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

Kaizer, József; Góger, Szabolcs; Speier, Gábor; Réglier, Marius; Giorgi, Michel

doi:10.1016/j.inoche.2005.11.011

Cited by 16 publications

(4 citation statements)

References 19 publications

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“…The addition of a nitrogen-containing ligand allows for a much lower catalyst loading, though high reaction temperatures are still needed (Scheme 314). 594 …”

Section: Reactions Of Carbonyls and Carbonyl Equivalentsmentioning

confidence: 99%

Aerobic Copper-Catalyzed Organic Reactions

et al. 2013

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24 peroxide [Cu I (pyr)(tpb)] 10 mol % TBHP, 1 atm O 2 , 1:2 AcOH/pyr, rt, 24 h ∼2.5 26 74 g 35 25 n-hexane aldehyde CuCl 2 , 18-crown-6 1 atm O 2 , MeCHO, CH 2 Cl 2 , 70 °C, 24 h 2.4 91 h 9 34a 26 n-decane aldehyde Cu II Cl 16 Pc-AM(PS) 3 equiv of PhCHO, MeCN, 1 atm O 2 , 50 °C 15.4 100 i 61 a See Chart 2 for ligand structures. b Also 28% cyclohexene. c Also 26% cyclohexene. d Mixture of alcohol and hydroperoxide. e Remainder of product is cyclohexene. f Approximately 93:7 of 1-adamantol/2-adamantol. g Approximately 98:2 of 1-adamantol/2-adamantol. h Afforded oxidation products in an approximately 1:1 ratio at the 2-and 3-positions. i Mixture of decanones.

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“…The addition of a nitrogen-containing ligand allows for a much lower catalyst loading, though high reaction temperatures are still needed (Scheme 314). 594 …”

Section: Reactions Of Carbonyls and Carbonyl Equivalentsmentioning

confidence: 99%

Aerobic Copper-Catalyzed Organic Reactions

et al. 2013

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“…In this regard, Speier and co‐workers reported that the dioxygenation of the bound flavonolate substrate was promoted by the addition of excess carboxylate (potassium salt), the role of which was attributed to the alternation of the binding mode of the bound flavonolate from bidentate to monodentate , . To date, several ligands containing a carboxylate group have been developed, but the effects of the carboxylate group in the ligands have yet to be addressed in detail.…”

Section: Introductionmentioning

confidence: 99%

Dioxygenation of Flavonol Catalyzed by Copper(II) Complexes Supported by Carboxylate‐Containing Ligands: Structural and Functional Models of Quercetin 2,4‐Dioxygenase

Sun

Huang

et al. 2017

Eur J Inorg Chem

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To obtain insights into the role of the carboxylate group of Glu73 in the active site of quercetin 2,4-dioxygenase (2,4-QD), the copper(II) complexes [Cu II Ln(AcO)] [1 (Ln = L1), 2 (Ln = L2), 3 (Ln = L3), and 4 (Ln = L4)] supported by a series of carboxylate-containing ligands [L1H = 2-{[bis(pyridin-2ylmethyl)amino]methyl}benzoic acid; L2H = 3-{[bis(pyridin-2ylmethyl)amino]methyl}benzoic acid,; L3H = 2-({bis[2-(pyridin-2yl)ethyl]amino}methyl)benzoic acid; L4H = 3-({bis[2-(pyridin-2yl)ethyl]amino}methyl)benzoic acid] as well as the ternary Cu II flavonolate (fla -) complexes [Cu II Ln(fla)] [5 (Ln = L1), 6 (Ln = L2), 7 (Ln = L3), and 8 (Ln = L4)] were synthesized and characterized as structural and functional models for the active site[a] 1845 Scheme 2. Structures of ligands LnH.Figure 2. ORTEP drawings of (a) [CuL1(AcO)]·CH 3 OH·H 2 O (1), (b) [CuL2(H 2 O)] 2 [ClO 4 ] 2 ·2H 2 O (2′), (c) [CuL3(AcO)]·2H 2 O (3), and (d) {[CuL4Cl]·H 2 O} n (4′); 50 % probability thermal ellipsoids are shown for 1, and 30 % probability ellipsoids are shown for the others. The non-coordinating counteranions and the hydrogen atoms attached to the carbon atoms are omitted for clarity. Scheme 4. Dioxygenation of the ternary complexes [Cu II Ln(fla)].

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“…Transition metal complexes derived from such Schiff bases have been widely investigated due to their potential biological activities, especially the antimicrobial activity [5][6][7][8]. Copper(II) is an important life element, which also possesses interesting biological activities [9][10][11]. Thiocyanate anion is a versatile bridging group [12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structures, and antimicrobial activity of two thiocyanato-bridged dinuclear copper(II) complexes derived from 2,4-dibromo-6-[(2-diethylaminoethylimino)methyl]phenol and 4-nitro-2-[(2-ethylaminoethylimino)methyl]phenol

Hong

2008

Transition Met Chem

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A pair of structurally similar thiocyanatobridged dinuclear Cu(II) complexes derived from the Schiff bases 2,4-dibromo-6-[(2-diethylaminoethylimino) methyl]phenol and 4-nitro-2-[(2-ethylaminoethylimino) methyl]phenol has been prepared and characterized by physico-chemical and spectroscopic methods. Each Cu atom is five-coordinate in a square-pyramidal geometry, with one O and two N atoms of one Schiff base ligand and one N atom of a bridging thiocyanate ligand defining the basal plane, and with one terminal S atom of another bridging thiocyanate ligand occupying the apical position. Antimicrobial activities of the Schiff bases and the two complexes have been tested.

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

Cited by 16 publications

References 19 publications

Aerobic Copper-Catalyzed Organic Reactions

Aerobic Copper-Catalyzed Organic Reactions

Dioxygenation of Flavonol Catalyzed by Copper(II) Complexes Supported by Carboxylate‐Containing Ligands: Structural and Functional Models of Quercetin 2,4‐Dioxygenase

Synthesis, crystal structures, and antimicrobial activity of two thiocyanato-bridged dinuclear copper(II) complexes derived from 2,4-dibromo-6-[(2-diethylaminoethylimino)methyl]phenol and 4-nitro-2-[(2-ethylaminoethylimino)methyl]phenol

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