  
pp. 1086-1098 ◽  
Author(s):  
Karel Šindelář ◽  
Emil Svátek ◽  
Jiří Holubek ◽  
Miroslav Ryska ◽  
Jiřina Metyšová ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Alkaline Hydrolysis ◽  
Title Compound ◽  
Polyphosphoric Acid ◽  
Titanium Tetrachloride ◽  
Keto Acid ◽  
Methanesulfonyl Chloride ◽  
Trifluoromethyl Derivative ◽  
By Products ◽  
Central Depressant

Reaction of 3-fluorothiophenol with (2-iodophenyl)acetic acid gave the acid VIII which was cyclized with polyphosphoric acid to the ketone XII. The first title compound VI was prepared via the intermediates XV and XVIII. Treatment of the ketone XII with 1-methylpiperazine in the presence of titanium tetrachloride resulted in the enamine XXIII. The similarly prepared acid IX was cyclized to the ketone XIII. By-products were the di-acid X and the enol-lactone XXIV, affording by alkaline hydrolysis the keto acid XXV. The synthesis of the second title compound VII was carried out from the ketone XIII via the intermediates XVI and XIX. 10,11-Dihydrodibenzo[b,f]thiepin-3,11-diol (XVII) gave by treatment with methanesulfonyl chloride and by the following reaction with 1-methylpiperazine the salt of 1-methylpiperazine with dibenzo[b,f]thiepin-3-ol (XXII) and 1-methyl-4-(methylsulfonyl)piperazine (XXVI)). Whereas the compound VI has low central depressant and cataleptic activity, the corresponding enamine XXIII is very potent in both lines. The trifluoromethyl derivative VII has the character of a neuroleptic but its depressant and cataleptic activity are ten times lower than those of the 8-trifluoromethyl isomer.

Fluorinated tricyclic neuroleptics with prolonged action: 8-Methoxy, 8-ethoxy, 8-ethylthio and 8-hydroxy derivatives of 3-fluoro-10-(4-methylpiperazino)-10,11-dihydrodibenzo[b,f]thiepin

1982 ◽  
Vol 47 (5) ◽  
pp. 1382-1391 ◽  
Author(s):  
Jiří Jílek ◽  
Josef Pomykáček ◽  
Jiřina Metyšová ◽  
Miroslav Protiva
Keyword(s):  
Acetic Acid ◽  
Polyphosphoric Acid ◽  
Prolonged Action ◽  
Substitution Reactions ◽  
Methoxy Derivative ◽  
Chloro Derivatives ◽  
Boron Tribromide ◽  
Derivatives Of ◽  
Central Depressant ◽  
Boiling Toluene

Acids IIa-c were prepared by reactions of (4-fluoro-2-iodophenyl)acetic acid with 4-methoxythiophenol, 4-ethoxythiophenol and 4-(ethylthio)thiophenol and cyclized with polyphosphoric acid in boiling toluene to dibenzo[b,f]thiepin-10(11H)-ones IIIa-c. Reduction with sodium borohydride afforded the alcohols IVa-c which were treated with hydrogen chloride and gave the chloro derivatives Va-c. Substitution reactions with 1-methylpiperazine resulted in the title compounds Ia-c out of which the methoxy derivative Ia was transformed by demethylation with boron tribromide to the phenol Id. Compounds Ia-d are very potent neuroleptics exhibiting a clear prolongation of the central depressant and some prolongation of the cataleptic activity.

Fluorinated analogues of tricyclic neuroleptics: 6,9-difluoro derivative of 10-(4-methylpiperazino)-10,11-dihydrodibenzo[b,f]thiepin

1980 ◽  
Vol 45 (10) ◽  
pp. 2688-2694 ◽  
Author(s):  
Irena Červená ◽  
Marta Hrubantová ◽  
Emil Svátek ◽  
Jiří Holubek ◽  
Miroslav Ryska ◽  
...  
Keyword(s):  
Acetic Acid ◽  
Title Compound ◽  
Substitution Reaction ◽  
Polyphosphoric Acid ◽  
Satisfactory Yield ◽  
Chloro Derivative ◽  
Cns Activity

The acid VI, obtained from 2,5-difluorothiophenol (IV) and (2-iodophenyl)acetic acid, afforded by cyclization with polyphosphoric acid 6,9-difluorodibenzo[b,f]thiepin-10(11H)-one (VII) in a satisfactory yield. Two further steps led to the chloro derivative X giving by a substitution reaction with 1-methylpiperazine the title compound III. This substance exhibits some 10% incoordinating activity of the unsubstituted compound I and an indication of cataleptic activity, in contrast to the inactive analogous dichloro compound II. The bulky atom of chlorine in the vicinity of the methylpiperazine residue interferes evidently with the CNS activity; the influence of the atom of fluorine is much less pronounced in this line.

Excess molar volumes of binary mixtures of acetic acid and propionic acid with some members of homologous series of alkanes

1991 ◽  
Vol 56 (4) ◽  
pp. 736-744 ◽  
Author(s):  
Ondřej Drábek ◽  
Ivan Cibulka
Keyword(s):  
Acetic Acid ◽  
Propionic Acid ◽  
Alkyl Chain ◽  
Excess Molar Volumes ◽  
Liquid Mixtures ◽  
Entire Concentration Range ◽  
Molar Volumes ◽  
Binary Liquid ◽  
Alkane Molecule ◽  
Increasing Temperature

Excess molar volumes of binary liquid mixtures of (acetic or propionic acid = hexane) at 25 and 35°C, and (acetic or propionic acid + heptane or octane) and (acetic acid + dodecane) at 25°C, measured with a tilting dilution dilatometer, are reported. The excess volumes are positive over the entire concentration range for all mixtures and increase with increasing length of an alkane molecule, decrease with increasing of the alkyl chain in a molecule of carboxylic acid, and increase with increasing temperature.

Vapour-liquid equilibrium in the ternary system cyclohexane-acetic acid-propionic acid

1989 ◽  
Vol 54 (11) ◽  
pp. 2840-2847 ◽  
Author(s):  
Ivona Malijevská ◽  
Alena Maštalková ◽  
Marie Sýsová
Keyword(s):  
Acetic Acid ◽  
Ternary System ◽  
Propionic Acid ◽  
Activity Coefficients ◽  
Error Propagation ◽  
Analytical Techniques ◽  
Liquid Equilibrium ◽  
Consistency Test ◽  
Propagation Law ◽  
Equilibrium Data

Isobaric equilibrium data (P = 101.3 kPa) for the system cyclohexane-acetic acid-propionic acid have been measured by two different analytical techniques. Activity coefficients calculated by simultaneous solving of equations for the chemical and phase equilibria were subjected to a consistency test based on inaccuracies determined from the error propagation law, and were correlated by Wilson’s equation. The activity coefficients measured were compared with those calculated from binary vapour-liquid equilibrium data and with values predicted by the UNIFAC method.

scholarly journals Pilot Study of the Effects of Polyphenols from Chestnut Involucre on Methane Production, Volatile Fatty Acids, and Ammonia Concentration during In Vitro Rumen Fermentation

Animals ◽  
2021 ◽  
Vol 11 (1) ◽  
pp. 108
Author(s):  
Yichong Wang ◽  
Sijiong Yu ◽  
Yang Li ◽  
Shuang Zhang ◽  
Xiaolong Qi ◽  
...  
Keyword(s):  
Fatty Acids ◽  
Acetic Acid ◽  
Propionic Acid ◽  
Acid Content ◽  
Volatile Fatty Acids ◽  
Rumen Fermentation ◽  
Gas Production ◽  
Quadratic Response ◽  
In Vitro Rumen Fermentation

Nutritional strategies can be employed to mitigate greenhouse emissions from ruminants. This article investigates the effects of polyphenols extracted from the involucres of Castanea mollissima Blume (PICB) on in vitro rumen fermentation. Three healthy Angus bulls (350 ± 50 kg), with permanent rumen fistula, were used as the donors of rumen fluids. A basic diet was supplemented with five doses of PICB (0%–0.5% dry matter (DM)), replicated thrice for each dose. Volatile fatty acids (VFAs), ammonia nitrogen concentration (NH3-N), and methane (CH4) yield were measured after 24 h of in vitro fermentation, and gas production was monitored for 96 h. The trial was carried out over three runs. The results showed that the addition of PICB significantly reduced NH3-N (p < 0.05) compared to control. The 0.1%–0.4% PICB significantly decreased acetic acid content (p < 0.05). Addition of 0.2% and 0.3% PICB significantly increased the propionic acid content (p < 0.05) and reduced the acetic acid/propionic acid ratio, CH4 content, and yield (p < 0.05). A highly significant quadratic response was shown, with increasing PICB levels for all the parameters abovementioned (p < 0.01). The increases in PICB concentration resulted in a highly significant linear and quadratic response by 96-h dynamic fermentation parameters (p < 0.01). Our results indicate that 0.2% PICB had the best effect on in-vitro rumen fermentation efficiency and reduced greenhouse gas production.

scholarly journals Insights into the interactions and dynamics of a DES formed by phenyl propionic acid and choline chloride

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Parisa Jahanbakhsh Bonab ◽  
Alireza Rastkar Ebrahimzadeh ◽  
Jaber Jahanbin Sardroodi
Keyword(s):  
Diffusion Coefficient ◽  
Liquid Phase ◽  
Propionic Acid ◽  
Structural Parameters ◽  
Choline Chloride ◽  
Self Diffusion ◽  
Phenyl Propionic Acid ◽  
Donor And Acceptor ◽  
Experimental Values ◽  
Self Diffusion Coefficient

AbstractDeep eutectic solvents (DESs) have received much attention in modern green chemistry as inexpensive and easy to handle analogous ionic liquids. This work employed molecular dynamics techniques to investigate the structure and dynamics of a DES system composed of choline chloride and phenyl propionic acid as a hydrogen bond donor and acceptor, respectively. Dynamical parameters such as mean square displacement, liquid phase self-diffusion coefficient and viscosity are calculated at the pressure of 0.1 MPa and temperatures 293, 321 and 400 K. The system size effect on the self-diffusion coefficient of DES species was also examined. Structural parameters such as liquid phase densities, hydrogen bonds, molecular dipole moment of species, and radial and spatial distribution functions (RDF and SDF) were investigated. The viscosity of the studied system was compared with the experimental values recently reported in the literature. A good agreement was observed between simulated and experimental values. The electrostatic and van der Waals nonbonding interaction energies between species were also evaluated and interpreted in terms of temperature. These investigations could play a vital role in the future development of these designer solvents.

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