861213-76-5

Upstream product

• 16732-64-2 4-bromo-1H-indole-2-carboxylic acid 
• 90002-36-1 2-ethylphenyl boronic acid 
• 608510-29-8 ethyl 3-(2-bromo-6-nitrophenyl)-2-oxopropanoate 
• 55289-35-5 2-bromo-6-nitrotoluene 
• 103858-52-2 4-bromo-1H-Indole-2-carboxylic acid ethyl ester 

Downstream Products

• 1210054-46-8 C₂₉H₂₉N₃O₅ 
• 1182349-08-1 (R)-2-benzyloxycarbonylamino-3-{[4-(2-ethyl-phenyl)-1H-indole-2-carbonyl]amino}propionic acid benzyl ester 

Relevant academic research and scientific papers

Improved synthetic route for the GluN2-specific NMDA receptor glycine site agonist AICP

(R)-2-Amino-3-(4-(2-ethylphenyl)-1H-indole-2-carboxamido)propanoic acid (AICP) is a N-methyl-D-aspartate (NMDA) receptor glycine site agonist with unprecedented high potency in the low nanomolar range, and a GluN2 subunit-dependent pharmacological profile in terms of potency and agonist efficacy (Jessen et al., 2017 [1]). Here, we report a scalable, practical and cost-efficient synthetic route for AICP, which is an improvement compared to the previously reported route. This improved synthetic route includes a versatile diphenylmethylester (DPM) protection for the amino acid moiety, which can be widely used in the synthesis of other amino acid ligands. Further functional evaluation of AICP at the different ionotropic glutamate receptor (iGluR) classes demonstrates that high affinity binding of AICP to the orthosteric binding site is selective for NMDA receptors over AMPA and kainate receptors. Furthermore, high affinity binding of AICP is not observed at GluN3A, GluN3B, and GluD2 subunits, which also bind glycine and D-serine. Thus, the new approach described here enables scalable synthesis of AICP for the use as a pharmacological tool compound to study the involvement of neuronal NMDA receptor subtypes in normal brain function and disease.

Drug design, in vitro pharmacology, and structure-activity relationships of 3-acylamino-2-aminopropionic acid derivatives, a novel class of partial agonists at the glycine site on the N-methyl-D-aspartate (NMDA) receptor complex

Retaining agonistic activity at the glycine coagonist site of the NMDA receptor in molecules derived from glycine or D-serine has proven to be difficult because in the vicinity of the α-amino acid group little substitution is tolerated. We have solved thi

INDOL-ALANINE DERIVATIVES AS SELECTIVE S1P4-AGONISTS

The present invention relates to agonists of the S1P4 receptor, which are selective for the S1P4 receptor over one or more of the S1P1, S1P2, S1P3 or S1P5 receptors of at least 10 fold, in particular new indol-alanine derivatives of structure (I), process