Clemente, Francesca published the artcilePiperidine Azasugars Bearing Lipophilic Chains: Stereoselective Synthesis and Biological Activity as Inhibitors of Glucocerebrosidase (GCase), Name: (2-Methoxyphenyl)methanamine, the publication is Journal of Organic Chemistry (2021), 86(18), 12745-12761, database is CAplus and MEDLINE.
We report a straightforward synthetic strategy for the preparation of trihydroxypiperidine azasugars, e.g. I, decorated with lipophilic chains at both the nitrogen and the adjacent carbon as potential inhibitors of the lysosomal enzyme glucocerebrosidase (GCase), which is involved in Gaucher disease. The procedure relies on the preparation of C-erythrosyl N-alkylated nitrones reaction of aldehyde and primary amines followed by oxidation of the imines formed in situ with the methyltrioxorhenium catalyst and urea hydrogen peroxide. The addition of octyl-MgBr to nitrone provided access to both epimeric hydroxylamines with opposite configuration at the newly created stereo-center in a stereo-divergent and completely stereoselective way, depending on the absence or presence of BF3·Et2O, and reductive amination. Hydroxypiperidine I was the best ligand for GCase (IC50 = 15μM), in agreement with MD simulations that allowed us to identify the chair conformation corresponding to the best binding affinity.
Journal of Organic Chemistry published new progress about 6850-57-3. 6850-57-3 belongs to ethers-buliding-blocks, auxiliary class Amine,Benzene,Ether, name is (2-Methoxyphenyl)methanamine, and the molecular formula is C8H11NO, Name: (2-Methoxyphenyl)methanamine.
Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem