20531-36-6

Basic information

• Product Name: (R)-(-)-N-(PHENYLSULPHONYL)GLUTAMIC ACID
• Synonyms: (-)-N-BENZENESULFONYLGLUTAMIC ACID;(+)-N-BENZENESULFONYLGLUTAMIC ACID;(S)-(+)-N-(PHENYLSULPHONYL)GLUTAMIC ACID;(R)-(-)-N-(PHENYLSULPHONYL)GLUTAMIC ACID;(-)-N-(PHENYLSULFONYL)GLUTAMIC ACID, 97%;N-(Phenylsulfonyl)-L-glutamic acid
• CAS NO: 20531-36-6
• Molecular Formula: C₁₁H₁₃NO₆S
• Molecular Weight: 287.29
• Mol File: 20531-36-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 137-140 °C(lit.)
• Boiling Point: 531.7°C at 760 mmHg
• Flash Point: 275.4°C
• Appearance: /
• Density: 1.468g/cm³
• Vapor Pressure: 3.89E-12mmHg at 25°C
• Refractive Index: 1.585
• CAS DataBase Reference: (R)-(-)-N-(PHENYLSULPHONYL)GLUTAMIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-N-(PHENYLSULPHONYL)GLUTAMIC ACID(20531-36-6)
• EPA Substance Registry System: (R)-(-)-N-(PHENYLSULPHONYL)GLUTAMIC ACID(20531-36-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 20531-36-6(Hazardous Substances Data)

Usage

Description

(R)-(-)-N-(PHENYLSULPHONYL)GLUTAMIC ACID, a derivative of glutamic acid, is a stereospecific inhibitor of glutamate carboxypeptidase II (GCPII), a zinc metallopeptidase that plays a role in the hydrolysis of N-acetylaspartylglutamate (NAAG). (R)-(-)-N-(PHENYLSULPHONYL)GLUTAMIC ACID has potential therapeutic applications in various neurological disorders and prostate cancer due to its ability to inhibit GCP II, which is overexpressed in these conditions.

Uses

Used in Pharmaceutical Industry:
(R)-(-)-N-(PHENYLSULPHONYL)GLUTAMIC ACID is used as a therapeutic agent for the treatment of neurological disorders such as neuropathic pain, stroke, and neurodegenerative diseases. Its application is based on its ability to inhibit GCP II, a potential therapeutic target in these conditions.
Used in Oncology:
(R)-(-)-N-(PHENYLSULPHONYL)GLUTAMIC ACID is used as an anticancer agent, particularly in the treatment of prostate cancer. (R)-(-)-N-(PHENYLSULPHONYL)GLUTAMIC ACID targets GCP II, which is overexpressed in prostate cancer cells, making it a promising candidate for cancer therapy.
Used in Central Nervous System (CNS) Disorders:
(R)-(-)-N-(PHENYLSULPHONYL)GLUTAMIC ACID is used as a potential treatment for CNS disorders due to its inhibitory effect on GCP II, which is involved in the regulation of neurotransmission and has been linked to various neurological conditions.

InChI:InChI=1/C11H13NO6S/c13-10(14)7-6-9(11(15)16)12-19(17,18)8-4-2-1-3-5-8/h1-5,9,12H,6-7H2,(H,13,14)(H,15,16)/t9-/m1/s1

Upstream product

• 32677-01-3 L-glutamic acid di-tert-butyl ester hydrochloride 
• 98-09-9 benzenesulfonyl chloride 
• 1301109-76-1 C₁₉H₂₉NO₆S 
• 110-94-1 1,5-pentanedioic acid 
• 7647-01-0 hydrogenchloride 
• 64-18-6 formic acid 
• 56-86-0 L-glutamic acid 
• 617-65-2 Glutamic acid 

Downstream Products

• 1165869-58-8 C₈H₁₇NO₂*C₁₁H₁₃NO₆S 
• 46857-11-8 1-(benzenesulfonyl)-5-oxopyrrolidine-2-carboxylic acid 
• 463314-98-9 2-(benzenesulfonyl)-L-glutamic acid dichloride 
• 46857-11-8 1-benzenesulphonyl-5-oxopyrrolidine-2-carboxylic acid 
• 12328-61-9 Cu⁽²⁺⁾*(C₆H₅SO₂NHCH(CH₂CH₂COO)COO)^(2-)*H₂O=Cu(C₆H₅SO₂NHCH(CH₂CH₂COO)COO)*H₂O 

Relevant articles and documents

Possible anticancer agents: synthesis, pharmacological activity, and molecular modeling studies on some 5-N -Substituted-2-N-(substituted benzenesulphonyl)-L(+)Glutamines

On the basis of our earlier work, fortyone 5-N-substituted-2N-(substituted benzenesulphonyl)-L(+)glutamines were synthesized and screened for cancer cell inhibitory activity. The best active compounds showed 91% tumor cell inhibition, whereas other three compounds showed more than 80% inhibition. Two-dimensional quantitative structure–activity relationship modeling and three-dimensional quantitative structure–activity relationship k-nearest neighbor molecular field analysis studies were done to get an insight into structural requirements toward further improved anticancer activity. Considering the fact that these compounds are competitive inhibitors of glutaminase, a molecular docking study followed by molecular dynamic simulation analysis were performed. The work may help to develop new anticancer agents.

Syntheses, biological evaluation and QSAR study on antitumor activity of 1,5-N,N′-disubstituted-2-(substituted benzenesulphonyl) glutamamides

We have reported [unpublished data] the synthesis and QSAR of 5-substituted-2-(substituted benzenesulphonyl) glutamines which have shown the importance of steric factor on the aliphatic chain. N-Phthalyl isoglutamine, having the substitution at position 1 of the glutamic acid moiety, is the metabolite of recently approved thalidomide for different types of tumors by US FDA. Based on these, 36 new 1,5-N,N′-disubstituted-2-(substituted benzenesulphonyl) glutamamides were synthesized, as tools for further elucidation of the structural requirements for antitumor activity. All the synthesized compounds were tested for antitumor activity against Ehrlich Ascites Carcinoma (EAC) in Swiss albino mice using tumor weight as inhibitory parameter. Quantitative structure-activity relationship (QSAR) studies of these analogues revealed that the electron donating groups on the phenyl ring are found to be mandatory for the activity which was also proved by the negative coefficient of indicator parameter I3, for NO2 group on the phenyl ring. Molecular volume (MV) and steric factor at R5 position also plays a role in ligand-receptor interactions.

Synthesis, characterization and biological activity of Cu(II) chelates with some amino acid derivatives

The complexing behaviour of seventeen amino acid derivatives towards Cu(II) has been studied.Complexes of the types Cu(RH)*xH2O, Cu(RH).Cu(OH)2*xH2O and Cu(R'H)2*yH2O have been prepared and characterized by IR, ESR, electronic spectral, magnetic moment and analytical data.On the basis of differences and direction of the shifts in the IR frequencies of vas OCO and vs OCO modes and ESR spectra, bonding modes of carboxylate group have been established.Biological activitu of complexes is more than that of the free metal ion and the ligands.