Synthesis of bioorganometallic nanomolar-potent CB2 agonists containing a ferrocene unit
Synthesis of bioorganometallic nanomolar-potent CB2 agonists containing a ferrocene unit
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.
3361-3368
Sansook, Supojjanee
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Tuo, Wei
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Lemaire, Lucas
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Tourteau, Aurélien
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Barczyk, Amélie
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Dezitter, Xavier
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Klupsch, Frédérique
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Leleu-Chavain, Natascha
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Tizzard, Graham J.
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Coles, Simon J
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Millet, Régis
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Spencer, John
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10 October 2016
Sansook, Supojjanee
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Tuo, Wei
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Lemaire, Lucas
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Tourteau, Aurélien
8aff7153-e0a3-40af-baaa-0f8cbbef070b
Barczyk, Amélie
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Dezitter, Xavier
f2cbc72d-c925-436a-90ca-3c8e02152eda
Klupsch, Frédérique
8abf0455-c8ac-4e54-b6e1-7981f6214854
Leleu-Chavain, Natascha
fce9b89e-6279-40d2-82a5-ea831c3c19e4
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Coles, Simon J
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Millet, Régis
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Spencer, John
a3cf55cd-a4c7-4af6-b16c-96c8fb8c4cf4
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 and Spencer, John
(2016)
Synthesis of bioorganometallic nanomolar-potent CB2 agonists containing a ferrocene unit.
Organometallics, 35 (19), .
(doi:10.1021/acs.organomet.6b00575).
Abstract
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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e-pub ahead of print date: 22 September 2016
Published date: 10 October 2016
Identifiers
Local EPrints ID: 403974
URI: http://eprints.soton.ac.uk/id/eprint/403974
ISSN: 0276-7333
PURE UUID: aa206c17-384b-49cc-9544-154ffb2a3352
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Date deposited: 19 Dec 2016 11:22
Last modified: 16 Mar 2024 03:22
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Contributors
Author:
Supojjanee Sansook
Author:
Wei Tuo
Author:
Lucas Lemaire
Author:
Aurélien Tourteau
Author:
Amélie Barczyk
Author:
Xavier Dezitter
Author:
Frédérique Klupsch
Author:
Natascha Leleu-Chavain
Author:
Régis Millet
Author:
John Spencer
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