2146146-58-7Relevant academic research and scientific papers
P -Toluenesulfonic Acid Induced Conversion of Fluorinated Trimethylsilylethynylanilines into Aminoacetophenones: Versatile Precursors for the Synthesis of Benzoazaheterocycles
Politanskaya, Larisa,Tretyakov, Evgeny
, p. 555 - 564 (2017/11/03)
A simple and efficient approach to the synthesis of fluorinated amino-substituted acetophenones in good to excellent yields is reported. The heart of the proposed method consists of conversion of a Me 3 Si-C≡C- moiety into a MeC(=O)- group in the presence of p -tolu ene sulfonic acid (p -TSA) passing a stage of ethynylaniline formation. The reaction is metal-free, proceeds under mild conditions, and uses readily available starting compounds (trimethylsilylarylacetylene derivatives). The reaction provides access to amino-substituted acetophenones, which may serve as precursors for the synthesis of polyfluorinated azaheterocycles, having potential anticarcinogenic activity.
LpxC Inhibitors: Design, Synthesis, and Biological Evaluation of Oxazolidinones as Gram-negative Antibacterial Agents
Kurasaki, Haruaki,Tsuda, Kosuke,Shinoyama, Mariko,Takaya, Noriko,Yamaguchi, Yuko,Kishii, Ryuta,Iwase, Kazuhiko,Ando, Naoki,Nomura, Masahiro,Kohno, Yasushi
supporting information, p. 623 - 628 (2016/07/06)
Herein we report a scaffold-hopping approach to identify a new scaffold with a zinc binding headgroup. Structural information was used to give novel oxazolidinone-based LpxC inhibitors. In particular, the most potent compound, 23j, showed a low efflux ratio, nanomolar potencies against E. coli LpxC enzyme, and excellent antibacterial activity against E. coli and K. pneumoniae. Computational docking was used to predict the interaction between 23j and E. coli LpxC, suggesting that the interactions with C207 and C63 contribute to the strong activity. These results provide new insights into the design of next-generation LpxC inhibitors.
