3665-51-8Relevant articles and documents
Vilsmeier-Haack reagent: An efficient reagent for the transformation of substituted 1,3-naphthoxazines into xanthene-type dyes
Farat, Oleg K.,Ananyev, Ivan V.,Varenichenko, Svetlana A.,Tatarets, Anatoliy L.,Markov, Victor I.
, p. 2832 - 2842 (2019)
Derivatives of 1,3-naphthoxazines containing from five to seven-membered spiro ring – under Vilsmeier–Haack reaction conditions are rearranged into novel xanthene-type compounds. All synthesized aminochromene derivatives fluoresce in organic solvents with extra large Stokes shifts (100–133 nm). It was found that compounds containing five-membered annulated aliphatic rings in methanol solution have the best spectral characteristics. These compounds have moderate quantum yields of 28.36–28.94%, and extra large Stokes shifts 106 and 115 nm.
Bi-aryl analogues of salicylic acids: Design, synthesis and sar study to ameliorate endoplasmic reticulum stress
Kim, Ye Eun,Kim, Dong Hwan,Choi, Ami,Jang, Seoul,Jeong, Kwiwan,Kim, Young-Mi,Nam, Tae-Gyu
, p. 3593 - 3604 (2021/08/30)
Introduction: Endoplasmic reticulum (ER) stress condition is characterized as the accu-mulation of misfolded or unfolded proteins in lumen of ER. This condition has been implicated in various diseases and pathologies including β-cell apoptosis, Alzheimer’s disease and atherosclerosis. We have reported that hydroxynaphthoic acids (HNA), naphtha-lene analogues of salicylic acid (SA), reduced ER stress. In this study, we explored structural modification to bi-aryl analogues of SA. Methods: Palladium-catalyzed cross-coupling was applied to synthesize bi-aryl analogues of SA. Anti-ER stress activity was monitored by using our cell-based assay system where ER stress is induced by tunicamycin. To monitor ER stress markers, ER stress was induced physiologically relevant palmitate system. Results: Many analogues decreased ER stress signal induced by tunicamycin. Compounds creating dihedral angle between Ar group and SA moiety generally increased the activity but gave some cytotoxicity to indicate the crucial role of flat conformation of aromatic region. The best compound (16e) showed up to almost 6-fold and 90-fold better activity than 3-HNA and tauro-ursodeoxycholic acid, positive controls, respectively. ER stress markers such as p-PERK and p-JNK were accordingly decreased in Western blotting upon treatment of 16e under palmitate-induced condition. Conclusion: Anti-ER stress activity and toxicity profile of bi-aryl analogues of SA could provide a novel platform for potential therapy for protein misfolding diseases.
Method for producing naphthalene carboxylic acid amide compound
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Page/Page column 9, (2008/06/13)
The present invention provides a method for producing a naphthalenecarboxylic acid amide compound represented by formula [1] comprising, reacting a naphthalenecarboxylic acid halide compound represented by formula [2] with ammonium acetate in a solvent having an ether bond. According to the method of the present invention, a naphthalene carboxylic acid amide compound can be obtained at high yield and at low cost.