179328-07-5

Upstream product

• 153435-96-2 ethyl-3-formyl-4,6-dichloro-indole-2-carboxylate 
• 179106-70-8 (Z)-3-(2-bromo-2-(tert-butoxycarbonyl)vinyl)-4,6-dichloro-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester 
• 179106-92-4 4,6-dichloro-3-formyl-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester 
• 179328-06-4 3-(2-tert-butoxycarbonyl-2-thiophen-2-yl-vinyl)-4,6-dichloro-1-(toluene-4-sulfonyl)-1H-indole-2-carboxylic acid ethyl ester 
• 53995-82-7 4,6-dichloro-indole-2-carboxylic acid,ethyl 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.

HETEROCYCLE SUBSTITUTED PROPENOIC ACID DERIVATIVES AND PHARMACEUTICAL COMPOSITIONS THEREOF

The present invention is new 3-(heterocyclic)-propenoic acid derivatives and pharmaceutical compositions thereof. These new 3-(heterocyclic)-propenoic acid derivatives are useful as NMDA antagonist.