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Synthesis of novel 2-(1-adamantanylcarboxamido)thiophene derivatives. Selective cannabinoid type 2 (CB2) receptor agonists as potential agents for the treatment of skin inflammatory disease.

Abstract：

:A set of CB2R ligands, based on the thiophene scaffold, was synthesized and evaluated in in vitro assays. Compounds 8c-i, k, l, bearing the 3-carboxylate and 2-(adamantan-1-yl)carboxamido groups together with apolar alkyl/aryl substituents at 5-position or at 4- and 5-positions of the thiophene ring possess high CB2R affinity at low nanomolar concentration, good receptor selectivity, and agonistic functional activity. The full agonist 8g, showing the best balance between receptor affinity and selectivity, was tested in vitro in an experimental model of allergic contact dermatitis and proved to be able to block the release of MCP-2 in HaCaT cells at 10 μM concentration.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Mugnaini C,Rabbito A,Brizzi A,Palombi N,Petrosino S,Verde R,Di Marzo V,Ligresti A,Corelli F

doi

10.1016/j.ejmech.2018.09.070

subject

Has Abstract

pub_date

2019-01-01 00:00:00

pages

239-251

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(18)30857-2

journal_volume

161

pub_type

杂志文章

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