This paper reports the preparation of new benzoyl and/or benzyl substituted 1,2,3-triazole derivatives and their pharmacological evaluation as potential BK channel openers, as a part of a research program which hypothesized a pharmacophoric structure containing the 1,2,3-triazole ring. The synthetic procedures consist essentially with the 1,3-dipolar cycloaddition of aryl or benzyl azides to the asymmetric alkyne benzoylacetylene to give the wished 4-benzoyl-1,2,3-triazole isomers in larger amount. The pharmacological results show that the 1-(2- hydroxybenzyl)-4-benzyl-1H-1,2,3-triazole possesses high vasorelaxing activity involving the opening of the BK channels. Therefore the structure–activity relationships concerning this pharmacophoric structure confirm the usefulness of a phenolic function in the ortho position of the aromatic ring and would suggest a 1,2,3-triazole model bearing benzyl substituents. In addition such substituents appear more flexible and able to take different conformations with respect to phenyl groups which have higher trend to coplanar conformations.

Benzoyl and/or benzyl substituted 1,2,3-triazoles as potassium channel activators. VIII / Calderone, V; Giorgi, I; Livi, O; Martinotti, E; Mantuano, Elisabetta; Martelli, A; Nardi, A.. - In: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY. - ISSN 0223-5234. - STAMPA. - 40:(2005), pp. 521-528. [10.1016/j.ejmech.2005.01.010]

Benzoyl and/or benzyl substituted 1,2,3-triazoles as potassium channel activators. VIII.

MANTUANO, ELISABETTA;
2005

Abstract

This paper reports the preparation of new benzoyl and/or benzyl substituted 1,2,3-triazole derivatives and their pharmacological evaluation as potential BK channel openers, as a part of a research program which hypothesized a pharmacophoric structure containing the 1,2,3-triazole ring. The synthetic procedures consist essentially with the 1,3-dipolar cycloaddition of aryl or benzyl azides to the asymmetric alkyne benzoylacetylene to give the wished 4-benzoyl-1,2,3-triazole isomers in larger amount. The pharmacological results show that the 1-(2- hydroxybenzyl)-4-benzyl-1H-1,2,3-triazole possesses high vasorelaxing activity involving the opening of the BK channels. Therefore the structure–activity relationships concerning this pharmacophoric structure confirm the usefulness of a phenolic function in the ortho position of the aromatic ring and would suggest a 1,2,3-triazole model bearing benzyl substituents. In addition such substituents appear more flexible and able to take different conformations with respect to phenyl groups which have higher trend to coplanar conformations.
Potassium channels, Potassium channel openers, BK-activators, 1; 2; 3-Triazoles, Vasodilator activity
01 Pubblicazione su rivista::01a Articolo in rivista
Benzoyl and/or benzyl substituted 1,2,3-triazoles as potassium channel activators. VIII / Calderone, V; Giorgi, I; Livi, O; Martinotti, E; Mantuano, Elisabetta; Martelli, A; Nardi, A.. - In: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY. - ISSN 0223-5234. - STAMPA. - 40:(2005), pp. 521-528. [10.1016/j.ejmech.2005.01.010]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/769676
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