168560-79-0Relevant articles and documents
Syntheses of compounds active toward glutamate receptors: I. New preparative synthesis of aminoindandicarboxylic acid (AIDA)
Matveeva,Podrugina,Zefirova,Alekseev,Bachurin,Pellicciari,Zefirov
, p. 1764 - 1768 (2002)
A preparative procedure has been developed for the synhtesis of 1-aminoindan-1,5-dicarboxylic acid which is a new group I metabotropic glutamate receptor antagonist.
Organocatalytic enantioselective synthesis of metabotropic glutamate receptor ligands
Suri, Jeff T.,Steiner, Derek D.,Barbas III, Carlos F.
, p. 3885 - 3888 (2007/10/03)
(Chemical Equation Presented) (R)-Proline catalyzes the amination reaction of functionalized indane carboxaldehydes and allows for the efficient enantioselective synthesis (>99% ee) of the metabotropic glutamate receptor ligands (S)-AIDA and (S)-APICA.
Asymmetric synthesis of (S)-1-aminoindan-1,5-dicarboxylic acid and related analogues via intramolecular acylation of enantiopure α,α-disubstituted amino acids
Ma, Dawei,Ding, Ke,Tian, Hongqi,Wang, Baomin,Cheng, Dongliang
, p. 961 - 970 (2007/10/03)
α,α-disubstituted amino acid derivatives are synthesized either by a self-regeneration of stereocenter strategy or using the asymmetric Strecker reaction/alkylation method. Of the four types of substrates tested for intramolecular acylation, those with a
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
Ma, Dawei,Tian, Hongqi,Zou, Guixiang
, p. 120 - 125 (2007/10/03)
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.