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Nanoporous Gold Catalyst for the Oxidative N‐Dealkylation of Drug Molecules: A Method for Synthesis of N‐Dealkylated Metabolites
Author(s) -
Alipour Najmi Ali,
JafariyehYazdi Elchin,
Hadian Mojgan,
Hermans Jos,
Bischoff Rainer,
Yue Jun,
Dömling Alexander,
Wittstock Arne,
Permentier Hjalmar P.
Publication year - 2022
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.202200040
Subject(s) - catalysis , chemistry , adme , alkylation , combinatorial chemistry , nanoporous , molecule , drug , demethylation , organic chemistry , biochemistry , pharmacology , in vitro , medicine , gene expression , dna methylation , gene
Abstract A novel method for the selective catalytic N‐dealkylation of drug molecules on a nanoporous gold (NPG) catalyst producing valuable N‐dealkylated metabolites and intermediates is described. Drug metabolites are important chemical entities at every stage of drug discovery and development, from exploratory discovery to clinical development, providing the safety profiles and the ADME (adsorption, distribution, metabolism, and elimination) of new drug candidates. Synthesis was carried out in aqueous solution at 80 °C using air (oxygen source) as oxidant, in single step with good isolated yields. Different examples examined in this study showed that aerobic catalytic N‐dealkylation of drug molecules on NPG has a broad scope supporting N‐deethylation, N‐deisopropylation and N‐demethylation, converting either 3° amines to 2° amines, or 2° amines to 1° amines.