104163-34-0Relevant articles and documents
Convenient one-pot methodology for the primary aminomethylation of electron rich heterocycles
Katritzky,Wang,Yang
, p. 2631 - 2637 (1995)
Primary aminomethyl groups were introduced into the 2-position of electron rich heterocycles in moderate to good yields by a one-pot sequence involving lithiation, transmetalation into an organozinc reagent and treatment with 1-(triphenylphosphoroylideneaminomethyl)benzotriazole (betmip).
Development of Glucose Regulated Protein 94-Selective Inhibitors Based on the BnIm and Radamide Scaffold
Crowley, Vincent M.,Khandelwal, Anuj,Mishra, Sanket,Stothert, Andrew R.,Huard, Dustin J. E.,Zhao, Jinbo,Muth, Aaron,Duerfeldt, Adam S.,Kizziah, James L.,Lieberman, Raquel L.,Dickey, Chad A.,Blagg, Brian S. J.
, p. 3471 - 3488 (2016/05/19)
Glucose regulated protein 94 (Grp94) is the endoplasmic reticulum resident of the heat shock protein 90 kDa (Hsp90) family of molecular chaperones. Grp94 associates with many proteins involved in cell adhesion and signaling, including integrins, Toll-like receptors, immunoglobulins, and mutant myocilin. Grp94 has been implicated as a target for several therapeutic areas including glaucoma, cancer metastasis, and multiple myeloma. While 85% identical to other Hsp90 isoforms, the N-terminal ATP-binding site of Grp94 possesses a unique hydrophobic pocket that was used to design isoform-selective inhibitors. Incorporation of a cis-amide bioisostere into the radamide scaffold led to development of the original Grp94-selective inhibitor, BnIm. Structure-activity relationship studies have now been performed on the aryl side chain of BnIm, which resulted in improved analogues that exhibit better potency and selectivity for Grp94. These analogues also manifest superior antimigratory activity in a metastasis model as well as enhanced mutant myocilin degradation in a glaucoma model compared to BnIm.
Functionalization of photochromic dithienylmaleimides
Wutz,Falenczyk,Kuzmanovic,K?nig
, p. 18075 - 18086 (2015/03/04)
Photochromic dithienylmaleimides are well known molecular switches, but for applications the suitable functionalization of the photochromic scaffold is required. We report here synthetic routes to dithienylmaleimides, which are functionalized at three different positions: at each of the thiophene moieties and the maleimide nitrogen. A Perkin-type condensation of two thiophene precursors is used as the key step to assemble the maleimide core, which allows the synthesis of non-symmetrically substituted dithienylmaleimides, such as photochromic amino acids. A different approach to the maleimide core is provided by the reaction of a dithienylmaleic anhydride with amines or hydrazides leading to maleimide protected dithienylmaleimides and photochromic labeled natural amino acids. The photochromic properties of the new photoswitches were investigated showing reversible photochromism in polar organic solvents. This journal is
