Abstract
The preparation, spectroscopic properties, and crystal structure of [Cu(ind)(mco)] [ind is the anion of 1,3-bis(2-pyridylimino)isoindoline and mco is the anion of 3-hydroxy-(4H)-benzopyran-4-one] are reported. The complex exhibits a distorted square pyramidal geometry. The oxygenation of the title compound results in oxidative cleavage of the heterocyclic ring to give the (acetylsalicylato)copper(II) complex [Cu(asp)(ind)] (asp is the anion of acetylsalicylic acid) and CO as primary products, which reaction resembles the enzymatic reaction of quercetinase.
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References
E. Wollenweber, in J.B. Harborne and T.J. Mabry, (Eds.) Flavonoids: Advances in Research, Chapman & Hall, London, New York, 1982, pp. 189–259.
J.B. Harborne and C.A. Williams, in J.B. Harborne and T.J. Mabry, (Eds.) Flavonoids: Advances in Research, Chapman & Hall, London, New York, 1982, pp. 261–311.
E. Wollenweber, Prog. Clin. Biol. Res., 2850, 45 (1988).
W. Bors, W. Heller, C. Michel and M. Saran, in L. Packer and A.N. Glazer, (Eds.) Method. Enzymol. Academic: New York, (1990), Vol. 186, p. 343.
M.G.L. Hertog, E.J.M. Feskens, P.C.H. Hollman, M.B. Katan and D. Kromhout, Lancet, 342, 1007 (1993).
S. Hattori and I. Noguchi, Nature, 184, 1145 (1959).
H.K. Hund, J. Breuer, F. Lingens, J. Hüttermann, R. Kappl and S. Fetzner, Eur. J. Biochem., 263, 871 (1999).
D.W.S. Westlake, J.M. Roxburgh and G. Talbot, Nature, 189, 510 (1961).
H.G. Krishnamurty and F.J. Simpson, J. Biol. Chem., 245, 1467 (1970).
F. Fusetti, K.H. Schröter, R.A. Steiner, P.I. van Noort, T. Pijning, H.J. Rozeboom, K.H. Kalk, M.R. Egmond and B.W. Dijkstra, Structure, 10, 259 (2002).
L. Barhács, J. Kaizer and G. Speier, J. Org. Chem., 65, 3449 (2000).
L. Barhács, J. Kaizer and G. Speier, J. Mol. Catal. A: Chem., 172, 117 (2001).
É. Balogh-Hergovich, J. Kaizer, G. Speier, G. Argay and L. Párkányi, J. Chem. Soc., Dalton Trans., 3847 (1999).
É. Balogh-Hergovich, J. Kaizer, G. Speier, V. Fülöp and L. Párkányi, Inorg. Chem., 38, 3787 (1999).
É. Balogh-Hergovich, J. Kaizer, G. Speier, G. Huttner and A. Jacobi, Inorg. Chem., 39, 4224 (2000).
É. Balogh-Hergovich, J. Kaizer, J. Pap, G. Speier, G. Huttner and L. Zsolnai, Eur. J. Inorg. Chem., 2287 (2002).
D.D. Perrin, W.L. Armarego, D.R. Perrin, Purification of Laboratory Chemicals, 2nd edit., Pergamon, New York, 1990.
M. Ferrali, D. Donati, S. Bambagioni, M. Fontani, G. Giorgi and A. Pietrangelo, Bioorg. Med. Chem., 9, 3041 (2001).
W.O. Siegl, J. Org. Chem., 42, 1872 (1977).
R.W. Adams, E. Bishop, R.L. Martin and G. Winter, Aust. J. Chem., 19, 207 (1966).
A. Altamore, G. Cascarano, C. Giacovazzo, A. Guagliardi, M.C. Burla, G. Polidori and M. Camalli, J. Appl. Cryst., 27, 435 (1994).
G.M. Sheldrick, SHELXL-97, Program for the Refinement of Crystal Structures, University of Göttingen, Germany, 1997.
A.W. Addison, T.N. Rao, J. Reedijk, J. van Rijn and G.C. Vershoor, J. Chem. Soc., Dalton Trans., 1349 (1984).
M. Ferrali, S. Bambagioni, A. Ceccanti, D. Donati, G. Giorgi, M. Fontani, F. Laschi, P. Zanello, M. Casolaro and A. Pietrangelo, J. Med. Chem., 45, 5776 (2002).
R.R. Gagné and D.N. Marks, Inorg. Chem., 23, 65 (1984).
R.J. Letcher, W. Zhang, C. Bensimon and R.J. Crutchley, Inorg. Chim. Acta., 210, 183 (1993).
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Kaizer, J., Pap, J., Speier, G. et al. Synthesis, properties, and crystal structure of a novel 3-hydroxy-(4H)-benzopyran-4-one containing copper(II) complex, and its oxygenation and relevance to quercetinase. Transition Metal Chemistry 29, 630–633 (2004). https://doi.org/10.1007/s11243-004-2794-8
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DOI: https://doi.org/10.1007/s11243-004-2794-8