397-60-4Relevant academic research and scientific papers
An isoxazole derivative ShU00238 suppresses colorectal cancer growth through miRNAs regulation
Wang, Haoyu,Ma, Yurui,Lin, Yifan,Liu, Jiajie,Chen, Rui,Xu, Bin,Liang, Yajun
, (2019)
Colorectal cancer (CRC) is a leading cause of cancer-related deaths worldwide. Isoxazoline and isoxazole derivatives represent an important class of five-membered heterocycles, which play a pivotal role in drug discovery. In our previous study, we develop
Chemoselective Transfer Hydrogenation of Enamides Using Ru Pincer Complexes for the Synthesis of α-Amino Acids
Nielsen, Martin,Pinheiro, Danielle L. J.
, (2022/03/14)
The chemoselective reduction of enamides to α-amino acids with iPrOH and EtOH as H-donors and solvents catalyzed by Ru pincer complexes is demonstrated. A range of α-amino acids is synthesized in good to excellent yields. Applications, large scale, and a one-pot experiment are also reported. Finally, deuterium-labeling experiments show high regioselectivity between the α-and β-positions of the alkene unit.
Base Induced Condensation of Malononitrile with Erlenmeyer Azlactones: An Unexpected Synthesis of Multi-Substituted Δ2-Pyrrolines and Their Cytotoxicity
Anil, Seegehalli M.,Kiran, Kuppalli R.,Rajeev, Narasimhamurthy,Sadashiva, Maralinganadoddi P.,Shobith, Rangappa,Sudhanva, Muddenahalli S.,Swaroop, Toreshettahally R.,Vinayaka, Ajjampura C.
, (2020/04/29)
An efficient, metal free approach to synthesize multi-substituted Δ2-pyrroline derivatives by mild base catalyzed cyclocondensation of malononitrile with Erlenmeyer azlactones via 1,2 addition was developed. The modularity of this reaction was used to assemble a range of poly-substituted pyrrolines. Further, synthesized products were screened for cytotoxic properties on different cancer cell lines such as A549 (Human lung adenocarcinoma cells), HeLa (Human cervical adenocarcinoma cells), Jurkat (Human chronic myeloid leukemia cells) and K562 (Human leukemic T cell Lymphoblast cells). Among the synthesized library of compounds, 6f and 6q displayed potent cytotoxic activity.
Synthesis of 2-substituted 4-arylidene-5(4h)-oxazolones as potential cytotoxic agents in the presence of lemon juice as a biocatalyst
Anand, Krishnan,Jonnalagadda, Sreekantha B.,Katari, Naresh K.,Lakshmi, Chapala V.,Pal, Manojit,Prasad, Malavattu G.
, p. 625 - 634 (2020/01/21)
Background: The oxazolone class of compounds is known to exert a profound effect on malignant cell proliferation, tumor angiogenesis and /or on the established neoplastic vasculature. Additionally, these compounds are generally known to have a low tendenc
Copper nitrate-mediated synthesis of 3-aryl isoxazolines and isoxazoles from olefinic azlactones
Lin, Yifan,Zhang, Ke,Gao, Mingchun,Jiang, Zheyi,Liu, Jiajie,Ma, Yurui,Wang, Haoyu,Tan, Qitao,Xiao, Junjie,Xu, Bin
supporting information, p. 5509 - 5513 (2019/06/14)
A copper nitrate-mediated [2 + 2 + 1] cycloaddition reaction was developed for the expedient synthesis of pharmacologically interesting 3-aryl substituted isoxazolines and isoxazoles through CC bond cleavage. Copper nitrate is employed as a reaction promoter and precursor of nitrile oxides. The given approach features a new mode of cycloaddition from olefinic azlactones, copper nitrate and unsaturated compounds with wide substrate scope, good functional group tolerance and operational simplicity.
Catalytic aza-wittig reaction of acid anhydride for the synthesis of 4H-benzo[d][1,3]oxazin-4-ones and 4-benzylidene-2-aryloxazol-5(4H)-ones
Wang, Long,Xie, Yi-Bi,Huang, Nian-Yu,Yan, Jia-Ying,Hu, Wei-Min,Liu, Ming-Guo,Ding, Ming-Wu
, p. 4010 - 4016 (2016/07/06)
Compared to the aza-Wittig reaction of aldehydes, ketones, amides, and esters, the aza-Wittig reaction of acid anhydride was always overlooked, which should be an important part of Wittig reactions. Here, the aza-Wittig reaction of anhydride and catalytic aza-Wittig reaction of anhydride were both developed with high yields, which provides an efficient method to synthesize of 4H-benzo[d][1,3]oxazin-4-ones and 4-benzylidene-2-aryloxazol-5(4H)-ones. The strategy of copper-catalyzed reduction of phosphine oxide was used and found effective for this transformation. Additionally, the one-pot catalytic aza-Wittig reaction of carboxylic acids was achieved. Furthermore, NMR experiments and Hammett plot recorded the process of catalytic aza-Wittig reaction of anhydride, which provides direct proof that the copper-catalyzed reduction of waste phosphine oxide is the key step in this transformation.
Synthesis and quantitative structure-activity relationships study for phenylpropenamide derivatives as inhibitors of hepatitis B virus replication
Yang, Jing,Ma, Min,Wang, Xue-Ding,Jiang, Xing-Jun,Zhang, Yuan-Yuan,Yang, Wei-Qing,Li, Zi-Cheng,Wang, Xi-Hong,Yang, Bin,Ma, Meng-Lin
, p. 82 - 91 (2015/07/27)
A series of new phenylpropenamide derivatives containing different substituents was synthesized, characterized and evaluated for their anti-hepatitis B virus (HBV) activities. The quantitative structure eactivity relationships (QSAR) of phenylpropenamide compound have been studied. The 2D-QSAR models, based on DFT and multiple linear regression analysis methods, revealed that higher values of total energy (TE) and lower entropy (Sθ) enhanced the anti-HBV activities of the phenylpropenamide molecules. Predictive 3D-QSAR models were established using SYBYL multifit molecular alignment rule. The optimum models were all statistically significant with cross-validated and conventional coefficients, indicating that they were reliable enough for activity prediction.
Phenylpropenamide derivatives: Anti-hepatitis B virus activity of the Z isomer, SAR and the search for novel analogs
Wang, Peiyuan,Naduthambi, Devan,Mosley, Ralph T.,Niu, Congrong,Furman, Phillip A.,Otto, Michael J.,Sofia, Michael J.
scheme or table, p. 4642 - 4647 (2011/09/12)
Phenylpropenamides have been reported to be a class of non-nucleoside inhibitors of the hepatitis B virus (HBV). This class of compounds was explored with the objective of developing potent anti-HBV agents, with a novel mechanism of action, that could be combined with nucleos(t)ide analogs currently used to treat HBV infection. To accomplish this objective a series of substituted arylpropenamide derivatives were prepared and the E and Z geometrical isomers were separated. The structural identity of each of the E and Z isomers was determined by single crystal X-ray crystallography. Contrary to previous reports, the activity of this class of molecules resides in the Z isomer. Further structure-activity relationship studies around the active Z isomer identified compounds that displayed potent antiviral activity against HBV with EC90 value of approximately 0.5 μM in vitro. Attempts to develop ring constrained analogs did not lead to active HBV inhibitors.
An improved "one-pot" procedure for synthesis of fluorinated DL-phenylalanines
Samet, Alexander V.,Coughlin, Daniel J.,Buchanan III,Gakh, Andrei A.
, p. 941 - 946 (2007/10/03)
DL-arylalanines were synthesized from corresponding aromatic aldehydes by an efficient "one-pot" procedure involving Erlenmeyer reaction and subsequent reduction of the resulting oxazolones (without prior isolation) using P/HI.
Phenylpropenamide derivatives as inhibitors of hepatitis B virus replication
Perni, Robert B.,Conway, Samuel C.,Ladner, Stephanie K.,Zaifert, Katie,Otto, Michael J.,King, Robert W.
, p. 2687 - 2690 (2007/10/03)
A non-nucleoside class of compounds that inhibits the replication of hepatitis B virus (HBV) in cell culture has been discovered. A series of substituted analogues of phenylpropenamide 6 has been prepared and evaluated in the HepAD38 cellular assay. Structure-activity relationships of this series are discussed. (C) 2000 Elsevier Science Ltd.
