79537-70-5Relevant academic research and scientific papers
Synthesis of Thiourea and Sulfonylurea Derivatives of Chalcones and Flavones and their Biological Evaluation
Pratap, Ram,Satyanarayana, Mavurapu,Shukla, Poonam,Srivastava, Arvind K,Tiwari, Priti,Tripathi, Brajendra K
, p. 341 - 345 (2021/11/22)
Chalcone and flavone derivatives based on thiourea and sulfonylurea (6, 7a and 7b, 13a and 13b) were synthesized and confirmed by spectral data. All the target compounds were evaluated for in vivo antihyperglycemic activity in sucrose loaded model (SLM) a
Rational modification, synthesis and biological evaluation of 3,4-dihydroquinoxalin-2(1H)-one derivatives as potent and selective c-Jun N-terminal kinase 3 (JNK3) inhibitors
Dou, Xiaodong,Huang, Huixia,Jiang, Lan,Jiao, Ning,Jin, Hongwei,Liu, Zhenming,Zhang, Liangren,Zhang, Lihe,Zhu, Guiwang
, (2020/07/03)
The c-Jun N-terminal kinase 3 (JNK3) plays key roles in a wide range of diseases, including neurodegeneration diseases, inflammation diseases, cancers, cardiovascular diseases, and metabolic disorders. Previously, we have identified a lead compound, (Z)-3
Contra-thermodynamic E → Z isomerization of cinnamamides via selective energy transfer catalysis
Becker, Marc R.,Morack, Tobias,Robertson, Jack,Metternich, Jan B.,Mück-Lichtenfeld, Christian,Daniliuc, Constantin,Burley, Glenn A.,Gilmour, Ryan
supporting information, (2020/05/25)
A bio-inspired, photocatalytic E → Z isomerization of cinnamides is reported using inexpensive (?)-riboflavin (vitamin B2) under irradiation at λ = 402 nm. This operationally simple transformation is compatible with a range of amide derivatives including –NR2, –NHSO2R and N(Boc)2 (up to 99:1 Z:E). Selective energy transfer from the excited state photocatalyst to the starting E-isomer ensures that directionality is achieved: The analogous process with the Z-isomer is inefficient due to developing allylic strain causing chromophore deconjugation. This is supported by X-ray analysis and Stern-Volmer photo-quenching studies. Preliminary validation of the method in manipulating the conformation of a simple model Leu-enkephalin penta-peptide is disclosed via the incorporation of a cinnamamide-based amino acid.
Metal-Free Photoinduced Transformation of Aryl Halides and Diketones into Aryl Ketones
Yao, Qiuli,Liu, Wenbo,Liu, Peng,Ren, Linjing,Fang, Xuehong,Li, Chao-Jun
supporting information, p. 2721 - 2724 (2019/01/14)
The acylation of aryl halides to prepare aryl ketones without metal catalyst represents an important yet challenging topic towards more sustainable ketone synthesis. Herein, we describe a simple and efficient metal-free protocol for the acylation of aryl halides with diketone under the irradiation of light utilizing N-methylpiperidine as base under an air atmosphere. This reaction can tolerate a wide range of functional groups and the corresponding ketones can be obtained in modest to good yields.
T790M mutant EGFR inhibitors and its application in the preparation of antineoplastic
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Paragraph 0090; 0092; 0094; 0095, (2018/03/25)
The invention provides a T790M mutant EGFR inhibitor and an application of the same in preparation of antitumor drugs. The inhibitor is a pyrimidine compound with structural characteristics of a formula (I). The compound can inhibit various tumor cells and particularly can act on EGFR L858R/T790M and EGFR E 745_A750/T790M lung cancer cells selectively, and the IC 50 of the compound is 10 timers and even 100 times higher than that of wild cancer cells. The compound is the protease inhibitor which is capable of overcoming prior EGFR-TKI drug resistance and has selectivity and can be applied to preparation of antitumor drugs. (img file= 'DDAS0000708455660000011. TIF' wi= '716' he= '576'/).
Applying the designed multiple ligands approach to inhibit dihydrofolate reductase and thioredoxin reductase for anti-proliferative activity
Ng, Hui-Li,Chen, Shangying,Chew, Eng-Hui,Chui, Wai-Keung
, p. 63 - 74 (2016/04/05)
The development of multi-targeting drugs is currently being explored as an attractive alternative to combination therapy, especially for the treatment of complex diseases such as cancer. Dihydrofolate reductase (DHFR) and thioredoxin reductase (TrxR) are enzymes belonging to two unrelated cellular pathways that are known to contribute towards cancer cell growth and survival. In order to evaluate whether simultaneous inhibition of DHFR and TrxR by dihydrotriazines (DHFR-targeting) and chalcones (TrxR-targeting) may be beneficial, breast MCF-7 and colorectal HCT116 carcinoma cells were treated with combinations of selected dihydrotriazines and chalcones at a 1:1 M ratio. Two combinations demonstrated synergy at low-to-moderate concentrations. Based on this result, four merged dihydrotriazine-chalcone compounds were designed and synthesized. Two compounds, 11a [DHFR IC50 = 56.4 μM, TrxR IC50 (60 min) = 12.6 μM] and 11b [DHFR IC50 = 2.4 μM, TrxR IC50 (60 min) = 10.1 μM], demonstrated in vitro inhibition of DHFR and TrxR. The compounds showed growth inhibitory activity against MCF-7 and HCT116 cells, but lacked cytotoxicity. Molecular docking experiments showed 11b to possess rational binding modes to both the enzymes. In conclusion, this study has not only identified the dihydrotriazine and chalcone scaffolds as good starting points for the development of dual inhibitors of DHFR and TrxR, but also demonstrated the synthetic feasibility of producing a chemical entity that could result in simultaneous inhibition of DHFR and TrxR. Future efforts to improve the antiproliferative profiles of such compounds will look at alternative ways of integrating the two pharmacophoric scaffolds.
Highly ortho-Selective Chlorination of Anilines Using a Secondary Ammonium Salt Organocatalyst
Xiong, Xiaodong,Yeung, Ying-Yeung
supporting information, p. 16101 - 16105 (2016/12/26)
An organocatalytic, highly facile, efficient, and regioselective ortho-chlorination of anilines is described. A secondary ammonium chloride salt has been employed as the catalyst and the reaction can be conducted at room temperature without protection from air and moisture. In addition, the reaction is readily scalable and the catalyst can be recycled and reused. This catalytic protocol has been applied to the efficient synthesis of a highly potent c-Met kinase inhibitor. Mechanistic studies revealed that unique structural features of the secondary ammonium chloride salt are important for both the catalysis and regioselectivity of the electrophilic ortho-chlorination.
COMPOUNDS COMPRISING 1,1',2,5'-TETRAHYDROSPIRO[INDOLE-3,2'-PYRROLE]-2,5'-DIONE SYSTEM AS INHIBITORS P53-MDM2 PROTEIN-PROTEIN INTERACTION
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Page/Page column 29; 30, (2016/01/01)
A spirooxoindole compound represented by the formula selected from the group consisting of Formula (IA) and (IB), wherein all symbols are as defined in the description. The compound can find use in a method of prevention and/or treatment of diseases selec
Pd-catalyzed amidation of aryl(Het) halides with tert-butyl carbamate
Qin, Lijin,Cui, Hongmeng,Zou, Dapeng,Li, Jingya,Wu, Yangjie,Zhu, Zhiwu,Wu, Yusheng
experimental part, p. 4445 - 4448 (2010/09/12)
Pd-catalyzed cross-coupling reaction of tert-butyl carbamate with various aryl(Het) halides with Cs2CO3 as base in 1,4-dioxane as solvent was investigated, which resulted in the formation of the desired compounds in moderate to excellent yields.
Room-temperature Pd-catalyzed amidation of aryl bromides using tert-butyl carbamate
Bhagwanth, Swapna,Waterson, Alex G.,Adjabeng, George M.,Hornberger, Keith R.
supporting information; experimental part, p. 4634 - 4637 (2009/09/08)
(Chemical Equation Presented) The scope of Pd-catalyzed synthesis of N-Boc-protected anilines from aryl bromides and commercially available tertbutyl carbamate is described. For the first time, this process can be conducted at room temperature (17-22°C) u
