Abstract
N-aminorhodanine as well as isatin are highly solicited motifs known for their wide potential for biological activity. The objective of this work was to synthesize hybrid molecules as kinase inhibitors from these two motifs. In order to study the reactivity of the two active centers in aminorhodanine (N-amino group and the 5-methylene group) toward two carbonyl groups (aromatic aldehyde and ketone of isatin), we decided to carry out a one-pot multi-component reaction by simultaneously introducing aminorhodanine, isatin, and an aromatic aldehyde in ethanol in the presence of AcOEt. Under these conditions, this reaction led to a single adduct. The reaction product structure was confirmed by 1H, 13C-NMR, X-ray single crystal analysis, and high-resolution mass HRMS analysis. As a result, the method used has been very effective and totally stereo- and regioselective.
Highlights
The combination of two or more targeted therapeutic pharmacophores with different mechanisms of action into a single so-called hybrid molecule is one of the alternatives of conventional treatments of complex diseases that are multifactorial disorders involving various potential targets associated with their pathogenesis
Among the most requested pharmacophores in recent years due to their broad spectrum of biological activity are isatin and rhodamine, which share certain bioactivities such as the inhibition of kinases [1,2,3]. This is why there is interest in combining these two pharmacophores in hybrid molecules to study the evolution of their kinase inhibitory potency
Such protein-ligand complex must be more rigorously evaluated using two or more experimental methods to avoid false results. In light of these findings, we were interested in the design, synthesis, and evaluation of a new. In light of these findings, we were interested in the design, synthesis, and evaluation of a new series of hybrid molecules by combining the two pharmacophoric elements: N-aminorhodanine and series of hybrid molecules by combining the two pharmacophoric elements: N-aminorhodanine and isatin, which are present in a number of natural and synthetic agents
Summary
The combination of two or more targeted therapeutic pharmacophores with different mechanisms of action into a single so-called hybrid molecule is one of the alternatives of conventional treatments of complex diseases that are multifactorial disorders involving various potential targets associated with their pathogenesis. Among the most requested pharmacophores in recent years due to their broad spectrum of biological activity are isatin and rhodamine, which share certain bioactivities such as the inhibition of kinases [1,2,3] This is why there is interest in combining these two pharmacophores in hybrid molecules to study the evolution of their kinase inhibitory potency. Several numbers of successful isatin–rhodanine examples of pharmacophore hybridization strategies for drug design, discovery, and development have been reported [4,5,6,7] Some of these have shown potent inhibitor activity against the UDP-Galactopyranose mutase UGM [8], β-lactamase infectious [9], and histone acetyltransferases [5] (a wide range of diseases).
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