Abstract
A series of 2-thiohydantoins were prepared as somatostatin subtype 4 (sst4) ligands. Reaction of a Nsubstituted- L-tryptophan methyl ester with an isothiocyanate in the presence of triethylamine readily afforded the target compounds. The 2-thiohydantoins were evaluated for binding affinities in cell lines expressing somatostatin receptor subtypes 2A (sst2A) and 4 (sst4). Compared to the thiourea NNC-26-9100 (3), all 2-thiohydantoins demonstrated lower binding affinities at sst4. Incorporation of the thiourea moiety into the more rigid 2-thiohydantoin nucleus leads to a loss of conformational freedom and may prevent optimal interaction with sst4.
Keywords: 2-Thiohydantoins, Somatostatin, Isothiocyanates, L-tryptophan methyl ester, Somatostatin receptors, Binding affinity, thiourea, triethylamine, SRIF, gastrointestinal tract, neuromodulator, structurally-related receptors , triethylamine, G-protein-coupled superfamily
Letters in Drug Design & Discovery
Title:Synthesis of 2-Thiohydantoins as Somatostatin Subtype 4 Receptor Ligands
Volume: 9 Issue: 7
Author(s): Xin Wang, David Mealer, Lacey Rodgers, Karin Sandoval, Ken Witt, Carsten Stidsen, Michael Ankersen and A. Michael Crider
Affiliation:
Keywords: 2-Thiohydantoins, Somatostatin, Isothiocyanates, L-tryptophan methyl ester, Somatostatin receptors, Binding affinity, thiourea, triethylamine, SRIF, gastrointestinal tract, neuromodulator, structurally-related receptors , triethylamine, G-protein-coupled superfamily
Abstract: A series of 2-thiohydantoins were prepared as somatostatin subtype 4 (sst4) ligands. Reaction of a Nsubstituted- L-tryptophan methyl ester with an isothiocyanate in the presence of triethylamine readily afforded the target compounds. The 2-thiohydantoins were evaluated for binding affinities in cell lines expressing somatostatin receptor subtypes 2A (sst2A) and 4 (sst4). Compared to the thiourea NNC-26-9100 (3), all 2-thiohydantoins demonstrated lower binding affinities at sst4. Incorporation of the thiourea moiety into the more rigid 2-thiohydantoin nucleus leads to a loss of conformational freedom and may prevent optimal interaction with sst4.
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Cite this article as:
Wang Xin, Mealer David, Rodgers Lacey, Sandoval Karin, Witt Ken, Stidsen Carsten, Ankersen Michael and Michael Crider A., Synthesis of 2-Thiohydantoins as Somatostatin Subtype 4 Receptor Ligands, Letters in Drug Design & Discovery 2012; 9 (7) . https://dx.doi.org/10.2174/157018012801319445
DOI https://dx.doi.org/10.2174/157018012801319445 |
Print ISSN 1570-1808 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-628X |
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