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2004 | 2 | 3 | 425-433
Tytuł artykułu

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

Treść / Zawartość
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
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.
Słowa kluczowe
Wydawca

Czasopismo
Rocznik
Tom
2
Numer
3
Strony
425-433
Opis fizyczny
Daty
wydano
2004-09-01
online
2004-09-01
Twórcy
  • Faculty of Chemistry, Warsaw University, Pasteur St. 1, 02-093, Warsaw, Poland
  • Department of Cellular and Structural Biology, University of Texas Health Science Center, 78229, San Antonio, Texas, USA
autor
  • Department of Cellular and Structural Biology, University of Texas Health Science Center, 78229, San Antonio, Texas, USA
  • Faculty of Chemistry, Warsaw University, Pasteur St. 1, 02-093, Warsaw, Poland
  • Faculty of Chemistry, Warsaw University, Pasteur St. 1, 02-093, Warsaw, Poland
autor
Bibliografia
  • [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. http://dx.doi.org/10.1021/jm010491d[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. http://dx.doi.org/10.1016/S0031-9422(99)00494-X[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. http://dx.doi.org/10.1038/sj.bjc.6600197[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. http://dx.doi.org/10.1021/jo971702i[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. http://dx.doi.org/10.1034/j.1600-079X.2003.02112.x[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. http://dx.doi.org/10.1385/CBB:34:2:237[Crossref]
  • [10] M. Nakagawa, J. Chiba and T. Hino: “Sensitized photooxygenation of melatonin and related compounds”, Heterocycles, Vol. 9, (1978), pp. 371–382. http://dx.doi.org/10.3987/R-1978-04-0385[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. http://dx.doi.org/10.1016/S0045-2068(02)00511-4[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. http://dx.doi.org/10.1016/S0166-1280(02)00098-2[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. http://dx.doi.org/10.1016/S0166-1280(03)00100-3[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. http://dx.doi.org/10.1006/bbrc.1998.9826[Crossref]
  • [16] G.M. Sheldrick: SHELXL-97 Program for X-ray Structure Refinement, University of Göttingen, Germany, 1997.
Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_BF02476198
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