Synthesis and complexation properties of two new curcuminoid molecules bearing a diphenylmethane linkage

Bis-curcuminoids 3 and 4, bearing a diphenylmethane bridge for both compounds and a crown ether chain adapted to complex Li + for compound 4, were synthesized and characterized by mass and NMR spectroscopies. By their preorganized geometry, they represent a new class of curcuminoids able to complex...

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Bibliographic Details
Published in:Journal of molecular structure 2003-04, Vol.649 (1), p.177-190
Main Authors: Sundaryono, Agus, Nourmamode, Aziz, Gardrat, Christian, Fritsch, Alain, Castellan, Alain
Format: Article
Language:English
Subjects:
Calculated structures
Complexation
Curcumin
Curcuminoids
Transition metals
UV–visible absorption
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Summary:Bis-curcuminoids 3 and 4, bearing a diphenylmethane bridge for both compounds and a crown ether chain adapted to complex Li + for compound 4, were synthesized and characterized by mass and NMR spectroscopies. By their preorganized geometry, they represent a new class of curcuminoids able to complex transition metal cations. Their absorption spectra in DMF by comparison with those of curcumin 1 and dimethylcurcumin 2 have shown that the phenolate forms in the two halves are in interaction in compound 3 and are independent in compound 4. Complexation studies have revealed a poor selectivity of curcuminoids for transition metals. Nevertheless complexation of Cu (II), studied by UV–visible absorption spectroscopy, has shown subtle differences between curcumin 1 and bis-curcuminoid 3. These observations were supported by quantum mechanic calculations to establish the most probable structures of non- and complexed compounds.
ISSN:0022-2860
1872-8014
DOI:10.1016/S0022-2860(03)00050-4