New tryptamine 5, 7 and β-carboline derivatives 3 were preparated by palladium-catalyzed coupling reaction of 5-bromotryptamine 1 with aryl boronic acids.
Institute for Organic Chemistry and Research, Group for Alkaloid Chemistry of the Hungarian Academy of Sciences, Budapest University of Technology and Economics, Budapest, Hungary
Institute for Organic Chemistry and Research, Group for Alkaloid Chemistry of the Hungarian Academy of Sciences, Budapest University of Technology and Economics, Budapest, Hungary
Institute for Organic Chemistry and Research, Group for Alkaloid Chemistry of the Hungarian Academy of Sciences, Budapest University of Technology and Economics, Budapest, Hungary
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]