132971-92-7Relevant academic research and scientific papers
Electronic effect control of regioselectivity in the Michael-Addition inspired cascade reaction of 1,3-dimethyl-6-amino-uracil and 2-hydroxychalcones
Cui, Xin,Huang, Chao,Li, Jing-Peng,Lin, Jun-Jie,Wang, Shuang,Xia, Xian-Song
supporting information, (2022/01/15)
An unexpected Brosnted acid-catalyzed cascade reaction of 1,3-dimethyl-6-aminouracil with 2-hydroxychalcone has been developed to afford pyrido[2,3–d]pyrimidine-2,4-diones derivatives and 2,8-dioxabicyclo[3.3.1]nonane derivatives in moderate to good yield
Palladium-Catalyzed Cascade Reactions of 2-(Cyanomethoxy)chalcones with Arylboronic Acids: Selective Synthesis of Emissive Benzofuro[2,3- c]pyridines
Xiong, Wenzhang,Hu, Kun,Lei, Yunxiang,Zhen, Qianqian,Zhao, Zhiwei,Shao, Yinlin,Li, Renhao,Zhang, Yetong,Chen, Jiuxi
supporting information, p. 1239 - 1243 (2020/01/11)
The Pd(II)-catalyzed cascade reactions of 2-(cyanomethoxy)chalcones with arylboronic acids were demonstrated, allowing the rapid construction of benzofuro[2,3-c]pyridine skeletons with excellent selectivity. These transformations involve the domino-style formation of C-C/C-C/C-N bonds through nitrile carbopalladation, intramolecular Michael addition, cyclization, and aromatization. This chemistry allows for the reactions of 2-(cyanomethoxy)chalcones with thiophen-3-ylboronic acid, providing 3-aryl-1-(thiophen-3-yl)benzofuro[2,3-c]pyridines in moderate to good yields. In addition, the resulting products represent a new class of emissive fluorophores.
The design, synthesis, in vitro biological evaluation and molecular modeling of novel benzenesulfonate derivatives bearing chalcone moieties as potent anti-microtubulin polymerization agents
Shen, Yu-Ning,Lin, Lin,Qiu, Han-Yue,Zou, Wen-Yan,Qian, Yong,Zhu, Hai-Liang
, p. 23767 - 23777 (2015/04/14)
A series of novel 3,4-dimethoxylbenzenesulfonate derivatives containing a chalcone structure were synthesized and evaluated for their anti-proliferative activities against HepG2, HCT-116, MCF-7 and HeLa cell lines, as well as the effects of compound 10b on mitotic arrest and cell cycle of MCF-7 carcinoma cell line. Most importantly, the results of DAPI staining under co-focal microscope justified that compound 10b functioned even at relatively low concentration. The analogues showed a potent bio-activity towards tumor cells with IC50 values at nano-mole class, compared with those of positive control drug Colchicine, whose IC50 were 150.4 nM for MCF-7, 123.9 nM for HepG2, 125.4 nM for HCT-116 and 131.4 nM for HeLa cells. Also, a molecular docking modeling was utilized to reveal the binding mode of derivatives and microtubule. Among all the synthesized compounds, compound 10b stands out as IC50 values against all the selected cell lines were at average 80 nM (in which the values against MCF-7 and HepG2 were similar; about 79.2 nM). In this research, we gave strong evidence upon the optimized stratagem for ligands targeting the colchicine-binding site on microtubules, explaining the attribution that the analogues were designed upon the structure of chalcone and combretastatin A-4.
Synthesis of functionalized 2-aryl-4-(indol-3-yl)-4H-chromenes via iodine-catalyzed domino Michael addition-intramolecular cyclization reaction
Yin, Guodong,Fan, Ling,Ren, Tianbing,Zheng, Chunyang,Tao, Qing,Wu, Anxin,She, Nengfang
, p. 8877 - 8883 (2013/01/15)
An efficient synthesis of novel functionalized 2-aryl-4-(indol-3-yl)-4H- chromenes has been developed, in the presence of a catalytic amount of iodine, from easily available starting materials, 2-hydroxychalcone derivatives. Indole, substituted indoles and 7-azaindole are suitable for this transformation. The possible domino Michael addition-intramolecular cyclization reaction mechanism is proposed.
Synthesis of some novel 2,3,4,8,9-pentahydro-7-(4-haloaryl)-pyrazolo[5,1-e] benzo[1,5]oxazocines and 2,3(erythro), 7,8-tetrahydro-2-aryl-3-(4-fluoro-3- methylbenzoyl)-6-(4-haloaryl)pyrazolo[5,1-d] benzo[1,4]oxazepines via solid-liquid PTC
Pathak, Vijai N.,Gupta, Ragini,Tiwari, Ranjana,Gupta, Rekha,Sareen, Vineeta,Varshney, Bindu
, p. 977 - 984 (2007/10/03)
In this communication, a simple and straightforward procedure for the heterocyclization of 1H-4,5-dihydro-3-(4-haloaryl)-5-substituted phenylpyrazoles (4) with 1-bromo-3-chloropropane and 2,3-dibromo-1-(4-fluoro-3-methylphenyl)-3- phe- nylpropanone affording 2,3,4,8,9-pentahydro-7-(4-haloaryl)pyrazolo[5,1-e] benzo[1,5] oxazocines 5 and regioselective synthesis of 2,3(erythro),7,8- tetrahydro-2- aryl-3-(4-fluoro-3-methylbenzoyl)-6-(4-halophenyl)pyrazolo[5,1-d] benzo[1,4]oxa- zepines 6, respectively, via solid-liquid PTC is reported. All the synthesized compounds have been characterized on the basis of their spectral studies (IR, PMR, and MS) and analytical data. Copyright Taylor & Francis Group, LLC.
New spiro-piperidines as 5-HT2B receptor antagonists
Bienayme, Hugues,Chene, Laurent,Grisoni, Serge,Grondin, Antonio,Kaloun, El-Bachir,Poigny, Stephane,Rahali, Houcine,Tam, Eric
, p. 4830 - 4833 (2007/10/03)
A functional screening highlighted a series of spiro-piperidines as 5-HT2B receptor antagonists. Preliminary structure-activity relationship has been explored driving to potent antagonists (IC50 = 1 nM) and indicating directions for
Polarographic Investigations on α,β-Unsaturated Ketones: 1-(4'-Fluorophenyl)-3-phenyl-2-propenones
Katiyar, Sarvagya S.,Latithambica, M.
, p. 956 - 960 (2007/10/02)
The reduction of various substituted 1-(4'-fluorophenyl)-3-phenyl-2-propenones at the dropping mercury electrode has been examined.In 50percent ethanol-water buffered media fluorochalkones give two well-defined waves in acid media and three waves in neutral and alkaline media.The one-electron electroreduction in the first two steps results in the formation of dihydrochalcone, which subsequently gets further reduced to the secondary alcohol.A large variety of substituents on the benzylidene moiety of 1-(4'-fluorophenyl)-3-phenyl-2-propenone, affect the half-wave potentials according to the relation E1/2 = a + b.Substituents with a positive ? value render the reduction easier and shift the E1/2 to more positive values, whereas groups with negative ? values make the electroreduction more difficult, resulting in more negative E1/2 compared to the parent compound.A comparison of the E1/2 values of o- and p-chloro substituted 1-(4'-fluorophenyl)-3-phenyl-2-propenones shows that o-substituted derivative undergoes reduction at a more positive potential indicating a positive ortho effect for this system.
