29753-26-2Relevant articles and documents
Binding of filamentous actin and winding into fibrillar aggregates by the polyphenolic C-glucosidic ellagitannin vescalagin
Quideau, Stephane,Douat-Casassus, Celine,Delannoy Lopez, Daniela Melanie,Di Primo, Carmelo,Chassaing, Stefan,Jacquet, Remi,Saltel, Frederic,Genot, Elisabeth
, p. 5099 - 5104 (2011)
Winding it up: The plant polyphenolic metabolite vescalagin fulfills all the requirements for use as an antiactin agent in cellular biological investigations. Despite its high hydrophilicity, it rapidly enters cells and disturbs the organization of the actin cytoskeleton in a dose-dependent reversible manner by binding fibrillar actin and forcing the actin filaments (left) to wind themselves into ball-like fibrillar aggregates (right). Copyright
Microwave-Assisted Synthesis of N-Substituted Maleimide Derivatives as Exogenous Antioxidant Agents
Rammohan, Aluru,Mallikarjuna Reddy, Guda,Raul Garcia, Jarem,Zyryanov, Grigory V.,Sravya, Gundala,Bakthavatchala Reddy, Nemallapudi,Yuvaraja, Gutha
, p. 470 - 476 (2019)
A series of N-substituted maleimide derivatives have been developed via acetic acid-mediated microwave reaction pathway, which was identified as the incomparable method for this maleimide compounds. All the synthesized compounds were tested for antioxidant activity by DPPH and H2O2 methods. Compounds 5h and 5m were displayed with higher antioxidant activity in two methods. The structure–activity relationship demonstrated that the compounds having electron releasing substitutions 5h and 5m generally show beneficial activity than electron capture substitution cores. Thus, compounds 5h and 5m may be useful as an exogenous antioxidant.
Design, synthesis and biochemical evaluation of novel ethanoanthracenes and related compounds to target burkitt’s lymphoma
Byrne, Andrew J.,Bright, Sandra A.,McKeown, James P.,O’brien, John E.,Twamley, Brendan,Fayne, Darren,Williams, D. Clive,Meegan, Mary J.
, (2020/01/31)
Lymphomas (cancers of the lymphatic system) account for 12% of malignant diseases worldwide. Burkitt’s lymphoma (BL) is a rare form of non-Hodgkin’s lymphoma in which the cancer starts in the immune B-cells. We report the synthesis and preliminary studies on the antiproliferative activity of a library of 9,10-dihydro-9,10-ethanoanthracene based compounds structurally related to the antidepressant drug maprotiline against BL cell lines MUTU-1 and DG- 75. Structural modifications were achieved by Diels-Alder reaction of the core 9-(2- nitrovinyl)anthracene with number of dienophiles including maleic anhydride, maleimides, acrylonitrile and benzyne. The antiproliferative activity of these compounds was evaluated in BL cell lines EBV? MUTU-1 and EBV+ DG-75 (chemoresistant). The most potent compounds 13j, 15, 16a, 16b, 16c, 16d and 19a displayed IC50 values in the range 0.17–0.38 μM against the BL cell line EBV? MUTU-1 and IC50 values in the range 0.45–0.78 μM against the chemoresistant BL cell line EBV+ DG- 75. Compounds 15, 16b and 16c demonstrated potent ROS dependent apoptotic effects on the BL cell lines which were superior to the control drug taxol and showed minimal cytotoxicity to peripheral blood mononuclear cells (PBMCs). The results suggest that this class of compounds merits further investigation as antiproliferative agents for BL.
Production method of maleimide biphenol-type benzoxazine monomer
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Paragraph 0050-0051; 0054-0055; 0058-0059; 0062-0063; 0066-, (2020/01/12)
The invention provides a production method of a maleimide biphenol-type benzoxazine monomer, and belongs to the technical field of organic synthesis. The provided production method of the maleimide biphenol-type benzoxazine monomer comprises the following steps: in a protective atmosphere, mixing N-(4-nitrophenyl)maleimide, a catalyst and hydrochloric acid, and carrying out a catalytic reduction reaction to obtain N-(4-aminophenyl)maleimide; in the protective atmosphere, mixing the N-(4-aminophenyl)maleimide and a first solvent, adding an obtained N-(4-aminophenyl)maleimide solution into formaldehyde dropwise, and carrying out a cyclization reaction to obtain a triazine compound; and in the protective atmosphere, mixing the triazine compound, paraformaldehyde, biphenol and a second solvent, and carrying out a substitution reaction to obtain the maleimide biphenol-type benzoxazine monomer. The provided production method is high in product yield, high in product purity, and suitable forindustrial production.
Chemoselective Hydrogenation of Nitroarenes Catalyzed by Molybdenum Sulphide Clusters
Pedrajas, Elena,Sorribes, Iván,Gushchin, Artem L.,Laricheva, Yuliya A.,Junge, Kathrin,Beller, Matthias,Llusar, Rosa
, p. 1128 - 1134 (2017/03/27)
Herein, we describe an atom efficient and general protocol for the chemoselective hydrogenation of nitroarenes to anilines catalyzed by well-defined diimino and diamino cubane-type Mo3S4 clusters. The novel diimino [Mo3S4Cl3(dnbpy)3]+ ([5]+) (dnbpy=4,4′-dinonyl-2,2′-dipyridyl, L1) trinuclear complex was synthesized in high yields by simple ligand substitution reactions starting from the thiourea (tu) [Mo3S4(tu)8(H2O)]Cl4?4 H2O (3) precursor. This strategy has also been successfully adapted for the isolation of the diamino [Mo3S4Cl3(dmen)3](BF4) ([6](BF4)), (dmen=N,N′-dimethylethylenediamine) salt. Applying these catalysts, high selectivity in the hydrogenation of functionalized nitroarenes has been accomplished. Over thirty anilines bearing synthetically functional groups have been synthesized in 70 to 99 % yield. Notably, the integrity of the cluster core is preserved during catalysis. Based on kinetic studies on the hydrogenation of nitrobenzene and other potential reaction intermediates, the direct reduction to aniline is the preferential route.
Highly selective transfer hydrogenation of functionalised nitroarenes using cobalt-based nanocatalysts
Jagadeesh, Rajenahally V.,Banerjee, Debasis,Arockiam, Percia Beatrice,Junge, Henrik,Junge, Kathrin,Pohl, Marga-Martina,Radnik, J?rg,Brückner, Angelika,Beller, Matthias
supporting information, p. 898 - 902 (2015/03/04)
Anilines are important feedstock for the synthesis of a variety of chemicals such as dyes, pigments, pharmaceuticals and agrochemicals. The chemoselective catalytic reduction of nitro compounds represents the most important and prevalent process for the manufacture of functionalized anilines. Consequently, the development of selective catalysts for the reduction of nitro compounds in the presence of other reducible groups is a major challenge and is crucial. In this regard, herein we show that the cobalt oxide (Co3O4-NGr@C) based nano-materials, prepared by the pyrolysis of cobalt-phenanthroline complexes on carbon constitute highly selective catalysts for the transfer hydrogenation of nitroarenes to anilines using formic acid as a hydrogen source. Applying these catalysts, a series of structurally diverse and functionalized nitroarenes have been reduced to anilines with unprecedented chemo-selectivity tolerating halides, olefins, aldehyde, ketone, ester, amide and nitrile functionalities.
Solvent-free synthesis of arylamides and arylimides, analogues of acetylcholine
Trujillo-Ferrara,Correa-Basurto, Jose,Espinosa, Judith,Garcia, Jazmin,Martinez, Francisco,Miranda, Rene
, p. 2017 - 2023 (2007/10/03)
Several arylamides and arylimides, novel inhibitors of acetylcholinesterase, were obtained under solventless conditions; the target molecules were produced with a good overall yield and short reaction times. 2017-2023 Copyright Taylor & Francis, Inc.
NEW EFFECTOR CONJUGATES, PROCESS FOR THEIR PRODUCTION AND THEIR PHARMACEUTICAL USE
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Page/Page column 47, (2010/02/06)
Conjugates of epothilones and epothilone derivatives (as effectors) with suitable biomolecules (as recognition units) are described. Their production is carried out by the effectors being reacted with suitable linkers, and the compounds that are produced are conjugated to the recognition units. The pharmaceutical use of the conjugates for treating proliferative or angiogenesis-associated processes is described.
Selectivity control by chemical modification of the recognition sites in two-point binding molecularly imprinted polymer
Lee, Kangwon,Ki, Chang Do,Kim, Hasuck,Chang, Ji Young
, p. 5544 - 5549 (2007/10/03)
We demonstrated the possibility of modifying the selectivity of a two-point binding imprinted polymer by chemical modification of the binding sites inside the cavities. We used a thermally reversible bond for the preparation of the monomer-template complex, which allowed us to remove the template easily by means of a simple thermal reaction and to simultaneously introduce various functional groups into the cavity. A phenylmaleimide having an azidocarbonyl group was reacted with diethylstilbestrol (DES, template) to yield a monomer, where the template was linked to two polymerizable maleimido groups via a thermally reversible urethane bond. The polymerization of the monomer was carried out in the presence of ethylene glycol dimethacrylate (EGDMA) by the initiation with 2,2-azobis(isobutyronitrile) (AIBN) at 54°C in DMF. The polymers were refluxed in 1,4-dioxane in the presence of a nucleophile such as water, methanol, or aniline. In this extraction step, the template molecules were removed from the polymer matrix, and simultaneously the isocyanato groups, which were generated by the thermal cleavage of the urethane bond, were converted to amino, urethane, or urea groups through their reaction with water, methanol, or aniline, respectively. The specific recognition ability of the imprinted polymers for the template and its structural analogues was dependent on the space between the two binding points as well as on the nature of the functional group. This method is especially propitious for developing artificial receptors for molecules lacking strongly interactive groups.
Functionalized Keggin- and Dawson-Type Cyclopentadienyltitanium Heteropolytungstate Anions: Small, Individually Distinguishable Labels for Conventional Transmission Elactron Microscopy. 2. Reactions
Keana, John F. W.,Ogan, Marc D.,Lue, YiXin,Beer, Michael,Varkey, J.
, p. 7957 - 7963 (2007/10/02)
Our goal is to develop a series of small, highly electron dense reagents to label substrate molecules covalently and chemoselectively for subsequent visualisation by using conventional transmission electron microscopy (CTEM).Starting with the organic functionalized cyclopentadienyltitanium (CpTi) substituted Keggin- and Dawson-type heteropolytungstate (HPT) anions prepared in the accompanying paper, it was first established that the HPT unit as well as the Cp-Ti bond in those anions are stable under a variety of reaction conditions that lead to modification (esterification, acylation, reduction, reductive amination, oxidation, and cycloaddition reactions) of the organic appendage.A Diels-Alder reaction between either Keggin HPT diene 34 or Dawson HPT diene 18 and one of several substituted N-phenylmaleimides (27-33) was a versatile method for the attachment of a variety of protein-reactive groups to the HPT anions.Thus prepared were HPT maleimides 20 and 35, bromoacetamides 21 and 36, biotin derivative 22, isothiocyanate 24, and N-hydroxysuccinimide esters 37 and 40.Additionally, the new heterobifunctional dienophiles 29, 30, 32 and 33 should act as protein cross-linking agents, complementing those already available.Acylating agent 40 is noteworthy in that two Dawson HPT units are tethered in close proximity to each other in this reagent.By analogy to the EM image of "dimeric" HPT 23, the EM image of 40 is expected to be recognizable morphologically as dumbells.HPT-labeled ATP derivative 42 was prepared by a reductive amination of Dawson benzaldehyde 10 with N6-methyl>ATP (Li salt).Both Keggin and Dawson HPTs are visible individually by using CTEM.Their stability in the electron beam is high.
