104-03-0Relevant articles and documents
A novel one pot synthesis of o-nitrophenylacetic acid and unexpected p-nitrobenzoic acid by HNO3-mediated CH2 extrusion reaction of phenylacetic acid
Sohail, Muhammad,Raza, Abdul Rauf
, p. 353 - 356 (2012)
The HNO3-mediated CH2 extrusion reactions of phenylacetic acid lead to one pot synthesis of unexpected commercially important product 4-nitrobenzoic acid through the formation of 4-nitrophenylacetic acid and 2-nitrophenylacetic acid. Copyright
The electrochemical behavior of 4-nitrobenzyl bromide and its catalytic activity for reduction of CO2 in the acetonitrile solvent at the Cu/Pd/rGO/GCE surface
Benvidi, Ali,Ghobadi, Kobra,Khoshro, Hossein,Mohammadzadeh, Safoora,Zare, Hamid R.
, (2020)
In this study, 4-nitrobenzyl bromide was used as a catalyst for reduction of CO2 and as an initial substrate for electrosynthesis of 4-nitrophenylacetic acid. Cu nanoparticles/Pd nanoparticles/reduced graphene oxide nanocomposite modified glassy carbon electrode (Cu/Pd/rGO/GCE) was used to promote electroactivation of CO2. rGO film was fabricated via electrochemical reduction of dispersed GO nanosheets on the GCE surface. Cyclic voltammetry procedure was applied in two steps to deposit Pd and Cu nanoparticles on the rGO/GCE surface. The morphology and structure of the nanocomposites were characterized using FESEM, EDS, AFM and XRD analysis. FTIR, 1H and 13C NMR spectral characteristics were used to identify the final products of the catalytic process. The electrocarboxylation of 4-nitrobenzyl bromide occurs at a potential which is less negative than those reported for other aryl halides. The results indicate that 4-nitrobenzyl bromide, as a catalyst, plays a dual role in the electrosynthesis of 4-nitrophenylacetate. The dual role includes the electrocatalytic reduction of CO2 and reaction of produced CO2 ?? with 4-nitrobenzyl bromide radical anion. Finally, an EC'C mechanism is proposed for the electrosynthesis of 4-nitrophenylacetate.
Novel carbazole-stilbene hybrids as multifunctional anti-Alzheimer agents
Chaudhary, Bharat N.,Gandhi, Pallav M.,Joshi, Prashant D.,Kanhed, Ashish M.,Patel, Dushyant V.,Patel, Kirti V.,Patel, Kishan B.,Patel, Nirav R.,Patel, Sagar P.,Prajapati, Navnit K.,Teli, Divya M.,Yadav, Mange Ram
, (2020)
Molecules capable of engaging with multiple targets associated with pathological condition of Alzheimer's disease have proved to be potential anti-Alzheimer's agents. In our goal to develop multitarget-directed ligands for the treatment of Alzheimer's disease, a novel series of carbazole-based stilbene derivatives were designed by the fusion of carbazole ring with stilbene scaffold. The designed compounds were synthesized and evaluated for their anti-AD activities including cholinesterase inhibition, Aβ aggregation inhibition, antioxidant and metal chelation properties. Amongst them, (E)-1-(4-(2-(9-ethyl-9H-carbazol-3-yl)vinyl)phenyl)-3-(2-(pyrrolidin-1-yl)ethyl)thiourea (50) appeared to be the best candidate with good inhibitory activities against AChE (IC50 value of 2.64 μM) and BuChE (IC50 value of 1.29 μM), and significant inhibition of self-mediated Aβ1–42 aggregation (51.29% at 25 μM concentration). The metal chelation study showed that compound (50) possessed specific copper ion chelating property. Additionally, compound (50) exhibited moderate antioxidant activity. To understand the binding mode of 50, molecular docking studies were performed, and the results indicated strong non-covalent interactions of 50 with the enzymes in the active sites of AChE, BuChE as well as of the Aβ1-42 peptide. Additionally, it showed promising in silico ADMET properties. Putting together, these findings evidently showed compound (50) as a potential multitarget-directed ligand in the course of developing novel anti-AD drugs.
Substituted 9-Diethylaminobenzo[ a]phenoxazin-5-ones (Nile Red Analogues): Synthesis and Photophysical Properties
Hornum, Mick,Mulberg, Mads W.,Szomek, Maria,Reinholdt, Peter,Brewer, Jonathan R.,Wüstner, Daniel,Kongsted, Jacob,Nielsen, Poul
, p. 1471 - 1488 (2021)
Nile Red is a benzo[a]phenoxazone dye containing a diethylamino substituent at the 9-position. In recent years, it has become a popular histological stain for cellular membranes and lipid droplets due to its unrivaled fluorescent properties in lipophilic environments. This makes it an attractive lead for chemical decoration to tweak its attributes and optimize it for more specialized microscopy techniques, e.g., fluorescence lifetime imaging or two-photon excited fluorescence microscopy, to which Nile Red has never been optimized. Herein, we present synthesis approaches to a series of monosubstituted Nile Red derivatives (9-diethylbenzo[a]phenoxazin-5-ones) starting from 1-naphthols or 1,3-naphthalenediols. The solvatochromic responsiveness of these fluorophores is reported with focus on how the substituents affect the absorption and emission spectra, luminosity, fluorescence lifetimes, and two-photon absorptivity. Several of the analogues emerge as strong candidates for reporting the polarity of their local environment. Specifically, the one- and two-photon excited fluorescence of Nile Red turns out to be very responsive to substitution, and the spectroscopic features can be finely tuned by judiciously introducing substituents of distinct electronic character at specific positions. This new toolkit of 9-diethylbenzo[a]phenoxazine-5-ones constitutes a step toward the next generation of optical molecular probes for advancing the understanding of lipid structures and cellular processes.
Synthesis, optical and nonlinear optical properties of new pyrazoline derivatives
Mysliwiec,Szukalski,Sznitko,Miniewicz,Haupa,Zygadlo,Matczyszyn,Olesiak-Banska,Samoc
, p. 63 - 70 (2014)
We report on synthesis and optical properties of new organic compounds based on substituted pyrazole ring. The investigated pyrazoline derivatives (PRDs) exhibit efficient broadband photoluminescence which covers nearly whole visible spectrum. The experimental results are compared to quantum chemical calculations. Amplified spontaneous emission and photodegradation measurements were performed for hybrid systems based on selected PRDs doped into poly(methyl methacrylate) matrix proving the potential utility of such systems in lasing applications. Two-photon absorption (TPA) properties were characterized by the femtosecond Z-scan technique.
Regio- and chemoselective enzymatic N-oxygenation in vivo, in vitro, and in flow
Winkler, Robert,Richter, Martin E. A.,Knuepfer, Uwe,Merten, Dirk,Hertweck, Christian
, p. 8016 - 8018 (2006)
(Chemical Equation Presented) Action by the para: Evaluation of the nitro-group-forming N-oxygenase AurF in vivo, in vitro, and immobilized as a fusion protein with simply H2O2 as oxidant (peroxide shunt) reveals para-regioselective oxygenation of aromatic amines (see scheme). This effect includes the selective oxygenation of diamino compounds.
Design, synthesis and biological evaluation of novel sesquiterpene mustards as potential anticancer agents
Xu, Yuan-Zhen,Gu, Xue-Yan,Peng, Shou-Jiao,Fang, Jian-Guo,Zhang, Ying-Mei,Huang, De-Jun,Chen, Jian-Jun,Gao, Kun
, p. 284 - 297 (2015)
Several novel series of sesquiterpene mustards (SMs) bearing nitrogen mustard and glutathione (GSH)-reactive α-methylene-γ-butyrolactone groups were successfully prepared for the first time and showed excellent antiproliferative activities in vitro. Among them, compounds 2e and 2g displayed the highest antiproliferative properties with IC50 values ranging from 2.5 to 8.7 μM. The selectivity of these two compounds was evaluated by SRB method against human cancer and normal hepatic cells (HepG2 and L02). The induction of apoptosis and effects on the cell cycle distribution with compounds 2e and 2g were investigated by Hoechst 33,258 staining and flow cytometry, which exhibited that they could induce selective cell apoptosis and cell cycle arrest in HepG2 and L02 cells. In addition, further investigation showed that compounds 2e and 2g could obviously inhibit the proliferation of HepG2 cells by inducing significant DNA cross-linking and depleting GSH in cell media. The good cytotoxicity and selectivity of compounds 2e and 2g pointed them as promising leads for anticancer drug design.
Pd(OH)2/C, a Practical and Efficient Catalyst for the Carboxylation of Benzylic Bromides with Carbon Monoxide
Wakuluk-Machado, Anne-Marie,Dewez, Damien F.,Baguia, Hajar,Imbratta, Miguel,Echeverria, Pierre-Georges,Evano, Gwilherm
, p. 713 - 723 (2020/02/04)
A simple, efficient, cheap, and broadly applicable system for the carboxylation of benzylic bromides with carbon monoxide and water is reported. Upon simple reaction with only 2.5 wt % of Pearlman's catalyst and 10 mol % of tetrabutylammonium bromide in tetrahydrofuran at 110 °C for 4 h, a range of benzylic bromides can be smoothly converted to the corresponding arylacetic acids in good to excellent yields after simple extraction and acid-base wash. The reaction was found to be broadly applicable, scalable, and could be successfully extended to the use of ex situ-generated carbon monoxide and applied to the synthesis of the nonsteroidal anti-inflammatory drug diclofenac.
Preparation method of phenylacetic acid type compound
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Paragraph 0113; 0114; 0115, (2019/02/21)
The invention discloses a preparation method of a phenylacetic acid type compound. The preparation method of the phenylacetic acid type compound I comprises the following steps that in a solvent and aCO gas phase system, a benzyl halide type compound II, pyridine-2-cobalt carboxylate, palladium acetate and alkaline neutralizers take carbonylation reaction to obtain the phenylacetic acid type compound I. A mixed catalytic system has a synergistic effect; the whole use quantity of catalysts is greatly reduced. When the mixed catalyst is used, a better catalytic effect can be achieved; the characteristics of easily obtaining the catalyst, avoiding the production safety risk of toxic three wastes and the like, reducing the reaction pressure, realizing mild reaction conditions, reducing the production risk, facilitating the production and the like are realized. The formulas are shown in description.
Preparation method of methyl p-aminophenylacetate
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, (2019/01/14)
An embodiment of the invention provides a preparation method of methyl p-aminophenylacetate and relates to the field of chemical synthesis. According to the preparation method, benzyl cyanide is adopted as a starting material and subjected to nitration, hydrolysis, esterification, reduction and other steps in sequence, and methyl p-aminophenylacetate is obtained with high yield. The preparation method adopts a reasonable route, is simple to operate, does not have quite high requirement for equipment and is suitable for large-scale industrial production, and the raw material is widely sourced.
