389888-02-2

Basic information

• Product Name: (S)-ALPHA-AMINO-2,3,4,5,6,7-HEXAHYDRO-2,4-DIOXO-1H-CYCLOPENTAPYRIMIDINE-1-PROPANOIC ACID
• Synonyms: (S)-ALPHA-AMINO-2,3,4,5,6,7-HEXAHYDRO-2,4-DIOXO-1H-CYCLOPENTAPYRIMIDINE-1-PROPANOIC ACID;(S)-CPW 399;(S)-α-Amino-2,3,4,5,6,7-hexahydro-2,4-dioxo-1H-cyclopentapyrimidine-1-propanoicacid;(2S)-2-amino-3-(2,4-dioxo-6,7-dihydro-5H-cyclopenta[d]pyrimidin-1-yl)propanoic acid
• CAS NO: 389888-02-2
• Molecular Formula: C10H13N3O4
• Molecular Weight: 239.23
• Mol File: 389888-02-2.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Storage Temp.: Desiccate at -20°C
• Solubility: Aqueous Acid (Slightly, Heated, Sonicated), DMSO (Slightly)
• CAS DataBase Reference: (S)-ALPHA-AMINO-2,3,4,5,6,7-HEXAHYDRO-2,4-DIOXO-1H-CYCLOPENTAPYRIMIDINE-1-PROPANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-ALPHA-AMINO-2,3,4,5,6,7-HEXAHYDRO-2,4-DIOXO-1H-CYCLOPENTAPYRIMIDINE-1-PROPANOIC ACID(389888-02-2)
• EPA Substance Registry System: (S)-ALPHA-AMINO-2,3,4,5,6,7-HEXAHYDRO-2,4-DIOXO-1H-CYCLOPENTAPYRIMIDINE-1-PROPANOIC ACID(389888-02-2)

Safety Data

• Hazardous Substances Data: 389888-02-2(Hazardous Substances Data)

Usage

Uses

(S)-CPW 399 is a subtype-selective weakly desensitising AMPA agonist.

Biological Activity

Novel subtype-selective and weakly desensitizing AMPA receptor partial agonist (K i values are 44, 109, 223, 1890 and 2090 nM at GluR5, GluR1, GluR2, GluR3 and GluR4 receptors respectively). Exhibits potent agonist activity at GluR1 and GluR2 subunit-containing AMPA receptors (EC 50 values are 24.9 and 13.9 μM respectively) and is excitotoxic in vitro .

references

[1]. campiani g, morelli e, nacci v, et al. characterization of the 1h-cyclopentapyrimidine-2,4(1h,3h)-dione derivative (s)-cpw399 as a novel, potent, and subtype-selective ampa receptor full agonist with partial desensitization properties. j med chem, 2001, 44(26): 4501-4504.[2]. sinclair c, reavy h, grieve a, et al. inherent desensitisation-preventing properties of a novel, subtype-selective ampa receptor agonist, (s)-cpw 399, as a possible explanation for its excitotoxic action in cultured cerebellar granule cells. neurochem int, 2003, 42(6): 499-510.[3]. salonen v, kallinen s, lopez-picon fr, et al. ampa/kainate receptor-mediated up-regulation of gabaa receptor delta subunit mrna expression in cultured rat cerebellar granule cells is dependent on nmda receptor activation. brain res, 2006, 1087(1): 33-40.[4]. butini s, pickering ds, morelli e, et al. 1h-cyclopentapyrimidine-2,4(1h,3h)-dione-related ionotropic glutamate receptors ligands. structure-activity relationships and identification of potent and selective iglur5 modulators. j med chem, 2008, 51(20): 6614-6618.

Upstream product

• 611-10-9 2-ethoxycarbonyl-1-cyclopentanone 
• 35563-27-0 2-sulfanylidene-1,2,3,4,6,7-hexahydro-5H-cyclopenta[d]pyrimidin-4-one 
• 5466-00-2 1,5,6,7-tetrahydro-cyclopentapyrimidine-2,4-dione 
• 98541-64-1 (S)-3-(tert-butoxycarbonylamino)-oxetan-2-one 

Relevant articles and documents

Characterization of the 1H-cyclopentapyrimidine-2,4(1H,3H)-dione derivative (S)-CPW399 as a novel, potent, and subtype-selective AMPA receptor full agonist with partial desensitization properties

(S)-CPW399 (2b) is a novel, potent, and subtype-selective AMPA receptor full agonist that, unlike (S)-willardiine and related compounds, in mouse cerebellar granule cells, stimulated an increase in [Ca2+]i, and induced neuronal cell death in a time- and concentration-dependent manner. Compound 2b appears to be a weakly desensitizing, full agonist at AMPA receptors and therefore represents a new pharmacological tool to investigate the role of AMPA receptors in excitotoxicity and their molecular mechanisms of desensitization.