174574-69-7Relevant articles and documents
Indolylglycines Backbones in the Synthesis of Enantiopure 3,3-Spiroindolenines, Indolyl Tetracyclic Hemiaminals, and 3-Indolyl-maleimides Frameworks
Markus, Jozef,Ferko, Branislav,Berke?, Du?an,Moncol, Ján,Lawson, Ata Martin,Othman, Mohamed,Da?ch, Adam
, p. 5662 - 5677 (2019/08/08)
This paper describes the synthesis of novel N-substituted 3-indolylglycines (3IGs), in high yields and optical purity via three-component Mannich reaction (3CR) of indole and free glyoxylic acid in the presence of primary and secondary aliphatic amines. By using this efficient approach, a series of racemic 3-indolylglycines (3IGs) as well as the optically pure (S)-3-indolylglycine ((S)-3IG) in multigram synthesis using (R-1-phenylethylamine ((R)-α-PEA) as chiral pool were synthetized. In parallel investigations, 3IGs were used as the starting material for the highly stereoselective synthesis of spiroindolenines bearing three controlled contiguous stereogenic centers. Despite our expectations, the N-chloroacetyl esters of 3IGs did not provide the expected spiroindolenine derivatives but led us to the discovery of a new methodology for the preparation of 3-indolylmaleimides (3IMs); compounds known for their broad range of important biological and fluorescence activities.
Discovery and structural insight of a highly selective protein kinase inhibitor hit through click chemistry
Gu, Guoxian,Wang, Huihui,Liu, Pi,Fu, Chenzeng,Li, Zhonghua,Cao, Xuefeng,Li, Yunping,Fang, Qinghong,Xu, Feng,Shen, Jie,Wang, Peng George
supporting information; experimental part, p. 2788 - 2790 (2012/04/23)
Novel bisaryl maleimide derivatives to mimic natural kinase inhibitors were prepared through click chemistry. A highly selective hit was discovered in a 124-kinase-assay, and docking studies revealed a π-π stacking interaction with the Phe67 at the P-loop of GSK-3β kinase. The Royal Society of Chemistry 2012.
Synthesis of new aza-analogs of staurosporine, K-252a and rebeccamycin by nucleophilic opening of C2-symmetric bis-aziridines
Delarue-Cochin, Sandrine,McCort-Tranchepain, Isabelle
supporting information; experimental part, p. 706 - 716 (2009/06/19)
Stable, water-soluble aminosugar staurosporine, K-252a and rebeccamycin analogs have been prepared by nucleophilic opening of C2-symmetric N-activated bis-aziridines by bis-indolylmaleimides. This divergent strategy allows the synthesis of unsymmetrical substituted derivatives and provides an easy access to the piperidine and pyrrolidine analogs.
