40856-80-2

Usage

Uses

Used in Pharmaceutical Industry:
2,4-Imidazolidinedione, 5-(1H-indol-3-ylmethyl)-, (S)is used as a key intermediate in the synthesis of Tryptophan (CAS# 73-22-3), an essential amino acid that serves as a building block for proteins and has various biological functions.
Used in Membrane Transport Proteins:
2,4-Imidazolidinedione, 5-(1H-indol-3-ylmethyl)-, (S)is involved in ligand recognition mechanisms for membrane transport proteins, which are crucial for the movement of molecules across cell membranes and maintaining cellular homeostasis.

Upstream product

• 590-28-3 potassium cyanate 
• 7524-52-9 (S)-tryptophan methyl ester hydrochloride 
• 917-61-3 sodium isocyanate 
• 73-22-3 L-Tryptophan 
• 89595-64-2 N-carbamoyl-L-tryptophan 

Relevant academic research and scientific papers

Mechanochemical preparation of hydantoins from amino esters: Application to the synthesis of the antiepileptic drug phenytoin

The eco-friendly preparation of 5- and 5,5-disubstituted hydantoins from various amino ester hydrochlorides and potassium cyanate in a planetary ball-mill is described. The one-pot/two-step protocol consisted in the formation of ureido ester intermediates, followed by a base-catalyzed cyclization to hydantoins. This easy-handling mechanochemical methodology was applied to a large variety of α- and β-amino esters, in smooth conditions, leading to hydantoins in good yields and with no need of purification steps. As an example, the methodology was applied to the "green" synthesis of the antiepileptic drug Phenytoin, with no use of any harmful organic solvent.

Privileged scaffolds or promiscuous binders: A comparative study on rhodanines and related heterocycles in medicinal chemistry

Rhodanines and related five-membered heterocycles with multiple heteroatoms have recently gained a reputation of being unselective compounds that appear as "frequent hitters" in screening campaigns and therefore have little value in drug discovery. However, this judgment appears to be based mostly on anecdotal evidence. Having identified various rhodanines and related compounds in screening campaigns, we decided to perform a systematic study on their promiscuity. An amount of 163 rhodanines, hydantoins, thiohydantoins, and thiazolidinediones were synthesized and tested against several targets. The compounds were also characterized with respect to aggregation and electrophilic reactivity, and the binding modes of rhodanines and related compounds in published X-ray cocrystal structures were analyzed. The results indicate that the exocyclic, double bonded sulfur atom in rhodanines and thiohydantoins, in addition to other structural features, offers a particularly high density of interaction sites for polar interactions and hydrogen bonds. This causes a promiscuous behavior at concentrations in the "screening range" but should not be regarded as a general knockout criterion that excludes such screening hits from further development. It is suggested that special criteria for target affinity and selectivity are applied to these classes of compounds and that their exceptional and potentially valuable biomolecular binding properties are consequently exploited in a useful way.

Efficient syntheses of 13C- and 14C-labelled 5-benzyl and 5-indolylmethyl L-hydantoins

Robust and straightforward methods are described for the first syntheses of highly pure 13C- and 14C-labelled L-5-benzylhydantoin (L-BH) and L-5-indolylmethylhydantoin (L-IMH) by cyclizing the amino acids L-phenylalanine and L-trypto