Novel 7-phenylsulfanyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indoles as dual serotonin 5-HT2C and 5-HT6 receptor ligands

N Krogsgaard-Larsen; A A Jensen; J Kehler

doi:10.1016/j.bmcl.2010.07.105

Novel 7-phenylsulfanyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indoles as dual serotonin 5-HT2C and 5-HT6 receptor ligands

Bioorg Med Chem Lett. 2010 Sep 15;20(18):5431-3. doi: 10.1016/j.bmcl.2010.07.105. Epub 2010 Aug 3.

Authors

N Krogsgaard-Larsen¹, A A Jensen, J Kehler

Affiliation

¹ Department of Medicinal Chemistry, The Faculty of Pharmaceutical Sciences, University of Copenhagen, 2 Universitetsparken, DK-2100, Denmark.

PMID: 20719507
DOI: 10.1016/j.bmcl.2010.07.105

Abstract

Novel 7-phenylsulfanyl-1,2,3,4,10,10a-hexahydro-pyrazino[1,2-a]indoles are synthesized using a six-step protocol. Notably, the synthesis route make use of a new and improved ring-closing methodology for the assembly of the hexahydro-pyrazino[1,2-a]indole scaffold, which is based on intramolecular C-H insertion of a carbene. The compounds act as dual serotonin 5-HT2C- and 5-HT6-ligands.

MeSH terms

Cell Line
HeLa Cells
Humans
Indoles / chemical synthesis
Indoles / chemistry*
Indoles / pharmacology*
Ligands
Protein Binding
Pyrazines / chemical synthesis
Pyrazines / chemistry*
Pyrazines / pharmacology*
Receptor, Serotonin, 5-HT2C / metabolism*
Receptors, Serotonin / metabolism*
Structure-Activity Relationship

Substances

Indoles
Ligands
Pyrazines
Receptor, Serotonin, 5-HT2C
Receptors, Serotonin
serotonin 6 receptor