Synthesis Of New Ethyl Research Articles

Design, Synthesis, and Anticancer Potential of the Enzyme (PARP-1) Inhibitor with Computational Studies of New Triazole, Thiazolidinone, - Thieno [2, 3-d] Pyrimidinones

Background: Thienopyrimidine, triazole and thiazolidinone derivatives have recently gained attention due to their effective pharmacological activities. They show antioxidant, antitumor, antimicrobial, antiviral, anti-inflammatory and analgesic properties. Objective: Synthesis of new ethyl 2-amino-4-isopropyl-5-methylthiophene-3-carboxylate (2) was used as a starting material to produce 2-mercapto-methylthienopyrimidinone (3), (4) and 2- hydrazinyl-methylthienopyrimidinone (5), through high yields and evaluating anticancer activities. Method: A series of novel Schiff's bases (6-9) were produced after treatment of (5) with aldehydes. Triazolopyrimidinones (6a, 7a, 8a, 9a) were produced from cyclization of benzylidene (6-9) using Br2 / AcOH or dry pyridine /Ac2O. Thiazolidinones (6b, 7b, 8b, 9b) were synthesized from benzylidene (6-9) with mercaptoacetic acid. Results: All the compounds were synthesized in good yields (55-85%) in a regularly actual system under mild condition. The new compounds have been established by means of diverse spectroscopic ways as IR, NMR and MS. The newly synthesized compounds were evaluated for their antiproliferative activity against the breast MCF-7 carcinoma cell line. Compound (7) showed promising anticancer activity with IC50 of 6.9 μM, and 40.8% of antioxidant effect as DPPH inhibition. Molecular docking of (7) showed ΔG values of-20.54 kcal/ mol and -25.60 kcal/ mol. Molecular dynamics simulation of (7) in complex with PARP-1 revealed RMSD of 3.00 Ǻ. Conclusion: The QSAR study confirmed the presence of a relationship between anticancer activity and subdivided surface area descriptors with coefficient r2 = 0.98 with high predictive power.

New synthesis of ethyl 6-amino-4-aryl-5-cyano-1,4-dihydropyrano[2,3-c]pyrazole-3-carboxylates

Ethyl 6-amino-4-aryl-5-cyano-1,4-dihydropyrano[2,3-c]pyrazol-3-carboxylates were synthesized by a reaction of diethyloxalacetate sodium salt with aromatic aldehyde, hydrazine hydrate, and malononitrile in the presence of acetic acid.

Synthesis of New Ethyl 4‐[3‐(Dimethylamino)‐propylmethylamino]pyrrolo[1,2‐a]quinoxaline‐2‐carboxylate Derivatives and Preliminary CNS Pharmacological Evaluation in Mice

The synthesis of new ethyl 4-[3-(dimethylamino)propylmethylamino]pyrrolo[1,2-a]-quinoxaline-2-carboxylate derivatives is described. Proconvulsant, convulsant and anticonvulsant activities were observed. Structure-activity relationships are discussed.

ChemInform Abstract: Synthesis and Structure of Acetyl‐Substituted Oxocyclohexanecarboxylates.

Dicarbonyl-substituted hydroxycyclohexanones with similar substituents (Ac or COOR) have been studied in sufficient detail [1]. Much less data are available on analogous compounds having different substituent groups (COR and COOR) [2]. However, such derivatives are promising from the viewpoint of their biological activity and design of carboand heterocyclic systems with specified functionalization pattern. We now report on the synthesis of new ethyl 3-acetyl-2-aryl-4-hydroxy-4-methyl-6-oxocyclohexanecarboxylates Ia–Ic whose structure was determined by spectral methods and chemical transformations. Compounds Ia–Ic were synthesized by condensation of aromatic aldehydes with ethyl acetoacetate or acetylacetone to give ethyl 2-benzylidene-3-oxobutanoate (IIa) or 3-arylmethylidenepentane-2,4-diones IIb and IIc, followed by Michael addition. Intramolecular aldolization of intermediate A gave cyclohexanecarboxylates Ia–Ic in up to 80% yield. The spectral data (IR and H NMR) for the synthesized compounds confirmed only the presence of carbonyl-containing fragments but not their position, so

Synthesis and structure of acetyl-substituted oxocyclohexanecarboxylates

Dicarbonyl-substituted hydroxycyclohexanones with similar substituents (Ac or COOR) have been studied in sufficient detail [1]. Much less data are available on analogous compounds having different substituent groups (COR and COOR) [2]. However, such derivatives are promising from the viewpoint of their biological activity and design of carboand heterocyclic systems with specified functionalization pattern. We now report on the synthesis of new ethyl 3-acetyl-2-aryl-4-hydroxy-4-methyl-6-oxocyclohexanecarboxylates Ia–Ic whose structure was determined by spectral methods and chemical transformations. Compounds Ia–Ic were synthesized by condensation of aromatic aldehydes with ethyl acetoacetate or acetylacetone to give ethyl 2-benzylidene-3-oxobutanoate (IIa) or 3-arylmethylidenepentane-2,4-diones IIb and IIc, followed by Michael addition. Intramolecular aldolization of intermediate A gave cyclohexanecarboxylates Ia–Ic in up to 80% yield. The spectral data (IR and H NMR) for the synthesized compounds confirmed only the presence of carbonyl-containing fragments but not their position, so

Pictet‐Spengler Condensation of N,N‐Dimethylsulfamoyl‐β‐Phenethylamines with Methylthioacetic Acid Ethyl Ester. New Synthesis of Ethyl 1,2,3,4‐Tetrahydroisoquinoline‐1‐Carboxylates

AbstractThe reaction of N,N‐dimethylsulfamoyl‐β‐phenethylamines with methylthioacetic acid ethyl ester using phenyliodine(III) bis(trifluoroacetate) gives moderate to good yields of the corresponding ethyl 1,2,3,4‐tetrahydroisoquinoline‐1‐carboxylates.

Synthesis of new ethyl 9-methylene-13 E and 13 Z-retinoates via the Julia olefination reaction

Synthesis of new ethyl 9-methylene-13 E and 13 Z-retinoates via the 9-methylene C-15 sulphone 5 is reported. The Julia olefination strategy was used for building the C-20 skeleton.

Clean solvent-free dipolar cycloaddition reactions assisted by focused microwave irradiations for the synthesis of new ethyl 4-cyano-2-oxazoline-4-carboxylates

1,3-Dipolar cycloaddition reactions without solvent under focused microwave irradiation are reported. Imidate 3, derived from ethyl α-cyano α-amino acetate as potential azomethine ylide, undergoes highly regioselective cycloadditions to a wide range of aldehydes 4a–f as dipolarophiles in short reaction times. This simple, efficient and environmentally-friendly methodology has been applied to the synthesis of new ethyl 4-cyano-2-oxazoline-4-carboxylates 6a–f in good yields (81–98%) and moderate diastereoisomeric ratios.

V-Triazolines. Part 36. New synthesis of ethyl 1-alkyl-1,4,5,6-tetrahydro-6-oxopyridine-3-carboxylates and 1-alkyl-1,4,5,6-tetranydro-6-oxopyridine-3-carbonitriles through reduction of N-2-nitroarylamidines

Ethyl 1-alkyl-1,4-dihydropyridine-3-carboxylates 2a–d and 1-alkyl-1,4-dihydropyridine-3-carbonitriles 2e,f were allowed to react with 2-nitrophenyl azide 3 to give tertiary amidines 4 by spontaneous rearrangement of the triazoline cycloadducts. Ready catalytic hydrogenation with Pd–C of 4 gave the corresponding ethyl 1-alkyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carboxylates 5a–d and 1-alkyl-6-oxo-1,4,5,6-tetrahydropyridine-3-carbonitriles 5e,f.

A Convenient Synthesis of Ethyl (Diethoxyphosphoryl) fluoroacetate from Ethyl Fluoroacetate

A new synthesis of ethyl (diethoxyphosphoryl) fluoroacetate starting from ethyl fluoroacetate is described for a mole scale. This synthesis does not require the use of special equipment for fluorine chemistry since no hydrogen fluoride is evolved

A new synthesis of ethyl 2-methyl-4-oxocyclohex-2-enecarboxylate (Hagemann's ester) and its methyl and t-butyl analogues

Regioselective cyclisations of esters of 2-acetyl-5-oxohexanoic acid led to (i) alkyl 2-methyl-4-oxocyclohex-2-enecarboxylates (alkyl = But,Et or Me)(catalysed by pyrrolidinium acetate), (ii) esters of 4-pyrrolidino-2-methyl-cyclohexa-1,3-dienecarboxylic acid (in the presence of pyrrolidine), and (iii) alkyl 4-methyl-2-oxocyclohex-3-enecarboxylates (catalysed by hydrogen chloride).