1-Benzhydryl-3-phenylurea and 1-benzhydryl-3-phenylthiourea derivatives: New templates among the CB1 cannabinoid receptor inverse agonists

Giulio G. Muccioli; Johan Wouters; Gerhard K E Scriba; Wolfgang Poppitz; Jacques H. Poupaert; Didier M. Lambert

doi:10.1021/jm0503906

1-Benzhydryl-3-phenylurea and 1-benzhydryl-3-phenylthiourea derivatives: New templates among the CB₁ cannabinoid receptor inverse agonists

Giulio G. Muccioli, Johan Wouters, Gerhard K E Scriba, Wolfgang Poppitz, Jacques H. Poupaert, Didier M. Lambert

Unite de recherche en chimie physique, theorique et structurale

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

Résumé

New 1-benzhydryl-3-phenylurea derivatives and their 1-benzhydryl-3- phenylthiourea isosteres were synthesized and evaluated for their human CB ₁ and CB₂ cannabinoid receptor affinity. These compounds proved to be selective CB₁ cannabinoid receptor ligands, acting as inverse agonists in a [³⁵S]-GTPγS assay. The affinity of 3,5,5′-triphenylimidazolidine-2,4-dione and 3,5,5′-triphenyl-2- thioxoimidazolidin-4-one derivatives, possessing the 1-benzhydryl-3-phenylurea and 1-benzhydryl-3-phenylthiourea moiety, respectively, was also evaluated. In conclusion, the 1-benzhydryl-3-phenylurea scaffold seems to be a new interesting template of CB₁ cannabinoid receptor inverse agonists.

langue originale	Anglais
Pages (de - à)	7486-7490
Nombre de pages	5
journal	Journal of Medicinal Chemistry
Volume	48
Numéro de publication	23
Les DOIs	https://doi.org/10.1021/jm0503906
Etat de la publication	Publié - 17 nov. 2005

Accès au document

10.1021/jm0503906

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Contient cette citation

@article{9916ffd2c93549dab1736d710c7f91cd,

title = "1-Benzhydryl-3-phenylurea and 1-benzhydryl-3-phenylthiourea derivatives: New templates among the CB1 cannabinoid receptor inverse agonists",

abstract = "New 1-benzhydryl-3-phenylurea derivatives and their 1-benzhydryl-3- phenylthiourea isosteres were synthesized and evaluated for their human CB 1 and CB2 cannabinoid receptor affinity. These compounds proved to be selective CB1 cannabinoid receptor ligands, acting as inverse agonists in a [35S]-GTPγS assay. The affinity of 3,5,5′-triphenylimidazolidine-2,4-dione and 3,5,5′-triphenyl-2- thioxoimidazolidin-4-one derivatives, possessing the 1-benzhydryl-3-phenylurea and 1-benzhydryl-3-phenylthiourea moiety, respectively, was also evaluated. In conclusion, the 1-benzhydryl-3-phenylurea scaffold seems to be a new interesting template of CB1 cannabinoid receptor inverse agonists.",

author = "Muccioli, {Giulio G.} and Johan Wouters and Scriba, {Gerhard K E} and Wolfgang Poppitz and Poupaert, {Jacques H.} and Lambert, {Didier M.}",

year = "2005",

month = nov,

day = "17",

doi = "10.1021/jm0503906",

language = "English",

volume = "48",

pages = "7486--7490",

journal = "Journal of Medicinal Chemistry",

issn = "0022-2623",

publisher = "American Chemical Society",

number = "23",

}

1-Benzhydryl-3-phenylurea and 1-benzhydryl-3-phenylthiourea derivatives: New templates among the CB₁ cannabinoid receptor inverse agonists. / Muccioli, Giulio G.; Wouters, Johan; Scriba, Gerhard K E et al.
Dans: Journal of Medicinal Chemistry, Vol 48, Numéro 23, 17.11.2005, p. 7486-7490.

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

TY - JOUR

T1 - 1-Benzhydryl-3-phenylurea and 1-benzhydryl-3-phenylthiourea derivatives

T2 - New templates among the CB1 cannabinoid receptor inverse agonists

AU - Muccioli, Giulio G.

AU - Wouters, Johan

AU - Scriba, Gerhard K E

AU - Poppitz, Wolfgang

AU - Poupaert, Jacques H.

AU - Lambert, Didier M.

PY - 2005/11/17

Y1 - 2005/11/17

N2 - New 1-benzhydryl-3-phenylurea derivatives and their 1-benzhydryl-3- phenylthiourea isosteres were synthesized and evaluated for their human CB 1 and CB2 cannabinoid receptor affinity. These compounds proved to be selective CB1 cannabinoid receptor ligands, acting as inverse agonists in a [35S]-GTPγS assay. The affinity of 3,5,5′-triphenylimidazolidine-2,4-dione and 3,5,5′-triphenyl-2- thioxoimidazolidin-4-one derivatives, possessing the 1-benzhydryl-3-phenylurea and 1-benzhydryl-3-phenylthiourea moiety, respectively, was also evaluated. In conclusion, the 1-benzhydryl-3-phenylurea scaffold seems to be a new interesting template of CB1 cannabinoid receptor inverse agonists.

AB - New 1-benzhydryl-3-phenylurea derivatives and their 1-benzhydryl-3- phenylthiourea isosteres were synthesized and evaluated for their human CB 1 and CB2 cannabinoid receptor affinity. These compounds proved to be selective CB1 cannabinoid receptor ligands, acting as inverse agonists in a [35S]-GTPγS assay. The affinity of 3,5,5′-triphenylimidazolidine-2,4-dione and 3,5,5′-triphenyl-2- thioxoimidazolidin-4-one derivatives, possessing the 1-benzhydryl-3-phenylurea and 1-benzhydryl-3-phenylthiourea moiety, respectively, was also evaluated. In conclusion, the 1-benzhydryl-3-phenylurea scaffold seems to be a new interesting template of CB1 cannabinoid receptor inverse agonists.

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