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Issue 6, 2017
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Pyrazolo[3,4-d]pyrimidines as sigma-1 receptor ligands for the treatment of pain. Part 1: 4-acylamino derivatives

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Abstract

The synthesis of a new series of 4-acylaminopyrazolo[3,4-d]pyrimidines active on the sigma-1 receptor (σ1R) is reported. Compounds were efficiently prepared using a two to three step process starting from commercially available 1H-pyrazolo[3,4-d]pyrimidin-4-amine. A SAR study shows that the σ1R requires the presence of relatively highly lipophilic substituents at opposite sides of the central scaffold, while selectivity versus the σ2R can be improved by shortening the distance of the basic nitrogen to it. Compound 9a was among the most active and selective in vitro derivatives and exhibited potent antinociceptive properties in several pain models in mice, indicating its antagonistic behaviour.

Graphical abstract: Pyrazolo[3,4-d]pyrimidines as sigma-1 receptor ligands for the treatment of pain. Part 1: 4-acylamino derivatives

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Publication details

The article was received on 16 Feb 2017, accepted on 07 Apr 2017 and first published on 20 Apr 2017


Article type: Research Article
DOI: 10.1039/C7MD00077D
Citation: Med. Chem. Commun., 2017,8, 1235-1245
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    Pyrazolo[3,4-d]pyrimidines as sigma-1 receptor ligands for the treatment of pain. Part 1: 4-acylamino derivatives

    J. L. Díaz, J. Corbera, R. Cuberes, M. Contijoch, R. Enrech, S. Yeste, A. Montero, A. Dordal, X. Monroy and C. Almansa, Med. Chem. Commun., 2017, 8, 1235
    DOI: 10.1039/C7MD00077D

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