Alpha2-adrenoreceptors profile modulation. 3.1 (R)-(+)-m-nitrobiphenyline, a new efficient and alpha2C-subtype selective agonist. - Archive ouverte HAL Access content directly
Journal Articles Journal of Medicinal Chemistry Year : 2007

Alpha2-adrenoreceptors profile modulation. 3.1 (R)-(+)-m-nitrobiphenyline, a new efficient and alpha2C-subtype selective agonist.

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Abstract

To assess the stereochemical requirements for efficient alpha2C-adrenoreceptor activation, the enantiomeric forms of m-nitrobiphenyline [(+/-)-5] were prepared and tested on cells expressing the human alpha2-adrenoreceptor subtypes. The importance of chirality was confirmed, since the enantiomer (R)-(+)-5 was much more efficient than (S)-(-)-5 in producing alpha2C-activation. Surprising reversal of enantioselectivity was observed with respect to structurally similar biphenyline [(+/-)-1] whose (S)-(-)-form proved the preferred alpha2C-configuration.

Dates and versions

inserm-00409859 , version 1 (13-08-2009)

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Pierre-Antoine Crassous, Claudia Cardinaletti, Antonio Carrieri, Bruno Bruni, Massimo Di Vaira, et al.. Alpha2-adrenoreceptors profile modulation. 3.1 (R)-(+)-m-nitrobiphenyline, a new efficient and alpha2C-subtype selective agonist.. Journal of Medicinal Chemistry, 2007, 50 (16), pp.3964-8. ⟨10.1021/jm061487a⟩. ⟨inserm-00409859⟩
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