169209-65-8

Usage

Uses

MPPG is a potent antagonist of L-AP4-induced effects.

Biological Activity

Potent antagonist of L-AP4-induced effects in rat spinal cord, thalamic and hippocampal neurons, showing selectivity over (1S,3S)-ACPD-induced effects. Potent antagonist of mGlu receptors linked to adenylyl cyclase in adult rat cortical slices.

Upstream product

• 22818-40-2 D-4-hydroxyphenylglycine 
• 180715-66-6 (R)-4-Benzyloxyphenyl-N-methylglycinamide 
• 71336-83-9 Methyl-D-p-benzyloxyphenylglycinat 
• 69489-40-3 D-2-[p-(benzyloxy)phenyl]glycine 
• 220024-53-3 (S)-2-[Benzyloxycarbonyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-2-(4-bromo-phenyl)-propionic acid methyl ester 
• 220024-55-5 (S)-2-[Benzyloxycarbonyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-2-[4-(diethoxy-phosphoryl)-phenyl]-propionic acid methyl ester 
• 220024-56-6 N-[(R)-(2-hydroxy-1-phenylethyl)]-(S)-2-amino-2-methyl-(4'-diethylphosphonophenyl)acetic acid methyl ester 
• 201608-22-2 [4-((2R,4S)-3-Benzoyl-2-tert-butyl-1,4-dimethyl-5-oxo-imidazolidin-4-yl)-phenyl]-phosphonic acid diethyl ester 
• 201608-21-1 Trifluoro-methanesulfonic acid 4-((2R,4S)-3-benzoyl-2-tert-butyl-1,4-dimethyl-5-oxo-imidazolidin-4-yl)-phenyl ester 
• 201608-20-0 (2R,5S)-1-Benzoyl-5-(4-benzyloxyphenyl)-2-(tert-butyl)-3,5-dimethylimidazolidin-4-one 
• 201608-19-7 (2R,5R)-1-Benzoyl-5-(4-benzyloxyphenyl)-2-tert-butyl-3-methylimidazolidin-4-one 

Relevant academic research and scientific papers

Asymmetric strecker-type reaction of α-aryl ketones. Synthesis of (S)- αM4CPG, (S)-MPPG, (S)-AIDA, and (S)-APICA, the antagonists of metabotropic glutamate receptors

Heating a mixture of α-aryl ketone with (R)-phenylglycinol produces a mixture of imine and 1,3-dioxazolidine. Treatment of this mixture with trimethylsilyl cyanide followed by transformation of nitrile to ester gives Strecker-type reaction products. The diastereoselectivity of the generated α-amino esters is from 2/1 to 7/1, and the (R,S)isomer is found as the major product. The (R,S) and (R,R)isomers can be separated by conversion to their N-Cbz or cyclization derivatives. Using this methodology, four antagonists of metabotropic glutamate receptors, (S)-αM4CPG, (S)-MPPG, (S)AIDA, and (S)- APICA, are synthesized.

Stereoselective synthesis of (S)-MPPG, (S)-MTPG and (S)-(+)-αM4CPG from (R)-4-hydroxyphenylglycine

(R)-4-Hydroxyphenylgrycine was protected with a benzyl group and a methyl group was introduced at the α position by using the self-regeneration-of-stereocentre method. After the 4-hydroxy group had been converted into the corresponding trifluoromethanesulfonate (triflate), three palladium-catalyzed reactions were employed to furnish (S)-α-methyl-4-phosphonophenylglycine [(S)-MPPG], (S)-α-methyl-4-(tetrazol-5-yl)phenylglycine [(S)-MTPG] and (S)-4-carboxyphenyl-α-methylglycine [(S)-αM4CPG], a class of new and selective antagonists of metabotropic glutamate receptors.