Search

A new class of chiral pyrrolidinone was synthesized from (5S)-5-[(trityloxy)methyl] pyrrolidin-2-one (6) (Schemes 1 and 2). The synthetic design followed led to the insertion of various substituents at 1 and 5 of the pyrrolidinone moiety. Some of them possess two or three stereo centers, here configuration was retained under the mild condition. The new compounds also carry an imidazole moiety, which, along with the 2-pyrrolidinone template, may prove pivotal to several biological processes. The chiral pyrrolidinone (R) ring is incorporatedin various compounds with biological and pharmaceutical activities [1]. some of them are well known medicines, e.g., doxapram for patients with respiratory failure,piracetam for patients with Alzheimer’s seizures, and senile dementia, concussion and other neurological problems [2,3]. The properties and applications of pyroglutamic acid as a versatile building block in asymmetric synthesis has extensively been reviewed in the literature[4,5]. Some of them exhibited anti-inflammatory and antihypertensive activity [6,7]

The addition of malonates to trans-β-alkyl-β-nitrostyrenes in the presence of chiral Mg2+ bisoxazoline complex and Ni2+ and Co2+ bis((S,S)- or (R,R)-N,N′-dibenzylcyclohexane-1,2-diamine) complexes resulted in the formation of Michael adducts with two stereo-centers which were used as key precursors for the preparation of potentially biologically active enantiopure 4,5-disubstituted pyrrolidin-2-one derivatives.

International audience; Twenty-eight 5-pyrrolidine-2-ones decorated by hydrazine or acyl hydrazones groups have been designed, synthesized and evaluated as antifungal agents on a panel of twelve fungal strains and three non albicans candida yeasts species which have demonstrated reduced susceptibility to commonly used antifungal drugs. Half of the target compounds exhibited good to high antifungal activities on at least one strain with MIC50 lower than the control antifungal agent – hymexazol or ketoconazole. 5-Arylhydrazino-pyrrolidin-2-ones were found active and the –NH-NH- linker proved to be essential to maintain the antifungal potential. Compound 2a is a broad-spectrum antifungal, active on 60% of the tested strains. Replacing the hydrazine linker by an acylhydrazone one narrowed the spectrum of activity but pyroglutamylaryl hydrazones, mainly aromatic ones, exhibited good activity, adequate “fungicide-like” properties and were devoted of cytotoxicity.

A series of new spirooxindole derivatives were synthesized via 1,3 –dipolar cycloaddition. All the synthesized compounds were evaluated for antimicrobial activity. In antibacterial studies compound 4d demonstrated the most potent inhibitory activity (MIC = 12.5 lg/mL for K.pneumonia, B.cereus and S.typhi), which was compared with the positive control streptomycin. In antifungal studies compound 4e demonstrated the most potent inhibitory activity (MIC = 3.125 lg/mL for C.albicans and A.niger), which was related with the standard drug ketaconazole. In addition, molecular modeling studies were also performed to disclose the binding modes of the most active inhibitors to the amino acid residues that compose the active site of the glucosamine-6-phosphate synthase and crystal structure of human lanosterol 14-alpha dimethylase in complex with ketaconazole enzyme.

A facile regio and stereoselective synthesis of novel spiro[indolin-3,2′-pyrrolidin]-2-one’s have been accomplished through 1,3-dipolar cycloaddition of azomethine ylides generated in situ from the...

Present study reports, densities, speeds of sound, molar heat capacities, of binary 1-methylpiperidine (1) + cyclopentanone, cyclohexanone, cycloheptanone (3) and ternary 1-methylpiperidine (1) + pyrrolidin-2-one (2) + cyclopentanone, cyclohexanone, cycloheptanone (3) mixtures over entire mole fraction, x1; and x1, x2 at temperatures from (293.15 to 308.15) K in interval of 5 K. Excess thermodynamic properties like excess molar volumes, V E ; excess isentropic compressibilities, κ S E ; excess heat capacities, C P E of the current mixtures have been derived using experimental data. V E , κ S E and C P E for each of the mixture have been correlated to the composition of the constituent liquids via Redlich-Kister equation and standard deviations, adjustable parameters have also been estimated. Further, V E , κ S E and C P E data have been interpreted qualitatively and quantitatively (Graph theory) to characterize molecular interactions. Further, IR studies legitimized the purposed nature and extent of molecular interactions.

International audience; In this study, new benzoxazole-linked pyrrolidinone heterocyclic compounds were synthesized by an eco-efficient strategy using substituted benzylamines and 2-aminophenol under ultrasonic irradiation in the presence of a newly designed metal-free deep eutectic solvent (DES). This DES was prepared by using a eutectic mixture of urea and a synthesized glycine-derived ionic liquid. X-ray diffraction and infrared spectroscopy were employed to investigate the structure of the ionic liquid and characterize the DES, respectively. This method exhibited key advantages of high productivity, a short reaction time, and simple processing. Moreover, this DES was easily separated from reaction mixtures and can be recycled for multiple reactions.

A bifunctional phosphine-catalyzed highly enantioselective [2+4] cycloaddition of α-substituted allenoates with (E)-1-benzyl-4-olefinicpyrrolidine-2,3-diones has been achieved, giving pyrrolidin-2-one fused dihydropyran derivatives in moderate to good yields with excellent enantioselectivities (up to 98% ee). This reaction provides a useful catalytic asymmetric access to dihydropyran structural motifs.

We report herein the first synthesis of biologically active natural bromophenols, namely 1-(2,3,6-tribromo-4,5-dihydroxybenzyl)pyrrolidin-2-one (2), 2RS-1-(2,3-dibromo-4,5-dihydroxybenzyl)-5-oxopyrrolidine-2-carboxylic acid (3), and 2RS-methyl 1-(2,3-dibromo-4,5-dihydroxybenzyl)-5-oxopyrrolidine-2-carboxylate (4), along with their different derivatives (6 and 8-18). Among the synthesized compounds, , 4, and their derivatives (8 and 9) are yielded in racemic form. Radical scavenging assays of the synthesized molecules were investigated using various bioanalytical antioxidant methods including 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS$^{\bullet +})$ and 2,2-diphenyl-1-picrylhydrazyl (DPPH$^{\bullet })$. In addition, the reducing power of the novel bromophenols was investigated by Cu$^{2+}$-Cu$^{+}$ reducing, Fe$^{3+}$-Fe$^{2+}$ reducing, and [Fe$^{3+}$-(TPTZ)$_{2}$]$^{3+}$-[Fe$^{2+}$-(TPTZ)$_{2}$]$^{2+}$ reducing capacity and ferrous ions (Fe$^{2+})$ chelating abilities. The molecules demonstrated powerful antioxidant activities when compared to standard antioxidant compounds of $\alpha $-tocopherol, trolox, butylated hydroxyanisole (BHA), and butylated hydroxytoluene (BHT). Moreover, novel bromophenols were tested against cholinergic enzymes including acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes in the last part of this study. The presented novel bromophenols showed Ki values in the range of 2.60 $\pm $ 0.75-16.36 $\pm $ 2.67 nM against AChE and 13.10 $\pm $ 3.33-54.47 $\pm $ 13.53 nM against BChE.

Excess molar enthalpies, H ijk E of ternary 1-ethyl-3-methylimidazolium tetrafluoroborate (i) + Pyrrolidin-2-one (j) + Pyridine or Water (k); 1-ethyl-3-methylimidazolium tetrafluoroborate (i) 1-methyl pyrrolidin-2-one (j) + Pyridine or Water (k) and HE of Pyrrolidin-2-one (i) + Pyridine or Water (j); 1-methyl pyrrolidin-2-one (i) + Pyridine (j); 1-ethyl-3-methylimidazolium tetrafluoroborate (i) + Water (j) mixtures have been measured over entire mole fraction range at 298.15 K. The H ijk E value for 1-ethyl-3-methylimidazolium tetrafluoroborate (i) + Pyrrolidin-2-one (j) + Water (k); 1-ethyl-3-methylimidazolium tetrafluoroborate (i) + 1-methyl pyrrolidin-2-one (j) + Pyridine or Water (k) are positive over whole range of composition and for 1-ethyl-3-methylimidazolium tetrafluoroborate (i) + Pyrrolidin-2-one (j) + Pyridine (k) mixture, the sign of H ijk E values varies with change in composition of the components. The observed data have been analyzed in terms of (i) Graph; and (ii) Prigogine–Flory–Patterson (PFP) theories. Results indicate that HE and H ijk E values obtained by Graph theory are in good agreement with experimental data. The PFP theory correctly predict sign as well as magnitude of HE values for the binary mixtures. However, theory fails to predict the sign of H ijk E values for the ternary mixtures.

The excess heat capacities, C P E , of binary 1-methyl pyrrolidin-2-one (i) + pyridine or α- or β- or γ-picoline (j) mixtures have been measured as a function of composition at 293.15, 298.15 and 303.15 K using micro differential scanning calorimeter (Model – μDSC 7 Evo). The C P E data have been fitted to Redlich–Kister equation to calculate binary adjustable parameters and standard deviations. The measured property of the studied mixtures has been analyzed in terms of Graph (which deals with the topology of the constituent of mixtures) theory. It has been observed that Graph theory describes well the C P E data of the investigated binary mixtures.

The total synthesis of the pyrrolidinone alkaloid rigidiusculamide A is reported starting from L-tyrosine, using amidation, ring-closing metathesis, and dihydroxylation as the key reactions.

Excess molar volumes V E, excess molar enthalpies H E, and speeds of sound u for 1-methyl pyrrolidin-2-one (1) + water or propan-1-ol or propan-2-ol (2) binary mixtures have been measured over the entire composition range (at 308.15 K) using a dilatometer, calorimeter and interferometer. Speeds of sound data, u, of (1 + 2) binary mixtures have been utilized to determine excess isentropic compressibilities, $$ \kappa_{S}^{\text{E}} $$ . The observed V E, H E and $$ \kappa_{S}^{\text{E}} $$ data have been analyzed in terms of (1) Graph theory (which involves the topology of the constituents of mixture), and (2) the Prigogine–Flory–Patterson theory. Analysis of V E data in terms of Graph theory suggests that 1-methyl pyrrolidin-2-one, water, propan-1-ol, and propan-2-ol exist as associated molecular entities. IR studies lend additional support to the proposed molecular entities in (1 + 2) mixtures. It has been observed that V E, H E and $$ \kappa_{S}^{\text{E}} $$ values predicted by Graph theory compare well with their corresponding experimental values.

Tandem approaches for the synthesis of pyrrolidone precursor of allokainic acid and kainic acid are described. The synthesis of pyrrolidone intermediate of allokainic acid is achieved by tandem Wittig–Michael reaction and tandem amidation-Michael reaction while one pot amidation—Ene-esterification is employed for the synthesis of Ganem intermediate (2:1) of kainic acid.

An efficient catalyst-free synthesis of 3′-benzoyl-4′,5′-diphenyl-2H-spiro[acenaphthylene-1,2′-pyrrolidin]-2-one derivatives via one-pot 1,3-dipolar cycloaddition of acenaphthenequinone, arylmethyl amines, and chalcones with high regioselectivity is described. The structure of the cycloadducts were characterized by infrared, high-resolution mass spectrometry (electrospray ionization), 1H NMR, and 13C NMR spectra, and the structure of 4a was confirmed using x-ray single-crystal structure analysis.

Excess molar enthalpies, HE of 1-ethyl-3-methylimidazolium tetrafluoroborate (1) + pyrrolidin-2-one or 1-methyl pyrrolidin-2-one (2) binary mixtures at 298.15 K, densities, ρ, and speeds of sound, u, data of the same mixtures at (293.15, 298.15, 303.15, and 308.15) K have been measured over entire mole fraction range. The observed densities and speeds of sound data have been utilized to determine their excess molar volumes, VE, and excess isentropic compressibilities, κSE. The topology of the constituents of mixtures (graph theory) has been employed to calculate the VE, HE, and κSE of ionic liquid mixtures. The analysis of the measured data in terms of graph theory suggests that investigated (1 + 2) mixtures are characterized by interactions forming a 1:1 molecular complex, and VE, HE, and κSE values calculated by graph theory are close to the experimental ones.

Densities, ρ123, and speeds of sound, u123, of 1-methyl pyrrolidin-2-one (1) + benzene or methyl benzene or cyclohexane (2) + propan-2-ol (3) ternary mixtures have been measured over the entire composition range at 308.15 K and atmospheric pressure. The resulting ρ123 and \(V_{123}^{\mathrm{E}}\) data were utilized to predict excess isentropic compressibilities, \((\kappa_{S}^{\mathrm{E}})_{123}\), of the studied (1+2+3) mixtures. The observed \(V_{123}^{\mathrm{E}}\) and \((\kappa_{S}^{\mathrm{E}})_{123}\) data have been analyzed in terms of Graph theory (which involved the topology of a molecule). It has been observed that \(V_{123}^{\mathrm{E}}\) and \((\kappa_{S}^{\mathrm{E}})_{123}\) values determined by Graph theory compare well with their corresponding experimental values.

Excess molar volumes, \({V^{\rm E}_{ijk}}\), and speeds of sound, uijk, of pyrrolidin-2-one (2-Py) (i)+benzene or methyl benzene (j)+propan-1-ol (k) ternary mixtures and speeds of sound, uij, of benzene or methyl benzene (i)+propan-1-ol (j) binary mixtures have been measured dilatometrically and interferrometrically over the complete mole fraction range at 308.15 K. Speed-of-sound data have been utilized to evaluate excess isentropic compressibilities for binary and ternary mixtures. \({V^{\rm E}_{ijk}}\) and \({\left({\kappa_S^{\rm E}}\right)_{ijk}}\) values have been fitted to a Redlich–Kister equation to predict ternary adjustable parameters and standard deviations. Topological investigations employed for predicting excess molar volumes and excess isentropic compressibilities, \({\left({\kappa _S^{\rm E}} \right)_{ij}}\), of 2-Py + benzene or methyl benzene or propan-1-ol binary mixtures have been extended to ternary mixtures (by employing the concept of a connectivity parameter of third degree, 3ξ, of a molecule) to obtain an expression that describes well the measured \({V^{\rm E}_{ijk}}\) and \({\left({\kappa_S^{\rm E}}\right)_{ijk}}\) values.

The activity of a number of 1-[3-(4-arylpiperazin-1-yl)propyl]pyrrolidin-2-one antiarrhythmic (AA) agents was described using the quantitative structure-activity relationship model by applying it to 33 compounds. The molecular descriptors of the AA activity were obtained by quantum chemical calculations combined with molecular modeling calculations. The resulting model explains up to 91% of the variance and it was successfully validated by four tests (LOO, LMO, external test, and Y-scrambling test). Statistical analysis shows that the AA activity of the studied compounds depends mainly on the PCR and JGI4 descriptors. ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (doi:10.1007/s00044-010-9540-x) contains supplementary material, which is available to authorized users.

Excess molar volumes, $${V^{\rm E}_{ijk}}$$ , and speeds of sound, u ijk , of pyrrolidin-2-one (2-Py) (i)+benzene or methyl benzene (j)+propan-1-ol (k) ternary mixtures and speeds of sound, u ij , of benzene or methyl benzene (i)+propan-1-ol (j) binary mixtures have been measured dilatometrically and interferrometrically over the complete mole fraction range at 308.15 K. Speed-of-sound data have been utilized to evaluate excess isentropic compressibilities for binary and ternary mixtures. $${V^{\rm E}_{ijk}}$$ and $${\left({\kappa_S^{\rm E}}\right)_{ijk}}$$ values have been fitted to a Redlich–Kister equation to predict ternary adjustable parameters and standard deviations. Topological investigations employed for predicting excess molar volumes and excess isentropic compressibilities, $${\left({\kappa _S^{\rm E}} \right)_{ij}}$$ , of 2-Py + benzene or methyl benzene or propan-1-ol binary mixtures have been extended to ternary mixtures (by employing the concept of a connectivity parameter of third degree, 3 ξ, of a molecule) to obtain an expression that describes well the measured $${V^{\rm E}_{ijk}}$$ and $${\left({\kappa_S^{\rm E}}\right)_{ijk}}$$ values.

A practical synthesis of N-substituted Clausenamide analogues, including (-) and (+) CM1, Piracetam analogue 1 and Nefiracetam analogue 2, have been developed.

Molar excess volumes V ijk E and speeds of sound, uijk of 2-pyrrolidinone (i) + benzene (j) + toluene or o- or p-xylene (k) ternary mixtures have been measured as a function of composition at 308.15 K. The observed speeds of sound data have been utilized to calculate their excess isentropic compressibilities. The observed data have been fitted to Redlich–Kister equation to calculate ternary adjustable parameters and standard deviations. Molar excess volumes, V ijk E and excess isentropic compressibilities, ( κ S E ) ijk data for the investigated mixtures have been analyzed in terms of Graph theory and Flory theory. It has been observed that V ijk E and ( κ S E ) ijk values calculated by Graph theory compare well with their corresponding experimental values.

The activity of various 1-(3-(4-arylpiperazin-1-yl)-propyl)-pyrrolidin-2-ones α1-adrenergic receptors (α1-ARs) antagonists, was described using the quantitative structure–activity relationship (QSAR) model by applying it to 49 compounds. The molecular descriptors of the α1-ARs antagonists were obtained by quantum chemical calculations combined with molecular modeling calculations. The obtained model explains more than 88% of the variance and it was successfully validated by four tests (LOO, LMO, external test and Y-scrambling test). Statistical analysis shows that the α1-ARs activity of the studied compounds depends mainly on the PCR and Qindex descriptors.

The relative lipophilicity (\documentclass{aastex} \usepackage{amsbsy} \usepackage{amsfonts} \usepackage{amssymb} \usepackage{bm} \usepackage{mathrsfs} \usepackage{pifont} \usepackage{stmaryrd} \usepackage{textcomp} \usepackage{upgreek} \usepackage{portland,xspace} \usepackage{amsmath,amsxtra} \pagestyle{empty} \DeclareMathSizes{10}{9}{7}{6} \begin{document} $$R_M ^0$$ \end{document}) of fourteen 1-substituted pyrrolidin-2-one derivatives has been measured by use of RP-TLC plates and mixtures of acetonitrile and pH 7.0 Tris buffer with volume fractions of acetonitrile between 20 and 80% were used as mobile phases. Retention data ( R M ) obtained by this method were exponentially dependent on acetonitrile concentration and enabled estimation of the relative lipophilicity corresponding to pH 7.0 Tris buffer as mobile phase. 1-{2-Hydroxy-3-[4-(3-methoxyphenyl)piperazin-1-yl]propyl}pyrrolidin-2-one had the highest relative lipophilicity (1.33) and butylcarbamic acid 1-[4-(2-methoxyphenyl)piperazin-1-ylmethyl]...

The synthesis of enantiomers of 1-[3-(4-aryl-piperazin-1-yl)-2-hydroxy-propyl]-pyrrolidin-2-one derivatives is described. These enantiomers were synthesized starting from (R)- or (S)-1-chloro-2,3-dihydroxypropane using relevant cyclic sulfates as chiral intermediates. The enantiomeric purities of the final compounds were in the range of 99.3–100.0%, as determined by high performance liquid chromatography. The final compounds were found to display moderate potency as ligands for α1-adrenoreceptors.

Aryl amines react smoothly and efficiently with N-vinyl pyrrolidin-2-one in the presence of 4-nitro phthalic acid in acetonitrile to afford the corresponding 1-(2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)pyrrolidin-2-ones in good yields.

The surface tension of aqueous solutions of 2-pyrrolidinone, 1-methyl-2-pyrrolidinone, and 1-ethyl-2-pyrrolidinone has been measured at temperatures from (20 to 50) °C over the whole range of conce...

Pyrrolidin-2-one Structure Derivatives as Novel Ligands for Copper-based Atom Transfer Radical Polymerization (ATRP)

Novel aza-analogues of ganciclovir were obtained from 1,5,5-tris(pivaloyloxymethyl)pyrrolidin-2-one by a one-pot base silylation/nucleoside coupling procedure. The compounds were evaluated for, but found to be devoid of, antiviral activity in vitro.

A series of novel arylpiperazines bearing a pyrrolidin-2-one fragment was synthesized and evaluated for the binding affinity of the alpha(1)- and alpha(2)-adrenoceptors (AR) and for the antiarrhythmic and hypotensive activities of the compounds. The most potent and selective compound 1-[2-hydroxy-3-[4-[(2-hydroxyphenyl)piperazin-1-yl]propyl]pyrrolidin-2-one 8 binds with pK(i) = 6.71 for alpha(1)-AR. Derivative 8 was also the most active in the prophylactic antiarrhythmic test in adrenaline-induced arrhythmia in anaesthetized rats. Its ED(50 )value equals 1.9 mg/kg (i.v.). Compounds with substituents such as a fluorine atom 4, a methyl 5, or a hydroxyl 8 group, or two substituents such as fluorine/chlorine atoms and methoxy groups in the phenyl ring, significantly decreased the systolic and diastolic pressure in normotensive anesthetized rats at a dosages of 5-10 mg/kg (i.v.). It was found that the presence of the piperazine ring and a hydroxy group in the second position of the propyl chain are critical structural features in determining the affinity of the compounds tested.

Using the known peroxide oxidation of N‐benzyl‐3‐phenylseleno‐2‐pyrrolidinone with 30% hydrogen peroxide at −5°C after 3.5 h, we prepared the expected N‐benzyl‐3‐pyrrolin‐2‐one. However, reaction with 30% hydrogen peroxide for 12 h (−5°C→ambient) gave the unexpected product N‐benzyl‐5‐hydroxy‐3‐pyrrolidin‐2‐one in 84% isolated yield. This procedure is a new synthetic route to N‐benzyl‐5‐hydroxy‐3‐pyrrolidin‐2‐one.

A three step, convergent synthesis of 4-aryl-3-pyrrolin-2-ones from a tetramic acid has been developed. The key transformation utilized a Suzuki–Miyaura cross-coupling reaction between a 4-tosyloxy-3-pyrrolin-2-one and an arylboronic acid. This work also provides access to 4-arylpyrrolidin-2-ones, cyclic analogs of γ-aminobutyric acid (GABA). Hydrogenation of 4-(4′-chlorophenyl)-3-pyrrolin-2-one proceeded smoothly to give baclofen lactam.

Benzoxazoles 2 can be smoothly synthesized by treatment of starting materials of N -(2-hydroxyaryl) cyclopropyl amides 1 with PPh 3 /CCl 4 in acetonitrile in good yields. When PPh 3 /CBr 4 /MS 4 A was used in the reaction system, the corresponding ring-expanding products 3 were obtained in moderate to good yields in acetonitrile at 80 °C. Using DCE as a solvent in this reaction, the corresponding 2-(3-chloropropyl)benzoxazoles 5 were obtained as major products.

[reaction: see text] A facile method for the synthesis of pyrrolidin-2-one fused N-confused calix[4]phyrins is provided by reactions of 5,10,15,20-tetraaryl-2-aza-21-carbaporphyrin with acyl chlorides in the presence of triethylamine. The (1)H NMR and UV-vis spectra of products indicate their loss of macrocyclic aromaticity.

The apparent molar volumes and molar isentropic compressibilities of pyrrolidin-2-one (PY) with Triton X-45 (TX-45), Triton X-114 (TX-114), Triton X-100 (TX-100), Triton X-405 (TX-405) have been determined at 303.15 K. Excess molar volume V E is negative throughout the composition range and follows the order TX-45 > TX-114 > TX-100 > TX-405. Molar isentropic compressibility K S and its excess values K S E have been obtained by combining the ultrasonic velocity and excess volume data. The deviations in K S E are negative for TX-45, TX-114 and TX-100 and positive for TX-405 and vary in the order TX 405 > TX 100 > TX 114 > TX 45. The results are compared and discussed to gain insight into the interactions between tritons and pyrrolidin-2-one.

Dilatometric measurements of excess volume VE and ultrasonic speed u have been carried out for mixtures of mono-, di-, tri- and tetra(ethylene glycol)s in pyrrolidin-2-one (PY) over the whole mole fraction range at 303.15 K. In the mixture of PY and monoethylene glycol, the VE is positive except for slight negative variation at the high mole fraction of PY. The other three mixtures PY+di-, + tri- and + tetra(ethylene glycol)s show negative VE over the entire composition range in the order di

The excess volume, VE and velocity of sound, u have been measured for the mixtures of pyrrolidin-2-one and aromatic hydrocarbons (o-xylene, m-xylene, p-xylene and ethylbenzene) over the entire range of composition at 303.15 K. VE values are negative for all the mixtures and vary in the order: o-xylene>ethylbenzene>m-xylene>p-xylene. The results have been analysed by using the well-known Prigogine–Flory–Patterson theory. Molar isentropic compressibility KS and its excess values KSE have been obtained from the ultrasonic velocity data in combination with density values (calculated from excess volume). The KSE is negative for all the systems over the entire range of composition and vary in the order o-xylene>m-xylene>ethylbenzene>p-xylene. The partial and apparent quantities have also been estimated. The results are compared and discussed to gain insight into the interactions between the respective components.

The aim of this study was to examine the anticonvulsant activity of some novel pyrrolidin-2-one derivatives with considerable affinity to serotonin 5-HT1A and α1-adrenergic receptors.The maximal electroshock-induced seizure (MES) and pentetrazole (PTZ)-induced seizure models in mice were performed.As a results of the conducted studies, three compounds showing anticonvulsant activity were selected. The EP-40 molecule significantly reduced incidence of seizures in the maximal electroshock test. The EP-42 and EP-46 compounds demonstrated activity in the pentetrazole-induced seizures.The results may indicate that the decrease in the susceptibility to seizures induced by the new pyrrolidin-2-one derivatives is related to the significant affinity to serotonergic or α1-adrenergic receptors. Also putative mechanism of action of the test compounds can be linked with their GABA-ergic activity, because these novel derivatives are GABA analogs.

Excess molar volumes, VmE and viscosities, η have been measured as a function of mole fraction at atmospheric pressure and 298.15 K for binary mixtures of n-alkoxyethanol + pyrrolidin-2-one. The alkoxyethanols were 2-methoxyethanol (CH3OCH2CH2OH), 2-(2- methoxyethoxy)ethanol [CH3(OCH2CH2)2OH], 2-{2-(2-methyoxyethoxy)ethoxy}ethanol [CH3(OCH2CH2)3OH], 2-(2-ethoxyethoxy)ethanol [C2H5(OCH2CH2)2OH], and 2-(2-butoxyethoxy)ethanol [C4H9(OCH2CH2)2OH]. In all mixtures the excess molar volumes are negative over the entire composition range. From the experimental results, deviation in the viscosity, Δnη and excess energies of activation for viscous flow, ΔG∗E have been calculated. The experimental and calculated quantities are used to discuss the mixing behaviour of the components.

The asymmetric synthesis of 1-[2-hydroxy-3-(4-phenyl-1-piperazinyl)-propyl]-pyrrolidin-2-one 1 is described. Enantiomers of compound 1 were obtained using the Sharpless asymmetric dihydroxylation (AD) or hydrolytic kinetic resolution (HKR) methods. The enantiomers of compound 1, which were obtained by HKR had higher enantiomeric excesses than those which were synthesized by AD and epoxidation. The enantiomeric purity of the synthesized compounds was determinated by capillary electrophoresis.

The synthesis of a series of novel trifluoromethylated β-acetal- gem -diols, 4-alkoxy-4-ethoxy-1,1,1-trifluoro-butane-2,2-diols ( 4a = methoxy , 4b = ethoxy , 4c = allyloxy , 4d = ynyloxy ) and 1-(2-alkoxytetrahydro-furan-3-yl)-2,2,2-trifluoro-ethane-1,1-diols ( 6a = methoxy , 6b = ethoxy , 6c = allyloxy , 6d = ynyloxy ) from the reaction of 4-ethoxy-1,1,1-trifluoro-3-buten-2-one ( 1 ) and 1-(4,5-dihydro-furan-3-yl)-2,2,2-trifluoro-ethanone ( 2 ) with sodium azide in hydro-alcoholic medium, is presented. From these reactions, a small amount (ca. of 20%) of the parent trifluoromethylated β-acetal-ketones, 4-alkoxy-4-ethoxy-1,1,1-trifluoro-butan-2-ones ( 3a – d ) and 2,2,2-trifluoro-1-(2-alkoxy-tetrahydro-furan-3-yl)-ethanones ( 5a – d ) were also obtained. The synthetic potential of the trifluoromethylated β-acetal-diols was demonstrated by its application to the synthesis of 3-ethoxy-5-hydroxy-5-trifluoromethyl-pyrrolidin-2-one ( 7 ).

In order to obtain constrained analogues of tryptophane, five-membered lactams and lactones bearing 4-indolyl and 3-carboxylic groups were prepared in a completely diastereoselective manner, resulting in a trans relationship. Furthermore, the use of chiral precursors in the synthesis yielded enantiomerically pure compounds with three contiguous chiral centres.

The absorption heat transformer (AHT) is a promising system for recovering waste heat. It can effectively recover about 50% of the waste heat and reuse it in industrial processes. However, there exists a need for identifying suitable working fluid combinations and for evaluating their relative performance characteristics. As an initial step, this paper presents a comparative performance study for the absorption heat transformer with H2O/LiBr, TFE(2,2,2-trifluoroethanol)/NMP(N-methy1-2-pyrrolidone), TFE/E181(dimethylether tetraethylene glycol) and TFE/PYR(2-pyrrolidone). The results show that the four working fluid combinations are all suitable for absorption heat transformers. H2O/LiBr is suitable at lower operating temperatures, while TFE/NMP, TFE/E181 and TFE/PYR are suitable at higher operating temperatures.

In the title compound, [Fe(C5H5)(C25H23N2O3)], the pyrrolidine ring adopts a twist conformation. The oxindole ring system is planar. The crystal packing is stabilized by N—H⋯O and C—H⋯π inter­molecular inter­actions.