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Parkinson’s disease (PD) is the second most common neurodegenerative disorder, mainly characterized by motor deficits correlated with progressive dopaminergic neuronal loss in the substantia nigra pars compacta (SN). Necroptosis is a caspase-independent f

Abstract: A simple synthetic protocol have been developed for the preparation of novelN-(4-benzylidene-5-oxo-2-phenyl-4,5-dihydro-1H-imidazol-1-yl)-N′-phenylthiourea derivatives by the reaction of4-benzylidene-2-phenyl-4,5-dihydro-1,3-oxazol-5-ones with N

An efficient, metal free approach to synthesize multi-substituted Δ2-pyrroline derivatives by mild base catalyzed cyclocondensation of malononitrile with Erlenmeyer azlactones via 1,2 addition was developed. The modularity of this reaction was used to assemble a range of poly-substituted pyrrolines. Further, synthesized products were screened for cytotoxic properties on different cancer cell lines such as A549 (Human lung adenocarcinoma cells), HeLa (Human cervical adenocarcinoma cells), Jurkat (Human chronic myeloid leukemia cells) and K562 (Human leukemic T cell Lymphoblast cells). Among the synthesized library of compounds, 6f and 6q displayed potent cytotoxic activity.

Inhibitors of carbonic anhydrase (CAIs) hold promise for addressing various diseases, including cancer, diabetes, and other metabolic syndromes. CAV is the only isoform present in the mitochondria and is considered a potential drug target for obesity. In

The first enantioselective decarboxylative [4 + 2]-annulation of ethynyl benzoxazinanones with azlactones has been developed under cooperative copper and bifunctional tertiary aminourea catalysis. This direct and modular approach combines dipolar copper-a

In this work, we present the synthesis and biological evaluation of novel series of diamide-based benzenesulfonamides 5a-h as inhibitors of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA I, II, IX and XII. The target tumor-associated i

Background: The present work describes antimicrobial, antimycobacterium and anti HIV-1 evaluation of newly synthesized 5-(4-Substituted-benzylidene)-3-[4-(5-methyl-benzothiazol2-yl)-phenyl]-2-phenyl-3,5-dihydro-imidazol-4-one (4a-o). The docking studies were performed in order to predict the potential binding affinities. Objective: The major aim of this study is to develop the new class of bezylidine candidate clubbed with benzothiazole with less toxicity and improved potency as antimicrobial, antitubercular and anti HIV-1. Methods: The titled compounds were characterized by spectral studies (IR, 1H NMR, 13C NMR and Mass). In vitro antimycobacterium activity was carried out using Lowenstein-Jensen medium method and antimicrobial activity using the broth microdilution method. The anti HIV-1 reverse transcriptase activity was determined by the colorimetric MTT method and inhibition of virusinduced cytopathogenicity in MT-4 cells. Results: Compound 4i (50 μM) showed better antifungal activity against A. clavatus. Compound 4g (50 μM) with 95% inhibition demonstrated good activity against M. tuberculosis H37Rv. Compound 4k showed CC50 (50 μM) against MT-4 (CD4+ Human T-cells containing an integrated HTLV-1 genome) cells by 50%, while 16 μM concentration value EC50 from the HIV-1 induced cytopathogenicity. Molecular docking study suggested that 4k interacted with the target with binding energy by Vina score (-10.3 Kcal/mol) Conclusion: The preliminary in vitro evaluation results revealed that some of the compounds have promising antimicrobial activities as well as antitubercular potency. Among the various substituents on benzylidene, the nitro group was the most beneficial for improving the anti-HIV-1 activity. Docking result suggested that 4k compound could be acting as a non-competitive or weak inhibitor of Reverse Transcriptase (RT).

Background: The oxazolone class of compounds is known to exert a profound effect on malignant cell proliferation, tumor angiogenesis and /or on the established neoplastic vasculature. Additionally, these compounds are generally known to have a low tendenc

A copper nitrate-mediated [2 + 2 + 1] cycloaddition reaction was developed for the expedient synthesis of pharmacologically interesting 3-aryl substituted isoxazolines and isoxazoles through CC bond cleavage. Copper nitrate is employed as a reaction promoter and precursor of nitrile oxides. The given approach features a new mode of cycloaddition from olefinic azlactones, copper nitrate and unsaturated compounds with wide substrate scope, good functional group tolerance and operational simplicity.

A simple, efficient and environmentally benign method for the synthesis of 4-benzylidene-2-phenyl oxazol-5(4H)-one derivatives by the reaction of aromatic aldehydes and hippuric acid using acetic anhydride as dehydrating agent and L-proline as catalyst ha

This study is focused on the catalytic activity of sulfanilic acid (SA) in the straightforward synthesis of 4-Arylidene-2-phenyl-5(4H)-oxazolones via condensation of aromatic aldehydes, hippuric acid, and acetic anhydride under green experimental conditio

An ionic liquid gel has been prepared by entrapping 1-butyl-3-methylimidazolium hydroxide ([Bmim]OH) in an aqueous agar gel. The ionic liquid gel has been characterized by Fourier transform infrared (FT-IR), Fourier transform Raman (FT-Raman) spectroscopy, scanning electron microscopy (SEM), thermogravimetric analysis (TGA) and energy dispersive X-ray analysis (EDX). The ionic liquid gel has been successfully employed as a heterogeneous catalyst in the Erlenmeyer-Plochl reaction involving aldehydes, hippuric acid and acetic anhydride as well as in the Henry reaction between aldehydes and nitromethane in ethanol at room temperature. The heterogeneity of the ionic liquid gel has been confirmed by conducting hot filtration tests and leaching studies. Additionally, the ionic liquid gel could be easily recovered by simple filtration and reused five times without significant loss in catalytic activity.

The first report of the preparation of symmetric and nonsymmetric diaminotruxinic derivatives through the photoredox [2 + 2] cycloadditions of Erlenmeyer azlactones is described, affording the desired compounds in high regio- and diastereocontrol (only head-to-head coupling). Mechanistic studies by DFT suggest that the reaction proceeds through a neutral photocatalytic pathway.

An efficient, straight-forward and eco-friendly synthetic strategy for the assembly of novel bisoxazolones via a four-component, sequential reaction of dialdehydes, glycine, benzoyl chloride and acetic anhydride, using ultrasound radiation, is described. Additionally, a diverse group of new bisimidazoles has been synthesized in good yields by the sonication of diamines and (Z)-4-Arylidene-2-phenyloxazol-5(4H)-ones. These approaches have resulted in a number of successful routes for the facile synthesis of bis-oxazolone and bis-imidazole frameworks within minutes of irradiation. Excellent outcomes using these environmentally-friendly parameters make these synthetic schemes ideal, sustainable, green-chemistry procedures and provide simple access towards the preparation of bisheterocycles. Formula parented.

5-Sulfosalicylic acid was found as an efficient catalyst in the synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones by condensation and cyclodehydration of aromatic aldehydes with hippuric acid and acetic anhydride at room temperature. The catalyst was eas

The efficient preparation of azlactones in the presence of zeolite NaY has been reported. This heterogeneous catalyst was used for efficient synthesis of azlactone derivatives with Ac2O as a condensing agent under microwave irradiation and solvent-free co

This study presents triphenylphosphine catalyzed process for the synthesis of azlactones and their derivatives using hippuric and substituted aromatic aldehydes. The methodology also found to be effective for the synthesis of azlactones from 5-(2,6-dichlorophenyl)-3-methyl-1,2-oxazol-4-yl carbonyl amino acetic acid and offers several advantages such as solvent-free conditions, excellent yields, simple procedure, mild conditions, and reduced environmental consequences.

We have developed simple, greener, safer multicomponent synthesis series of 4-arylidene-2-phenyl-5(4H) oxazolones 4(a-r) catalyzed by Bronsted acid ionic liquid as triethylammonium hydrogen sulfate [Et3NH][HSO4] and catalytic amount of acetic anhydride and sodium acetate with excellent yields (90–99%). The protocol offers economical, environmentally benign, solvent-free conditions, and recycle–reuse of the catalyst and easily available starting as benzoyl chloride 1, amino acid 2 and a variety of aldehydes 3. The cyclization followed by condensation of benzoyl chloride, amino acid, and a variety of aldehydes catalyzed by ILs [Et3NH][HSO4] and catalytic amount of acetic anhydride and sodium acetate. The final products were confirmed by their characterization data such as FTIR, 1H-NMR, 13C-NMR, Mass, high-resolution mass spectra and were compared with its reported method.

MgO/Al2O3 catalyzes the synthesis of azlactone derivatives from condensation reaction of aldehydes (or ketones) with hippuric acid and acetic anhydride as a dehydrating agent under microwave irradiation. The low toxicity, low cost, ease of handling, and high activity of MgO/Al2O3 make this procedure particularly attractive. Also, this catalyst can be easily recovered by decant and can be reused for this condensation five times in succession without considerable loss of its catalytic activity.

A novel cellulose supported ionic liquid phase catalyst containing hydroxide ions ([CellFemImi]OH) has been synthesized by covalent anchoring of 1-N-ferrocenylmethyl imidazole in the functionalized cellulose matrix followed by an anion metathesis reaction. The [CellFemImi]OH was characterized by various techniques including FT-IR, FT-Raman, 13C solid state NMR, X-ray diffraction, energy dispersive X-ray (EDX) analysis, field emission scanning electron microscopy (FESEM) and thermogravimetric analysis. The [CellFemImi]OH was effectively employed as a heterogeneous catalyst in the synthesis of oxazolones by cyclocondensation of aryl aldehydes with hippuric acid in the presence of acetic anhydride.

(Formula presented) A convenient and mild procedure for the synthesis of azlactones in the presence of catalytic amounts of calcium hydrogen phosphate as a green, inexpensive and environmentally benign catalyst has been demonstrated. The present protocol is operationally simple and offers some advantages such as good yields, short reaction time, simple work-up, low cost and reusability of catalyst, which makes this method mild and eco-friendly.

A facile and effective approach for the synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones has been developed. Under solvent-assisted grinding in the presence of 2,4,6-trichloro-1,3,5-triazine, catalytic triphenylphosphine, and sodium carbonate, dehydrati

Compared to the aza-Wittig reaction of aldehydes, ketones, amides, and esters, the aza-Wittig reaction of acid anhydride was always overlooked, which should be an important part of Wittig reactions. Here, the aza-Wittig reaction of anhydride and catalytic aza-Wittig reaction of anhydride were both developed with high yields, which provides an efficient method to synthesize of 4H-benzo[d][1,3]oxazin-4-ones and 4-benzylidene-2-aryloxazol-5(4H)-ones. The strategy of copper-catalyzed reduction of phosphine oxide was used and found effective for this transformation. Additionally, the one-pot catalytic aza-Wittig reaction of carboxylic acids was achieved. Furthermore, NMR experiments and Hammett plot recorded the process of catalytic aza-Wittig reaction of anhydride, which provides direct proof that the copper-catalyzed reduction of waste phosphine oxide is the key step in this transformation.

A series of novel tetrahydroimidazo[1,2-a]pyridine-5(1H)-one derivatives containing a electronegative pharmacophore (=CNO2) were synthesized via practical aza-ene reaction and characterized by 1H NMR, 13C NMR, 19F NMR and HRMS. Preliminary bioassays showed that some of the target compounds exhibited good insecticidal activity against brown planthopper (Nilaparvata lugens) and cowpea aphids (Aphis craccivora) at 500 mg L-1. Among them, compound 11h was active against brown planthopper at 100 mg L-1. The insecticidal activities varied significantly depending on the types and patterns of the substituents, which provided guidance for further investigation on structure modifications.

A series of new phenylpropenamide derivatives containing different substituents was synthesized, characterized and evaluated for their anti-hepatitis B virus (HBV) activities. The quantitative structure eactivity relationships (QSAR) of phenylpropenamide compound have been studied. The 2D-QSAR models, based on DFT and multiple linear regression analysis methods, revealed that higher values of total energy (TE) and lower entropy (Sθ) enhanced the anti-HBV activities of the phenylpropenamide molecules. Predictive 3D-QSAR models were established using SYBYL multifit molecular alignment rule. The optimum models were all statistically significant with cross-validated and conventional coefficients, indicating that they were reliable enough for activity prediction.

Substituted 2-phenyl-4-[phenylmethylidene]-1,3-oxazol-5(4H)-ones 1-27 were evaluated for their activity against Leishmania major. Compounds 1-27 demonstrated in vitro antileishmanial activities with IC50 values between 28.9 - 69.05 μM, as compared to standard drug pentamidine (IC50 = 5.09 ± 0.04 μM). Compounds 12 (IC50 = 28.90 ± 1.10 μM), 24 (IC50 = 31.4 ± 2.15 μM), 13 (IC50 = 35.0 ± 3.18 μM), 16 (IC50 = 35.0 ± 3.13 μM), and 25 (IC50 = 35.0 ± 3.18μM) displayed signifiant antileishmanial activities. Whereas, compounds 8-10, 15, 19, and 26 with IC50 values of 62.2 ± 3.36, 57.8 ± 2.30, 57.72 ± 5.02, 56.18 ± 4.40, 57.85 ± 2.25, 69.05 ± 6.20, 54.8 ± 1.50, and 57.8 ± 2.30 μM showed a moderate antileishmanial activities.

Titanium dioxide nanoparticles were prepared by a electrochemical reduction method using parameters such as current density, solvent polarity, distance between electrodes, and concentration of stabilizers to control the size of the nanoparticles. The nanoparticles were characterized by UV-Vis spectroscopy, X-ray diffraction, scanning electron microscopy and transmission electron microscopy, and their catalytic performance was tested for the synthesis of a series of 4-aryldiene-2-phenyl-5(4)-oxazolones from the cyclodehydration and condensation of the respective aldehyde, hippuric acid and acetic anhydride. Easy availability, reusability and eco-friendliness were some prominent features of the nanocrystalline titanium dioxide catalyst.

A straightforward and efficient copper(i)/amino acid-catalyzed intramolecular Ullmann-type C-O coupling reaction has been developed. This protocol affords a facile methodology for the synthesis of a series of novel 2,4,5-substituted oxazoles from readily accessible N-acyl-2-bromo enamides under mild conditions. This journal is the Partner Organisations 2014.

The synthesis, photophysics and photochemistry of a family of molecular switches inspired by the green fluorescent protein (GFP) chromophore is presented. These compounds can be synthesized in one step and good yields, their photophysical properties may b

Simple, effective, and high yield synthetic procedure for the synthesis of 4-ylidene-5(4H)-oxazolones 2a-m from arylidene-malononitriles under solvent-free conditions is described. The scope of this reaction was investigated, and it was found that the presence of anhydrous sodium acetate gave the corresponding oxazolones in excellent yields. The newly generated oxazolone derivative 2m underwent ring transformation into pyrroles, imidazoles, pyridazine, and triazines.

An efficient method to synthesize azalactone derivatives using ammonium metavanadate (NH4VO3) as catalyst was performed in the absence of solvent. This method is environmentally friendly and affords the product azalactones in high yi

A simple and efficient procedure for the synthesis of azlactones employing condensation reaction of aromatic aldehydes with hippuric acid has been developed by using the tosyl chloride (TsCl) and dimethylformamide (DMF) system as condensing agent in the absence of solvents under microwave irradiation. The present protocol is operationally simple and offers several advantages such as high yields, short reaction time, and simple workup.

A series of substituted (benzamidostyryl) benzimidazole (3a-r) were synthesized and evaluated for their possible anti-inflammatory and ulcerogenicity. The structures of the synthesized compounds were confirmed on the basis of their spectral data and elemental analysis. Majority of the compounds were active in carrageenaninduced hind paw edema method test and compounds 3b, 3k had shown high potency after 3 and 4 h time intervals (P0.001) almost equipotent to the standard drug indomethacin and showed less severity index than it. Springer Science+Business Media, LLC 2011.

A novel axially chiral spiro-phosphine-catalyzed highly regio-, diastereo- and enantioselective [3+2] cycloaddition of alkylidene azlactones with various allenic esters has been developed, affording the corresponding functionalized spirocyclic products in

2-Phenyl-4-benzylidene-5(4H)-oxazolones (1a-e) were used as versatile starting materials for the synthesis of fused compounds such as: 4H-3,1-benoxazin-4-ones (2a,b), imidazo[4,3-b]benzimidazoles (3,4), imidazo[1,5-b]1,2,4-triazoles (5a,b), and 7.

A series of (benzamidostyryl)benzimidazole derivatives were synthesized by hydrolyzing 2-phenyl-4-(substituted)benzylidene-5-oxazolones, the azlactone precursors in an acidic medium and treating the product with substituted o-phenylenediamine (OPDA) in si

Phenylpropenamides have been reported to be a class of non-nucleoside inhibitors of the hepatitis B virus (HBV). This class of compounds was explored with the objective of developing potent anti-HBV agents, with a novel mechanism of action, that could be combined with nucleos(t)ide analogs currently used to treat HBV infection. To accomplish this objective a series of substituted arylpropenamide derivatives were prepared and the E and Z geometrical isomers were separated. The structural identity of each of the E and Z isomers was determined by single crystal X-ray crystallography. Contrary to previous reports, the activity of this class of molecules resides in the Z isomer. Further structure-activity relationship studies around the active Z isomer identified compounds that displayed potent antiviral activity against HBV with EC90 value of approximately 0.5 μM in vitro. Attempts to develop ring constrained analogs did not lead to active HBV inhibitors.

Fourteen azalactones have been synthesized in excellent yields under solvent-free conditions by heating an aldehyde, hippuric acid, and acetic anhydride in the presence of molecular iodine as a catalyst in a microwave oven. The short reaction time, cleaner reaction, and easy workup make this protocol practical and economically attractive. Copyright

A new and efficient method to synthesize azlactone derivatives using alum ascatalyst was performed in the absence of additional solvent. This method is environmentally friendly and affords the product azlactones in high yields after simple workup.

A practical and efficient two reaction sequence one-pot process for the synthesis of Z-α-benzoylamino-acrylic acid methyl esters was developed. The process involves a potassium phosphate-catalyzed Erlenmeyer reaction of aromatic aldehydes with hippuric acid followed by an oxazolone ring-opening methanolysis. This process afforded a good overall yield and an excellent product quality via a simple workup.

An evaluation of organic base versus sodium acetate as the base in the Erlenmeyer Pl?chl reaction was performed. Aldehyde substituents play an important role in these reactions. Organic bases afford fast reactions, but other side reactions were observed. Alternatively, in the presence of solvent, sodium acetate could be used in catalytic amounts rather than the typical stoichiometric quantities. This Letter reports the comparative results for the use of organic bases versus sodium acetate in Erlenmeyer Pl?chl reactions.

A series of 2-(substituted aryloxy)-5-(substituted benzylidene)-3-phenyl-2, 5-dihydro-1H-[1,2,4] triazin-6-one were designed & synthesized using appropriate synthetic route keeping in view the structural requirement of pharmacophore and evaluated for anticonvulsant activity and CNS activities. After intraperitoneal injection to mice, some synthesized derivatives were examined in the maximal electroshock seizure (MES) and subcutaneous pentylenetetrazol (scPTZ) induced seizure and neurotoxicity screens. Those found potent were also evaluated for behavioural impairment and depression activity. Among the compound tested, 5 eIX showed protection from seizures in both the animal models at dose level of 30 mg/kg while 5 bII & 5 cII showed protection against scPTZ model at same dose level. Some titled compounds exhibited lesser CNS depression and neurotoxicity compared to clinically effective drug. A series of substituted [1,2,4] triazin-6-one derivatives were synthesized, evaluated for their anticonvulsant potency on two animal models along with CNS activity and neurotoxicity and also subjected to computational parameter.

A series of substituted cinnamoyl alanines were synthesized by condensation of substituted 4-benzylidene-2-phenyloxazol-5-ones with alanine. The chemical structures of synthesized compounds were confirmed by means of IR, 1H NMR, mass spectral and elementa

A series of 4-substituted benzylidene-2-phenyl-1-substituted phenyl-1H-imidazol-5(4H)-one were synthesized by condensation of substituted oxazolones with p-amino benzoic acid and benzocaine. The chemical structures of synthesized compounds were confirmed

A simple and efficient method for the synthesis of some new pyrazol-5-yl-1H-imidazoles 4a-h is described. In this method oxazolones 5a-h were produced as minor products. The X-ray analysis confirmed the structures of 4 and 5. The Japan Institute of Heterocyclic Chemistry.

We have recently developed a novel and efficient method for synthesising Erlenmeyer azlactones under mild and rapid conditions. The reaction is performed by reacting 2-phenyl-5-oxazolone with an aldehyde in dichloromethane using alumina as a catalyst. The materials react instantly at room temperature, negating the need for high temperatures and long reaction times. We have successfully used this method for both aliphatic, aromatic and heteroaromatic aldehydes, synthesising previously unmade Erlenmeyer azlactones in moderate to high yields.

(Chemical Equation Presented) A one-pot procedure for the synthesis of 4-arylidene-2-phenyl-5(4H)oxazolones directly from aryl aldehyde bisulfite adducts in the absence of Ac2O in good to excellent yields using phosphoryl chloride is reported. In addition, the observed chemoselectivity can be considered as a noteworthy advantage of this method.

We have found that dodecatungstophosphoric acid (H3PW 12O40), samarium or ruthenium(III) chloride act as efficient catalysts for the synthesis of unsaturated 2-phenyl-5(4H)oxazolone derivatives under solvent-free condition

(Chemical Equation Presented) A novel cascade reaction of 4-arylidene-2-phenyl-1,3-oxazol-5(4H)-one with 3-methyl-l-phenyl-1H-pyrazol-5- amine was described and a number of new pyrazolo[3,4-b]pyridine-6-one derivatives were synthesized. This new protocol has the advantages of shorter time, higher yields, and lower cost as well as easier operation.

The alkyl, aryl, and acyl substituent effects on the photoinduced electron transfer-initiated cyclization reaction of the title compounds (1) were investigated in polar solvents from mechanistic and synthetic points of view. The irradiation of (Z)-1 in me