37687-57-3Relevant articles and documents
Synthesis, biological evaluation and molecular modeling studies of substitutedN-benzyl-2-phenylethanamines as cholinesterase inhibitors
Carmona-Viglianco, Florencia,Enriz, Ricardo D.,Feresin, Gabriela E.,Garro, Adriana,Kurina-Sanz, Marcela,Orden, Alejandro A.,Parravicini, Oscar,Zaragoza-Puchol, Daniel
, p. 9466 - 9476 (2020/06/17)
In this work, we report the synthesis of a series of derivatives ofN-benzyl-2-phenylethanamine which is the framework of norbelladine, the natural common precursor of the Amaryllidaceae alkaloids. These compounds were assessed in the inhibition of both AChE and BChE which are the enzymes responsible for the breakdown of acetylcholine and hence they constitute targets in the palliative treatment of Alzheimer's disease. In particular, brominated derivatives exhibited the lowest IC50values against AChE. Interestingly, the presence of iodine in one of the aromatic rings highly increased the inhibition of BChE compared to its analogues, with an IC50value similar to that of galantamine, which is the reference compound currently used in the treatment of AD. A possible mechanism of action for these compounds was determined by molecular modeling studies using combined techniques of docking and molecular dynamics simulations.
4',5'-Dichloro-2',7'-dimethoxy-5(6)-carboxyfluorescein (JOE): Synthesis and spectral properties of oligonucleotide conjugates
Tsybulsky, Dmitry A.,Kvach, Maksim V.,Stepanova, Irina A.,Korshun, Vladimir A.,Shmanai, Vadim V.
scheme or table, p. 977 - 984 (2012/03/26)
A convenient procedure for the preparation of the fluorescent dye 4',5'-dichloro-2',7'-dimethoxy-5(6)-carboxyfluorescein (JOE) is reported; the overall yield achieved starting from isovanillin is 10 times higher (40% vs 4%) compared to the known procedure. Isomers (5- and 6-) are easily chromatographically separable as pentafluorophenyl esters of 3′,6′-O-bis(cyclohexylcarbonyl) derivatives. Four non-nucleoside JOE phosphoramidites based on 5- and 6-isomers and flexible 6-aminohexanol (AH) or rigid 4-trans-aminocyclohexanol (ACH) linkers have been prepared and used for oligonucleotide labeling. Spectral and photophysical properties of 5′-JOE-modified oligonucleotides have been studied. Fluorescence quantum yield of the dye correlates with the nature of the linker (rigid vs flexible) and with the presence of dG nucleosides in close proximity to a JOE residue.
Improved synthetic procedures for 4,7,2′,7′-tetrachloro- and 4′,5′-dichloro-2′,7′-dimethoxy-5(and 6)-carboxyfluoresceins
Lyttle, Matthew H.,Carter, Tim G.,Cook, Ronald M.
, p. 45 - 49 (2013/09/07)
Literature syntheses of 4,7,2′,7′-tetrachloro-5(and 6)-carboxyfluorescein ("5 and 6 TET") 1 and 4′,5′-dichloro-2′,7′-dimethoxy-5(and 6)-carboxyfluorescein ("5 and 6 JOE") 2 are reviewed, and new, preparatively useful methods are presented. A three-step synthesis of 1 was developed, which proved to be more efficient than the published seven step synthesis of this compound. The published synthesis of 2 also proved difficult to reproduce, and a better workup of the key intermediate 2-chloro-4-methoxy resorcinol was devised. Isolation of purified single isomers of both dyes is described.