Synthesis of novel tryptamine and β-carboline derivatives via palladium-catalyzed reaction of bromotryptamine with organic boronic acids

• Authors: Melinda Fekete , Pál Kolonits , Ngo Hien , Lajos Novák
• Languages of publication: EN

Abstracts

EN

New tryptamine 5, 7 and β-carboline derivatives 3 were preparated by palladium-catalyzed coupling reaction of 5-bromotryptamine 1 with aryl boronic acids.

Keywords

EN

Suzuki-type reaction; palladium catalyst; tryptamine derivatives; boronic acids

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2005
• Volume: 3
• Issue: 4
• Pages: 792-802

Dates

published

1 - 12 - 2005

online

1 - 12 - 2005

Contributors

author

Melinda Fekete

• Institute for Organic Chemistry and Research, Group for Alkaloid Chemistry of the Hungarian Academy of Sciences, Budapest University of Technology and Economics, Budapest, Hungary

author

Pál Kolonits

• Institute for Organic Chemistry and Research, Group for Alkaloid Chemistry of the Hungarian Academy of Sciences, Budapest University of Technology and Economics, Budapest, Hungary

author

Ngo Hien

• Institute for Organic Chemistry and Research, Group for Alkaloid Chemistry of the Hungarian Academy of Sciences, Budapest University of Technology and Economics, Budapest, Hungary

author

Lajos Novák

• Institute for Organic Chemistry and Research, Group for Alkaloid Chemistry of the Hungarian Academy of Sciences, Budapest University of Technology and Economics, Budapest, Hungary

References

• [1] M. Hese: Alcaloids, Verlag Helvetica Chimica Acta, Zürich, 2002.
• [2] K.A. Sporer: “The serotonin syndrome. Implicated drugs, pathophysiology and management”, Drug Safety, Vol. 13, (1995), pp. 94–104. [Crossref]
• [3] W.W. Blessing and B. Seaman: “5-hydroxytryptamine 2A receptors regulate sympathetic nerves constricting the cutaneous vascular bed in rabbits and rats”, Neuroscience, Vol. 117, (2003), pp. 939–948. http://dx.doi.org/10.1016/S0306-4522(02)00810-2[Crossref]
• [4] B.J. Ebersole, I. Visiers, H. Weinstein and S.C. Sealfou: “Molecular basis of partial agonism: orientation of indoleamine ligands in the binding pocket of the human serotonin 5-HT receptor determines relative efficacy”, Mol. Pharmacol., Vol. 63, (2003), pp. 36–43. http://dx.doi.org/10.1124/mol.63.1.36
• [5] M.M. Rapport: “The discovery of serotonin”, Perspect. Biol. Med., Vol. 40, (1997), pp. 260–273. [Crossref]
• [6] H. Lefebvre, P. Compagnon, V. Contesse, C. Hamel, C. Delame, C. Thuillez, H. Vaudry, J.M. Kuhn: “Production and metabolism of serotonin (5-HT) by the human adrenal gland”, Endocrine Res. Vol. 22, (1996), pp. 851–853.
• [7] R. Lane and D. Baldwin: “Selective serotonin reuptake inhibitor-induced serotonin syndrome”, J. Clinical Psychopharmacology, Vol. 17, (1997), pp. 208–221. http://dx.doi.org/10.1097/00004714-199706000-00012[Crossref]
• [8] P. Schloss and D.C. Williams: “The serotonin transporter: a primary target for antidepressant drugs”, J. Psychopharmacology, Vol. 12, (1998), pp. 115–121. [Crossref]
• [9] S.R. Chemler, D. Trauner and J.S. Danishefsky: “The B-alkyl Suzuki-Miyaura cross-coupling reaction: development, mechanistic study, and application in natural product synthesis”, Angew. Chem. Int. Ed., Vol. 40, (2001), pp. 4544–4568. http://dx.doi.org/10.1002/1521-3773(20011217)40:24<4544::AID-ANIE4544>3.0.CO;2-N[Crossref]
• [10] A. Suzuki: “The Suzuki reaction with arylboron compounds in arene chemistry”, In: Modern Arene Chemistry, Wiley-VHC Verlag Gmbh and Co., Weinheim, Germany, 2002.
• [11] A. Suzuki and H.C. Brown: Organic Syntheses Via Boranes, Vol. 3, Suzuki Coupling. Aldrich Chemical Company, Inc. Milwaukee, Wisconsin, 2003. http://dx.doi.org/10.1002/0471264180.os051.22[Crossref]
• [12] M. Fekete, P. Kolonits and L. Novak: “Preparation of New Vindoline Derivatives by Palladium-Catalyzed Cross-Coupling Reaction”, Heterocycles, Vol. 65, (2005), pp. 165–171. http://dx.doi.org/10.3987/COM-04-10224[Crossref]
• [13] S. Chackal, F. Dudonit, R. Houssin and J.-P. Henarch: “On the synthesis of two dimethoxy-1,3,4,5-tetrahydropynolo[4,3,2-de]quonoline regioisomers”, Heterocycles, Vol. 60, (2003), pp. 615–622.
• [14] D.S. Walker, T.E. Barder, J.R. Martinelli and S.L. Buchwald: “A rationally designed universal catalyst for Suzuki-Miyaura coupling processes”, Angew. Chem. Int. Ed., Vol. 43, (2004), pp. 1871–1876. http://dx.doi.org/10.1002/anie.200353615[Crossref]
• [15] T. Harayama: “Synthesis of benzo[c]phenanthridine alkaloids using a Palladium-catalyzed aryl-ary coupling reaction”, Heterocycles, Vol. 65, (2005), pp. 697–713. http://dx.doi.org/10.3987/REV-04-594[Crossref]

Identifiers

DOI

10.2478/BF02475205