149704-66-5Relevant articles and documents
Photoredox-catalyzed Direct Reductive Amination of Aldehydes without an External Hydrogen/Hydride Source
Alam, Rauful,Molander, Gary A.
, p. 2680 - 2684 (2018)
The direct reductive amination of aromatic aldehydes has been realized using a photocatalyst under visible light irradiation. The single electron oxidation of an in situ formed aminal species generates the putative α-amino radical that eventually delivers the reductive amination product. This method is operationally simple, highly selective, and functional group tolerant, which allows the direct synthesis of benzylic amines by a unique mechanistic pathway.
Design, synthesis, biological activity evaluation of 3-(4-phenyl-1H-imidazol-2-yl)-1H-pyrazole derivatives as potent JAK 2/3 and aurora A/B kinases multi-targeted inhibitors
Zheng, You-Guang,Wang, Jin-An,Meng, Long,Pei, Xin,Zhang, Ling,An, Lin,Li, Cheng-Lin,Miao, Ying-Long
, (2020/10/29)
In this study, a series of 3-(4-phenyl-1H-imidazol-2-yl)-1H-pyrazole derivatives were designed, synthesized, and evaluated for their biological activities. Upon performing kinase assays, most of the compounds exhibited potent inhibition against JAK2/3 and Aurora A/B with the IC50 values ranging from 0.008 to 2.52 μM. Among these derivatives, compound 10e expressed the most moderate inhibiting activities against all the four kinases with the IC50 values of 0.166 μM (JAK2), 0.057 μM (JAK3), 0.939 μM (Aurora A), and 0.583 μM (Aurora B), respectively. Moreover, most of the derived compounds exhibited potent cytotoxicity against human chronic myeloid leukemia cells K562 and human colon cancer cells HCT116, while compound 10e expressed antiproliferative activities against K562 (IC50=6.726 μM). According to western blot analysis, compound 10e down-regulated the phosphorylation of STAT3, STAT5, Aurora A, and Aurora B in a dose-dependent manner in K562 and HCT116 cells. Cell cycle analysis revealed that compound 10e inhibited the proliferation of cells by inducing cell cycle arrest in the G2 phase. The molecular modeling suggested that compound 10e could maintain a binding mode similar to the binding mode of AT9832, a common JAK 2/3 and Aurora A/B kinases multi-target kinase inhibitor. Therefore, compound 10e might be a potential agent for cancer therapy deserving further research.
3-(4-phenyl-1H-2-imidazolyl)-1H-pyrazole compound as well as preparation method and application thereof
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Paragraph 0080-0082, (2020/04/22)
The invention relates to a 3-(4-phenyl-1H-2-imidazolyl)-1H-pyrazole compound as well as a preparation method and application thereof, and belongs to the field of medicinal chemistry and pharmacotherapeutics. The invention provides application of a compound shown as a formula I or pharmaceutically acceptable salt thereof in preparation of drugs for treating tumor-related diseases, particularly an application in preparation of an Aurora A kinase specific inhibitor.
Direct Catalytic Decarboxylative Amination of Aryl Acetic Acids
Kong, Duanyang,Moon, Patrick J.,Bsharat, Odey,Lundgren, Rylan J.
supporting information, p. 1313 - 1319 (2019/12/15)
The decarboxylative coupling of a carboxylic acid with an amine nucleophile provides an alternative to the substitution of traditional organohalide coupling partners. Benzoic and alkynyl acids may be directly aminated by oxidative catalysis. In contrast, methods for intermolecular alkyl carboxylic acid to amine conversion, including amidate rearrangements and photoredox-promoted approaches, require stoichiometric activation of the acid unit to generate isocyanate or radical intermediates. Reported here is a process for the direct chemoselective decarboxylative amination of electron-poor arylacetates by oxidative Cu catalysis. The reaction proceeds at (or near) room temperature, uses native carboxylic acid starting materials, and is compatible with protic, electrophilic, and other potentially complicating functionality. Mechanistic studies support a pathway in which ionic decarboxylation of the acid generates a benzylic nucleophile which is aminated in a Chan–Evans–Lam-type process.
Iron-Catalysed Reductive Amination of Carbonyl Derivatives with Ω-Amino Fatty Acids to Access Cyclic Amines
Wei, Duo,Netkaew, Chakkrit,Carré, Victor,Darcel, Christophe
, p. 3008 - 3012 (2019/05/15)
An efficient method for the reductive amination of carbonyl derivatives with ω-amino fatty acids catalysed by an iron complex Fe(CO)4(IMes) [IMes=1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene] by means of hydrosilylation was developed. A variety of pyrrolidines, piperidines and azepanes were selectively synthesised in moderate-to-excellent yields (36 examples, 47–97 % isolated yield) with a good functional group tolerance.
Aminomethylation via cyclopalladated-ferrocenylimine-complexes-catalyzed Suzuki-Miyaura coupling of aryl halides with potassium N, N - dialkylaminomethyltrifluoroborates
Zou, Dapeng,Cui, Hongmeng,Qin, Lijin,Li, Jingya,Wu, Yangjie,Wu, Yusheng
scheme or table, p. 349 - 356 (2011/03/23)
Using cyclopalladated ferrocenylimine complexes (1-3 mol%) as catalysts, the Suzuki-Miyaura coupling of potassium N,N-dialkylaminomethyltrifluoroborates with aryl and heteroaryl halides were carried out in a 10:1 THF-H2O mixture at 80° in the presence of Cs2CO3 (3.0 equiv) as base, giving the desired cross-coupling products in 14-87% yields. A variety of potassium alkyltrifluoroborates were also examined. Georg Thieme Verlag Stuttgart New York.
Scope of aminomethylations via Suzuki-Miyaura cross-coupling of orsanotrifluoroborates
Molander, Gary A.,Gormisky, Paul E.,Sandrock, Deidre L.
, p. 2052 - 2057 (2008/09/19)
(Chemical Equation Presented) We previously reported the Suzuki-Miyaura reaction of N,N-dialkylaminomethyltrifluoroborates with aryl bromides. Herein, we report a further investigation of the scope and limitations of this palladium-catalyzed aminomethylation reaction. Aryl chlorides, iodides, and triflates coupled in good to excellent yields to give N,N-dialkylbenzylic amines. The aminomethylation of alkenyl bromides was also examined.
A new paradigm for biohydroxylation by Beauveria bassiana ATCC 7159
Holland, Herbert L.,Morris, Terence A.,Nava, Phillip J.,Zabic, Mirjana
, p. 7441 - 7460 (2007/10/03)
The biohydroxylation of a series of amides and related amino, keto and hydrocarbon substrates by the fungal biocatalyst Beauveria bassiana ATCC 7159 has been examined. The product distributions, together with data obtained from selective inhibition experiments using the cyt.P-450 inhibitors isosafrole, 1-aminobenzotriazole and phenylacetylene, suggest that B. bassiana contains a range of hydroxylase enzymes with different substrate specificities. A paradigm is presented for the interpretation of the results of microbial hydroxylation and for the application of existing active site models for B. bassiana.
