54060-30-9Relevant articles and documents
Preparation method of acetenyl aniline
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Paragraph 0055; 0058-0059; 0062-0063; 0066-0067; 0070-0071, (2021/04/14)
The invention discloses a preparation method of acetenyl aniline, wherein the preparation method comprises the following steps: by using nitroethylbenzene as a raw material and MBr-MBrO3-H2SO4 (M=Na or K) as a bromination reagent, carrying out free radical bromination reaction to prepare 1,1-dibromo-1-(nitrophenyl)ethane, carrying out elimination reaction under the action of alkali to obtain nitrophenylacetylene, and finally, carrying out Fe/HCl reduction to obtain acetenyl aniline. The preparation method provided by the invention has the advantages of cheap and easily available raw materials, simple and safe operation, good reaction selectivity, high product yield, less emission of three wastes and the like.
Differences in the selective reduction mechanism of 4-nitroacetophenone catalysed by rutile- And anatase-supported ruthenium catalysts
Gu, Xianmo,Pei, Linjuan,Wang, Jie,Zhang, Jin,Zheng, Zhanfeng,Zhu, Pengqi
, p. 1518 - 1528 (2020/03/26)
Ru/TiO2 catalysts exhibit excellent catalytic performance for selective reduction of 4-nitroacetophenone to 4-aminoacetophenone at normal temperature and atmospheric hydrogen pressure. Moreover, 99.9% selectivity to 4-aminoacetophenone can be obtained over 2.7 wt% Ru/TiO2(anatase) catalyst even in a relatively wide temperature (55-115 °C) and time (1-12 h) range. Its excellent catalytic performance is derived from the activation of H2 on the Ru nanoparticles at atmospheric pressure and the strong interaction of nitro groups with the support surface. Additionally, Ru nanoparticles supported on different crystalline TiO2 phases (anatase and rutile) result in different reaction pathways for 4-nitroacetophenone. Since the Ti-Ti distance on the rutile surface is smaller than that on the anatase surface, the hydroxylamine species adsorbed on the Ti atoms of rutile are more susceptible to the coupling reaction. Therefore, Ru/TiO2(rutile) causes a series of intermediates to accumulate during the conversion process, while Ru/TiO2(anatase) allows the highly selective conversion of 4-nitroacetophenone to 4-aminophenone. In addition, Ru/TiO2(anatase) can achieve chemoselective reduction of nitroaromatics to the corresponding anilines in the presence of -CN, -CHO, and -COOH, especially nitroaromatics containing CC and CC, indicating the excellent applicability.
Design, synthesis and biological evaluation of novel uracil derivatives bearing 1, 2, 3-triazole moiety as thymidylate synthase (TS) inhibitors and as potential antitumor drugs
Lu, Guo-qing,Li, Xin-yang,Mohamed O, Kamara,Wang, Depu,Meng, Fan-hao
, p. 282 - 296 (2019/03/27)
Research on thymidylate synthase inhibitors has been a hot spot for anticancer drug development. Here, based on the structures and pharmacological properties of two types of TS inhibitors, through a molecular assembly principle of drugs design, we designed and synthesized a series of 30 novel uracil derivatives as TS inhibitors. The antiproliferative ability of these compounds was evaluated against four cancer cell lines (A549, OVCAR-3, SGC-7901, and HepG2) by the MTT assay. Most of them showed excellent activities against all the tested cell lines. Furthermore, hTS assay results showed that these compounds have the unique ability to inhibit hTS activity in vitro. Notably, compound 13j exhibited the most potent activity against A549 cells (IC50 = 1.18 μM) and extremely prominent enzyme inhibition (IC50 = 0.13 μM), which was superior to the pemetrexed (PTX, IC50 = 3.29 μM and IC50 = 2.04 μM). Flow cytometric analysis showed the compound 13j could inhibit A549 cells proliferation by arresting the cell cycle in the G1/S phase, then induced the cell apoptosis. Further western blot analysis showed that compound 13j could down-regulate the cycle checkpoint proteins cyclin D1 and cyclin E to inhibit the cell cycle progression, and then induce intrinsic apoptosis by activating caspase-3, and reducing the ratio of bcl-2/bax. All of these results demonstrated that this new structure has potential drug-making properties and provides new ideas for drug development.