Preferences help
enabled [disable] Abstract
Number of results
2004 | 2 | 3 | 425-433
Article title

The synthesis and the structure elucidation of N,O-diacetyl derivative of cyclic 3-hydroxymelatonin

Title variants
Languages of publication
Melatonin was subjected to an oxidation to give 3-hydroxymelatonin. All spectroscopic data for this compound were collected. Ab initio calculations for both possible configurations were performed. X-ray data on N,O-diacetyl derivative of 3-hydroxymelatonin allowed the unambigous structure determination.
Physical description
1 - 9 - 2004
1 - 9 - 2004
  • [1] N. Lysek, E. Rachor and T. Lindel: “Isolation and structure elucidation of deformylflustrabromine from the North Sea bryozoan Flustra foliacea”, Z. Naturforsch, Vol. 57c, (2002), pp. 1056–1061.
  • [2] Q.S. Yu, X.X. Zhu, H.W. Halloway, N.F. Whittaker, A. Brossi and N.F. Greig: “Anticholinesterase activity of compounds related to geneserine tautomers. N-oxides and 1,2-oxazines”, J. Med. Chem., Vol. 45, (2002), pp. 3684–3691.[Crossref]
  • [3] M.S.C. Pedras, F.I. Okanga, I.L. Zaharia and A.Q. Khan: “Phytoalexins from crucifers: synthesis, biosynthesis, and biotransformation”, Phytochemistry, Vol. 53, (2002), pp. 161–176.[Crossref]
  • [4] M. Sabol, P. Kutschy, L. Siegfried, A. Mirossay, M. suchy, H. Hrbkova, M. Dzurilla, R. Maruskova, J. Starkova and E. Paulikova: “Cytotoxic effect of cruciferous phytoalexins against murine L1210 leukemia and B16 melanoma”, Biologia, Vol. 55, (2000), pp. 701–707.
  • [5] R. Mezencev, J. Mojzis, M. Pilatova and P. Kutschy, “Antiproliferative and cancer chemopreventive activity of phytoalexins: focus on indole phytoalexins from crucifers”, Neoplasma, Vol. 50, (2003), pp. 239–245.
  • [6] G.A. Potter, L.H. Patterson, E. Wanogho, P.J. Perry, P.C. Butler, T. Ijaz, K.C. Ruparelia, J.H. Lamb, P.B. Farmer, L.A. Stanley and M.D. Burke: “The cancer preventive agent resveratrol is converted to the anticancer agent piceatannol by the cytochrome P450 enzyme CYPIBI”, Brit. J. Cancer, Vol. 86, (2002), pp. 774–778.[Crossref]
  • [7] M.S.C. Pedras and F.I. Okanga: “Probing the phytopathogenic blackleg fungus with a phytoalexin homolog”, J. Org. Chem., Vol. 63, (1998), pp. 416–417.[Crossref]
  • [8] M. Allegra, R.J. Reiter, D.X. Tan, C. Gentile, L. Tesoriere and M.A. Livrea: “The chemistry of melatonin’s interaction with reactive species”, J. Pineal Res., Vol. 34, (2003), pp. 1–10.[Crossref]
  • [9] R.J. Reiter, D.X. Tan, L.C. Manchester and W. Qi: “Biochemical reactivity of melatonin with reactive oxygen and nitrogen species-A review of the evidence”, Cell Biochem. Biophys., Vol. 34, (2001), pp. 237–256.[Crossref]
  • [10] M. Nakagawa, J. Chiba and T. Hino: “Sensitized photooxygenation of melatonin and related compounds”, Heterocycles, Vol. 9, (1978), pp. 371–382.[Crossref]
  • [11] J.A. Horstman, M.Z. Wrona and G. Dryhurst: “Futher insights into the reaction of melatonin with hydroxyl radical”, Bioorg. Chem., Vol. 30, (2002), pp. 371–382.[Crossref]
  • [12] S. Erkoc, F. Erkoc and N. Keskin: “Theoretical investigation of melatonin and its hydroxy isomers”, J. Mol. Struct (Theochem), Vol. 587, (2002) pp. 73–79.[Crossref]
  • [13] M.D. Carter and D.F. Weaver: “Ab initio molecular modeling of imadazolium interaction with 5-hydroxy-and 5-methoxyindole: implications for melatonin-based inhibition of alzheimer beta-amyloid fibril formation”, J. Mol. Struct. (Theochem), Vol. 626, (2003), pp. 279–285.[Crossref]
  • [14] PC Spartan Pro software, version 1.0.5, Aug 16, 2000. Wavefunction, Inc., Irvine, California.
  • [15] D. Tan, L.C. Manchester, R.J. Reiter, B.F. Plummer, L.J. Hardies, S.T. Weintraub and A.M.M. Shepherd: “A novel melatonin metabolite, cyclic 3-hydroxymelatonin: a biomarker of in vivo hydroxyl radical generation”, Biochem. Biophys Res. Commun., Vol. 253, (1998), pp. 614–620.[Crossref]
  • [16] G.M. Sheldrick: SHELXL-97 Program for X-ray Structure Refinement, University of Göttingen, Germany, 1997.
Document Type
Publication order reference
YADDA identifier
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.