We report on the fluorinated form of Cpd 5 as a cell growth inhibitor. This compound is 3-fold more potent than the parent Cpd 5 and is predicted, using the semi-empirical AM1 method to be only an arylator of cysteine-containing proteins, without generating reactive oxygen species.
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http://dx.doi.org/10.1016/j.bmcl.2004.05.009 | DOI Listing |
Angew Chem Int Ed Engl
November 2024
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory for Organic Solids, Institute of Chemistry, Chinese Academy of Sciences, Beijing, 100190, China.
Dicyanomethylene-terminated quinoidal materials are promising n-type organic semiconductors featuring excellent electron mobilities and air stability. Traditional synthetic methods of these materials such as Takahashi reaction, require the use of expensive palladium catalyst and halogenated substrates. However, for electron-rich fused aromatic compounds, the poor stability after halogenation renders their halogenated derivatives unsuitable as reaction precursors.
View Article and Find Full Text PDFActa Crystallogr E Crystallogr Commun
August 2024
Department of Chemistry New Mexico Highlands University,Las Vegas New Mexico 87701 USA.
The crystal structures of two inter-mediates, 4-amino-3,5-di-fluoro-benzo-nitrile, CHFN (), and ethyl 4-amino-3,5-di-fluoro-benzoate, CHFNO (), along with a visible-light-responsive azo-benzene derivative, diethyl 4,4'-(diazene-1,2-di-yl)bis-(3,5-di-fluoro-benzoate), CHFNO (), obtained by four-step synthetic procedure, were studied using single-crystal X-ray diffraction. The mol-ecules of and demonstrate the quinoid character of phenyl rings accompanied by the distortion of bond angles related to the presence of fluorine substituents in the 3 and 5 () positions. In the crystals of and , the mol-ecules are connected by N-H⋯N, N-H⋯F and N-H⋯O hydrogen bonds, C-H⋯F short contacts, and π-stacking inter-actions.
View Article and Find Full Text PDFJ Org Chem
November 2022
Department of Chemical Science and Technologies, University of Rome Tor Vergata, Via della Ricerca Scientifica, 00133 Rome, Italy.
A chemoselective photocatalytic system to perform thioether oxidation to sulfoxide is presented. The light-induced oxidation process is here promoted by a metal-free quinoid catalyst, namely 1-hexylKuQuinone (KuQ). Reactions performed in a fluorinated solvent (i.
View Article and Find Full Text PDFChemistry
April 2022
Department of Chemistry & Biochemistry and Materials Science Institute, University of Oregon, Eugene, Oregon, 97403-1253, USA.
Chem Res Toxicol
April 2021
State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences University of Chinese Academy of Sciences, Beijing 100085, P. R. China.
Pyridinium aldoximes are best-known therapeutic antidotes used for clinical treatment of poisonings by organophosphorus nerve-agents and pesticides. Recently, we found that pralidoxime (2-PAM, a currently clinically used nerve-agent antidote) could also detoxify tetrachloro-1,4-benzoquinone (TCBQ), which is a carcinogenic quinoid metabolite of the widely used wood preservative pentachlorophenol under normal physiological conditions, via an unusually mild and facile Beckmann fragmentation mechanism accompanied by radical homolysis. However, it is not clear whether the less-chlorinated benzoquinones (BQs, ≤ 3) act similarly; if so, what is the structure-activity relationship? In this study, we found that (1) The stability of reaction intermediates produced by different BQs and 2-PAM was dependent not only on the position but also the degree of Cl-substitution on BQs, which can be divided into TCBQ- and DCBQ (dichloro-1,4-benzoquinone)-subgroup; (2) The p value of hydroxlated quinones (BQ-OHs, the hydrolysis products of BQs), determined the stability of corresponding intermediates, that is, the decomposition rate of the intermediates depended on the acidity of BQ-OHs; (3) The p value of the corresponding BQ-OHs could also determine the reaction ratio of Beckmann fragmentation to radical homolysis in BQs/2-PAM.
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