midazoline Binding Sites (IBS) Profile Modulation:  Key Role of the Bridge in Determining I1-IBS or I2-IBS Selectivity within a Series of 2-Phenoxymethylimidazoline Analogues

Gentili, F.; Bousquet, P.; Brasili, Livio; Dontenwill, M.; Feldman, J.; Ghelfi, F.; Giannella, M.; Piergentili, A.; Quaglia, W.; Pigini, M.

The α- and β-methyl derivatives of 2-phenylethylimidazoline (compounds 7 and 8) and the corresponding enantiomers were prepared and tested with the purpose of studying the role played by the ethylene bridge in modulating I1- and I2-IBS selectivity. The α-methylation appeared to be extremely critical regarding the affinity and selectivity for the I1-IBS subtypes (I1/I2 = 186 for imidazoline 7) and the stereospecificity of interaction (eudismic ratio (S)-(−)-7/(R)-(+)-7 = 5888). Instead, even if in a more limited fashion, the β-methylation tended toward I2-IBS selectivity (I2/I1 = 50 for imidazoline 8). The unsubstituted compound 4 (I2/I1 = 1479) proved to be considerably more potent and selective with respect to I2-IBS subtypes.

midazoline Binding Sites (IBS) Profile Modulation: Key Role of the Bridge in Determining I1-IBS or I2-IBS Selectivity within a Series of 2-Phenoxymethylimidazoline Analogues / F., Gentili; P., Bousquet; Brasili, Livio; M., Dontenwill; J., Feldman; F., Ghelfi; M., Giannella; A., Piergentili; W., Quaglia; M., Pigini. - In: JOURNAL OF MEDICINAL CHEMISTRY. - ISSN 0022-2623. - STAMPA. - 46(2003), pp. 2169-2176.

Data di pubblicazione:	2003
Titolo:	midazoline Binding Sites (IBS) Profile Modulation: Key Role of the Bridge in Determining I1-IBS or I2-IBS Selectivity within a Series of 2-Phenoxymethylimidazoline Analogues
Autore/i:	F., Gentili; P., Bousquet; Brasili, Livio; M., Dontenwill; J., Feldman; F., Ghelfi; M., Giannella; A., Piergentili; W., Quaglia; M., Pigini
Autore/i UNIMORE:	F. Gentili P. Bousquet BRASILI, Livio M. Dontenwill J. Feldman F. Ghelfi M. Giannella A. Piergentili W. Quaglia M. Pigini mostra contributor esterni nascondi contributor esterni
Rivista:	JOURNAL OF MEDICINAL CHEMISTRY
Volume:	46
Pagina iniziale:	2169
Pagina finale:	2176
Codice identificativo Scopus:	2-s2.0-0038248835
Codice identificativo Pubmed:	12747788
Citazione:	midazoline Binding Sites (IBS) Profile Modulation: Key Role of the Bridge in Determining I1-IBS or I2-IBS Selectivity within a Series of 2-Phenoxymethylimidazoline Analogues / F., Gentili; P., Bousquet; Brasili, Livio; M., Dontenwill; J., Feldman; F., Ghelfi; M., Giannella; A., Piergentili; W., Quaglia; M., Pigini. - In: JOURNAL OF MEDICINAL CHEMISTRY. - ISSN 0022-2623. - STAMPA. - 46(2003), pp. 2169-2176.
Tipologia	Articolo su rivista

File in questo prodotto:

Non ci sono file associati a questo prodotto.

Utilizza questo identificativo per citare o creare un link a questo documento:
http://hdl.handle.net/11380/596090

Citazioni

I documenti presenti in Iris Unimore sono rilasciati con licenza Creative Commons Attribuzione - Non commerciale - Non opere derivate 3.0 Italia, salvo diversa indicazione.
In caso di violazione di copyright, contattare Supporto Iris