168766-62-9

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 4299-70-1 L-tryptophan methyl ester 

Downstream Products

• 300766-76-1 methyl N-tert-butoxycarbonyl-N'-(p-methoxybenzyl)-(S)-alanyl-(S)-tryptophanate 
• 1401015-07-3 5-(1H-indol-3-yl)methyl-1-(4-methoxybenzyl)-3-(4-(pyridin-2-ylamino)butyl)-2-thioxoimidazolidin-4-one 

Relevant academic research and scientific papers

Synthesis of 2-thiohydantoins as somatostatin subtype 4 receptor ligands

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.

Synthesis of a seco analogue of ardeemin

(1S,4S)-1-Indolylmethyl-4-methyl-2,4-dihydro-1H-pyrazino[2,1-b]-q uinazaline-3,6-dione, a seco analogue of ardeemin, was synthesized in six steps from L-tryptophan methyl ester via an N-protected 2,5-piperazinedione and using an aza-Wittig reaction for the preparation of the quinazoline system. The final acid-promoted deprotection required tuning of the reaction conditions in order to minimize a side reaction involving loss of the indolylmethyl side chain.