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Enantioselective copper-catalyzed reductive coupling of alkenylazaarenes with ketones

Catalytic enantioselective methods for the preparation of chiral azaarene-containing compounds are of high value. By combining the utility of copper hydride catalysis with the ability of C=N-containing azaarenes to activate adjacent alkenes toward nucleophilic additions, the enantioselective reductive coupling of alkenylazaarenes with ketones has been developed. The process is tolerant of a wide variety of azaarenes and ketones, and provides aromatic heterocycles bearing tertiary-alcohol-containing side chains with high levels of diastereo- and enantioselection.

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Quinoxaline – Wikipedia,
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Recent advances in the synthesis of benzimidazol(on)es: Via rearrangements of quinoxalin(on)es

This is the first review describing all the quinoxaline-benzimidazole rearrangements as a whole and the new quinoxalinone-benzimidazol(on)e rearrangements in particular when exposed to nucleophilic rearrangements for the synthesis of various biheterocyclic motifs. The scope of the rearrangements is illustrated by way of numerous examples of their application, and in doing so, the review contains over 131 references and covers all of the literature, from the first report of the rearrangement of 2,3-diphenylquinoxaline by Ogg and Bergstrom in 1931 up to more recent examples in the past few years. The mechanisms for the selected transformations are also discussed.

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Synthesis of 1,3-dithiol-2-ones as proligands related to molybdopterin

The reaction of suitably disubstituted alkynes with diisopropyl xanthogen disulfide gives differentially substituted 4,5-disubstituted-1,3-dithiol-2-ones as proligands for metal complexes related to the molybdenum cofactor.

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AWTHRANILIC ACID DERIVATIVES AND THEIR USE IN TREATMENT OF DISEASES OF LIPID METABOLISM, IN PARTICULAR DYSLIPIDAEMIA

Therapeutically active anthranilic acid derivatives of Formula (I) wherein R1, R2, W, Y and Z are as defined in the specification, processes for the preparation of said derivatives, pharmaceutical formulations containing the active compounds and the use of the compounds in therapy, particularly in the treatment of diseases in which under-activation of the HM74A receptor contributes to the disease or in which activation of the receptor will be beneficial, are disclosed.

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A segmented flow platform for on-demand medicinal chemistry and compound synthesis in oscillating droplets

We report an automated flow chemistry platform that can efficiently perform a wide range of chemistries, including single/multi-phase and single/multi-step, with a reaction volume of just 14 muL. The breadth of compatible chemistries is successfully demonstrated and the desired products are characterized, isolated, and collected online by preparative HPLC/MS/ELSD.

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Development of second-generation small-molecule RhoA inhibitors with enhanced water solubility, tissue potency, and significant in vivo efficacy

RhoA, a member of the Rho GTPases, is involved in a variety of cellular functions and could be a suitable therapeutic target for the treatment of cardiovascular diseases. However, few small-molecule RhoA inhibitors have been reported. Based on our previously reported lead compounds, 32 new 2-substituted quinoline (or quinoxaline) derivatives were synthesized and tested in biological assays. Six compounds showed high RhoA inhibitory activities, with IC50 values of 1.17-1.84 muM. Among these, (E)-3-(3-(ethyl(quinolin-2-yl)amino)phenyl)acrylic acid (26b) and (E)-3-(3-(butyl(quinolin-2-yl)amino)phenyl)acrylic acid (26d) demonstrated noticeable vasorelaxation effects against phenylephrine-induced contraction in thoracic aorta artery rings, and compound 26b had good water solubility and showed significant in vivo efficacy, which was similar to that of 5-(1,4-diazepane-1-sulfonyl)isoquinoline (fasudil) in a subarachnoid hemorrhage-cardiovascular model. To the best of our knowledge, compound 26b is the first example of a small-molecule RhoA inhibitor with potent in vivo efficacy, which could serve as a good lead for designing cardiovascular agents.

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Quinoxaline – Wikipedia,
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Antimicrobial evaluation and action mechanism of chalcone derivatives containing quinoxaline moiety

Abstract: A series of chalcone derivatives containing quinoxaline moieties were synthesized, and their antibacterial activities were evaluated. Antibacterial bioassays indicated that some of the compounds exhibited significant antibacterial activity against Xanthomonas axonopodis pv. Citri (Xac), Xanthomonas oryzae pv. oryzae (Xoo), and Ralstonia solanacearum (Rs) at the concentrations of 50 or 100 mug/cm3. 50% effective concentration (EC50) values of (E)-3-(pyridin-2-yl)-1-[4-(quinoxalin-2-yloxy)phenyl]prop-2-en-1-one against Xac, Xoo, and Rs were 6.72, 15.17, and 9.29 mug/cm3, respectively, which were better than those of bismerthiazol (44.31, 42.46, and 62.36 mug/cm3, respectively). Scanning electron microscopy (SEM) was employed to analyze the mechanism of antibacterial action of that compound toward Xac. Graphical abstract: [Figure not available: see fulltext.].

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Application of 1448-87-9, Catalysts function by providing an alternate reaction mechanism that has a lower activation energy than would be found in the absence of the catalyst. In some cases, the catalyzed mechanism may include additional steps.In a article, 1448-87-9, molcular formula is C8H5ClN2, introducing its new discovery.

Mild and general conditions for Negishi cross-coupling enabled by the use of palladacycle precatalysts

A wide range of biaryls were synthesized by palladium-catalyzed Negishi cross-couplings at ambient temperature or with low catalyst loading. This protocol features the use of a recently reported aminobiphenyl palladacycle precatalyst to generate the catalytically active XPhosPd0 species. Significantly, a wide range of challenging heterocyclic and polyfluorinated aromatic substrates can be employed to give products in excellent yields. Copyright

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Quinoxaline – Wikipedia,
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Direct alkylation of heteroaryls using potassium alkyl- and alkoxymethyltrifluoroborates

A direct alkylation of various heteroaryls using stoichiometric potassium alkyl- and alkoxymethyltrifluoroborates has been developed. This method leads to the synthesis of complex substituted heterocycles, which have been obtained with yields up to 89%.

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Synthesis, antiviral and antibacterial activities and action mechanism of penta-1,4-dien-3-one oxime ether derivatives containing a quinoxaline moiety

A series of penta-1,4-dien-3-one oxime ether derivatives containing a quinoxaline moiety were synthesized and their antibacterial and antiviral activities were evaluated. Bioassay activity indicated that some of the compounds displayed significant antibacterial and antiviral activities. In particular, some title compounds were found to show remarkable antiviral activities against tobacco mosaic virus (TMV). Compound 6i showed remarkable curative, protective and inactivation activity against TMV, with a 50% effective concentration (EC50) of 287.1, 157.6 and 133.0 mug mL-1, respectively. These results were better than or comparable to those of ningnanmycin (356.3, 233.7 and 121.6 mug mL-1, respectively). Microscale thermophoresis (MST) also showed that the binding of compound 6i to TMV coat protein (TMV-CP) gave a Kd value of 0.115 ± 0.092 mumol L-1, which was better than that of ningnanmycin (0.523 ± 0.254 mumol L-1). Meanwhile, the EC50 values of compound 6k against Xanthomonas axonopodis pv. Citri (Xac) and Xanthomonas oryzae pv. oryzae (Xoo) were 16.8 and 33.4 mug mL-1 respectively, and that of compound 6i against Ralstonia solanacearum (Rs) was 33.9 mug mL-1. These results were better than those of bismerthiazol (44.3, 42.5 and 62.4 mug mL-1, respectively). The mechanism of antibacterial action of compound 6k against Xac was analysed through scanning electron microscopy (SEM). This study indicated that the title compounds are valuable in the search for novel agrochemicals.

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Quinoxaline – Wikipedia,
Quinoxaline | C8H6N721 | ChemSpider