42001-07-0Relevant academic research and scientific papers
Synthesis of 4-(alkoxyamino)chroman-2-ones via 6-exo-trig cyclization of carbon-centered radicals into oxime ethers
Bejarano, Carlos A.,Díaz, John E.,Loaiza, Alix E.
, p. 177 - 182 (2016)
[Figure not available: see fulltext.] 4-(Alkoxyamino)chroman-2-ones were synthesized via a 6-exo-trig cyclization of alkyl radicals obtained from α-bromoesters containing an oxime ether group. In the case of secondary bromides, the best results were achie
Boronic acids facilitate rapid oxime condensations at neutral pH
Schmidt, Pascal,Stress, Cedric,Gillingham, Dennis
, p. 3329 - 3333 (2015/05/27)
We report here the discovery and development of boron-assisted oxime formation as a powerful connective reaction for chemical biology. Oximes proximal to boronic acids form in neutral aqueous buffer with rate constants of more than 104 M-1
Synthesis, biological evaluation, and molecular docking studies of 2,6-dinitro-4-(trifluoromethyl)phenoxysalicylaldoxime derivatives as novel antitubulin agents
Zhao, Ting-Ting,Lu, Xiang,Yang, Xian-Hui,Wang, Li-Ming,Li, Xi,Wang, Zhong-Chang,Gong, Hai-Bin,Zhu, Hai-Liang
experimental part, p. 3233 - 3241 (2012/07/14)
A series of 2,6-dinitro-4-(trifluoromethyl)phenoxysalicylaldoxime derivatives (1h-20h) have been designed and synthesized, and their biological activities were also evaluated as potential antiproliferation and tubulin polymerization inhibitors. Among all the compounds, 2h showed the most potent activity in vitro, which inhibited the growth of MCF-7, Hep-G2 and A549 cell lines with IC50 values of 0.70 ± 0.05, 0.68 ± 0.02 and 0.86 ± 0.05 μM, respectively. Compound 2h also exhibited significant tubulin polymerization inhibitory activity (IC50 = 3.06 ± 0.05 μM). The result of flow cytometry (FCM) demonstrated that compound 2h induced cell apoptosis. Docking simulation was performed to insert compound 2h into the crystal structure of tubulin at colchicine binding site to determine the probable binding model. Based on the preliminary results, compound 2h with potent inhibitory activity in tumor growth may be a potential anticancer agent.
Synthesis and Antimicrobial Activities of Oximes Derived from O- Benzylhydroxylamine as FabH Inhibitors
Luo, Yin,Zhang, Li-Rong,Hu, Yang,Zhang, Shuai,Wang, Xiao-Ming,Zhu, Hai-Liang,Fu, Jie
, p. 1587 - 1593,7 (2020/08/31)
Forty-three oxime derivatives were synthesized by allowing O-benzylhydroxylamines to react with primary benzaldehydes or salicylaldehydes; these products were gauged as potential inhibitors of β-ketoacyl-(acyl-carrier-protein) synthaseIII (FabH). Among the 43 compounds, 38 are reported herein for the first time. These compounds were assayed for antimicrobial activities against Escherichia coli, Pseudomonas aeruginosa, Pseudomonas fluorescens, Bacillus subtilis, Staphylococcus aureus, and Enterococcus faecalis. Compounds with prominent antibacterial activities were tested for their E. coli FabH inhibitory activities. 3-((2,4 Dichlorobenzyloxyimino) methyl) benzaldehyde O-2,4-dichlorobenzyl oxime (44) showed the best antibacterial activity, with minimum inhibitory concentrations of 3.13-6.25μgmL-1 against the tested bacterial strains, exhibiting the best E. coli FabH inhibitory activity, with an IC50 value of 1.7mM. Docking simulations were performed to position compound 44 into the E. coli FabH active site in order to determine the most probable binding conformation.
Scope of the radical addition-cyclization-elimination reaction of oxime ether towards the synthesis of tricyclic lactam derivatives
Rahaman, Habibur,Shirai, Atsushi,Miyata, Okiko,Naito, Takeaki
, p. 5789 - 5792 (2008/12/22)
The synthesis of tricyclic lactam building blocks by the radical addition-cyclization-elimination (RACE) reaction is presented. A range of oxime ethers carrying unsaturated ester part have been tested for the radical reaction. A variety of substituents were incorporated around the aromatic backbones and their effect on the RACE reaction has been examined. In addition, the power of RACE reaction is demonstrated by preparation of a key intermediate for the synthesis of constrained analogue of methoctramine.
Intermolecular alkyl radical addition to the carbon-nitrogen double bond of oxime ethers and hydrazones
Miyabe, Hideto,Shibata, Ryouhei,Sangawa, Masato,Ushiro, Chikage,Naito, Takeaki
, p. 11431 - 11444 (2007/10/03)
Intermolecular carbon radical addition to the carbon-nitrogen double bond of oxime ethers and hydrazones was studied. The reaction of unactivated aldoxime ethers proceeded smoothly in the presence of BF3·OEt2 to give the alkylated products in high yields via the free radical-mediated carbon- carbon bond-forming process.
REACTIONS OF VINYLNITROSONIUM IONS WITH SOME AROMATIC HETEROCYCLES - ELECTROPHILIC SUBSTITUTION VS CYCLOADDITION.
Holzapfel, C. W.,Dyk, M. S. van
, p. 1349 - 1362 (2007/10/02)
Reaction of N-cyclohexyl-N-propenyl-nitrosonium ion and N-cyclohexyl-N-ethenylnitrosonium ion with indole and N-methylindole resulted in electrophilic substitution while reaction of the former with skatole, benzothiophene and benzofuran resulted in cycloaddition.
