180690-86-2Relevant academic research and scientific papers
Synthesis and Structure-Activity Studies of a Series of salicylates as Inhibitors of EGF Receptor-Associated Tyrosine Kinase Activity
Chen, Huixiong,Boiziau, Janine,Parker, Fabienne,Maroun, Rachid,Tocque, Bruno,et al.
, p. 4094 - 4098 (1993)
The synthesis and structure-activity relationships of a series of salicylates and a series of salicylates as inhibitors of EGF receptor-associated tyrosine kinase activity are described.Their inhibitory potency was evaluated in vitro using ER 22 cell membranes (CCL 39 cells transfected with EGF receptor) as an enzyme source and the tridecapeptide RRSrc (RRLIEDAEYAARG) as substrate.Their cellular activity was measured by inhibition of the EGF-stimulated DNA synthesis of ER 22 cells.Chemical modifications were made to analyze the role of the different substituents.The amino series was found to be more active than the imino series.The hydroquinone moiety appears to be essential for tyrosine kinase inhibitory activity in the series of 5-salicylates.Comparison of the imino and amino series by molecular modeling techniques provides further evidence in support of the hypothesis that the important reduced linking chain, CH2NH allows the correct positioning of the 2,5-dihydroxybenzyl ring, possibly in a cis-like conformational arrangement.
Metal-free synthesis of fluorinated indoles enabled by oxidative dearomatization
Vitaku, Edon,Smith, David T.,Njardarson, Jon T.
supporting information, p. 2243 - 2247 (2016/02/18)
Nitrogen heterocycles are found in a majority of approved small-molecule pharmaceuticals, and the number of approved fluorinated drugs is increasing each decade. Therefore, new approaches for accessing fluorinated nitrogen heterocycles are of great significance. A novel, scalable, and metal-free method for accessing a wide range of fluorinated indoles is described. This oxidative-dearomatization-enabled approach assembles 2-trifluoromethyl NH-indole products from simple commercially available anilines with hexafluoroacetylacetone in the presence of an organic oxidant. The nature of the aniline N-capping group is critical for the success of this new reaction. Furthermore, the indole products contain a 3-trifluoroacetyl group, which can be exploited to access a plethora of useful functional groups.
