32402-63-4Relevant academic research and scientific papers
5-Hydroxyindole-based EZH2 inhibitors assembled via TCCA-catalyzed condensation and Nenitzescu reactions
Chen, Guoliang,Du, Fangyu,Sun, Wenjiao,Wang, Lihui,Wu, Chunfu,Yang, Cheng,Zhou, Qifan
, (2020/05/16)
5-Hydroxyindole derivatives have various demonstrated biological activities. Herein, we used 5-hydroxyindole as a synthetic starting point for structural alterations in a combinatorial process to synthesize 22 different compounds with EZH2 inhibitor pharmacophores. A series of 5-hydroxyindole-derived compounds were screened inhibitory activities against K562 cells. According to molecular modeling and in vitro biological activity assays, the preliminary structure-activity relationship was summarized. Compound L–04 improved both the H3K27Me3 reduction and antiproliferation parameters (IC50 = 52.6 μM). These findings revealed that compound L–04 is worthy of consideration as a lead compound to design more potent EZH2 inhibitors. During the preparation of compounds, we discovered that trichloroisocyanuric acid (TCCA) is a novel catalyst which demonstrates condensation-promoting effects. To gain insight into the reaction, in situ React IR technology was used to confirm the reactivity. Different amines were condensed in high yields with β-diketones or β-ketoesters in the presence of TCCA to afford the corresponding products in a short time (10~20 min), which displayed some advantages and provided an alternative condensation strategy.
Indole ring-containing IDO inhibitor and preparation method thereof
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Paragraph 0184; 0186-0188, (2019/01/20)
The invention discloses an indole ring-containing IDO inhibitor and a preparation method thereof. A drug utilizing the compound as an active component can be used for treating immune activation and inflammation diseases, cardiovascular diseases and the li
Bimetallic Ag-Cu alloy nanoparticles as a highly active catalyst for the enamination of 1,3-dicarbonyl compounds
Rout, Lipeeka,Kumar, Aniket,Dhaka, Rajendra S.,Dash, Priyabrat
, p. 49923 - 49940 (2016/06/15)
Bimetallic nanoparticles, particularly those based on copper, have recently attracted a great deal of attention for the development of low cost and highly active catalysts due to the synergistic interaction between individual metal components. In this work, bimetallic Ag-Cu alloy nanoparticles were explored as a highly active and reusable catalyst for the enamination of 1,3-dicarbonyls using diverse amines. The nanocatalysts were intensively characterized by ultraviolet-visible (UV-Vis) spectroscopy, X-ray diffraction (XRD), high-resolution transmission electron microscopy-energy-dispersive spectroscopy (HRTEM-EDS) and valence band and core level X-ray photoelectron spectroscopy (XPS) to study the effect of the bimetallic structure and composition. In comparison to monometallic Ag and Cu nanoparticles, the alloyed Ag-Cu nanoparticles showed a high catalytic performance and the resultant catalytic activity was dependant on the Ag to Cu ratio. This enhanced catalytic activity should be related to the electronic interaction between Ag and Cu nanoparticles formed due to the intimate contact between them. Our study may serve as a foundation for designing efficient alloyed nanocatalysts for fine chemical synthesis via enamination reactions.
Effect of solvent ratio and counter ions on the morphology of copper nanoparticles and their catalytic application in β-enaminone synthesis
Gajengi, Aravind L.,Sasaki, Takehiko,Bhanage, Bhalchandra M.
, p. 101800 - 101807 (2016/11/09)
This work reports the synthesis of shape selective copper nanoparticles (NPs) using a microwave irradiation method, using diverse ratios of an ethylene glycol (EG)/water system. The solvent ratio of EG/water plays a pivotal role in the selective formation of CuO NPs. The alteration of the counter ion of the copper precursor leading to the selective synthesis of copper (CuO, Cu2O, Cu(OH)2) NPs has been observed. The synthesized copper NPs are well characterized using FEG-SEM, TEM, XRD, XPS, NH3-TPD and BET surface area. The prepared CuO NPs show high activity towards the synthesis of β-enaminones and β-enamino esters from 1,3 diketones and amines.
Three naphthalenedisulfonate polymers with imidazole-containing ligands: Synthesis, structure and heterogeneously catalytic performance in reactions of enamination of β-dicarbonyl compounds
Wang, Li,Liu, Jing,Guo, Hui,Deng, Dongsheng,Yao, Tian,Wang, Xingwei,Wang, Xinyi,Wu, Hongli
supporting information, p. 253 - 260 (2015/04/14)
Three new naphthalenedisulfonate polymers, [Cd(2,6-nds)(bib)]n (1), [Cd(1,5-nds)(bib)]n (2), and [Cu(2,6-nds)0.5(tpim)]n (3), have been successfully synthesized by hydrothermal reactions of corresponding metal salts with naphthalenedisulfonate (nds) and imidazole-containing ligands 1,4-bis(imidazol-1-ylmethyl)benzene (bib) and 2,4,5-tri(4-pyridyl)-imidazole (tpim). The structures of these polymers were determined by single crystal X-ray diffraction analysis. Polymers 1 and 2 crystallize in the same space group and have similar cell parameters, and thus show same three-dimensional (3D) framework architecture. Complex 3 has the same 2D layer structure. The photoluminescent properties of the complexes 1 and 2 were investigated. Catalytic tests indicate that complex 3 has chemo-and regio-selective catalytic activity towards enamination of β-ketoesters.
Iodine-Promoted Construction of Polysubstituted 2,3-Dihydropyrroles from Chalcones and β-Enamine Ketones (Esters)
Li, Yujin,Xu, Hui,Xing, Mengming,Huang, Fang,Jia, Jianhong,Gao, Jianrong
supporting information, p. 3690 - 3693 (2015/08/18)
A novel approach for the synthesis of a variety of polysubstituted trans-2,3-dihydropyrroles from a wide range of chalcones and β-enamine ketones (esters) via iodine-promoted tandem Michael/cyclization sequence has been developed, affording the desired products in moderate to excellent yields. This methodology is a highly efficient, convenient way to access functionalized 2,3-dihydropyrroles from readily accessible substrates under mild reaction conditions.
Fabrication of Ag/γ-Fe2O3@TiO2 hollow magnetic core-shell nanospheres as highly efficient catalysts for the synthesis of β-enaminones
Huo, Hongfei,Li, Xinzhe,Zhou, Xingchun,Jiao, Lixin,Zhao, Shiling,Zhang, Le,Li, Wenzhu,Li, Shuwen,Li, Rong
, p. 73612 - 73618 (2015/09/15)
Herein, we describe a method to prepare hollow magnetic mesoporous sphere catalysts (Ag/γ-Fe2O3@meso-TiO2). The core-shell strategy efficiently prevents the aggregation of Ag NPs in the high temperature calcination process and the leaching of Ag NPs for the catalytic reaction in the liquid phase. The catalyst is characterized by TEM, XRD and ICP-AES. Moreover, the catalyst exhibited improved activity for the synthesis of β-enaminones, and it could be easily recovered by an external magnet from the reaction mixture and recycled five times without any significant loss in activity.
An efficient and convenient synthesis of 1,2,3-trisubstituted pyrroles via iodocyclization from ethyl acetoacetate
Xu, Pengfei,Huang, Kunzhu,Liu, Zhiguo,Zhou, Ming,Zeng, Wenbin
supporting information, p. 2929 - 2933 (2013/06/27)
A novel and efficient methodology for the synthesis of 1,2,3-trisubstituted pyrroles by one-pot two-step reaction has been developed. The iodocyclization of a series of β-enamino esters followed by dehydroiodination, led to the formation of corresponding pyrroles. This approach provides an easy access to a wide range of 1,2,3-trisubstituted pyrroles.
A new copper-based metal-organic framework as a promising heterogeneous catalyst for chemo- and regio-selective enamination of β-ketoesters
Zhao, Ying,Deng, Dong-Sheng,Ma, Lu-Fang,Ji, Bao-Ming,Wang, Li-Ya
supporting information, p. 10299 - 10301 (2013/10/22)
Assembly of 5-nitro-1,2,3-benzenetricarboxylic acid (H3nbta) with CuII in the presence of 1,3-bis(1,2,4-triazol-1-yl)propane (1,3-btp) leads to a new metal-organic framework, [Cu(Hnbta)(1,3-btp)] ·2H2O (A1), which is shown to be an efficient and recyclable heterogeneous catalyst for enamination of β-ketoesters with excellent product yields and selectivity.
Ecofriendly and facile Nano ZnO catalyzed solvent-free enamination of 1,3-dicarbonyls
Indulkar, Utkarsha U.,Kale, Sandip R.,Gawande, Manoj B.,Jayaram, Radha V.
supporting information; experimental part, p. 3857 - 3860 (2012/08/27)
Nano zinc oxide (Nano-ZnO) was explored as a reusable catalyst for the enamination of 1,3-dicarbonyls using diverse amines. To make the process environmentally viable, the reaction was carried out under solvent-free conditions and found to give good yield of desired products. The catalyst was characterized by various analytical techniques such as UV-spectroscopy, XRD, and TEM. The catalyst was found to be reusable up to four catalytic cycles without any appreciable loss in activity.
