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Design, Synthesis, and Cholinesterase Inhibitory Activity of 4‐Substituted‐6‐(trihalomethyl)‐2‐methylsulfanyl Pyrimidines
Author(s) -
Da Silva Andreia M. P. W.,
Mittersteiner Mateus,
Da Silva Fabio M.,
D'Avila Fernanda,
Nogara Pablo A.,
Nogara Karise F.,
Rocha João B. T.,
Bonacorso Helio G.,
Martins Marcos A. P.,
Zanatta Nilo
Publication year - 2021
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202100125
Subject(s) - chemistry , moiety , pyrimidine , nucleophile , cholinesterase , acetylcholinesterase , inhibitory postsynaptic potential , stereochemistry , ring (chemistry) , aché , butyrylcholinesterase , combinatorial chemistry , enzyme , organic chemistry , catalysis , pharmacology , medicine , neuroscience , biology
A chemoselective approach is reported for the synthesis of 4‐(bromo/chloro)methyl‐2‐methylsulfanyl‐6‐trihalomethyl pyrimidines and subsequent nucleophilic substitution of the halomethyl moiety with aminoalcohols. The final compounds were choline derivatives (bearing a pyrimidine ring). These were tested as AChE and BChE inhibitors, and presented IC 50 values in the range of 13.8–81.6 μM. Remarkably, the trichloromethyl pyrimidines were the most active compounds. Docking studies and ADMET properties are also reported.