83472-62-2Relevant academic research and scientific papers
Design, synthesis, biological evaluation and cellular imaging of imidazo[4,5-b]pyridine derivatives as potent and selective TAM inhibitors
Baladi, Tom,Aziz, Jessy,Dufour, Florent,Abet, Valentina,Stoven, Véronique,Radvanyi, Fran?ois,Poyer, Florent,Wu, Ting-Di,Guerquin-Kern, Jean-Luc,Bernard-Pierrot, Isabelle,Garrido, Sergio Marco,Piguel, Sandrine
, p. 5510 - 5530 (2018/10/15)
The TAM kinase family arises as a new effective and attractive therapeutic target for cancer therapy, autoimmune and viral diseases. A series of 2,6-disubstituted imidazo[4,5-b]pyridines were designed, synthesized and identified as highly potent TAM inhib
Microwave-Assisted C-2 Direct Alkenylation of Imidazo[4,5-b]pyridines: Access to Fluorescent Purine Isosteres with Remarkably Large Stokes Shifts
Baladi, Tom,Granzhan, Anton,Piguel, Sandrine
, p. 2421 - 2434 (2016/06/01)
We describe herein the first C-2 direct alkenylation of the valuable 3H-imidazo[4,5-b]pyridine promoted by microwave-assisted Pd/Cu co-catalysis. The reaction is rapid and compatible with a wide range of functional groups either on the imidazo[4,5-b]pyridine ring or on the styryl bromides thereby leading to the isolation of 23 compounds with moderate to good yields. The relevance of this method is demonstrated by its application to the synthesis of new cross-conjuguated push-pull 2-vinyl- and 2-alkynylimidazo[4,5-b]pyridines characterized by satisfactory fluorescence quantum yields and remarkable solvatofluorochromic properties.
Direct Alkynylation of 3H-Imidazo[4,5-b]pyridines Using gem-Dibromoalkenes as Alkynes Source
Aziz, Jessy,Baladi, Tom,Piguel, Sandrine
, p. 4122 - 4133 (2016/06/09)
C2 direct alkynylation of 3H-imidazo[4,5-b]pyridine derivatives is explored for the first time. Stable and readily available 1,1-dibromo-1-alkenes, electrophilic alkyne precursors, are used as coupling partners. The simple reaction conditions include an inexpensive copper catalyst (CuBr·SMe2 or Cu(OAc)2), a phosphine ligand (DPEphos) and a base (LiOtBu) in 1,4-dioxane at 120 °C. This C-H alkynylation method revealed to be compatible with a variety of substitutions on both coupling partners: heteroarenes and gem-dibromoalkenes. This protocol allows the straightforward synthesis of various 2-alkynyl-3H-imidazo[4,5-b]pyridines, a valuable scaffold in drug design.
