54060-30-9Relevant articles and documents
Preparation method of m-aminophenylacetylene
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, (2021/05/29)
The invention discloses a preparation method of m-aminophenylacetylene, belonging to the technical field of organic synthesis. The method comprises the following steps of: subjecting m-nitroacetophenone serving as a raw material to reacting with triethyl phosphite under the action of a catalyst, continuously converting the m-nitroacetophenone into enol form, and condensing the enol form with the triethyl phosphite to obtain condensation ester, wherein the condensation ester is easy to separate and high in purity, m-nitrophenylacetylene is generated from the ester under the action of strong base, and m-aminophenylacetylene is generated from the ester through reduction. Compared with an acetophenone chlorination method, the method of the invention has the advantages that phosphorus oxychloride does not need to be used for changing oxygen of the m-nitroacetophenone into chlorine, pollution is small, purity is high ( 98% or more), the use of high-pollution raw material reagents is avoided, operation is simple, the environment-friendly effects are realized, and industrial production can be conveniently realized.
Fast heck-cassar-sonogashira (hcs) reactions in green solvents
Cabri, W.,Corbisiero, D.,Daka, A.,Fantoni, T.,Ferrazzano, L.,Martelli, G.,Ricci, A.,Tolomelli, A.,Viola, A.
supporting information, p. 3969 - 3973 (2020/06/08)
The replacement of toxic solvents with greener alternatives in Heck-Cassar-Sonogashira (HCS) cross-couplings was investigated. The fine-tuning of the HCS protocol allowed to achieve complete conversions and high speed under mild conditions. N-Hydroxyethylpyrrolidone (HEP) gave the best results. Moreover, the methodology was successfully applied to the synthesis of an intermediate of the anticancer drug Erlotinib, demonstrating the versatility of the new green protocol.
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.
