(O-Benzoylsalicylato)copper(II) complexes as synthetic enzyme-product models for flavonol 2,4-dioxygenase

Mononuclear complexes of the type [CuII(BPEA)(O-bs)], [CuII(BnBPA)(O-bs)]ClO4, and [CuII(Bn-6Me2BPA)(O-bs)]ClO4 [O-bsH = O-benzoylsalicylic acid, BPEAH = N,N-bis(2-pyridylmethyl)amino-2-ethanoic acid, BnBPA = N-benzyl-N,N-bis(2-pyridylmethyl)amine, Bn-6Me2BPA = N-benzyl-N,N-bis(6-methyl-2-pyridylmethyl)amine] were synthesized as synthetic enzyme-depside complexes, and characterized by spectroscopic measurements and X-ray crystal analysis. The oxygenation of flavonol using the above-mentioned complexes as catalyst results in the oxidative cleavage of the heterocyclic ring to give a O-benzoylsalicylic acid and CO as a mimic of quercetinase action.

Graphical abstractThe molecular structure of [CuII(O-bs)(BPEA)], [CuII(O-bs)(BnBPA)]ClO4, and [CuII(O-bs)(Bn-6Me2BPA)]ClO4 [O-bsH = O-benzoylsalicylic acid, BPEAH = N,N-bis(2-pyridylmethyl)amino-2-ethanoic acid, BnBPA = N-benzyl-N,N-bis(2-pyridylmethyl)amine, Bn-6Me2BPA = N-benzyl-N,N-bis(6-methyl-2-pyridylmethyl)amine] was fully determined by IR, UV–Vis, and X-ray crystal analysis. The oxygenation of flavonol using the above-mentioned copper complexes as a catalyst results in the oxidative cleavage of the heterocyclic ring to give a O-benzoylsalicylic acid and CO as a mimic of quercetinase action.Figure optionsDownload full-size imageDownload as PowerPoint slide