205646-87-3

Upstream product

• 179106-27-5 (Z)-2-(3-aminophenyl)-3-(2-carboethoxy-4,6-dichloroindol-3-yl)-propenoic acid, methyl ester 
• 109-94-4 formic acid ethyl ester 
• 179106-22-0 3-methoxy-2-(3-nitrophenyl)-propenoic acid methyl ester 
• 53995-82-7 4,6-dichloro-indole-2-carboxylic acid,ethyl ester 
• 10268-12-9 methyl 3-nitrophenylacetate 
• 179106-25-3 (E)-2-(3-Nitrophenyl)-3-(2-carboethoxy-4,6-dichloroindol-3-yl-2)propenoic acid, methyl ester 

Relevant academic research and scientific papers

CoMFA, synthesis, and pharmacological evaluation of (E)-3-(2-carboxy-2- arylvinyl)-4,6-dichloro-1H-indole-2-carboxylic acids: 3-[2-(3-Aminophenyl)-2- carboxyvinyl]-4,6-dichloro-1H-indole-2-carboxylic acid, a potent selective glycine-site NMDA receptor antagonist

(E)-3-(2-Carboxy-2-phenylvinyl)-4,6-dichloro-1H-indole-2-carboxylic acid, 1, is a potent and selective antagonist of the glycine site of the N-methyl-D-aspartate (NMDA) receptor. Using 3D comparative molecular field analysis (CoMFA) to guide the synthetic effort, a series of aryl diacid analogues of 1 were synthesized to optimize in vivo potency, duration of action, and binding activity. It was found that the incorporation of a substituted aromatic with an electron withdrawing group or a heterocyclic group at the 2-position of the 3-propenyl moiety of 1 gave compounds with better affinity and potency in the murine stroke model. Ultimately this led to the discovery of 3-[2-(3-aminophenyl)-2-carboxyvinyl]-4,6-dichloro-1H-indole-2-carboxylic acid, 19, as a new potent selective glycine-site NMDA receptor antagonist.

NMDA (N-METHYL-D-ASPARTATE) ANTAGONISTS

The present invention is new excitatory amino acid antagonists (herein referred to as compounds of formula (1)). These new antagonists are useful as NMDA (N-methyl-D-aspartate) antagonists.