Affiliation:
1. Laboratoire Hétérochimie Fondamentale et Appliquée UMR CNRS 5069 Université Toulouse III – Paul Sabatier 118 route de Narbonne 31062 Toulouse Cedex 9 France
2. Centre RAPSODEE Université de Toulouse IMT Mines Albi, UMR CNRS 5302 Campus Jarlard 81013 Albi Cedex 9 France
3. Laboratoire des IMRCP Université de Toulouse CNRS UMR 5623 Université Toulouse III – Paul Sabatier 118 route de Narbonne 31062 Toulouse Cedex 9 France
Abstract
AbstractTerpene‐derived alkaloids show a variety of biological activities, including antioxidant, anti‐inflammatory, antimicrobial and cytotoxicity effects. In this work, homologated monoterpene amines have been prepared via a rhodium‐catalyzed hydroaminomethylation of biomass‐based alkenes, such as (R)‐limonene, linalool, myrcene and camphene, in combination with secondary amines of aliphatic and aromatic nature, namely morpholine and N‐methylaniline, leading to highly chemo‐ and regioselective processes. The as‐prepared amines were obtained in 50–99 % overall yields, and in vitro tested on a human colon cancer cell line (HCT‐116) to evaluate their cytotoxic potential. The lead compound of the series (3 a) showed cytotoxicity in the micromolar range (IC50 52.46 μM) via the induction of cell death by apoptosis, paving the way towards further structure‐activity relationship studies.
Funder
Université Toulouse III - Paul Sabatier
Centre National de la Recherche Scientifique