Nanoporous Gold Catalyst for the Oxidative N-Dealkylation of Drug Molecules: A Method for Synthesis of N-Dealkylated Metabolites

Ali Alipour Najmi, Elchin Jafariyeh-Yazdi, Mojgan Hadian, Jos Hermans, Rainer Bischoff, Jun Yue, Alexander Dömling, Arne Wittstock, Hjalmar P Permentier*

*Corresponding author for this work

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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.

Original languageEnglish
Article numbere202200040
Number of pages4
JournalChemMedChem
Volume17
Issue number11
Early online date2022
DOIs
Publication statusPublished - 3-Jun-2022

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