Document Detail

Indene-based frameworks targeting the 5-HT6 serotonin receptor: ring constraint in indenylsulfonamides using cyclic amines and structurally abbreviated counterparts.
MedLine Citation:
PMID:  19758807     Owner:  NLM     Status:  MEDLINE    
Further studies in quest of 5-HT(6) serotonin receptor ligands led to the design and synthesis of a few selected examples of N-(inden-5-yl)sulfonamides with a ring-constrained aminoethyl side chain at the indene 3-position, some of which exhibited a high binding affinity, such as the pyrrolidine analogue 28 (K(i)=3nM). Moreover, the structurally abbreviated N-(inden-5-yl)sulfonamides showed K(i) values > or = 43 nM, which indicates that neither the N,N-aminoethyl nor the conformationally restricted aminoethyl side arm at the indene 3-position are required for binding. Selected compounds were then tested in a functional cAMP stimulation assay and found to act as 5-HT(6) antagonists, although with moderate potency at the micromolar level.
Ermitas Alcalde; Neus Mesquida; Sara L??pez-P??rez; Jordi Frigola; Ramon Merc??; J??rg Holenz; Marta Pujol; Enrique Hern??ndez
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2009-08-08
Journal Detail:
Title:  Bioorganic & medicinal chemistry     Volume:  17     ISSN:  1464-3391     ISO Abbreviation:  Bioorg. Med. Chem.     Publication Date:  2009 Oct 
Date Detail:
Created Date:  2009-10-06     Completed Date:  2010-01-19     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  9413298     Medline TA:  Bioorg Med Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  7387-97     Citation Subset:  IM    
Laboratori de Qu??mica Org??nica, Departament de Farmacologia i Qu??mica Terap??utica, Facultat de Farm??cia, Universitat de Barcelona, Avda. Joan XXIII s/n, 08028 Barcelona, Spain.
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MeSH Terms
Amines / chemistry*
Cell Line
Cyclic AMP / chemistry
Indenes / chemistry*
Magnetic Resonance Spectroscopy
Molecular Structure
Receptors, Serotonin / chemistry*
Spectrometry, Mass, Electrospray Ionization
Sulfonamides / chemistry*
Reg. No./Substance:
0/Amines; 0/Indenes; 0/Receptors, Serotonin; 0/Sulfonamides; 0/serotonin 6 receptor; 60-92-4/Cyclic AMP

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