Journal
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
Volume 46, Issue 9, Pages 3867-3876Publisher
ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
DOI: 10.1016/j.ejmech.2011.05.056
Keywords
Ullmann; Ullmann-Finkelstein; Copper-catalyzed; AT1-receptor antagonists; Pyrazoles. C to N bioisosterism; Patent escaping
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Funding
- CAMPLP
- Fondation pour la Recherche Medicale
- Nord-Pas-de-Calais [RAD07001EEA]
- PRIM (Pole de Recherche Interdisciplinaire pour le Medicament)
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Ullmann-type reactions are becoming a major tool in medicinal chemistry. In this article, we describe the use of these Copper-catalyzed reactions with various precursors, acyl-heteroarylamines or pyrazoles of interest for pharmacomodulation. To the medicinal chemist they offer new, usually untapped disconnection approaches to compounds of interest. They thus open the way to new original analogues of bioactive compounds possibly not patented, from common building-blocks. They also allow C to N bioisosteric replacements, which sometimes are synthetically challenging. We report for the first time the critical effect of acetylamino substituents on the regioselective arylation of unsymmetrical pyrazoles that are useful for medicinal chemists. Finally, we have applied this strategy to the design of novel AT, receptor antagonists. Though this family has been extensively investigated in the past 30 years, N-arylation and C to N replacement made possible by Ullmann chemistry, can produce original antagonists. (C) 2011 Elsevier Masson SAS. All rights reserved.
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