101-18-8Relevant articles and documents
A survey on the reactivity of phenyliodonium ylide of 2-hydroxy-1,4- naphthoquinone with amino compounds
Spagou, Konstantina,Malamidou-Xenikaki, Elizabeth,Spyroudis, Spyros
, p. 226 - 237 (2005)
The phenyliodonium ylide of 2-hydroxy-1,4-naphthoquinone reacts with aminoesters, ureas, aminoalcohols and aminophenols in refluxing dichloromethane to afford good yields of indanedione 2-carboxamido compounds, that in solution exist in an enol-amide form. The same reactants in a copper-catalyzed reaction afford mainly the corresponding N-arylo compounds. Arylhydrazines are mainly oxidized by the ylide and arylation occurs only in a low yield.
3-Hydroxy-2-(trialkylsilyl)phenyl Triflate: A Benzyne Precursor Triggered via 1,3-C-sp2-to-O Silyl Migration
Kwon, Yong-Ju,Jeon, Young-Kyo,Sim, Ha-Bin,Oh, In-Young,Shin, Inji,Kim, Won-Suk
, p. 6224 - 6227 (2017)
3-Hydroxy-2-(trialkylsilyl)phenyl triflates are presented as new versatile hydroxyaryne precursors. These are base-activated aryne precursors induced via a C-sp2-to-O 1,3-Brook rearrangement. The reaction of various arynophiles and 3-trialkylsiloxybenzyne generated from 3-hydroxy-2-(trialkylsilyl)phenyl triflate efficiently afforded highly regioselective phenol derivatives. Furthermore, through crossover experiments, the intramolecular mechanism of silyl migration was demonstrated.
Discovery of 4-(3,5-dimethoxy-4-(((4-methoxyphenethyl)amino)methyl)phenoxy)-N-phenylaniline as a novel c-myc inhibitor against colorectal cancer in vitro and in vivo
Cao, Chaoguo,Lan, Suke,Li, Rui,Liu, Yuanyuan,Luo, Dan,Luo, Meng,Ma, Xinyu,Shan, Huifang,Yang, Jie,Yu, Su,Zhong, Xinxin
, (2020)
Proto-oncogene c-Myc plays an essential role in the development of colorectal cancer (CRC), since downregulation of c-Myc inhibits intestinal polyposis, which is the most cardinal pathological change in the development of CRC. Herein, a series of novel phenoxy-N-phenylaniline derivatives were designed and synthesized. The cytotoxicity activities of all the derivatives were measured by MTT assay in different colon cancer cells, 4-(3,5-dimethoxy-4-(((4-methoxyphenethyl)amino)methyl)phenoxy)-N-phenylaniline (42) was discovered, the lead compound 42 with excellent cytotoxicity activity of IC50 = 0.32 μM, IC50 = 0.51 μM, in HT29 and HCT 15 cells, respectively. Compound 42 had a good inhibitory activity of c-Myc/MAX dimerization and DNA binding. Besides, compound 42 could effectively induce apoptosis and induced G2/M arrest in low concentration and G0/G1 arrest in high concentration to prevent the proliferation and differentiation in colon cancer cells. Western blot analysis confirmed the 42 strongly down-regulated expression of c-Myc. Furthermore, during 30 days treatment 42 exhibited excellent efficacy in HT29 tumor xenograft model without causing significant weight loss and toxicity. Consequently, 42 could be a promising drug candidate for CRC therapy.
N-arylation of amines: C-N coupling of amines with arylboronic acids using Fe3O4 magnetic nanoparticles-supported EDTA-Cu(ii) complex in water
Mostafalu, Ramin,Kaboudin, Babak,Kazemi, Foad,Yokomatsu, Tsutomu
, p. 49273 - 49279 (2014)
Fe3O4 magnetic nanoparticles-supported EDTA-copper(ii) complex (Fe3O4-EDTA-Cu(ii)) has been prepared and characterized by TEM, SEM, XRD, VSM, TGA, and FT-IR spectrometers. The catalyst was applied for the C-N coupling of arylboronic acids with amines for the preparation of N-aryl compounds. Recovery tests confirm that the catalyst can be easily recovered and reused up to eight times without significant loss of its catalytic activity.
Phenoxy-N-phenylaniline derivative and application thereof
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Paragraph 0064; 0067; 0069; 0071, (2020/06/05)
The invention relates to a phenoxy-N-phenylaniline derivative and an application thereof, and belongs to the technical field of novel colorectal cancer drugs. The present invention addresses the problem of providing some novel compounds having c-Myc inhibitory activity. The structural formula of the compound is shown as a formula I in the specification. According to the invention, a series of novel phenoxy-N-phenylaniline derivatives are designed and synthesized, and the compounds can be used as c-Myc inhibitors, have a good inhibition effect on the proliferation of colorectal cancer cells, and provide a new choice for colorectal cancer drugs.
Synthesis process of sulfonic-group rhodamine compound
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Paragraph 0043; 0045; 0048; 0050; 0053; 0055, (2019/04/26)
The invention discloses a synthesis process of a sulfonic-group rhodamine compound. The process comprises the steps: mixing saccharin and a protonic acid catalyst, performing heating for a reaction soas to obtain a compound shown in a formula (I), performing a reaction between a compound shown in a formula (II) and resorcinol through heating under the action of the protonic acid catalyst so as toobtain a compound shown in a formula (III), performing a reaction between the compound of the formula (I) and the compound in the formula (III) through heating under the action of a Lewis acid catalyst under the conditions of nitrogen protection and light shielding so as to obtain the sulfonic-group rhodamine compound shown in a formula (IV). Through the synthesis process, the use of thionyl chloride in a conventional process is avoided, the operation is simplified, the production safety is improved, the pollution to the environment is little, the reaction can be carried out under normal pressure, and the reaction has a high selectivity; and the chemical structural formulas of the compounds represented separately by the formula (I), the formula (II), the formula (III) and the formula (IV)are shown.
A meta-substituted phenol compounds and its preparation method and application
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Paragraph 0051-0055, (2019/05/21)
The invention relates to the field of organic synthesis, in particular relates to a meta-substituted phenol derivative molecule and its preparation method and application. The invention discloses a meta-substituted phenol molecule preparation method, including formula I compounds of the formula II with a compound represented by a plurality of times of oxidative dehydrogenation coupling reaction, a compound represented by formula III. The invention provides a meta-substituted phenol derivative molecule and its preparation method and application, solves the technical intermediate substituted phenol derivatives molecular synthesis reaction and the cost is high, the reaction stability is not high, and the reaction of complex technical issues.
Intermolecular Multiple Dehydrogenative Cross-Couplings of Ketones with Boronic Acids and Amines via Copper Catalysis
Wang, Tianzhang,Chen, Guowei,Lu, Yu-Jing,Chen, Qian,Huo, Yanping,Li, Xianwei
supporting information, p. 3886 - 3892 (2019/07/19)
An efficient and versatile oxidative coupling reaction was developed for the synthesis of valuable β-functionalized unsaturated ketones and meta-substituted phenols. In the case of intramolecular reactions, achieving rapid molecular complexity through multiple dehydrogenative couplings is already a well-established strategy. Herein, we report an intermolecular multiple dehydrogenative coupling between ketones and nucleophilic amines or boronic acids using inexpensive copper(I) oxide as a catalyst. This method provides a facile access to highly desirable chemical products such as α,β-unsaturated ketones, enaminones, and synthetically relevant meta-substituted phenols. (Figure presented.).
Synthesis of Di(hetero)arylamines from Nitrosoarenes and Boronic Acids: A General, Mild, and Transition-Metal-Free Coupling
Roscales, Silvia,Csák?, Aurelio G.
, p. 1667 - 1671 (2018/03/23)
The synthesis of di(hetero)arylamines by a transition-metal-free cross-coupling between nitrosoarenes and boronic acids is reported. The procedure is experimentally simple, fast, mild, and scalable and has a wide functional group tolerance, including carbonyls, nitro, halogens, free OH and NH groups. It also permits the synthesis of sterically hindered compounds.
Copper(ii)-catalyzed Chan-Lam cross-coupling: chemoselective N-arylation of aminophenols
Siva Reddy,Ranjith Reddy,Nageswar Rao,Jaladanki, Chaitanya K.,Bharatam, Prasad V.,Lam, Patrick Y. S.,Das, Parthasarathi
supporting information, p. 801 - 806 (2017/02/05)
Copper(ii)-catalyzed boronic acid promoted chemoselective N-arylation of unprotected aminophenols has been developed. Selective N-arylation of 3-aminophenol is achieved with a Cu(OAc)2/AgOAc combination in MeOH at rt, whereas the chemoselective N-arylated products of 4-aminophenol can be obtained with a Cu(OAc)2/Cs2CO3 system and benzoic acid as an additive. These ligand-free conditions and “open-flask” chemistry are robust and compatible with a wide range of functional groups. The mechanistic investigation for this selective N-arylation has been studied by considering Density Functional Theory (DFT) calculations.
