latest CB2 organometallics clean.pdf (604.64 kB)
Synthesis of bioorganometallic nanomolar-potent CB2agonists containing a ferrocene unit
journal contribution
posted on 2023-06-09, 03:06 authored by Supojjanee Sansook, Wei Tuo, Lucas Lemaire, Aurélien Tourteau, Amélie Barczyk, Xavier Dezitter, Frédérique Klupsch, Natascha Leleu-Chavain, Graham J Tizzard, Simon J Coles, Régis Millet, John SpencerJohn SpencerA 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.
Funding
Royal Thai Government PhD
History
Publication status
- Published
File Version
- Accepted version
Journal
OrganometallicsISSN
0276-7333Publisher
American Chemical SocietyExternal DOI
Issue
19Volume
35Page range
3361-3368Department affiliated with
- Chemistry Publications
Full text available
- Yes
Peer reviewed?
- Yes