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α2-Adrenoreceptors Profile Modulation. 3. (R)-(+)-m-Nitrobiphenyline, a New Efficient and α2C-Subtype Selective Agonist

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journal contribution
posted on 09.08.2007, 00:00 by Pierre-Antoine Crassous, Claudia Cardinaletti, Antonio Carrieri, Bruno Bruni, Massimo Di Vaira, Francesco Gentili, Francesca Ghelfi, Mario Giannella, Hervé Paris, Alessandro Piergentili, Wilma Quaglia, Stéphane Schaak, Cristian Vesprini, Maria Pigini
To assess the stereochemical requirements for efficient α2C-adrenoreceptor activation, the enantiomeric forms of m-nitrobiphenyline [(±)-5] were prepared and tested on cells expressing the human α2-adrenoreceptor subtypes. The importance of chirality was confirmed, since the enantiomer (R)-(+)-5 was much more efficient than (S)-(−)-5 in producing α2C-activation. Surprising reversal of enantioselectivity was observed with respect to structurally similar biphenyline [(±)-1] whose (S)-(−)-form proved the preferred α2C-configuration.