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Efficient regioselective synthesis and potential antitumor evaluation of isoxazolo[5,4-b]pyridines and related annulated compounds

The reaction of 5-amino-3-methylisoxazole with appropriate alpha,beta-unsaturated ketones gave the corresponding isoxazolo[5,4-b] pyridines. Treatment of 1 with 2,6-dibenzylidenecyclohexanone or 2-benzylidenedimedone afforded the corresponding isoxazolo[5,4-b]quinoline derivatives. 4,6,8,9-Tetrahydroisoxazolo[5,4-b]quinolin-5-one derivative was also obtained by multicomponent condensation reaction of 1 with dimedone and benzaldehyde. Heterocyclic annulation of the isoxazolo[5,4-b]pyridine system was achieved via reaction of 1 with benzylidene derivatives of indandione, quinuclidone, pyrazolone, and oxazolone. A representative of some newly synthesized compounds was evaluated as antitumor agents.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Studies on the synthesis of spiroheterocycles and their derivatives using dimedone as synthetic precursor

Diarylidene ketones 1a?c, formed by the condensation of acetone with diverse appropriate aryl aldehydes undergo Micheal reaction with dimedone to afford the desired spiro compounds 2a?c. The spirodiarylidene derivatives 3a?l on cyclisation with hydrazine, phenyl hydrazine, hydroxyl amine, urea, thiourea and guanidine carbonate furnish the respective insitu oxidized pyrazole 4a?l, phenylpyrazole 5a?l, isoxazole 6a?l, pyrimidine 7a?l, aminopyrimidine 8a?l. The antibacterial activities of the synthesized compounds have been investigated against the gram negative Escherichia coli and gram positive bacteria Staphylococcus aureus.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

Discovery of C17H14O

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Stable and Reusable Palladium Nanoparticles-Catalyzed Conjugate Addition of Aryl Iodides to Enones: Route to Reductive Heck Products

An efficient, binaphthyl-backbone-stabilized palladium nanoparticles (Pd-BNP) catalyst for the 1,4-addition of aryl halides to enones has been developed. The scope of the reaction has been studied with various substituted and sterically hindered aryl halides and enones to afford the conjugate addition products in good to excellent yields. The catalyst has been recovered and reused up to five times without any appreciable change in particle size or reactivity. (Figure presented.).

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Stereoselective debromination and selective reduction of vic-dibromides with nickel boride

A simple procedure is reported for the stereoselective debromination of vic-dibromides with nickel boride at ambient temperature. Debromination with concomitant reduction of vic-dibromides to give dihydro products in a one-pot reaction is also reported. alpha,beta-Dibromoketones can also be converted to their corresponding alcohols.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Anti-neoplastic activity of 1,3-diaza-2-functionalized-adamantan-6-one compounds against melanoma cells

Four series of 1,3-diaza-2-functionalized-adamantan-6-one derivatives, bearing at the 2 position SO, SO2, POCl and PO2H functional groups, were synthesized via a key quadruple Mannich reaction, followed by transformation of an aminal functionality into the final 2-thia- and 2-phospha compounds. The compounds were tested for cytotoxic activity against the mouse B16-F10 melanoma cell line. Malignant melanoma is notorious for its high resistance to chemotherapy, and new anti-melanoma drugs are urgently needed. The 2-thia compounds exhibited poor proliferation inhibition activity, but the 2-phospha derivatives showed significant activity, with IC50 values of 10-60 M. The compounds induced cell death by G2/M cell cycle arrest, which led to apoptosis, as determined by Annexin V-FITC/PI staining, mitochondrial membrane potential changes assessed by the JC-1 reagent, caspases 3 and 7 activation, and morphological changes.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Synthesis of Isomerically Pure (E)- and (Z)-1,3-Disubstituted 1,3-Dienes

The (E)-dienes 1a – p were prepared in >98percent purity by dehydrative decarboxylation of the corresponding 4,5-unsaturated 3-hydroxycarboxylic acids 3 with dimethylformamide dimethylacetal (11).The (Z)-isomers 6a – m were obtained by stereouncontrolled Wittig reaction of the phosphorane 18 with the aldehydes 7 and subsequent thermolysis of the resulting (E)-/(Z)-diene mixture.Under these conditions 1 was quantitatively converted into its dimer 5, whereas 6 remained unchanged and was readily separated from 5 by vacuum distillation or column chromatography.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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The cascade synthesis of alpha,beta-unsaturated ketones via oxidative C-C coupling of ketones and primary alcohols over a ceria catalyst

We herein report the oxidative C-C coupling of ketones and primary alcohols to produce alpha,beta-unsaturated ketones in the absence of base additives. This cascade synthetic reaction was conducted at 150 C in 12 h using a heterogeneous CeO2 catalyst. The conversion of acetophenone reached 74% with 89% selectivity to chalcone. A correlation between the CeO2 crystal plane and catalytic performance is established as the catalytic activities decrease in the sequence of (110) > (111) > (100). Characterization using Raman spectroscopy, CO2 temperature-programmed desorption (CO2-TPD), and in situ active site-capping tests has shown that the unusual catalysis of the CeO2 catalyst is attributed to the coexistence of basic and redox active sites. These sites synergistically catalyze the oxidation of alcohols to aldehydes and the aldol condensation to ketones. Moreover, the CeO2 catalyst can be reused several times after calcination to remove the surface-adsorbed substances.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Cationic Alkynyl Heck Reaction toward Substituted Allenes Using BobCat: A New Hybrid Pd(0)-Catalyst Incorporating a Water-Soluble dba Ligand

The cationic alkynyl Heck reaction between aryl triflates and alkynes to give substituted allenes is described. Key to the success of this method was the discovery and development of a new hybrid Pd(0)-catalyst, BobCat, that incorporates a water-soluble dba-ligand and biaryl phosphine ligand to provide substituted allenes in good yields under mild reaction conditions.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Catalytic asymmetric chloroamination reaction of alpha,beta-Unsaturated gamma-keto esters and chalcones

Highly efficient catalytic chloroamination reaction of alpha,beta- unsaturated gamma-keto esters and chalcones has been developed via a chloronium-based mechanism to deliver anti-regioselective vicinal chloroamines instead of the aziridinium intermediates delivered aminochlorides. The combination of TsNCl2 and TsNH2 as reagents made the transformation highly efficient, delivering the gamma-carbonyl-beta-chloro- alpha-amino acid derivatives and alpha-chloro-beta-amino-ketone derivatives in nearly quantitative yields with up to 99% ee and 99:1 dr under 0.05-0.5 mol % catalyst loading. TsNHCl was demonstrated to act as the key reactive species to form a bridged chloronium ion intermediate in the presence of a chiral scandium complex. The method might provide useful information for further realization of other haloamination reactions.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Antimicrobial Activity of Monoketone Curcuminoids Against Cariogenic Bacteria

We evaluated the antimicrobial activity of 25 monoketone curcuminoids (MKCs) against a representative panel of cariogenic bacteria in terms of their minimum inhibitory concentration (MIC) values. Curcumin A (10) displayed promising activity against Streptococcus mutans (MIC = 50 mug/ml) and Streptococcus mitis (MIC = 50 mug/ml) as well as moderate activity against S. sanguinis (MIC = 100 mug/ml), Lactobacillus casei (MIC = 100 mug/ml), and Streptococcus salivarius (MIC = 200 mug/ml). Results indicated higher activity of compound 10 than that of its bis-beta-diketone analog. Additionally, compounds 3a (1,5-bis(4-methylphenyl)pentan-3-one) and 7b (1,5-bis(4-bromophenyl)pentan-3-ol) were moderately active against S. mitis (MIC = 100 mug/ml) and S. salivarus (MIC = 200 mug/ml).

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate