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Synthesis and biological evaluation of ferrocene-based cannabinoid receptor 2 ligands

Synthesis and biological evaluation of ferrocene-based cannabinoid receptor 2 ligands
Synthesis and biological evaluation of ferrocene-based cannabinoid receptor 2 ligands
Ferrocene analogues of known fatty acid amide hydrolase inhibitors and CB2 ligands have been synthesized and characterized spectroscopically and crystallographically. The resulting bioorganometallic isoxazoles were assayed for their effects on CB1 and CB2 receptors as well as on FAAH. None had any FAAH activity but compound 3, 5-(2-(pentyloxy)phenyl)-N-ferrocenylisoxazole- 3-carboxamide, was found to be a potent CB2 ligand (Ki = 32.5 nM).
isoxazole, ferrocene, cannabinoids, FAAH
1756-8919
Sansook, Supojjanee
b5e89a15-b73e-4b73-b985-e0725f3f4d8a
Tuo, Wei
dfaea1ae-ded9-4eea-b3b1-fb7f1089549c
Bollier, Mélanie
c78ccfa5-acff-4fd5-82d4-bf8b8924ab88
Barczyk, Amélie
8c442017-1e79-4033-afc4-88b51572113d
Dezitter, Xavier
f2cbc72d-c925-436a-90ca-3c8e02152eda
Klupsch, Fredérique
02b3f8e9-e9d4-42ba-9132-74d9d6fea778
Leleu-Chavain, Natascha
dbf21857-f59c-4412-a995-6ab1c89550e6
Farce, Amaury
120c8529-fcf4-4bc9-bc74-acf55189a1e2
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Spencer, John
a3cf55cd-a4c7-4af6-b16c-96c8fb8c4cf4
Millet, Régis
034f1a84-30ad-4f1d-9260-a85a1aa1bcd6
Sansook, Supojjanee
b5e89a15-b73e-4b73-b985-e0725f3f4d8a
Tuo, Wei
dfaea1ae-ded9-4eea-b3b1-fb7f1089549c
Bollier, Mélanie
c78ccfa5-acff-4fd5-82d4-bf8b8924ab88
Barczyk, Amélie
8c442017-1e79-4033-afc4-88b51572113d
Dezitter, Xavier
f2cbc72d-c925-436a-90ca-3c8e02152eda
Klupsch, Fredérique
02b3f8e9-e9d4-42ba-9132-74d9d6fea778
Leleu-Chavain, Natascha
dbf21857-f59c-4412-a995-6ab1c89550e6
Farce, Amaury
120c8529-fcf4-4bc9-bc74-acf55189a1e2
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Spencer, John
a3cf55cd-a4c7-4af6-b16c-96c8fb8c4cf4
Millet, Régis
034f1a84-30ad-4f1d-9260-a85a1aa1bcd6

Sansook, Supojjanee, Tuo, Wei, Bollier, Mélanie, Barczyk, Amélie, Dezitter, Xavier, Klupsch, Fredérique, Leleu-Chavain, Natascha, Farce, Amaury, Tizzard, Graham J., Coles, Simon J., Spencer, John and Millet, Régis (2018) Synthesis and biological evaluation of ferrocene-based cannabinoid receptor 2 ligands. Future Medicinal Chemistry, 10 (6). (doi:10.4155/fmc-2017-0200).

Record type: Article

Abstract

Ferrocene analogues of known fatty acid amide hydrolase inhibitors and CB2 ligands have been synthesized and characterized spectroscopically and crystallographically. The resulting bioorganometallic isoxazoles were assayed for their effects on CB1 and CB2 receptors as well as on FAAH. None had any FAAH activity but compound 3, 5-(2-(pentyloxy)phenyl)-N-ferrocenylisoxazole- 3-carboxamide, was found to be a potent CB2 ligand (Ki = 32.5 nM).

Text final CB2 FMC paper - Accepted Manuscript
Restricted to Repository staff only until 11 March 2019.
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More information

Accepted/In Press date: 11 December 2017
e-pub ahead of print date: 8 February 2018
Published date: 1 March 2018
Keywords: isoxazole, ferrocene, cannabinoids, FAAH

Identifiers

Local EPrints ID: 416391
URI: https://eprints.soton.ac.uk/id/eprint/416391
ISSN: 1756-8919
PURE UUID: e7beac9b-ee1d-4fe1-8248-2b1c70436093
ORCID for Graham J. Tizzard: ORCID iD orcid.org/0000-0002-1577-5779
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 15 Dec 2017 17:30
Last modified: 22 Mar 2018 17:31

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Contributors

Author: Supojjanee Sansook
Author: Wei Tuo
Author: Mélanie Bollier
Author: Amélie Barczyk
Author: Xavier Dezitter
Author: Fredérique Klupsch
Author: Natascha Leleu-Chavain
Author: Amaury Farce
Author: Simon J. Coles ORCID iD
Author: John Spencer
Author: Régis Millet

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