66924-63-8Relevant academic research and scientific papers
Continuous flow as an enabling technology: a fast and versatile entry to functionalized glyoxal derivatives
Lima, Fabio,Meisenbach, Mark,Schenkel, Berthold,Sedelmeier, Joerg
supporting information, p. 2420 - 2424 (2021/04/02)
We herein report two complementary strategies employing organolithium chemistry for the synthesis of glyoxal derivatives. Micro-mixer technology allows for the generation of unstable organometallic intermediates and their instantaneous in-line quenching with esters as electrophiles. Selective mono-addition was observedviaputative stabilized tetrahedral intermediates. Advantages offered by flow chemistry technologies facilitate direct and efficient access to masked 1,2-dicarbonyl compounds while mitigating undesired by-product formation. These two approaches enable the production of advanced and valuable synthetic building blocks for heterocyclic chemistry with throughputs of grams per minute.
Dichloroacetophenones targeting at pyruvate dehydrogenase kinase 1 with improved selectivity and antiproliferative activity: Synthesis and structure-activity relationships
Zhang, Shao-Lin,Yang, Zheng,Hu, Xiaohui,Tam, Kin Yip
supporting information, p. 3441 - 3445 (2018/09/29)
Dichloroacetophenone is a pyruvate dehydrogenase kinase 1 (PDK1) inhibitor with suboptimal kinase selectivity. Herein, we report the synthesis and biological evaluation of a series of novel dichloroacetophenones. Structure-activity relationship analyses (SARs) enabled us to identify three potent compounds, namely 54, 55, and 64, which inhibited PDK1 function, activated pyruvate dehydrogenase complex, and reduced the proliferation of NCI-H1975 cells. Mitochondrial bioenergetics assay suggested that 54, 55, and 64 enhanced the oxidative phosphorylation in cancer cells, which might contribute to the observed anti-proliferation effects. Collectively, these results suggested that 54, 55, and 64 could be promising compounds for the development of potent PDK1 inhibitors.
Chemoselective Reduction of Trichloromethyl Compounds to gem-Dichloromethyl Groups Following Appel's Reaction Protocol
Romero-Reyes, Moises A.,Zaragoza-Galicia, Ivann,Olivo, Horacio F.,Romero-Ortega, Moises
, p. 9515 - 9519 (2016/10/14)
A simple and easy reduction of trichloroacetyl compounds following the modification of Appel's reaction protocol, using triphenylphosphine and methanol, afforded the corresponding dichloroacetyl compounds, with the exception of trichloroacetylmorpholine,
Ozone-mediated Nitration of Aromatic Ketones and Related Compounds with Nitrogen Dioxide
Suzuki, Hitomi,Murashima, Takashi
, p. 903 - 908 (2007/10/02)
Alkyl aryl ketones react smoothly with nitrogen dioxide at low temperatures in the presence of ozone to give ortho- and meta-nitro derivatives as the principal products, the former usually being predominant (ortho:meta = 1.1-3.8:1.0).No attack was observed on the alkyl side chains.
