1029802-02-5Relevant articles and documents
Substituent effects on the basicity (p: K a) of aryl guanidines and 2-(arylimino)imidazolidines: Correlations of pH-metric and UV-metric values with predictions from gas-phase ab initio bond lengths
Dardonville, Christophe,Caine, Beth A.,Navarro De La Fuente, Marta,Martín Herranz, Guillermo,Corrales Mariblanca, Beatriz,Popelier, Paul L. A.
, p. 11016 - 11028 (2017/10/03)
The dissociation constants of two related series of 2-(arylimino)imidazolidine and aryl guanidine α2-adrenoceptor antagonists (35 compounds in total) were measured by potentiometric titrations and by UV-spectrophotometry using the 96-well microtitre plate method. The experimental values obtained using both methods were quite consistent and showed a very good agreement with the pKa values calculated using the AIBLHiCoS methodology, which uses only a single bond length obtained using ab initio calculations at a low level of theory. The prediction power of the imidazolidine and guanidine set of compounds was very good with deviations typically a units, and a mean absolute error (MAE) of 0.23 and 0.29, respectively. The study of the quantitative effect of diverse substituents on the basicity of aryl guanidine and 2-(arylimino)imidazolidine derivatives is useful for medicinal chemists working with biologically relevant guanidine-containing molecules.
Guanidine and 2-aminoimidazoline aromatic derivatives as α2-adrenoceptor antagonists. 2. Exploring alkyl linkers for new antidepressants
Rodriguez, Fernando,Rozas, Isabel,Ortega, Jorge E.,Erdozain, Amaia M.,Meana, J. Javier,Callado, Luis F.
supporting information; experimental part, p. 3304 - 3312 (2009/04/07)
The preparation of a number of (bis)guanidine and (bis)2-aminoimidazoline derivatives as potential α2-adrenoceptor antagonists for the treatment of depression is presented. Human brain tissue was used to measure their affinity toward the α2-adrenoceptors in vitro. Compounds 6b, 8b, 9b, 10b, 15b, 17b, 18b, 20b, and 21b displayed a good affinity (pK i > 7) and were evaluated in in vitro functional [ 35S]GTPγS binding assays in human prefrontal cortex to determine their agonistic or antagonistic activity. Among these compounds, 17b and 20b showed the expected behavior for an antagonist and were subject to in vivo microdialysis experiments in rats. Significantly, these experiments confirmed the antagonistic properties of 17b and 20b, and therefore both compounds can be considered as potential antidepressants.
