28-Sep-2021 News Top Picks: new discover of 15804-19-0

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Methods of treating or preventing neuronal loss associated with stroke, ischemia, CNS trauma, hypoglycemia, and surgery, as well as treating neurodegenerative diseases including Alzheimer’s disease, amyotrophic lateral sclerosis, Huntington’s disease, and Down’s syndrome, treating or preventing the adverse consequences of the hyperactivity of the excitatory amino acids, as well as treating anxiety, chronic pain, convulsions, and inducing anesthesia are disclosed by administering to an animal in need of such treatment an alkyl or azido-substituted 1,4-dihydroquinoxaline-2,3-dione or pharmaceutically acceptable salts thereof, which have high binding to the glycine receptor.

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The present invention relates to the discovery that specific human taste receptors in the T2R taste receptor family respond to particular bitter compounds present in, e.g., coffee. Also, the invention relates to the discovery of specific compounds and compositions containing that function as bitter taste blockers and the use thereof as bitter taste blockers or flavor modulators in, e.g., coffee and coffee flavored foods, beverages and medicaments. Also, the present invention relates to the discovery of a compound that antagonizes numerous different human T2Rs and the use thereof in assays and as a bitter taste blocker in compositions for ingestion by humans and animals.

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A simple and efficient method has been developed for the synthesis of various 2-quinoxalinone-3-hydrazone derivatives using microwave irradiation technique. The series of 2-quinoxalinone-3-hydrazone derivatives synthesized, were structurally confirmed by analytical and spectral data and evaluated for their antimicrobial activities. The results showed that this skeletal framework exhibited marked potency as antimicrobial agents. The most active antibacterial agent was 3-{2-[1-(6-chloro-2-oxo-2H-chromen-3-yl)ethylidene]hydrazinyl}quinoxalin-2(1H)-one, 7 while 3-[2-(propan-2-ylidene)hydrazinyl]quinoxalin-2(1H)-one, 2 appeared to be the most active antifungal agent.

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27-Sep-2021 News Brief introduction of 15804-19-0

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Condensation of o-phenylenediamine (1) with propanoic acid under Phillips’ conditions gives 2-ethylbenzimidazole (2). Attempts to oxidise 2 to 2-acetylbenzimidazole (3) using H2O2, SeO2, KMnO4/acetone were unsuccessful. Condensation of 2 with benzaldehyde yields 2-(alpha-methylstyryl)benzimidazole (4) which on oxidation with KMnO4 gives benzimidazole-2-carboxylic acid (5) as the sole product. Reaction of 1 with pyruvic acid results in 3-methylbenzo-1H-dihydropyrazine-2-one (7) rather than 3 as the major product. Treatment of 1 with formic acid gives the known compound benzimidazole (9) which with acetic anhydride in the presence of NaOAc does not yield 3. Reaction of 1 with lactic acid under Phillips’ conditions gives 2-(alpha-hydroxyethyl)benzimidazole (10) which on oxidation with acid dichromate, however, yields 3. Studies on syntheses and spectral properties of related benzimidazoles are reported.

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Sep-21 News Discover the magic of the 15804-19-0

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o-Phenylenediamines 1 underwent a series of cascade condensations with 1,2-dicarbonyl compounds to afford quantitative yields (eight cases) of heterocycles in solid-state syntheses that avoided waste formation. The products were produced in pure form and did not require purifying workup. The components were ball-milled in stoichiometric ratio, or in exceptional cases they were melted together and heated in the absence of solvents (some of them giving quantitative yields). Benzils and 2-hydroxy-1,4-naphthoquinone afforded quinoxaline derivatives 3 and 5, 2-oxoglutaric acid gave a 3-oxodihydroquinoxaline 7, and oxalic acid afforded the dihydroquinoxaline-2,3-dione 9. This last condensed with la in the melt, to afford a mixture of bis(benzimidazolyl) 10 and fluoflavin 11. Alloxane hydrate provided a 100% yield of the 3-oxodihydroquinoxaline-2-carbonylureas 15/16 at room temperature. Parabanic acid required a melt reaction providing a 78% yield of 3-oxodihydroquinoxalinyl-2-urea 22 and side products. Despite numerous reaction steps, most of these uncatalyzed stoichiometric reactions proceeded quantitatively in the solid state to give only one product (plus water), with unsurpassed atom economy. If catalysis with HCl was tried, the results were inferior. If melt reactions were required it appeared to be advantageous to have the products crystallize directly at the reaction temperature. The synthetic results have been interpreted mechanistically and compared to some similar solution reactions that do not exhibit the benefits of the solid-state techniques. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).

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Sep-21 News Extended knowledge of 15804-19-0

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A number of N-glycidyl compounds derived from oxo-substituted nitrogen heterocycles such as diazines, triazines, diazoles, triazoles as well as condensed ring systems containing these units have been synthesized. All products were tested for their antitumor activity against leukaemia in the mouse. Almost all of the approx. 50 di- and triglycidyl compounds showed activity and 5 of them exhibited an increase of lifespan of 200% and more. The most active compound was 1,2,4-triglycidyl-urazol.

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26-Sep-2021 News New explortion of 15804-19-0

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o-Phenylenediamine 1 is condensed with oxalic acid using Phillips’ procedure to obtain quinoxaline-2, 3-dione 2. The latter on treatment with hydrazine hydrate gives the known 2-hydrazinoquinoxalin -3-one 3. Reaction of 3 with various acid chlorides (which were obtained from the corresponding carboxylic acids by reaction with thionyl chloride in the presence of catalytic amount of dimethyl formamide) in HMPA medium at 220C in one pot reaction yield the corresponding 1-substituted-4-dimethylamino[1, 2, 4]triazolo[4, 3-a]quinoxalines 4. This reaction has been shown to proceed through the intermediacy of 2-(N-acyl/aryl hydrazinoquinoxalin -3-one 5 and 1-substituted-4-oxo-[1, 2, 4] triazolo[4, 3-a]quinoxalines 6. An interesting observation here has been that 5 can be cyclised to 6 at a considerably lower temperature of 100C than the requisite 220C using catalytic amount of HCl.

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September 26, 2021 News New explortion of 15804-19-0

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The treatment of the diethyl ester of o-phenylenebis(oxamic acid) (opbaH2Et2) with 2/3 of an equivalent of MeNH2 in MeOH does not result in the formation of the methyl ester of o-phenylene(N?-methyloxamide)(oxamic acid) (opooH3Me, 1) in pure state, as reported previously. The colourless crude material formed by this reaction was confirmed to be composed of 1 (89% content), the dimethyl ester of o-phenylenebis(oxamic acid) (opbaH2Me2, 2, 6%), 1,4-dihydro-2,3-quinoxalinedione (3, 3%) and o-phenylenebis(N?- methyloxamide) (opboH4Me2, 4, 1%), respectively. The identities of 1-4 have been verified by IR, 1H and 13C NMR spectroscopy as well as elemental analysis. In addition, the solid state structures of 1 and 2·2DMSO, respectively, were determined by single-crystal X-ray diffraction studies. Successive recrystallization of the crude material from MeOH and MeOH : THF (1 : 1), respectively, does not give pure 1, but a mixture of 1 and 2. It is shown further that out of this mixture pure bis(oxamato) complexes cannot be obtained, as previously reported. Instead, treatment of the mixture with NiII or CuII salts, followed by the addition of [nBu4N]OH, results in the formation of two mixtures of [nBu4N]2[Ni(opba)] (5) and [nBu4N]2[Ni(opooMe)] (6) as well as [nBu4N]2[Cu(opba)] (7) and [nBu 4N]2[Cu(opooMe)] (8), respectively. The simultaneous formation of 5/6 and 7/8, respectively, has been verified by crystallization of the obtained mixtures and X-ray diffraction studies of the obtained single crystals. Co-crystallization of mixtures of 5/6 (99 mass%) and 7/8 (1 mass%), respectively, results in the formation of single-crystals of diamagnetically diluted 7 in the host lattice of 5 (7@5) accompanied by single-crystal formation of diamagnetically diluted 8 in the host lattice of 6 (8@6), as verified by EPR spectroscopy. It is finally shown that the ethyl ester of o-phenylene(N?- methyloxamide)(oxamic acid) (opooH3Et, 9), a homologue of 1, can be obtained in pure state by the treatment of opbaH2Et2 with 5/6 of an equivalent of MeNH2 in EtOH. The Royal Society of Chemistry 2013.

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9/23 News Archives for Chemistry Experiments of 15804-19-0

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In continuation of our previous work on the design and synthesis of topoisomerase II (Topo II) inhibitors and DNA intercalators, a new series of quinoxaline derivatives were designed and synthesized. The synthesized compounds were evaluated for their cytotoxic activities against a panel of three cancer cell lines (Hep G-2, Hep-2, and Caco-2). Compounds 18b, 19b, 23, 25b, and 26 showed strong potencies against all tested cell lines with IC50 values ranging from 0.26 ± 0.1 to 2.91 ± 0.1 muM, comparable with those of doxorubicin (IC50 values ranging from 0.65 ± 0.1 to 0.81 ± 0.1 muM). The most active compounds were further evaluated for their Topo II inhibitory activities and DNA intercalating affinities. Compounds 19b and 19c exhibited high activities against Topo II (IC50 = 0.97 ± 0.1 and 1.10 ± 0.1 muM, respectively) and bound the DNA at concentrations of 43.51 ± 2.0 and 49.11 ± 1.8 muM, respectively, whereas compound 28b exhibited a significant affinity to bind the DNA with an IC50 value of 37.06 ± 1.8 muM. Moreover, apoptosis and cell-cycle tests of the most promising compound 19b were carried out. It was found that 19b can significantly induce apoptosis in Hep G-2 cells. It has revealed cell-cycle arrest at the G2/M phase. Moreover, compound 19b downregulated the Bcl-2 levels, indicating its potential to enhance apoptosis. Furthermore, molecular docking studies were carried out against the DNA?Topo II complex to examine the binding patterns of the synthesized compounds.

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Co(II), Ni(II), Cu(II) and Zn(II) mixed ligand complexes have been synthesized from N2, N3-bis(4-nitrophenyl)quinoxaline-2,3-diamine and 1,10-phenanthroline. The compounds were characterized by elemental analyses, molar conductance, magnetic susceptibility, IR, UV-Vis., 1H NMR, mass and ESR spectra. Octahedral geometry has been assigned for Co(II), Ni(II) and Zn(II) complexes and distorted octahedral geometry for Cu(II) complex. Electrochemical behavior of the synthesized complexes was studied using cyclic voltammetry. Grain size and surface morphologies of the complexes were determined by powder XRD and SEM analyses. The mixed ligand metal complexes were screened for antimicrobial activity against bacterial species Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa and Staphylococcus aureus; fungal species Aspergillus niger, and Candida albicans by disc diffusion method. The DNA binding and DNA cleavage activities of the compounds were determined using electronic absorption titration and agarose gel electrophoresis respectively. The superoxide radical scavenging and free radical scavenging activities of the Cu(II) complex was also evaluated. Molecular docking studies of the synthesized mixed ligand metal complexes were carried out against B-DNA dodecamer and the protein Plasmodium falciparum dihydrofolate reductase (pf DHFR).

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