La chimie-<i>click</i> débusque les substrats d’ADAM10

Saurty, Mirca; Sanson, R D De; Amrane, Rania; Rubinstein, Eric

doi:10.1051/medsci/20163210015

Cited by 1 publication

(1 citation statement)

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“…In addition, click chemistry today constitutes an innovative and valuable tool in organic synthesis with applications in various domains, such as medicine [17], biology [18], biomedical field [19], and nanotechnology [20]. In the light of these observations and in the continuity of our previous work on the synthesis of α-heterocyclic phosphonic amino acids [21]- [25], we report in this paper the preparation of a new biheterocyclic phospohonic aminoester, entituled,…”

Section: Introductionmentioning

confidence: 91%

Synthesis and Characterization of the Structure of Diethyl [(4-{(1H-Benzo[d]Imidazol-1-yl)Methyl}-1H-1,2,3-Triazol-1-yl)(Benzamido)Methyl]Phosphonate Using 1D and 2D NMR Experiments

Khadir

Boukhssas

Achamlale³

et al. 2021

EJCHEM

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The biheterocyclic derivative of the phosphonic glycine analogue is prepared selectively by reaction between the α-azidoamino diethyl methylphosphonate and the 1-(prop-2-yn-1-yl)-1H-benzo[d]imidazole. The dipolar -1,3 cycloaddition reaction using Click Chemistry was carried out in a solvent water/ethanol mixture in a ratio of 1:1. Copper sulphate pentahydrate and sodium ascorbate are used in the reaction in catalytic amounts. The compound [diethyl [{4-[(1H-benzo[d]imidazol-1-yl)methyl]-1H-1,2,3-triazol-1-yl}(benzamido) methyl] phosphonate was isolated pure as a white powder, after chromatography on a silica gel column (ethyl acetate/hexane acetate: 1/1). The yield of pure product is 90%, after recrystallization in an ether/hexane mixture. The structure of the -1,4 isomer is attributed to the compound obtained by means of 1D and 2D NMR and based on data from the literature concerning the cycloaddition reaction via Click Chemistry. Two-dimensional NMR spectroscopy played a major role. The analysis of the different correlations between adjacent hydrogens and carbons, and also between hydrogens and distant carbons, confirmed the proposed structure.

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