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Zinc alumotitanate sorbents with various compositions were prepared through sol-gel synthesis with the use of ethyl acetoacetate as a chelating agent. The formation and decomposition of chelates, providing insight into sol-gel process advancement, have been successfully monitored via 1H NMR, 13C NMR, and FTIR spectroscopy. It has been established that Al(OBus)3 and Ti(OBun)4 react completely with Eaa, forming chelates after 1 h, while after 24 h hydrolysis is already advanced. Hydrolysis is accelerated in the presence of Zn(NO2)3·6H2O, supplying the water needed for hydrolysis. In dried gels, the amount of ethyl acetoacetate is greatly reduced, and it is mainly present unbound. According to XRD analysis, samples with none or less titania are composed of layered double hydroxide, while in samples with greater amounts of titania, crystal nitrates are present. In all samples except those without Al, the spinel phase with variable composition crystallizes. [ABSTRACT FROM AUTHOR]

In this investigation, 4-antipyrinecarboxaldhyde was reacted with methyl hydrazinecarbodithioate to afford the carbodithioate derivative 3. The as-prepared carbodithioate derivative 3 is considered to be a key molecule for the preparation of new antipyrine-1,3,4-thiadiazole-based molecules (4–9) through its reaction with the appropriate hydrazonoyl halides. Furthermore, a typical Biginelli three-component cyclocondensation reaction involving ethyl acetoacetate, 4-antipyrinecarboxaldhyde, and thiourea under the standard conditions is carried out in the presence of sulfuric acid to afford the corresponding antipyrine–pyrimidine hybrid molecule (10). The latter was submitted to react with hydrazine monohydrate to provide the corresponding hydrazide derivative (11) which, under reaction with ethyl acetoacetate in refluxing ethanol containing catalytic amount of acetic acid, afforded the corresponding derivative (12). The structure of the newly synthesized compounds was affirmed by their spectral and microanalytical data. We also screened for their antimicrobial potential (ZOI and MIC) and conducted a kinetic study. Additionally, the mechanism of biological action was assessed by a membrane leakage assay and SEM imaging technique. Moreover, the biological activities and the binding modes of these compounds were further supplemented by an in silico docking study against E. coli β-carbonic anhydrase. The amount of cellular protein released by E. coli is directly correlated to the concentration of compound 9, which was found to be 177.99 µg/mL following treatment with 1.0 mg/mL of compound 9. This finding supports compound 9's antibacterial properties and explains how the formation of holes in the E. coli cell membrane results in the release of proteins from the cytoplasm. The newly synthesized compounds represent acceptable antimicrobial activities with potential action against E. coli β-carbonic anhydrase. The docking studies and antimicrobial activity test proved that compound (9) declared a greater activity than the other synthesized compounds. [ABSTRACT FROM AUTHOR]

The synthesis of 4-methyl/phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-one 4 and 7 has been reported with ninhydrin via a reaction first with ethyl acetoacetate or ethyl benzoylacetate and then a reaction of the resultant esters with hydrazine hydrate. The mechanism of hydrazinolysis and cyclization to obtain tetraazafluoranthen-3(2H)-ones is ambiguous, and the previously proposed mechanism was not based on facts because the actual intermediates were not isolated. Herein, the important intermediates involved in the hydrazinolysis–cyclization mechanistic pathway were isolated and characterized using NMR and X-ray single-crystal analysis. The intermediates demonstrate that the reaction carried out via two hydrazinolysis–cyclization reactions, the first of which includes the condensation of one hydrazine molecule with two ketone groups and the second of which includes the reaction of another hydrazine molecule with the ester and then condensation with the other ketone group. The stability of hydrazide 11 enabled the hydrazine to reduce the carbonyl of the ketone group to form 12 via a Wolff–Kishner-like reduction. The structure of the three intermediates was confirmed using X-ray crystallographic analysis. It was found that the three fused ring systems deviated from planarity to different extents, with their deviation from being coplanar reaching up to 5.3°. The possible non-covalent interactions which control the molecular packing of these intermediates were elucidated with the aid of Hirshfeld analysis. [ABSTRACT FROM AUTHOR]

Pyrimidines play an important role in modern medical fields. They have a wide spectrum of biological activities such as antimicrobial, anticancer, anti-allergic, anti-leishmanial, antioxidant agents and others. Moreover, in recent years, 3,4-dihydropyrimidin-2(1H)ones have attracted researchers to synthesize them via Biginelli reaction and evaluate their antihypertensive activities as bioisosters of Nifedipine, which is a famous calcium channel blocker. Our new target compounds were prepared through one-pot reaction of thiourea 1, ethyl acetoacetate 2 and/or 1H-indole-2-carbaldehyde, 2-chloroquinoline-3-carbaldehyde, 1,3-diphenyl-1H-pyrazole-4-carbaldehyde, 3a–c in acid medium (HCl) yielding pyrimidines 4a–c, which in turn were hydrolyzed to carboxylic acid derivatives 5a–c which were chlorinated by SOCl2 to give acyl chlorides 6a–c. Finally, the latter were reacted with some selected aromatic amines, namely, aniline, p-toluidine and p-nitroaniline, producing amides 7a–c, 8a–c, and 9a–c. The purity of the prepared compounds was examined via TLC monitoring, and structures were confirmed by different spectroscopic techniques such as IR, 1HNMR, 13CNMR, and mass spectroscopy. The in vivo evaluation of the antihypertensive activity revealed that compounds 4c, 7a, 7c, 8c, 9b and 9c had comparable antihypertensive properties with Nifedipine. On the other hand, the in vitro calcium channel blocking activity was evaluated by IC50 measurement and results revealed that compounds 4c, 7a, 7b, 7c, 8c, 9a, 9b, and 9c had comparable calcium channel blocking activity with the reference Nifedipine. Based on the aforementioned biological results, we selected compounds 8c and 9c to be docked onto Ryanodine and dihydropyridine receptors. Furthermore, we developed a structure–activity relationship. The designed compounds in this study show promising activity profiles in reducing blood pressure and as calcium channel blockers, and could be considered as new potential antihypertensive and/or antianginal agents. [ABSTRACT FROM AUTHOR]

We hereby report a simple and efficient method for the preparation of 4-methylcoumarins series, including Coumarin 120 (7-amino-4-methylcoumarin) from phenols (or naphthols) and ethyl acetoacetate in the presence of 3 mol% InCl3. Coumarins were obtained in good yields (52–92%) through Pechmann condensation, under a rapid and environmentally friendly protocol using a high-speed ball mill mixer at room temperature, with short reaction times, under solvent-free conditions. [ABSTRACT FROM AUTHOR]

A series of new [1,2,4]triazolo[4,3-a]pyrimidine derivatives was prepared using a one-pot three-component synthesis from 5-amino-1-phenyl-1H-1,2,4-triazoles, aromatic aldehydes and ethyl acetoacetate. The compound structures were confirmed by IR, 1H-NMR, 13C-NMR, HRMS and X-ray analyses. The biological activity of these compounds as antitumor agents was evaluated. Their antitumor activities against cancer cell lines (MDA-MB-231 and MCF-7) were tested by the MTT in vitro method. Among them, compounds 4c and 4j displayed the best antitumor activity with IC50 values of 17.83 μM and 19.73 μM against MDA-MB-231 and MCF-7 cell lines, respectively, compared to the Cisplatin reference. [ABSTRACT FROM AUTHOR]

Dioxidovanadium(V) complex [VVO2(sal-aebmz)] (1) (where Hsal-aebmz = Schiff base derived from the condensation of salicylaldehyde and 2-aminoethylbenzimidazole) has been immobilized on chloromethylated polystyrene (PS-Cl) cross-linked with divinylbenzene to obtain [VVO2(sal-aebmz)]@PS (2), a heterogeneous complex. Both complexes, after characterization, have been used as catalysts to explore a single pot multicomponent (benzaldehyde or its derivatives, urea and ethyl acetoacetate) Biginelli reaction producing biologically active 3,4-dihydropyrimidin-2-(1H)-one (DHPM)-based biomolecules under solvent-free conditions in the presence of H2O2 as a green oxidant. Various reaction conditions such as amounts of catalyst and oxidant, temperature, time, and solvent have been optimized to obtain the maximum yield of DHPMs. The polymer-immobilized complex has been found to show excellent catalytic activity, giving ca. 95% yield of DHPMs under the optimized reaction conditions selectively. Oxidant plays an important role in enhancing the yield of DHPMs. [ABSTRACT FROM AUTHOR]

Many chemically synthesized xenobiotics can significantly inhibit the vitality of parasitic nematodes. However, there is yet too little research on the toxicity of such contaminating compounds toward nematodes. Compounds that are present in plants are able to inhibit the vitality of parasitic organisms as well. According to the results of our laboratory studies of toxicity, the following xenobiotics caused no decrease in the vitality of the larvae of Strongyloides papillosus and Haemonchus contortus: methanol, propan-2-ol, propylene glycol-1,2, octadecanol-1, 4-methyl-2-pen-tanol, 2-ethoxyethanol, butyl glycol, 2-pentanone, cyclopentanol, ortho-dimethylbenzene, dibutyl phthalate, succinic anhydride, 2-methylfuran, 2-methyl-5-nitroimidazole. Strong toxicity towards the nematode larvae was exerted by glutaraldehyde, 1,4-diethyl 2-methyl-3-oxobutanedioate, hexylamine, diethyl malonate, allyl acetoacetate, tert butyl carboxylic acid, butyl acrylate, 3-methyl-2-butanone, isobutyraldehyde, methyl acetoacetate, ethyl acetoacetate, ethyl pyruvate, 3-methylbutanal, cyclohexanol, cyclooctanone, phenol, pyrocatechin, resorcinol, naphthol-2, phenyl ether, piperonyl alcohol, 3-furoic acid, maleic anhydrid, 5-methylfurfural, thioacetic acid, butan-1-amine, dimethylformamide, 1-phenylethan-1-amine, 3-aminobenzoic acid. Widespread natural compounds (phytol, 3-hydroxy-2-butanone, maleic acid, oleic acid, hydroquinone, gallic acid-1-hydrate, taurine, 6-aminocaproic acid, glutamic acid, carnitine, ornithine monohydrochloride) had no negative effect on the larvae of S. papillosus and H. contortus. A powerful decrease in the vitality of nematode larvae was produced by 3,7-dimethyl-6-octenoic acid, isovaleric acid, glycolic acid, 2-oxopentanedioic acid, 2-methylbutanoic acid, anisole, 4-hydroxy-3-methoxybenzyl alcohol, furfuryl alcohol. The results of our studies allow us to consider 28 of the 62 compounds we studied as promising for further research on anti-nematode activity in manufacturing conditions. [ABSTRACT FROM AUTHOR]

In this study, pumice is used as a novel natural heterogeneous catalyst for the synthesis of 3,4-dihydropyrimidine-2-(1H)-ones/thiones via the one-pot multi-component condensation of aromatic aldehydes, urea/thiourea, and ethyl acetoacetate or acetylacetone in excellent yields (up to 98%). The physical and chemical properties of the catalyst were studied. Their geochemical analysis revealed a basaltic composition. Furthermore, X-ray diffraction showed that it is composed of amorphous materials with clinoptilolite and heulandites zeolite minerals in its pores. Moreover, pumice has a porosity range from 78.2–83.9% (by volume) and is characterized by a mesoporous structure (pore size range from 21.1 to 64.5 nm). Additionally, it has a pore volume between 0.00531 and 0.00781 m2/g and a surface area between 0.053 and 1.47 m2/g. The latter facilitated the reaction to proceed in a short time frame as well as in excellent yields. It is worth noting that our strategy tolerates the use of readily available, cheap, non-toxic, and thermally stable pumice catalyst. The reactions proceeded smoothly under solvent-free conditions, and products were isolated without tedious workup procedures in good yields and high purity. Indeed, pumice can be reused for at least five reuse cycles without affecting its activity. [ABSTRACT FROM AUTHOR]

New substituted 4-aryl-8-methyl-2-thioxo-1,2,3,4-tetrahydro-6H-pyrimido[1,2-a][1,3,5]triazin-6-one 8a–b and ethyl 4-aryl-6-oxo-2-thioxo-1,3,4,6-tetrahydro-2H-pyrimido[1,2-a][1,3,5]triazine-7-carboxylate 8c–e were synthesized by the reaction of the corresponding 4-oxopyrimidin-2-ylthioureas with arylaldehydes. The formation of only one regioisomer was proven using complex spectral data and its structure was characterized. It was found that the interaction of 6-amino-4-phenyl-3,4-dihydro-1,3,5-triazine-2(1H)-thione with ethyl acetoacetate and diethyl ethoxymethylenemalonate leads to the formation of the same regioisomer. That is, changing the sequence of stages in this cascade process does not affect the structure of the final reaction product. All synthesized compounds exhibit antibacterial activity against E. coli and S. aureus cultures at a concentration (MIC) of 256 µg/mL. [ABSTRACT FROM AUTHOR]

Sulphonamide motif is found extensively in numerous chemotherapeutic drug candidates, it acts by stopping the production of folate inside the bacterial cell. Current research has established the synthesis and characterization of new bioprecursor prodrugs of sulfadiazine. The first prodrug, 3, was synthesized via the coupling of diazonium salt of sulfadiazine with ethyl acetoacetate in AcONa at 0 °C. The second prodrug, sulfadiazine-pyrazole, 5, was furnished via cyclocondensation of the hydrazono derivative, 3, and 2-pyridyl hydrazine, 4. The generated data from the X-ray analysis is interpreted and refined to obtain the crystal structure of the target compound, 5. Density functional theory (DFT) method was used to calculate the optimized geometrical parameters, electronic state (HOMO–LUMO), and the electronic properties. Moreover, Hirshfeld analysis revealed that the most important contributions to the crystal packing of the prodrug 5 are H···H, O···H and H···C contacts. [ABSTRACT FROM AUTHOR]

Laccases from I Trametes versicolor i , I Myceliophthora thermophila i , I Bacillus subtilis i and laccase-like multicopper oxidase from I T. thermophila i have been investigated by Milovanovic et al. in the oxidation of 1,4-dihydropyridine-based hexahydroquinolines to the corresponding pyridine-containing tetrahydroquinolines and in the oxidation of 1,4-dihydropyridine-based decahydroacridines to the corresponding pyridine-based octahydroacridines [[9]]. The milestone of the 10th anniversary of I Catalysts i is a great time to reflect on past accomplishments, present progress and challenges, as well as to identify future challenges and opportunities. The enzymatic monoacetylation of diols catalyzed by I Candida antarctica i lipase B is a valuable desymmetrization methodology and has been applied by Madali'nska et al. [[1]] to prochiral phosphines and phosphine I P i -sulfides as a route towards P-chiral catalysts. [Extracted from the article]

A suitable methodology of synthesis of coumarin derivatives by Pechmann reaction over heterogeneous solid acid catalysts in a free solvent media under microwave irradiation is described. Resorcinol, phenol and ethyl acetoacetate were selected as model reactants in the Pechmann condensation. The catalytic activity of several materials--Amberlyst-15, zeolite β and sulfonic acid functionalized hybrid silica--in solvent-free microwave-assisted synthesis of the corresponding coumarin derivatives has been investigated in detail. 7-Hydroxy-4-methylcoumarin and 4-methylcoumarin were obtained in 97% and 43% yields, respectively, over Amberlyst-15. This was the most active catalyst in the Pechmann reaction under studied conditions. [ABSTRACT FROM AUTHOR]

An efficient one-pot synthesis of 1,2,3-triazole derivatives of dihydropyrimidinones has been developed using two multicomponent reactions. The aldehyde-1,2,3-triazoles were obtained in good yields from in situ-generated organic azides and O-propargylbenzaldehyde. The target heterocycles were synthesized through the Biginelli reaction in which the aldehyde-1,2,3-triazoles reacted with ethyl acetoacetate and urea in the presence of Ce(OTf)3 as the catalyst. The corrosion inhibition of steel grade API 5 L X52 in 1 M HCl by the synthesized compounds was investigated using the electrochemical impedance spectroscopy technique. The measurements revealed that these heterocycles are promising candidates to inhibit acidic corrosion of steel. [ABSTRACT FROM AUTHOR]

A rapid and efficient solvent-free one-pot synthesis of coumarin derivatives by Pechmann condensation reactions of phenols with ethyl acetoacetate using FeF3 as a catalyst under microwave irradiation is described. This one-pot synthesis on a solid inorganic support provides the products in good yields. The newly synthesized compounds were systematically characterized by IR, 1H-NMR, 13C-NMR, MS and elemental CHN analyses. The proposed solvent-free microwave irradiation method using the environmentally friendly catalyst FeF3 offers the unique advantages of high yields, shorter reaction times, easy and quick isolation of the products, excellent chemoselectivity, and a one-pot, green synthesis. The products were screened for antimicrobial activity, and the results showed that the compounds reacted against all the tested bacteria. [ABSTRACT FROM AUTHOR]

Biginelli reaction of ethyl acetoacetate, thiourea and the appropriate aromatic aldehyde was used to produce ethyl 4-aryl-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine- 5-carboxylates, that reacted with bromomalononitrile to give ethyl 3-amino-5- aryl-2-cyano-7-methyl-5H-thiazolo[3,2-a]pyrimidine-6-carboxylates rather than the isomeric 7H-thiazolo[3,2-a]pyrimidines. Thiazolopyrimidine derivatives reacted with carbon disulphide to yield ethyl 9-aryl-7-methyl-2,4-dithioxo-2,3,4,9-tetrahydro-1H-thiazolo[3,2-a:4,5-d']dipyrimidine-8-carboxylates, that reacted with phenacyl bromide to produce ethyl 8-methyl-10-(4-methoxyphenyl)-3-substituted-5-thioxo-2(un)subatituted-10H-thiazolo[3'',2'':1',2']pyrimido[4',5':4,5]thiazolo[3,2-a]pyrimidine-9-carboxylates. The aforementioned reactions were carried out using both conventional chemical methods and with the assistance of microwave irradaition. Comparison between both methods showed that the microwave assisted method is preferable because of the time reduction and yield improvements achieved. The new compounds were tested for their biological activity as antioxidants, antibacterial or antifungal agents. Some of the new compounds were found to have moderate to good antioxidant and antimicrobial activities. [ABSTRACT FROM AUTHOR]

Acridinediones were synthesized by the one-pot Hantzsch condensation of an aromatic aldehyde, 5,5-dimethyl-1,3-cyclohexanedione, and aniline/4-methylaniline in refluxing water. This method has then been extended to the four-component reaction of an aromatic aldehyde, 5,5-dimethyl-1,3-cyclohexanedione, ethyl acetoacetate and ammonium acetate for the synthesis of polyhydroquinoline derivatives. This is an environmentally friendly and efficient procedure providing good to excellent yields. [ABSTRACT FROM AUTHOR]

3-Aroyl and 3-heteroaroyl substituted 3-oxoalkanenitriles were synthesized by the reactions of activated aromatic and hetero-aromatic substances with cyanoacetic acid in the presence of acetic anhydride. As part of studies focusing on the preparation of cyanoacetyl-1-N-methylbenzimidazole, we observed that reaction of N-methyl-benzimidazole with the cyanoanhydride formed by condensation of cyanoacetic acid with acetic anhydride, leads to the formation of 2-(1,3-diacetyl-2,3-dihydro-1H-benzo[d]-imidazol-2-yl)acetonitrile (5), whose structure was confirmed by X-ray crystallographic analysis. 3-Oxoalkanenitriles 3a,b were observed to undergo condensation reactions with dimethylformamide dimethyl acetal (DMFDMA) to afford the corresponding enamino-nitriles, which react with malononitrile to give 2-dialkylaminopyridines through a pathway involving a new, unexpected rearrangement process. Reactions of 3-oxoalkanenitriles with ethyl acetoacetate were found to afford 2-oxopyran-3-carbonitriles, also occurring via this unexpected rearrangement process. Mechanisms to account for both rearrangement reactions are suggested. In addition, reactions of 3-oxoalkanenitriles with acetylacetone in acetic acid in the presence of ammonium acetate result in the formation of pyridine-3-carbonitriles. Finally, upon heating in the presence of zeolite 3-oxoalkanenitriles 3b,c self-trimerized to produce the corresponding aniline derivatives 23b,c. [ABSTRACT FROM AUTHOR]

The goal of the study was to evaluate the ability of filamentous fungi to biotransform the pentacyclic triterpene lupeol. The microbial transformations were carried out in shake flasks in different media. Experiments were also run with control flasks. Samples of each culture were taken every 24 hours, extracted with ethyl acetate, and analyzed by GC-MS. The biotransformation of lupeol by Aspergillus ochraceus and Mucor rouxii afforded two compounds in each culture, which were detected in the cultures developed for more than seven days only in the Koch's K1 medium. The obtained data demonstrated that A. ochraceus is a good biocatalyst to introduce double bonds in the lupeol structure, whereas M. rouxii exhibits ability to biocatalyze oxygen insertions in that pentacyclic triterpene. Mass spectrometry was demonstrated to be an efficient analytical method to select promising biocatalysts for the compound investigated in this study. The biotransformation processes were influenced by the culture medium and incubation period. The obtained results open the perspective of using A. ochraceus and M. rouxii in pentacyclic triterpene biotransformations. [ABSTRACT FROM AUTHOR]

Three phenolic compounds, p-hydroxybenzoic acid (1), isorhamnetin-3-O-β-Drutinoside (2), and 3,3′-di-O-methylquercetin (5), along with a phenolic mixture were successfully separated from the ethyl acetate crude extract of Halimodendron halodendron by high-speed counter-current chromatography (HSCCC) with chloroform-methanolwater- acetic acid (4:3:2:0.05, v/v) as the two-phase solvent system. The phenolic mixture from HSCCC was further separated by preparative HPLC and purified by Sephadex LH-20 to afford quercetin (3) and 3-O-methylquercetin (4). Seven hundred mg of ethyl acetate crude extract was separated by HSCCC to obtain six fractions which were then analyzed by high performance liquid chromatography (HPLC). The HSCCC separation obtained total of 80 mg of the mixture of quercetin (3) and 3-O-methylquercetin (4) (26.43% and 71.89%, respectively) in fraction 2, 14 mg of 3,3′-di-O-methylquercetin (5) at 95.14% of purity in fraction 3, 15 mg of p-hydroxybenzoic acid (1) at 92.83% of purity in fraction 5, 12 mg of isorhamnetin-3-O-β-D-rutinoside (2) at 97.99% of purity in fraction 6. This is the first time these phenolic compounds have been obtained from H. halodendron, and their chemical structures identified by means of physicochemical and spectrometric analysis. [ABSTRACT FROM AUTHOR]

A series of Ni-based catalysts were prepared using hydrogen reduction of Ni/Al hydrotalcite-like compounds (Ni/Al HTlcs) synthesized by coprecipitation. The physicochemical properties of Ni/Al hydrotalcite-like compounds and the corresponding Ni-based catalysts were characterized using inductively coupled plasma (ICP), BET surface areas, Xray diffraction (XRD), Fourier transform infrared (FTIR) spectroscopy and scanning electron microscopy (SEM) techniques. The results indicated that Ni/Al HTlcs with layered structures could be successfully prepared by the coprecipitation method, and the characteristic HTlcs reflections were also observed in the XRD analysis. The NiO and Ni0 phases were identified in all Ni-based catalysts, which displayed randomly interconnected pores and no layer structures. In addition, the studies also found the Ni/Al HTlcs and Nibased catalysts had high specific surface areas, low pore volumes and low pore diameters. The catalytic hydrogenation of ethyl acetate to ethanol with Ni-based catalysts was also investigated. Among the studied catalysts, RE1NASH-110-3 showed the highest selectivity and yield of ethyl acetate to ethanol, which were 68.2% and 61.7%, respectively. At the same time, a major by-product, butyl acetate, was formed due to an ester-exchange reaction. A proposed hydrogenation pathway for ethyl acetate over Ni-based catalysts was suggested. [ABSTRACT FROM AUTHOR]

Sorbus commixta Hedl. (Rosaceae) has been traditionally used in oriental countries for the treatment of asthma and other bronchial disorders. In this study, a chalcone glycoside was isolated from the ethyl acetate extract of the fruits of this plant. The compound was identified as neosakuranin based on the spectroscopic analysis and comparion with literature data. This is the first report of isolation of neosakuranin from Sorbus commixta. [ABSTRACT FROM AUTHOR]

3,5-Bis(4-chlorobenzylidene)-1-ethylpiperidin-4-one (1b) was condensed with malononitrile or cyanothioacetamide to yield pyranopyridine 2 and thiopyridopyridine 3b, respectively. Treatment of compound 3b with methyl iodide or ethyl chloroacetate in the presence of a base catalyst gave the corresponding compounds 4 and 5. Compound 3b was reacted with 2-chloro-N-arylacetamide derivatives to yield compounds 7a,b, which were reacted with benzoyl chloride or sodium nitrite to give the corresponding tetracyclic compounds 8a,b and 9a,b, respectively. Compound 2 was treated with acetic anhydride or formic acid to yield the corresponding N-acetylpyranopyridine 10 and pyranopyrimidine 11. Treatment of compound 2 with triethyl ortho-formate gave compound 12, which was cyclized with hydrazine hydrate to give N-aminopyrimidine 13. Some of the synthesized compounds showed high antiarrhythmic activities comparable with Procaine amide and Lidocaine as positive controls. [ABSTRACT FROM AUTHOR]

Objective: In this study, small molecules possessing tetrahydropyrimidine derivatives have been synthesized having halogenated benzyl derivatives and carboxylate linkage. As previously reported, FDA approved halogenated pyrimidine derivatives prompted us to synthesize novel compounds in order to evaluate their biological potential. Methodology: Eight pyrimidine derivatives have been synthesized from ethyl acetoacetate, secondary amine, aromatic benzaldehyde by adding catalytic amount of CuCl2·2H2O via solvent less Grindstone multicomponent reagent method. Molecular structure reactivity and virtual screening were performed to check their biological efficacy as an anti-oxidant, anti-cancer and anti-diabetic agent. These studies were supported by in vitro analysis and QSAR studies. Results: After combined experimental and virtual screening 5c, 5g and 5e could serve as lead compounds, having low IC50 and high binding affinity. [ABSTRACT FROM AUTHOR]

β-Phenylethylamine hydrochloride (PEA-HCl) and ethyl acetoacetate (EAA) are anti-microbials with applications in food processing. As food anti-microbials, the compounds will have to withstand the cooking process without changing to toxic compounds. With this Communication, we address the question of whether PEA and EAA are altered when heated to 73.9 °C or 93.3 °C. A combination of gas chromatography and mass spectrometry was used to analyze solutions of PEA(-HCl) or EAA in beef broth or water. In addition, the anti-microbial activity of PEA-HCl and EAA was compared between heated and unheated samples at a range of concentrations. The gas chromatograms of PEA(-HCl) and EAA showed one peak at early retention times that did not differ between the heated and unheated samples. The mass spectra for PEA and EAA were near identical to those from a spectral database and did not show any differences between the heated and unheated samples. We conclude that PEA(-HCl) and EAA formed pure solutions and were not altered during the heating process. In addition, the anti-microbial activity of PEA-HCl and EAA did not change after the heating of the compounds. Regardless of temperature, the minimal inhibitory concentrations (MICs) for PEA-HCl were 20.75 mmol mL−1 for Escherichia coli and Salmonella enterica serotype Typhimurium. For EAA, the MICs were 23.4 mmol mL−1 for E. coli and 15.6 mmol mL−1 for S. enterica. [ABSTRACT FROM AUTHOR]

To date, no fused heterocycles have been formed on folic acid molecules; for this reason, and others, our target is to synthesize new derivatives of folic acid as isolated or fused systems. Folic acid 1 reacted with ethyl pyruvate, triethyl orthoformate, ethyl chloroformate, thioformic acid hydrazide, and aldehydes to give new derivatives of folic acid 2–6a,b. Moreover, It reacted with benzylidene malononitrile, acetylacetone, ninhydrin, ethyl acetoacetate, ethyl cyanoacetate, and ethyl chloroacetate to give the pteridine fused systems 10–15, respectively. Ethoxycarbonylamino derivate 5 reacted with some nucleophiles containing the NH2 group, such as aminoguanidinium hydrocarbonate, hydrazine hydrate, glycine, thioformic acid hydrazide, and sulfa drugs in different conditions to give the urea derivatives 16–20a,b. Compound 4 reacted with the same nucleophiles to give the methylidene amino derivatives 21–24a,b. The fused compound 10 reacted with thioglycolic acid carbon disulfide, malononitrile, and formamide to give the four cyclic fused systems 25–30, respectively. The biological activity of some synthesized showed moderate effect against bacteria, but no effect shown towards fungi. [ABSTRACT FROM AUTHOR]

Ethyl 5-arylpyridopyrimidine-6-carboxylates 3a–d were prepared as a one pot three component reaction via the condensation of different aromatic aldehydes and ethyl acetoacetate with 6-amino-1-benzyluracil 1a under reflux condition in ethanol. Additionally, condensation of ethyl 2-(2-hydroxybenzylidene) acetoacetate with 6-amino-1-benzyluracil in DMF afforded 6-acetylpyridopyrimidine-7-one 3e; a facile, operationally, simple and efficient one-pot synthesis of 8-arylxanthines 6a–f is reported by refluxing 5,6-diaminouracil 4 with aromatic aldehydes in DMF. Moreover, 6-aryllumazines 7a–d was obtained via the reaction of 5,6-diaminouracil with the appropriate aromatic aldehydes in triethyl orthoformate under reflux condition. The synthesized compounds were characterized by spectral (1H-NMR, 13C-NMR, IR and mass spectra) and elemental analyses. The newly synthesized compounds were screened for their anticancer activity against lung cancer A549 cell line. Furthermore, a molecular-docking study was employed to determine the possible mode of action of the synthesized compounds against a group of proteins highly implicated in cancer progression, especially lung cancer. Docking results showed that compounds 3b, 6c, 6d, 6e, 7c and 7d were the best potential docked compounds against most of the tested proteins, especially CDK2, Jak2, and DHFR proteins. These results are in agreement with cytotoxicity results, which shed a light on the promising activity of these novel six heterocyclic derivatives for further investigation as potential chemotherapeutics. [ABSTRACT FROM AUTHOR]

Within a series of dipeptide derivatives (5–11), compound 4 was refluxed with d-glucose, d-xylose, acetylacetone, diethylmalonate, carbon disulfide, ethyl cyanoacetate, and ethyl acetoacetate which yielded 5–11, respectively. The candidates 5–11 were characterized and their biological activities were evaluated where they showed different anti-microbial inhibitory activities based on the type of pathogenic microorganisms. Moreover, to understand modes of binding, molecular docking was used of Nicotinoylglycine derivatives with the active site of the penicillin-binding protein 3 (PBP3) and sterol 14-alpha demethylase's (CYP51), and the results, which were achieved via covalent and non-covalent docking, were harmonized with the biological activity results. Therefore, it was extrapolated that compounds 4, 7, 8, 9, and 10 had good potential to inhibit sterol 14-alpha demethylase and penicillin-binding protein 3; consequently, these compounds are possibly suitable for the development of a novel antibacterial and antifungal therapeutic drug. In addition, in silico properties of absorption, distribution, metabolism, and excretion (ADME) indicated drug likeness with low to very low oral absorption in most compounds, and undefined blood–brain barrier permeability in all compounds. Furthermore, toxicity (TOPKAT) prediction showed probability values for all carcinogenicity models were medium to pretty low for all compounds. [ABSTRACT FROM AUTHOR]

Novel Mn–Ce–Ti–O composite aerogels with large mesopore size were prepared via a one-pot sol–gel method by using propylene oxide as a network gel inducer and ethyl acetoacetate as a complexing agent. The effect of calcination temperature (400, 500, 600, and 700 °C) on the NH3–selective catalytic reduction (SCR) performance of the obtained Mn–Ce–Ti–O composite aerogels was investigated. The results show that the Mn–Ce–Ti–O catalyst calcined at 600 °C exhibits the highest NH3–SCR activity and lowest apparent activation energy due to its most abundant Lewis acid sites and best reducibility. The NO conversion of the MCTO-600 catalyst maintains 100% at 200 °C in the presence of 100 ppm SO2, showing the superior resistance to SO2 poisoning as compared with the MnOx–CeO2–TiO2 catalysts reported the literature. This should be mainly attributed to its large mesopore sizes with an average pore size of 32 nm and abundant Lewis acid sites. The former fact facilitates the decomposition of NH4HSO4, and the latter fact reduces vapor pressure of NH3. The NH3–SCR process on the MCTO-600 catalyst follows both the Eley–Rideal (E–R) mechanism and the Langmuir–Hinshelwood (L–H) mechanism. [ABSTRACT FROM AUTHOR]

In the present study, acetoacetic ester-terminated polyether was selected as a modifier to prepare a new type of polyether phenolic resin, which was successfully prepared by pre-synthesis modification. It is used to prepare interpenetrating cross-linked network structure modified phenolic foam with excellent mechanical properties. Fourier transform infrared spectroscopy (FT-IR) and nuclear magnetic resonance (1H NMR, 13C NMR) were used to characterize the molecular structure of the polyether phenolic resin. The results showed that the acetoacetic ester-terminated polyether successfully modified the phenolic resin and introduced a polyether skeleton into the resin structure. The effect of changing the added amount of acetoacetic ester-terminated polyether from 10% to 20% of the phenol content on the mechanical properties and microstructure of the modified phenolic foam was investigated. The results showed that when the amount of acetoacetic ester-terminated polyether was 16% the amount of phenol, this resulted in the best toughness of the modified foam, which had a bending deflection that could be increased to more than three times that of the base phenolic foam. The modified phenolic foam cell diameter was reduced by 36.3%, and the distribution was more uniform, which formed a denser network structure than that of the base phenolic foam. The bending strength was increased by 0.85 MPa, and the pulverization rate was as low as 1.3%. [ABSTRACT FROM AUTHOR]

A new compound belonging to a dihydrotetrazolopyrimidine derivative, that is, ethyl 5-methyl-7-(4-morpholinophenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate, was successfully synthesized using a Biginelli reaction between 4-morpholinobenzaldehyde, ethyl acetoacetate, and 5-aminotetrazole with p-toluenesulfonic acid (pTSA) as a catalyst in ethanol under reflux. The molecular structure of the title compound was characterized on the basis of spectroscopic evidence, using FTIR, HRESI-MS, 1H- and 13C-NMR, and 2D NMR. [ABSTRACT FROM AUTHOR]

The title compound (Z)-4-[2-(3,4-difluorophenyl)hydrazono]-3-methyl-1H-pyrazol-5(4H)-one 4 was synthesized by the reaction of ethyl 2-[2-(3,4-difluorophenyl)hydrazono]-3-oxobutanoate 3 with hydrazine hydrate. The diazotization of 3,4-difluoroaniline, followed by the treatment with ethyl acetoacetate, afforded intermediate 3. The synthesized compound 4 was characterized by FTIR, 1H-NMR, 13C-NMR and LCMS, and it showed synergistic anti-inflammatory, antiproliferative and antibacterial activities. [ABSTRACT FROM AUTHOR]