Synthesis and pharmacological evaluation of chlorinated N-alkyl-3- and -5-(2-hydroxyphenyl)pyrazoles as CB1 cannabinoid ligands

被引：17

作者：

Silva, Vera L. M.

Silva, Artur M. S. ^{[1
]}

Pinto, Diana C. G. A.

Jagerovic, Nadine

Callado, Luis F.

Cavaleiro, Jose A. S.

Elguero, Jose

机构：

[1] Univ Aveiro, Dept Chem, P-3800 Aveiro, Portugal

[2] Inst Quim Med, CSIC, Inst Quim Med, Madrid, Spain

[3] Univ Basque Country, Dept Pharmacol, UPV EHU, Bizkaia, Spain

来源：

MONATSHEFTE FUR CHEMIE | 2007年 / 138卷 / 08期

关键词：

3-and 5-(2-hydroxyphenyl)-N-alkylpyrazoles; chloropyrazoles; NMR spectroscopy; CB1 cannabinoid receptors; radioligand;

D O I：

10.1007/s00706-007-0676-4

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The syntheses of several new 3- and 5-(4-chloro-2-hydroxyphenyl)-5- and -3-(2,4-dichlorophenyl)-1-alkylpyrazoles are reported. These syntheses started from simple chlorophenols, 2,4-dichlorobenzaldehyde or ethyl 2,4-dichlorobenzoate in order to prepare pyrazoles bearing three and four chloro substituents in certain positions. The affinity of these compounds towards the CB1 type cannabinoids receptors was then evaluated in human brain tissues (frontal cortex). The results showed that some of the compounds exhibit affinity towards this kind of receptors in the micromolar range.

引用

页码：797 / 811

页数：15

共 22 条

[1] Molecular rearrangement of some o-acyloxyacetophenones and the mechanism of the production of 3-acylchromones [J].