207508-60-9

Basic information

• Product Name: (4S)-4-(4-TRIFLUOROMETHYL-BENZYL)-L-GLUTAMIC ACID
• Synonyms: L-Glutamic acid, 4-[[4-(trifluoromethyl)phenyl]methyl]-, (4S)-
• CAS NO: 207508-60-9
• Molecular Formula: C13H14F3NO4
• Molecular Weight: 305.25
• Mol File: 207508-60-9.mol

Chemical Properties

• Boiling Point: 445.107°C at 760 mmHg
• Flash Point: 222.993°C
• Appearance: /
• Density: 1.417g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.524
• CAS DataBase Reference: (4S)-4-(4-TRIFLUOROMETHYL-BENZYL)-L-GLUTAMIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-4-(4-TRIFLUOROMETHYL-BENZYL)-L-GLUTAMIC ACID(207508-60-9)
• EPA Substance Registry System: (4S)-4-(4-TRIFLUOROMETHYL-BENZYL)-L-GLUTAMIC ACID(207508-60-9)

Safety Data

• Hazardous Substances Data: 207508-60-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
(4S)-4-(4-TRIFLUOROMETHYL-BENZYL)-L-GLUTAMIC ACID is used as a research tool for studying glutamate receptors, which are crucial in the central nervous system for processes like synaptic transmission and neuronal excitability.
Used in Drug Development for Neurological Disorders:
In the pharmaceutical industry, (4S)-4-(4-TRIFLUOROMETHYL-BENZYL)-L-GLUTAMIC ACID is used as a potential therapeutic agent for the treatment of neurological disorders such as epilepsy, Alzheimer's disease, and depression. Its unique structure allows it to potentially modulate glutamate signaling, which is implicated in these conditions.
Used in Medicinal Chemistry for Targeting Glutamate Signaling:
(4S)-4-(4-TRIFLUOROMETHYL-BENZYL)-L-GLUTAMIC ACID is utilized in the development of new drugs that target glutamate signaling pathways, which are involved in various cognitive functions and neurological processes. Its trifluoromethyl and benzyl groups may offer specific binding affinities or selectivity for certain receptors or enzymes, contributing to its therapeutic potential.
Note: The uses listed are speculative based on the compound's properties and potential applications in the field of medicinal chemistry and drug development. Actual uses may vary and are subject to ongoing research and development.

InChI:InChI=1/C13H14F3NO4/c14-13(15,16)9-3-1-7(2-4-9)5-8(11(18)19)6-10(17)12(20)21/h1-4,8,10H,5-6,17H2,(H,18,19)(H,20,21)/t8-,10-/m0/s1

Upstream product

• 153080-93-4 ethyl (2S,4S)-1-(tert-butoxycarbonyl)-4-(p-trifluoromethyl)benzylpyroglutamate 
• 144978-12-1 1-tert-butyl 2-ethyl (2R)-5-oxopyrrolidine-1,2-dicarboxylate 
• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 402-49-3 4-bromomethyltrifluoromethylbenzene 

Relevant articles and documents

4-Substituted D-glutamic acid analogues: The first potent inhibitors of glutamate racemase (MurI) enzyme with antibacterial activity

The first potent inhibitors of glutamate racemase (MurI) enzyme that show whole cell antibacterial activity are described. Optically pure 4-substituted D-glutamic acid analogues with (2R,4S) stereochemistry and bearing aryl-, heteroaryl-, cinnamyl-, or biaryl-methyl substituents represent a novel class of glutamate racemase inhibitors. Exploration of the D-Glu core led to the identification of lead compounds (-)-8 and 10. 2-Naphthylmethyl derivative 10 was found to be a potent competitive inhibitor of glutamate racemase activity (Ki = 16 nM, circular dichroism assay; IC50 = 0.1 μg/mL high-performance liquid chromatography (HPLC) assay). Thorough structure-activity relationship (SAR) studies led to benzothienyl derivatives such as 69 and 74 with increased potency (IC50 = 0.036 and 0.01 μg/mL, respectively, HPLC assay). These compounds showed potent whole cell antibacterial activity against S. pneumoniae PN-R6, and good correlation with the enzyme assay. Compounds 69, 74 and biaryl derivative 52 showed efficacy in an in vivo murine thigh infection model against Streptococcus pneumoniae. Data described herein suggest that glutamate racemase may be a viable target for developing new antibacterial agents.

(2S,3S)-2-Amino-3-(2,2-diphenylethyl)pentanedioic acid selective group 2 metabotropic glutamate receptor antagonist

(2S,4S)-2-Amino-4-(4,4-diphenylbut-1-yl)-pentane-1,5-dioic acid 1m, is a novel metabotropic glutamate receptor (mGluR) antagonist with insignificant ionotropic affinity. It is a selective antagonist of negatively-coupled cAMP-linked mGluRs with no effect