587-48-4Relevant academic research and scientific papers
CONJUGATED PROTEINS AND USES THEREOF
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Paragraph 0387; 0404-0405, (2020/09/16)
Disclosed herein, in certain embodiments, are protein-probe adducts and synthetic ligands that inhibit protein-probe adduct formation, in which the proteins are regulated by NRF2. In some instances, also described herein are protein-binding domains that interact with a probe and/or a ligand described herein, in which the proteins are regulated by NRF2.
Synthesis of acetamides via oxidative C–C bond cleavage of ketones catalyzed by Cu-immobilized magnetic nanoparticles
Yazdani, Elahe,Pazoki, Farzane,Salamatmanesh, Arefe,Nejad, Masoume Jadidi,Miraki, Maryam Kazemi,Heydari, Akbar
, (2020/07/27)
Copper supported on magnetite nanoparticles modified with environmentally friendly ligand tricine was devised for synthesis of acetamides via C–C oxidative cleavage of ketones with amines. The catalyst was characterized using different techniques, including Fourier transform infrared, X-ray diffraction, scannin electron microscopy, vibrating sample magnetometry, thermogravimetric analysis, and energy dispersive x-ray spectroscopy. The protocol showed relatively high yields of acetamide products. Furthermore, the magnetic recovery of the catalyst rendered the overall process fast and efficient. It was used in the reaction for six consecutive cycles with negligible loss of catalytic activity. This research is the first report of application of magnetic nanocatalysts for synthesis of acetamides from ketones of low activity through a C–C bond cleavage strategy.
A magnetically recoverable copper–salen complex as a nano-catalytic system for amine protection via acetylation using thioacetic acid
Yazdani, Elahe,Kazemi Miraki, Maryam,Salamatmanesh, Arefe,Azarnia, Jamshid,Azizi, Kobra,Ghandi, Leila,Heydari, Akbar
, p. 1775 - 1793 (2019/01/16)
A novel copper(II)–salen complex was immobilized on the surface of magnetite nanoparticles using chitosan as a linker. This system exhibits superior catalytic activity in acetyl protection of various amines with thioacetic acid as the acetylating reagent. The method has advantages over others in high selectivity, simple work-up, green reaction medium and the application of an easily recoverable heterogeneous catalyst.
Mild and eco-friendly chemoselective acylation of amines in aqueous medium using a green, superparamagnetic, recoverable nanocatalyst
Miraki, Maryam Kazemi,Yazdani, Elahe,Ghandi, Leila,Azizi, Kobra,Heydari, Akbar
, (2017/09/30)
Copper-grafted guanidine acetic acid-modified magnetite nanoparticles (Fe3O4@GAA-Cu(II)) as a green, superparamagnetic and recoverable nanocatalyst is found to promote quantitative N-acylation of various amines in a very short time with an equimolar amount of thioacetic acid in water at room temperature. This method is found to be highly selective for amines and not sensitive to other functional groups. Mild reaction condition, high selectivity, efficiency, simple workup and excellent yields are some of the major advantages of the procedure.
Scalable synthesis of 8-amino-3-hydroxy-6 H -benzo[ c ]chromen-6-one: Key intermediate for SEGRA via the Hurtley reaction
Kudo, Kazuhiro,Yamamoto, Noriyoshi
, p. 309 - 314 (2015/01/30)
A practical and scalable process for the preparation of 8-amino-3-hydroxy-6H-benzo[c]chromen-6-one in multihundred kilogram amounts has been developed. The key features of this synthesis are the application of the Hurtley reaction with a copper and base combination and the development of a purification process. The new synthesis improved the total yield from 49.0% to 59.5% and reduced the number of steps from three to two. Compared with the conventional medicinal route, manufacturing costs were reduced significantly by the use of inexpensive, easy to procure materials.
Kinetics and mechanism of the oxidation of substituted benzaldehydes with bis(pyridine)silver permanganate
Purohit, Trupti,Banerji, Jayshree,Kotai, Laszlo,Sajo,Banerji,Sharma, Pradeep K.
, p. 1045 - 1052 (2013/01/14)
The oxidation of thirty-six ortho-, meta- and para-substituted benzaldehydes by bis(pyridine)silver permanganate (BPSP) resulted in the formation of the corresponding benzoic acids. The reaction is first order with respect to both BPSP and aldehydes. The reaction is catalyzed by hydrogen ions. The rate of reaction increases with an increase in the amount of acetic acid in the solvent. The correlation analyses of the rate of oxidation of thirty-six aldehydes were performed in terms of Charton's LDR and LDRS equations. The rate of oxidation of meta- and para-substituted benzaldehydes showed excellent correlation with Charton's LDR equation. The rates of ortho-compounds showed excellent correlation with LDRS equation. The oxidation para-compounds is more susceptible to the delocalization effect. The oxidation of ortho- and meta-compounds exhibited a greater dependence on the field effect. The polar reaction constants are negative indicating an electron-deficient centre in the rate-determining step. A mechanism involving a nucleophilic attack on the carbonyl group by a permanganate-oxygen and a subsequent hydride transfer has been proposed.
"Meta elimination," a diagnostic fragmentation in mass spectrometry
Attygalle, Athula B.,Nishshanka, Upul,Weisbecker, Carl S.
experimental part, p. 1515 - 1525 (2012/05/05)
The diagnostic value of the "ortho effect" for unknown identification by mass spectrometry is well known. Here, we report the existence of a novel "meta effect," which adds to the repertoire of useful mass spectrometric fragmentation mechanisms. For example, the meta-specific elimination pathway described in this report enables unequivocal identification of meta isomers from ortho and para isomers of carboxyanilides. The reaction follows a specific path to eliminate a molecule of meta-benzyne, from the anion produced after the initial decarboxylation of the precursor. Consequently, in the CID spectra of carboxyanilides, a peak for the (R-CO-NH)- anion is observed only for the meta isomers. For example, the peaks observed at m/z 58, 86, 120, 128, and 170 from acetamido-, butamido-, benzamido, heptamido-, and decanamido-benzoates, respectively, were specific only to the spectra of meta isomers.
Structure-Reactivity correlation in the oxidation of substituted benzaldehydes by tetraethylammonium chlorochromate
Gehlot,Prasadrao,Sharma
experimental part, p. 1173 - 1178 (2012/01/05)
Oxidation of 36 monosubstituted benzaldehydes by tetraethylammonium chlorochromate in dimethyl sulphoxide, leads to the formation of corresponding benzoic acids. The reaction is of first order with respect to chlorochromate and aldehydes. The reaction is promoted by H+; the H+ dependence has the form kobs = a + b[H+]. The oxidation of duteriated benzaldehyde exhibits substantial primary kinetic isotope effect. The reaction was studied in 19 different organic solvents and the effect of solvent was analyzed using Taft's and Swain's multiparametric equations. The rates of the oxidation of para- and meta-substituted benzaldehydes showed excellent correlation in terms of Charton's triparametric LDR equation, whereas the oxidation of ortho-substituted benzaldehydes were correlated well with tetraperametric LDRS equation. The oxidation of para-substituted benzaldehydes is more susceptible to the delocalized effect than is the oxidation of ortho- and meta- substituted compounds, which display a greater dependence on the field effect. The positive value of h suggests the presence of an electron-deficient reaction centre in the rate-determining step. The reaction is subjected to steric acceleration by the orthosubstituents. A suitable mechanism has been proposed.
Synthesis and SAR of 2-aryl-3-aminomethylquinolines as agonists of the bile acid receptor TGR5
Herbert, Mark R.,Siegel, Dana L.,Staszewski, Lena,Cayanan, Charmagne,Banerjee, Urmi,Dhamija, Sangeeta,Anderson, Jennifer,Fan, Amy,Wang, Li,Rix, Peter,Shiau, Andrew K.,Rao, Tadimeti S.,Noble, Stewart A.,Heyman, Richard A.,Bischoff, Eric,Guha, Mausumee,Kabakibi, Ayman,Pinkerton, Anthony B.
scheme or table, p. 5718 - 5721 (2010/11/05)
Optimization of a screening hit from uHTS led to the discovery of TGR5 agonist 32, which was shown to have activity in a rodent model for diabetes.
Kinetics and products of the catalytic oxidation of acetamidotoluenes with ozone in acetic acid
Galstyan,Bushuev,Sementsov
experimental part, p. 516 - 520 (2011/01/07)
The kinetics of acetamidotoluene oxidation in glacial acetic acid in the presence of cobalt acetate is reported. At 95°C and atmospheric pressure, acetamidotoluenes are oxidized by molecular oxygen very slowly: oxidation is complete in 10-12 h, and the major reaction products are acetamidobenzoic acids (27-36% yield). The introduction of ozone into the reactive gas increases the reaction rate by one order of magnitude. The main role of ozone is to generate the active form of the catalyst.
