Reaction Of Ethyl Research Articles

Crystal and Physiochemical Properties of 2-Aminoethanaminium 2-(Ethoxycarbonyl)-4,6-Dinitrophenolate

The proton transfer reaction of Ethyl 3,5-dinitrosalicylate, ethyl ester of 3,5-dinitrosalicylic acid (DNS), and ethylenediamine has been investigated. The reaction stoichiometry was 1:1 giving a molecular salt namely 2-Ami- noethanaminium 2-(ethoxycarbonyl)-4,6-dinitrophenolate (AED). The single crystals were grown by the slow solvent evaporation technique using DMF- water as a solvent at room temperature and found in a dimeric form. The structure was confirmed by single crystal X-ray diffraction (XRD), Nuclear magnetic resonance (NMR), fourier-transform infrared (FT-IR), ultraviolet-visible (UV-Vis) spectroscopic techniques as well as thermal analysis (TGA/TDA). It is transparent between 460 - 1000 nm melts at 192°C and decomposes at 268°C and may found a suitable optical application. The title compound crystallizes in monoclinic crystal system with the centrosymmetric space group C2/c and the title compound has shown superior properties in reducing sugar quantification as compared to DNS method.

Design, synthesis, cytotoxic evaluation and molecular docking studies of novel thiazolyl α-aminophosphonates

A new class of thiazolyl α-aminophosphonate derivatives was synthesized by one-pot Kabachnik–Fields reaction of ethyl 2-(3-formyl-4-isobutoxyphenyl)-4-methylthiazole-5-carboxylate with various aryl amines and diethyl phosphite under solvent-free conditions using β-cyclodextrin supported sulfonic acid (β-CD-SO3H) as an efficient, reusable and heterogeneous solid acid catalyst. The products were obtained in good to excellent yields at shorter reaction time. All the title compounds were screened for cytotoxic activity against human breast cancer (MCF-7 and MDA-MB-231), prostate cancer (DU-145) liver cancer (HepG2) and HeLa cancer cell lines using sulfarodamine-B (SRB assay). Compounds (8b, –4OMe), (8h, –4NO2) and (8j, –2I, –4CF3) showed better anticancer activity when compared with standard drug Adriamycin. Further in-silico target hunting reveals the anticancer activity of the designed compounds by inhibiting DNA topoisomerase II.

Kinetic study of reaction C2H5 + HO2 in a photolysis reactor with time-resolved Faraday rotation spectroscopy

The rate constant and branching ratios of ethyl reaction with hydroperoxyl radical, C2H5 + HO2 (1), a key radical-radical reaction for intermediate temperature combustion chemistry, were measured in situ for the first time in a photolysis Herriott cell by using mid-IR Faraday rotation spectroscopy (FRS) and UV-IR direct absorption spectroscopy (DAS). The microsecond time-resolved diagnostic technique in this work enabled the direct rate measurements of the target reaction at 40 and 80 mbar and reduced the experimental uncertainty considerably. C2H5 and HO2 radicals were generated by the photolysis of (COCl)2/C2H5I/CH3OH/O2/He mixture at 266 nm. By direct measurements of the transient profiles of C2H5, HO2 and OH concentrations, the overall rate constant for this reaction at 297 K was determined as k1(40 mbar) = (3.8 ± 0.8) × 10−11 cm3 molecule−1 s−1 and k1(80 mbar) = (4.1 ± 1.0) × 10−11 cm3 molecule−1 s−1. The direct observation of hydroxyl radical (OH) indicated that OH formation channel was the major channel with a branching ratio of 0.8 ± 0.1.

Synthesis and antibacterial activity of new hybrid derivatives of 5-sulfamoyl-1H-indole and 4-thiazolidinone groups

The synthesis of a series of new 3-phenyl-5-sulfamoyl-N-(7/8/9-(non)substituted-3-oxo-1-thia-4-azaspiro[4.4]non/[4.5]dec-4-yl)-1H-indole-2-carboxamide derivatives and their subsequent testing for antibacterial activity is described in this paper. 4-Sulfamoylbenzenediazonium chloride was synthesized from diazotization of sulfanilamide and sodium nitrite in the presence of HCl and was further allowed to condense with ethyl 2-benzylacetoacetate to produce ethyl 2-benzyl-2-(4-sulfamoylphenyl)hydrazonoacetate. This compound was cyclized to ethyl 5-sulfamoyl-3-phenyl-1H-indole-2-carboxylate employing the Fischer-indole procedure. The reaction of ethyl 5-sulfamoyl-3-phenyl-1H-indole-2-carboxylate with hydrazine hydrate yielded sulfamoyl-3-phenyl-1H-indole-2-carbohydrazide. Through a cyclization process, the spirothiazolidinone derivatives were obtained from the reaction of suitable cyclic ketones with 5-sulfamoyl-3-phenyl-1H-indole-2-carbohydrazide in the presence of thioglycolic acid/thiolactic acid. Structural elucidation of the novel compounds was achieved with the help of UV, IR, 1H NMR, HSQC, ESI–MS, and as well as elemental analysis. Among all the synthesized compounds tested, four compounds displayed the most promising antibacterial activity. The influence of the substituents and their positions on the antibacterial activity was evaluated.

Efficient synthetic method of β-fluorocinnamate by arylboronic acids and ethyl 3,3,3-trifluoropropionate under palladium-catalyzed conditions

A convenient and efficient method for synthesizing β-fluorocinnamate and derivatives is reported. Palladium (II) catalysis was employed in β-F elimination and coupling reaction of phenylboronic acid and ethyl 3,3,3-trifluoropropionate with a high yield and E-selectivity. The reaction was conducted under mild conditions and could be widely adapted to boronic acid substrates.

Ethyl 11a,12-Dihydrobenzo[b]benzo[5,6][1,4]oxazino[2,3-e][1,4]oxazine-5a(6H)-carboxylate

The 11a,12-dihydrobenzo[b]benzo[5,6][1,4]oxazino[2,3-e][1,4]oxazine heterocyclic system has been used in the construction of heteropropellanes, which attracted much attention not only on the possible modification of drugs, but also for novel materials with unusual and important physical properties. In this communication, the reaction of ethyl 2-(hydroxyimino)propanoate 1 with disulfur dichloride and o-aminophenol, which gave ethyl 11a,12-dihydrobenzo[b]benzo[5,6][1,4]oxazino[2,3-e][1,4]oxazine-5a(6H)-carboxylate in moderate yield, was described. The structure of the newly synthesized compound was established by means of elemental analysis, high resolution mass-spectrometry, 1H, 13C NMR and IR spectroscopy, mass-spectrometry and X-ray analysis.

An efficient preparation and characterization of 1-(2-ethoxy-2-oxoethyl)imidazolium based ionic liquids derivatives as potential bioactive agents

A set of new 1-(2-ethoxy-2-oxoethyl)imidazolium-based ionic liquids (1–16) have been prepared via the alkylation reaction of ethyl 2-(1H-imidazol-1-yl)acetate with various type of substituted alkyl halides using a microwave irradiation reaction in yields above 90%. The chemical structures of the manufactured ILs (1–16) were analyzed by mass and NMR spectroscopy. The newly prepared ILs were examined for their in vitro anti-microbial activities towards different types of Gram (+) and Gram (−) bacteria, and also for their antifungal activities. The preliminary tests showed that most of the resultant ILs presented modest activities towards S. aureus and B. subtilis with IZ values ranging between 10 and 14 mm, while the E. coli activities was in the range of 16 and 20 mm. However, ILs (1–16) displayed poor activities against the C. albicans.

Synthesis of 2H-Thiopirano[3,4-c]pyrazol-7-one Derivatives as the First Example a New Heterocyclic System

A series of ethyl 4-[(Z)-(4-oxo-2-thioxo-1,3-thiazolidin-5-ylidene)methyl]-1-aryl-1H-pyrazole-3-carboxylates was obtained as a result of the reaction of ethyl 4-formyl-1-aryl-1H-pyrazole-3-carboxylates with rhodanine. Under the action of NaOH, the prepared pyrazole-3-carboxylates underwent recyclization to form 2-aryl-7-oxo-2,7-dihydrothiopyrano[3,4-c]pyrazole-5-carboxylic acids—the first representatives of new heterocyclic system.

Synthesis and Biological Activity of Ethyl 2-[8-Arylmethylidenehydrazino-3-Methyl-7-(1-Oxothietan-3-YL)Xanth-1-YL]Acetates

Ethyl 2-[8-Arylmethylidenehydrazino-3-methyl-7-(1-oxothietan-3-yl)xanth-1-yl]acetates (IV) were synthesized via reactions of ethyl 2-[8-hydrazino-3-methyl-7-(1-oxothietan-3-yl)xanth-1-yl]acetic acid (III) with various benzaldehydes and acetophenones. The structures of the compounds were elucidated using IR and NMR spectroscopy and elemental analysis. The antiplatelet, anticoagulation, antioxidant, and anti-inflammatory activities were assessed in vitro and in laboratory animals to identify promising compounds exhibiting antiplatelet (hydrazone IVd) and antioxidant properties (hydrazone IVb). Both IVb and IVd according to in silico calculations were characterized by the absence of toxic risks (mutagenicity, oncogenicity, reproductive toxicity, local irritation) and had acceptable topological polar surface area so that they were promising.

Densely functionalized cinnolines: Controlled microwave-assisted facile one-pot multi-component synthesis and in vitro anticancer activity via apoptosis induction.

There is an urging continuous need for novel anti-cancer agents due to persistent chemoresistance. Herein, newly synthesized cinnolines are evaluated for their possible anticancer activities and suggested mechanisms. In the current study, a simple and efficient synthesis of densely functionalized cinnolines has been developed that relied on multi-component reaction of ethyl 5-cyano-4-methyl-1-aryl-6-oxo-1,6-dihydropyridazine-3-carboxylates with aromatic aldehydes and nitromethane in dioxane/pipridine under controlled microwave heating. Selected cinnolines (4a-c, e, h, j-n, q-v) were tested for possible anticancer activity using in vitro one dose assay at National Cancer institute, USA. Only cinnoline 4b stood out as the most potent cinnoline derivative (mean GI%=26.33) with broad-spectrum antitumor activity against the most tested cancer cell lines from all subpanels. The target cinnoline 4b emerged as the most active derivative against both leukemia RPMI-8226 and melanoma LOX IMVI cell lines (GI% = 106.06 and 82.1) respectively, with IC50 values equal to 17.12±1.31 and 12.32±0.75μg/mL, which are comparable to those of staurosporin; 24.97±1.47 and 8.45±0.42μg/mL, respectively. Cinnoline 4b influenced cell cycle distribution causing pre-G1 apoptosis and cell growth arrest at G2/M phase. It also induced apoptosis in both cell lines as manifested by significant increase in the percent of annexin V-FITC positive apoptotic cells in leukemia RPMI-8226 cells (from 1.09% to 12.47%) and melanoma LOX IMVI (from 1.32% to 19.05%). In addition, it showed lower expression levels of anti-apoptotic Bcl-2 protein, and higher expression levels of pro-apoptotic proteins; Bax, p53, cytochrome c, caspases 3 and 9. CONCLUSION: Induction of mitochondrial intrinsic pathway of apoptosis is a possible mechanism by which cinnoline 4b may confer its anticancer activity.

Synthesis and Anticancer Activity of 2-Aryl-3-methylbenzofuro[3,2-b]pyrazolo[4,3-e]azepine-4,11(2H,10H)-dione and 2-Aryl-3,7,9-trimethylpyrido[3',2':4,5]thieno[3,2-b]pyrazolo[4,3-e]azepine-4,11(2H,10H)-diones

The reactions of ethyl 1-aryl-4-(2-bromoacetyl)-5-methyl-1H-pyrazolocarboxylates with ortho-hydroxybenzonitrile and 4,6-dimethyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile gave previously unknown 2-aryl-3-methylbenzofuro[3,2-b]pyrazolo[4,3-e]azepine-4,11(2H,10H)-diones and 2-aryl-3,7,9-trimethylpyrido[3',2':4,5]thieno[3,2-b]pyrazolo[4,3-e]azepine-4,11(2H,10H)-diones, respectively. It was found that this reaction occurred as a tandem process. The synthesized compounds were sceened for anticancer activity and exhibited moderate activity against the most part of malignant cancer cells.

Synthesis, Antitumor Evaluation, Molecular Modeling and Quantitative Structure-Activity Relationship (QSAR) of Novel 2-[(4-Amino-6-N-substituted-1,3,5-triazin-2-yl)methylthio]-4-chloro-5-methyl-N-(1H-benzo[d]imidazol-2(3H)-ylidene)Benzenesulfonamides.

A series of novel 2-[(4-amino-6-R2-1,3,5-triazin-2-yl)methylthio]-4-chloro-5-methyl-N-(5-R1-1H-benzo[d]imidazol-2(3H)-ylidene)benzenesulfonamides 6–49 was synthesized by the reaction of 5-substituted ethyl 2-{5-R1-2-[N-(5-chloro-1H-benzo[d]imidazol-2(3H)-ylidene)sulfamoyl]-4-methylphenylthio}acetate with appropriate biguanide hydrochlorides. The most active compounds, 22 and 46, showed significant cytotoxic activity and selectivity against colon (HCT-116), breast (MCF-7) and cervical cancer (HeLa) cell lines (IC50: 7–11 µM; 15–24 µM and 11–18 µM), respectively. Further QSAR (Quantitative Structure–Activity Relationships) studies on the cytotoxic activity of investigated compounds toward HCT-116, MCF-7 and HeLa were performed by using different topological (2D) and conformational (3D) molecular descriptors based on the stepwise multiple linear regression technique (MLR). The QSAR studies allowed us to make three statistically significant and predictive models for them. Moreover, the molecular docking studies were carried out to evaluate the possible binding mode of the most active compounds, 22 and 46, within the active site of the MDM2 protein.

Синтез и биологическая активность этиловых эфиров 2-[8-арилметилиденгидразино-3-метил-7-(1-оксотиетанил-3)-ксантинил-1]уксусных кислот

Этиловые эфиры 2-[8-арилметилиденгидразино-3-метил-7-(1-оксотиетанил-3)ксантинил-1]уксусных кислот (IV) синтезированы реакцией этилового эфира 2-[8-гидразино-3-метил-7-(1-оксотиетанил-3)ксантинил-1]уксусной кислоты (III) с различными бензальдегидами и ацетофенонами. Структура соединений установлена с помощью ИК-, ЯМР спектроскопии и элементного анализа. Исследования in vitro и на лабораторных животных для оценки антиагрегантной, антикоагулянтной, антиоксидантной и противовоспалительной активности выявили перспективные соединения, проявляющие антиагрегантные (гидразон IVd) и антиоксидантные (гидразон IVb) свойства. По расчётам in silico оба соединения IVb, d характеризуются отсутствием токсических рисков (мутагенности, онкогенности, репродуктивной токсичности и местного раздражающего действия) и приемлемой площадью топологической полярной поверхности (TPSA), поэтому эти соединения перспективны.

Hydrosilylation of Allyl Ethers in the Presence of Platinum(II) Immobilized on Polymethylene Sulfide

The reactions of allyl ethyl, allyl butyl, allyl glycidyl, allyl benzyl, and allyl phenyl ethers with 1,1,3,3-tetra-methyldisiloxane in the presence of platinum(II) immobilized on polymethylene sulfide have been studied.

Iodine catalyzed one-pot four component synthesis of coumarinyl phosphoramidates via sequential addition of reactants

An unprecedented synthetic route for the preparation of a library of novel coumarinyl phosphoramidate derivatives via iodine catalysed one-pot four component reactions of ethyl 4-bromo-3-oxo-alkanoate, sodium azide, trialkyl phosphites, and phenols in ethanol is reported.

Synthesis, in vitro and in silico Studies of Naphthalene Pyrazoline Prop-2-en-1-one Derivatives

The synthesized new naphthalene pyrazoline prop-2-en-1-one derivatives (NDPP 1-8) were obtained by the Michael addition reaction of ethyl propanoate, hydrazine hydrate with NPD as a multicomponent scaffold. (E)-1-(naphthalen-3-yl)-3-phenylprop-2-en-1-one (NPD) was formed from 2-acetyl naphthalene and substituted aldehyde via Claisen-Schmidt condensation reaction. The NDPP skeleton structures were confirmed by infrared, 1H & 13C NMR spectral data and elemental analysis. The structure of NDPP compounds was subjected to molecular docking and ADME studies. The result of ADME prediction, compound NDPP 2, which contains electron withdrawing -Cl group has high drug-likeness value 4.21 than the compounds NDPP 4 and 7 which had electron donating CH3 and OCH3 group shows the drug-likeness value 2.62. The NDPP 2 also has high drug score 0.63 than NDPP 4 and NDPP 7 have drug score 0.60 and 0.69, respectively. Docking studies shows that compound NDPP 5 which also contain electron withdrawing NO2 group has good binding affinity value -8.8 Kcal/mol were docked with 1UAG protein. These compounds showed good drug-likeness value 2.25 and drug score 0.65. in vitro Studies have a high inhibition value for the same NO2 substituted derivative. All the compounds have higher binding affinity value than standards binding affinity value.

Sodium 4‐amino‐5‐hydroxy‐7‐sulfonaphthalene‐2‐sulfonate an efficient ligand for click reaction in water: Synthesis of 1,2,3‐triazole pharmacophore linked‐quinazolinone scaffold

AbstractWater soluble sodium 4‐amino‐5‐hydroxy‐7‐sulfonaphthalene‐2‐sulfonate ligand was used successfully for the preparation of 1,2,3‐triazoles pharmacophore linked‐quinazolinone scaffold. The reaction of ethyl 4‐oxo‐3,4‐dihydroquinazoline‐2‐carboxylate and related amide compounds with propargyl bromide afforded ethyl 4‐oxo‐3‐(prop‐2‐yn‐1‐yl)‐3,4‐dihydroquinazoline‐2‐carboxylate and its amide derivatives. The reaction of propargylated compounds with azides catalyzed by copper (II) salt, in the presence of Sodium 4‐amino‐5‐hydroxy‐7‐sulfonaphthalene‐2‐sulfonate as a ligand in water produced novel 1,2,3‐triazole pharmacophore linked‐quinazolinone‐4‐one scaffold with high‐to‐excellent yields. The ligand assisted in the click reaction and reduced loading of copper salt to 2 mol%. Simplicity, short reaction times, use of water as green solvent, and low catalyst loading are the main advantages of this procedure.

Three-Dimensional Kinetic Trends in Zeolites Catalyzed Benzene Ethylation Reaction: A Descriptor-Based DFT Study Coupled with Microkinetic Modeling

In zeolite catalysis, both the Bronsted acidity (e.g., acid strength) and reaction conditions (e.g., temperature) have significant influence on catalytic performance. Because of the intimate coupli...

Synthesis and antimicrobial activity of new thiazole and thiadiazole derivatives via ethyl pyruvate

ABSTRACT Reaction of ethyl 2-(2-((methylthio)carbonothioyl)hydrazono)propanoate (2) and ethyl 2-(2-carbamothioyl-hydrazono)propanoate (3) with hydrazonoyl halides 4 a-e afforded the corresponding thiadiazoles 5 a-e. Also, treatment of compound 2 with α-ketohydrazonoyl halides 12a-f in absolute ethanol and in the presence of triethylamine gave the corresponding thiadiazoles 13a-f; while reaction of ethyl 2-(2-carbamothioyl-hydrazono)propanoate (3) with α-ketohydrazonoyl halide 12 gave thiazole derivatives 15. Also, the reaction of compound 3 with hydrazonoyl chloride 12f afforded thiazolone derivative 18. Antimicrobial studies are performed using two-gram positive bacteria and two-gram negative bacteria. Data revealed that thiazole derivative 17a achieved the lowest MIC values (high efficient derivative) against the sensitive bacterial strain S. aureus with MIC value 160 µg/ml.

Synthesis of New Fused Furo- and Thienopyridines

A method was developed for the synthesis of new fused derivatives of pyrano[4,3-b]thieno(furo)-pyridine, namely 8,8-dimethyl-11-(2-furyl)-7,10-dihydro-8H-pyrano[3″,4″:5′,6′]pyrido[3′,2′:4,5]thieno(furo)[3,2-d]- pyrimidine-4(3H)-ones, from 2,2-dimethyltetrahydropyran-4-one. Optimal conditions for carrying out the cyclization reaction of ethyl {7,7-dimethyl-4-(2-furyl-3-cyano-7,8-dihydro-5H-pyrano[4,3-b]pyridin-2-yl]oxy}acetate into the corresponding amino ester were determined.