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Synthesis and biological evaluation of coumarin based isoxazoles, pyrimidinthiones and pyrimidin-2-ones

The titled compounds (6?a?k), (7?a?k) and (8?a?k) were synthesized from chalcones (5a?k) having coumarin moiety. Cyclization of chalcones (5a?k) with hydroxyl amine hydrochloride, thiourea and urea resulted in corresponding isoxazoles (6?a?k), pyrimidinthiones (7?a?k) and pyrimidin-2-ones (8?a?k). Structures of newly synthesized compounds were established on the basis of their elemental analysis, IR, 1H NMR, 13C NMR, and mass spectral data. The synthesized analogs were evaluated for their antimycobacterial activity and antimicrobial activity against eight bacteria (Staphylococcus aureus, Bacillus cereus, Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumoniae, Salmonella typhi, Proteus vulgaris, and Shigella flexneri) and four fungi (Aspergillus niger, Candida albicans, Aspergillus fumigatus, and Aspergillus clavatus).

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146. 15N-NMR Spectra of Azoles with Two Heteroatoms

The 15N-NMR spctra of azoles, with natural isotope abundance, have been measured under different experimental conditions, and chemical shifts are reported for imidazoles, pyrazoles, oxazoles, isoxazoles, thiazoles and isothiazoles.General trends of substituent effects in this heterocyclic series are discussed based on the data of 67 substituted azoles, dihydro- and tetrahydroazoles. 15N, 1H spin-coupling constants have been determined from spectra obtained by (1H) -> 15N polarizationtransfer experiments, i.e. an application of INEPT and DEPT pulse sequences.Two-bond and three-bond coupling constants are fully assigned and are discussed in terms of the specific pathways in azoles.The potential of structural applications of the new data is illustrated for isomeric nitro-imidazoles and highly-substituted pyrazoles, and in the case of ring-chain tautomerism of 2-substituted tetrahydrooxazoles.

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SUBSTITUTE 1, 6-NAPHTHYRIDINES FOR USE AS SCD INHIBITORS

The present invention relates to substituted tetrahydronaphthyridine (THN) compounds of the formula (I) and salts thereof, to pharmaceutical compositions containing them and their use in medicine. In particular, the invention relates to compounds for inhibiting SCD activity

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Archives for Chemistry Experiments of Isoxazole

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An Efficient Four-Component Approach for the Synthesis of Novel 5-Methyl-4-(2-(3-methyl-4-nitroisoxazol-5-yl)- 1-arylethyl)-1H-pyrazol-3-ol Derivatives and their Antibacterial Study

A One pot four-component domino reactions were developed for the synthesis of 5-methyl-4-(2-(3-methyl-4-nitroisoxazol-5-yl)-1-arylethyl)-1H-pyrazol-3-ols derivatives in excellent yield from hydrazine hydrate (1), ethyl acetoacetate (2), aldehyde (3) and 3,5-dimethyl-4-nitro-isoxazole (4) using 10 mol% of piperidine. This method is simple, efficient and multiple bonds were generated (two C?C, one C?N, one O?H and one C=N) in a single step. These novel 5-methyl-4-(2-(3-methyl-4-nitroisoxazol-5-yl)-1-arylethyl)-1H-pyrazol-3-ol derivatives are evaluated as anti-bacterial agents.

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Palladium-catalyzed chelation-assisted ortho-tetra-acetoxylation of 1,3-diarylpyrazoles and 1,3-diarylindazoles

Palladium-catalyzed chelation-assisted acetoxylation of 1,3-diarylpyrazoles has been carried out with phenyliodonium diacetate (PIDA) to obtain the corresponding ortho-tetra-acetoxylated pyrazoles in good yields.

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Final Thoughts on Chemistry for Isoxazole

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Copper-Catalyzed Cascade Cyclization Reactions of Diazo Compounds with tert-Butyl Nitrite and Alkynes: One-Pot Synthesis of Isoxazoles

A novel copper-catalyzed [3 + 2] cycloaddition reaction of alkynes with nitrile oxides generated in situ from the coupling reaction of copper carbene and nitroso radical has been developed. The three-component reaction provides a simple and efficient method for the construction of isoxazoles in a highly regioselective manner in a single step. On the basis of the experimental results and density functional theory calculations, a catalytic cycle (CuI-CuII-Cu0-CuI) for this cascade cyclization reaction is proposed.

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Fragmentation of isoxazole molecules by electron impact in the energy range 10-85 eV

Fragmentation of isoxazole molecules by electron impact excitation, that produces excited atomic and molecular fragments, has been studied using the optical excitation technique. Excited hydrogen atoms H(n), n = 4-7, have been detected by observation of the Hbeta to H lines of the Balmer series. The diatomic CH(A2Delta) and CN(B2Sigma +) fragments have been identified by their A2Delta ? X2Pir and B2Sigma+ ? X2Sigma+ emission bands, respectively. The appearance energies for the H(n = 4), CH(A2Delta) and CN(B2Sigma +) have been measured to be 21.9, 14.0 and 10.6 eV, respectively. Absolute emission cross sections have been also obtained for the fragments in electron energy ranges from their respective appearance thresholds up to 85 eV. Possible fragmentation processes are discussed.

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Catalytic Lignin Depolymerization to Aromatic Chemicals

ConspectusIn recent decades, research on lignin depolymerization and its downstream product transformation has drawn an enormous amount of attention from academia to industry worldwide, aiming at harvesting aromatic compounds from this abundant and renewable biomass resource. Although the lignin conversion can be traced back to the 1930s and various noncatalytic and catalytic methods have been explored to depolymerize lignin via direct lignin conversion research or lignin models conversion studies, the complexity of the lignin structure, various linkages, the high stability of lignin bonds, and the diverse fragments condensation process make lignin depolymerization to monomers a highly challenging task. For the potential practical utilization of lignin, compared with lignin conversion to liquid fuel with extra H2 consumption, maintaining the aromatic structure and preparing high-value aromatic chemicals from renewable lignin is more profitable. Therefore, lignin depolymerization to easy-to-handle aromatic monomers with acceptable conversion and selectivity is of great importance. In this article, we present our recent studies on lignin’s catalytic conversion to aromatic chemicals. First, we introduce our research on protolignin depolymerization via a fragmentation-hydrogenolysis process in alcohol solvents. Then, focusing on the catalytic cleavage of lignin C-C and C-O bonds, we shed light on a recapitulative adjacent functional group modification (AFGM) strategy for the conversion of lignin models. AFGM strategy begins with the adjacent functional group modification of the target C-C or C-O bond to directly decrease the bond dissociation enthalpy (BDE) of targeted bonds or generate new substrate sites to introduce the cleavage reagent for further conversion. Subsequently, on the basis of these two concepts from AFGM, we summarize our strategies on lignin depolymerization, which highlight the effects of lignin structure, catalyst character, and reaction conditions on the efficiency of strategies. In short, the key point for lignin depolymerization to aromatics is promoting the lignin conversion and restraining the condensation. Compared with the complex research on direct lignin conversion, this bottom-up research approach, beginning with lignin model research, can make the conversion mechanism study clear and provide potential methods for the protolignin/technical lignin conversion. In addition, one of our perspectives for lignin utilization is that the products from lignin conversion can be used as monomers for artificial polymerization, such as the simple phenol (PhOH) and other potential acid compounds, or that lignin derivative molecules can be used to synthesize high-value synthetic building blocks.

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Induction of apoptosis and downregulation of ERalpha in DMBA-induced mammary gland tumors in Sprague?Dawley rats by synthetic 3,5-disubstituted isoxazole derivatives

Isoxazole derivatives are an important group of chemotherapeutic prototypes. In the current study, we have synthesized few isoxazole derivatives and tested them for their antiproliferative properties in cancer cell lines such as MCF7 and HeLa. The lead compound, 3-(3,4-dimethoxyphenyl)-5-(thiophen-2-yl)isoxazole (2b), showed considerable inhibition of proliferation of MCF7 and HeLa cells with the IC50 values of 19.5 and 39.2?muM, respectively. Cell cycle analyses and annexin-FITC staining in 2b-treated breast adenocarcinoma cells (MCF7) showed increased sub-G1 population and apoptosis. Furthermore, we tested the tumor inhibitory effect of 2b and estrogen receptor expression profile in DMBA-induced mammary tumors in Sprague?Dawley rats. The gross morphology of tumor studies was investigated by histopathology and ERalpha protein expression was evaluated by immunohistochemistry, which showed tumor regression and downregulation of ERalpha in tumor cells. The present results implicate that compound 2b could be used for the further derivatization for the treatment of breast cancer.

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The Literature of Heterocyclic Chemistry, Part XV, 2015

A systematized survey of reviews and monographs published in 2015 on all aspects of heterocyclic chemistry is given.

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