2379-55-7Relevant articles and documents
Optimisation of conoidin A, a peroxiredoxin inhibitor
Liu, Gu,Botting, Catherine H.,Evans, Kathryn M.,Walton, Jeffrey A. G.,Xu, Guogang,Slawin, Alexandra M. Z.,Westwood, Nicholas J.
, p. 41 - 45 (2010)
Lead optimisation: Interest in the inhibition of peroxiredoxin has been revitalised by their recently identified role in signalling cascades. Here, the synthesis and analysis of novel analogues of the peroxiredoxin inhibitor conoidin A is described. Computational methods are used to rationalise the generated SAR data. These studies lead to a proposed binding mode for this class of compounds that will aid the design of second generation inhibitors. (Figure Presented)
Isolation and determination of α-dicarbonyl compounds by RP-HPLC-DAD in green and roasted coffee
Daglia, Maria,Papetti, Adele,Aceti, Camilla,Sordelli, Barbara,Spini, Valentina,Gazzani, Gabriella
, p. 8877 - 8882 (2007)
Glyoxal, methylglyoxal, and diacetyl formed as Maillard reaction products in heat-treated food were determined in coffee extracts (coffee brews) obtained from green beans and beans with different degrees of roast. The compounds have been reported to be mutagenic in vitro and genotoxic in experimental animals in a number of papers. More recently, α-dicarbonyl compounds have been implicated in the glycation process. Our data show that small amounts of glyoxal and methylglyoxal occur naturally in green coffee beans. Their concentrations increase in the early phases of the roasting process and then decline. Conversely, diacetyl is not found in green beans and forms later in the roasting process. Therefore, light and medium roasted coffees had the highest glyoxal and methylglyoxal content, whereas dark roasted coffee contained smaller amounts of glyoxal, methylglyoxal, and diacetyl. For the determination of coffee α-dicarbonyl compounds, a reversed-phase high performance liquid chromatography with a diode array detector (RP-HPLC-DAD) method was devised that involved the elimination of interfering compounds, such as chlorogenic acids, by solid phase extraction (SPE) and their derivatization with 1,2-diaminobenzene to give quinoxaline derivatives. Checks of SPE and derivatization conditions to verify recovery and yield, respectively, resulted in rates of 100%. The results of the validation procedure showed that the proposed method is selective, precise, accurate, and sensitive.
POTENTIAL ALARM PHEROMONES FROM THE MEDITERRANEAN OPISTHOBRANCH SCAPHANDER LIGNARIUS
Cimino, G.,Spinella, A.,Sodano, G.
, p. 5003 - 5004 (1989)
Two new ω-phenyl conjugated trienones, lignarenone-A (2) and lignarenone-B (3), are the main metabolites isolated from the dorsum acetone extract of Scaphander lignarius.Their structures, closely related to 3-methyl navenone-B (1) a minor component of the alarm pheromone mixture of the opisthobranch Navanax inermis, were characterized by spectral methods.
-
Wasa,Musha
, p. 1617,1618 (1967)
-
In water organic synthesis: Introducing itaconic acid as a recyclable acidic promoter for efficient and scalable synthesis of quinoxaline derivatives at room temperature
Tamuli, Kashyap J.,Nath, Shyamalendu,Bordoloi, Manobjyoti
supporting information, p. 983 - 1002 (2021/02/27)
Substituted quinoxaline derivatives are traditionally synthesized by co-condensation of various starting materials. Herein, we describe a novel environmentally benign in water synthetic route for the synthesis of structurally and electronically diverse ninety quinoxalines with readily available substituted o-phenylenediamine and 1,2-diketones using cheap and biodegradable itaconic acid as a mild acid promotor in 1 hours. The reaction is performed at room temperature, which proceeds through cyclo-condensation reaction followed by obtaining the aforesaid nitrogen-containing heterocyclic adducts without performing the column chromatography up to 96% total yields. The simplicity, high efficiency, and reusable of the catalyst merits this reaction condition as “green synthesis” which enables it to be useful in synthetic transformations upto gram scale level.
Decarboxylation of Aromatic Carboxylic Acids by the Prenylated-FMN-dependent Enzyme Phenazine-1-carboxylic Acid Decarboxylase
Datar, Prathamesh M.,Marsh, E. Neil G.
, p. 11723 - 11732 (2021/09/28)
Phenazine-1-carboxylic acid decarboxylase (PhdA) is a member of the expanding class of prenylated-FMN-dependent (prFMN) decarboxylase enzymes. These enzymes have attracted interest for their ability to catalyze (de)carboxylation reactions on aromatic rings and conjugated double bonds. Here we describe a method to reconstitute PhdA with prFMN that produces an active and stable form of the holo-enzyme that does not require prereduction with dithionite for activity. We establish that oxidized phenazine-1-carboxylate (PCA) is the substrate for decarboxylation, withkcat= 2.6 s-1andKM= 53 μM. PhdA also catalyzes the much slower exchange of solvent deuterium into the product, phenazine, with an apparent turnover number of 0.8 min-1. The enzyme was found to catalyze the decarboxylation of a broad range of polyaromatic carboxylic acids, including anthracene-1-carboxylic acid. Previously described prFMN-dependent aromatic (de)carboxylases have utilized electron-rich phenolic or heterocyclic molecules as substrates. PhdA extends the substrate range of prFMN-dependent (de)carboxylases to electron-poor and unfunctionalized aromatic systems, suggesting that it may prove a useful catalyst for the regioselective (de)carboxylation of otherwise unreactive aromatic molecules.
Acceptorless dehydrogenative condensation: synthesis of indoles and quinolines from diols and anilines
Bellezza, Delia,Zaragozá, Ramón J.,José Aurell,Ballesteros, Rafael,Ballesteros-Garrido, Rafael
supporting information, p. 677 - 683 (2021/02/06)
The use of diols and anilines as reagents for the preparation of indoles represents a challenge in organic synthesis. By means of acceptorless dehydrogenative condensation, heterocycles, such as indoles, can be obtained. Herein we present an experimental and theoretical study for this purpose employing heterogeneous catalysts Pt/Al2O3and ZnO in combination with an acid catalyst (p-TSA) and NMP as solvent. Under our optimized conditions, the diol excess has been reduced down to 2 equivalents. This represents a major advance, and allows the use of other diols. 2,3-Butanediol or 1,2-cyclohexanediol has been employed affording 2,3-dimethyl indoles and tetrahydrocarbazoles. In addition, 1,3-propanediol has been employed to prepare quinolines or natural and synthetic julolidines.
