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Synthesis of bioorganometallic nanomolar-potent CB2agonists containing a ferrocene unit

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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 Spencer
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.

Funding

Royal Thai Government PhD

History

Publication status

  • Published

File Version

  • Accepted version

Journal

Organometallics

ISSN

0276-7333

Publisher

American Chemical Society

Issue

19

Volume

35

Page range

3361-3368

Department affiliated with

  • Chemistry Publications

Full text available

  • Yes

Peer reviewed?

  • Yes

Legacy Posted Date

2016-09-26

First Open Access (FOA) Date

2017-09-23

First Compliant Deposit (FCD) Date

2016-09-26

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