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Article Dans Une Revue European Journal of Medicinal Chemistry Année : 2015

Indenopyrazole oxime ethers: Synthesis and β1-adrenergic blocking activity

Résumé

This paper reports the synthesis and cardiac activity of new β-blockers derived from (Z/E)-indeno[1,2-c]pyrazol-4(1H)-one oximes (5a,b). The latter compounds were allowed to react with epichlorohydrin, followed by reacting the oxiranyl derivatives formed (6a,b) with some aliphatic amines to give the target compounds (Z/E)-1-phenyl-1H-indeno[1,2-c]pyrazol-4-one O-((2-hydroxy-3-(substituted amino)propyl)oxime (7a–c) and (Z/E)-1-methyl-1H-indeno[1,2-c]pyrazol-4-one O-((2-hydroxy-3-(substituted amino)propyl)oxime (8a–c). These final products 7a–c and 8a–c were evaluated for their ability to modulate the cardiac performance of a prototype mammalian heart. The results showed that, out of these molecules tested, 7b elicits a more potent depressant effect on contractility and relaxation, and competitively antagonizes β1-adrenergic receptors.

Dates et versions

hal-01116512 , version 1 (13-02-2015)

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Citer

Tomaso Angelone, Anna Caruso, Christophe Rochais, Angela Caputa, Maria Cerra, et al.. Indenopyrazole oxime ethers: Synthesis and β1-adrenergic blocking activity. European Journal of Medicinal Chemistry, 2015, 92, pp.672-681. ⟨10.1016/j.ejmech.2015.01.037⟩. ⟨hal-01116512⟩
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