168560-79-0

Basic information

• Product Name: AIDA
• Synonyms: 1-AMINO-2,3-DIHYDRO-1H-INDENE-1,5-DICARBOXYLIC ACID;(+/-)-1-AMINOINDAN-1,5-DICARBOXYLIC ACID;(+/-)-1-AMINOINDANE-1,5-DICARBOXYLIC ACID;AIDA;(RS)-1-AMINOINDAN-1,5-DICARBOXYLIC ACID;UPF 523;1-AMINOINDAN-1,5-DICARBOXYLIC ACID,UPF 5 23;(R,S)-1-Aminoindane-1,5-dicarboxylicacid
• CAS NO: 168560-79-0
• Molecular Formula: C11H11NO4
• Molecular Weight: 221.21
• Product Categories: Glutamate receptor
• Mol File: 168560-79-0.mol

Chemical Properties

• Boiling Point: 362.26°C (rough estimate)
• Flash Point: 238.3 °C
• Appearance: white/solid
• Density: 1.2818 (rough estimate)
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: 0-6°C
• Solubility: DMSO: 2 mg/mL
• CAS DataBase Reference: AIDA(CAS DataBase Reference)
• NIST Chemistry Reference: AIDA(168560-79-0)
• EPA Substance Registry System: AIDA(168560-79-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• WGK Germany: 3
• Hazardous Substances Data: 168560-79-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
AIDA is used as a pharmaceutical agent for its potent and selective agonist properties towards group I mGluR. This makes it a valuable compound in the development of drugs targeting specific receptors, potentially leading to more effective treatments for various conditions.
Used in Research and Development:
In the field of research and development, AIDA serves as a crucial tool for studying the functions and interactions of group I mGluR receptors. Its selective agonist properties allow scientists to investigate the roles these receptors play in cellular processes and signaling pathways, contributing to a deeper understanding of their mechanisms and potential therapeutic applications.
Used in Drug Design and Synthesis:
AIDA's properties as a potent and selective group I mGluR agonist make it a valuable compound in the design and synthesis of new drugs. Its unique interaction with specific receptors can be leveraged to create novel therapeutic agents with improved efficacy and selectivity, potentially leading to better treatment options for patients.

Biological Activity

A relatively potent and selective antagonist of group I metabotropic glutamate receptors (mGlu 1a ), having no effect on group II (mGlu 2 ) or group III (mGlu 4 ) receptors expressed individually in baby hamster kidney cells. Has no effect on ionotropic glutamate receptors. Centrally active following systemic administration in vivo .

Upstream product

• 220024-58-8 C₁₈H₁₆BrNO₂ 
• 220024-59-9 C₂₁H₂₁NO₄ 
• 473930-89-1 (S)-1-(methoxycarbonylamino)-3-oxoindan-1,5-dicarboxylic acid dimethyl ester 
• 473930-88-0 (S)-2-(methoxycarbonylamino)-5-dibromomethyl-3-oxoindan-1-carboxylic acid methyl ester 
• 473930-86-8 (S)-2-(methoxycarbonylamino)-2-(4-methylphenyl)succinic acid 1-methyl ester 
• 473930-87-9 (S)-2-(methoxycarbonylamino)-5-methyl-3-oxoindan-1-carboxylic acid methyl ester 
• 473930-83-5 (3RS,5R)-3-(4-methylphenyl)-5-phenyl-2-morpholinone 
• 104-87-0 4-methyl-benzaldehyde 
• 865172-68-5 (S)-methyl 1-formyl-1-[1,2-hydrazinedicarboxylic acid-bis(phenylmethyl)ester]-2,3-dihydro-1H-indene-5-carboxylate 
• 865172-67-4 methyl 1-formyl-2,3-dihydro-1H-indene-5-carboxylate 
• 865172-69-6 C₂₉H₂₈N₂O₈ 
• 473930-90-4 (S)-1-(methoxycarbonylamino)indan-1,5-dicarboxylic acid dimethyl ester 
• 220024-60-2 (S)-1-((S)-2-Hydroxy-1-phenyl-ethylamino)-indan-1,5-dicarboxylic acid dimethyl ester 
• 68634-02-6 methyl 2,3-dihydro-1-oxo-1H-indene-5-carboxylate 

Relevant articles and documents

Syntheses of compounds active toward glutamate receptors: I. New preparative synthesis of aminoindandicarboxylic acid (AIDA)

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

(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

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

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.