111359-62-7Relevant articles and documents
A convenient and efficient synthesis of 2,6-dihydroxynaphthalene
Cui, Jia-Hua,Li, Shao-Shun
, p. 675 - 677 (2012)
A convenient synthesis of 2,6-dihydroxynaphthalene from 6-bromo-2-naphthol has been achieved with high overall yield (52%) and good purity (95.7%) based on the conversion of 6-(methoxymethoxy)-2-naphthaldehyde to 6- (methoxymethoxy)-2-naphthol formate by a Baeyer-Villiger oxidation- rearrangement. Compared with the reported methods, the reaction conditions are milder and the work-up of each step is much simpler. Moreover, 6-bromo-2-naphthol as the starting material for the synthesis is readily available.
Synthesis and Biochemical Evaluation of Noncyclic Nucleotide Exchange Proteins Directly Activated by cAMP 1 (EPAC1) Regulators
Wang, Pingyuan,Luchowska-Stańska, Urszula,Van Basten, Boy,Chen, Haiying,Liu, Zhiqing,Wiejak, Jolanta,Whelan, Padraic,Morgan, David,Lochhead, Emma,Barker, Graeme,Rehmann, Holger,Yarwood, Stephen J.,Zhou, Jia
, p. 5159 - 5184 (2020/06/03)
Exchange proteins directly activated by cAMP (EPAC) play a central role in various biological functions, and activation of the EPAC1 protein has shown potential benefits for the treatment of various human diseases. Herein, we report the synthesis and biochemical evaluation of a series of noncyclic nucleotide EPAC1 activators. Several potent EPAC1 binders were identified including 25g, 25q, 25n, 25u, 25e, and 25f, which promote EPAC1 guanine nucleotide exchange factor activity in vitro. These agonists can also activate EPAC1 protein in cells, where they exhibit excellent selectivity toward EPAC over protein kinase A and G protein-coupled receptors. Moreover, 25e, 25f, 25n, and 25u exhibited improved selectivity toward activation of EPAC1 over EPAC2 in cells. Of these, 25u was found to robustly inhibit IL-6-activated signal transducer and activator of transcription 3 (STAT3) and subsequent induction of the pro-inflammatory vascular cell adhesion molecule 1 (VCAM1) cell-adhesion protein. These novel EPAC1 activators may therefore act as useful pharmacological tools for elucidation of EPAC function and promising drug leads for the treatment of relevant human diseases.
Iron-Catalyzed C-Allylating Partial Dearomatization of Naphthols
Heid, Berenice,Plietker, Bernd
supporting information, p. 340 - 350 (2016/01/28)
The iron complex Bu4N[Fe(CO)3(NO)] (TBA[Fe]) catalyzes the intermolecular allylation of naphthol derivatives to give the corresponding partially dearomatized allylated chromenones in good to excellent yields. The scope and limitations are reported. An efficient decarboxylative intramolecular C-allylation, starting from allyl naphthyl carbonates, was developed. From a mechanistic point of view, the overall process is the result of a fast O-allylation followed by a sigmatropic rearrangement to the desired product.
