Synthesis of bioorganometallic nanomolar-potent CB2agonists containing a ferrocene unit

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Sansook, Supojjanee ; Tuo, Wei ; Lemaire, Lucas ; Tourteau, Aurélien ; Barczyk, Amélie ; Dezitter, Xavier ; Klupsch, Frédérique ; Leleu-Chavain, Natascha ; Tizzard, Graham J ; Coles, Simon J ; Millet, Régis ; Spencer, John (2016)

A small library of ferrocene-containing amides has been synthesized using standard amide coupling chemistry with ferrocenylamine. Ferrocene analogues of known bioactive adamantylamides were shown to be effective cannabinoid receptor (CB1 and CB2) agonists, displaying, in many cases, single-digit nanomolar potency. Three final ferrocene-containing derivatives have been characterized in the solid state by X-ray crystallography and display intramolecular hydrogen bonding of the type NH---C═O. N-Methylation of the amide, confirmed by X-ray crystallography, leads to both loss of hydrogen bonding and biological activity.
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