1401015-13-1Relevant articles and documents
Synthesis of 2-thiohydantoins as somatostatin subtype 4 receptor ligands
Wang, Xin,Mealer, David,Rodgers, Lacey,Sandoval, Karin,Witt, Ken,Stidsen, Carsten,Ankersen, Michael,Crider, A. Michael
, p. 655 - 662 (2012/09/22)
A series of 2-thiohydantoins were prepared as somatostatin subtype 4 (sst4) ligands. Reaction of a N-substituted-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.