46857-11-8

Basic information

• Product Name: 5-oxo-1-(phenylsulphonyl)-L-proline
• Synonyms: 5-oxo-1-(phenylsulphonyl)-L-proline;5-Oxo-1-(phenylsulfonyl)-L-proline
• CAS NO: 46857-11-8
• Molecular Formula: C₁₁H₁₁NO₅S
• Molecular Weight: 269.27374
• EINECS: 256-284-3
• Mol File: 46857-11-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 496.2°C at 760 mmHg
• Flash Point: 253.9°C
• Appearance: /
• Density: 1.531g/cm³
• Vapor Pressure: 1.16E-10mmHg at 25°C
• Refractive Index: 1.627
• CAS DataBase Reference: 5-oxo-1-(phenylsulphonyl)-L-proline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-oxo-1-(phenylsulphonyl)-L-proline(46857-11-8)
• EPA Substance Registry System: 5-oxo-1-(phenylsulphonyl)-L-proline(46857-11-8)

Safety Data

• Hazardous Substances Data: 46857-11-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H11NO5S/c13-10-7-6-9(11(14)15)12(10)18(16,17)8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,14,15)/t9-/m0/s1

Upstream product

• 20531-36-6 2-(benzenesulfonyl)-L-glutamic acid 
• 35418-16-7 L-t-butyl pyroglutamate 
• 56-86-0 L-glutamic acid 
• 98-09-9 benzenesulfonyl chloride 
• 378238-37-0 tert-butyl N-benzenesulfonyl-(S)-pyroglutamate 

Downstream Products

• 83870-92-2 (S)-2-Benzenesulfonylamino-4-pentylcarbamoyl-butyric acid 
• 474433-43-7 1-Allyl-9-((S)-1-benzenesulfonyl-5-oxo-pyrrolidine-2-carbonyl)-1,9-dihydro-β-carboline-2-carboxylic acid 2,2,2-trichloro-ethyl ester 
• 378238-38-1 9-[N-(benzenesulfonyl)-(S)-pyroglutamyl]-β-carboline 
• 83870-88-6 N-methyl-2-benzenesulphonyl-L-glutamine 
• 83870-95-5 (S)-2-Benzenesulfonylamino-4-benzylcarbamoyl-butyric acid 
• 83870-96-6 (S)-2-Benzenesulfonylamino-4-phenylcarbamoyl-butyric acid 
• 83870-91-1 (S)-2-Benzenesulfonylamino-4-butylcarbamoyl-butyric acid 
• 83870-87-5 benzenesulphonyl-L-glutamine 
• 83870-89-7 (S)-2-Benzenesulfonylamino-4-ethylcarbamoyl-butyric acid 
• 83870-94-4 (S)-2-Benzenesulfonylamino-4-cyclohexylcarbamoyl-butyric acid 
• 83870-93-3 (S)-2-Benzenesulfonylamino-4-hexylcarbamoyl-butyric acid 
• 83870-90-0 (S)-2-Benzenesulfonylamino-4-propylcarbamoyl-butyric acid 

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.

Synthesis, screening and quantitative structure-activity relationship (QSAR) studies of some glutamine analogues for possible anticancer activity

We described the syntheses, biological activities and QSAR studies of 36 new 5-n-substituted-2-(substituted benzenesulphonyl) glutamines 6-41 with different substitutions. These compounds were designed as structural analogues of most reactive amino acid, 'glutamine' (GLN), especially in the tumor cells. They present the new basic lateral chains at R5 position as well as different substitutions at 2′, 3′, 4′, and 5′ positions on the benzene ring. The synthesized compounds have been tested for antitumor activity against Ehrlich ascites carcinoma (EAC) in Swiss albino mice using percentage inhibition of tumor weight as inhibitory parameter. In order to elucidate the structural requirements for antitumor activity, quantitative structure-activity relationship (QSAR) studies have been performed using extra thermodynamic model of Hansch. QSAR equations showed that the electronic parameter (σ) on the aromatic ring system, steric parameter (Es) and to some extent Sterimol length of the substituent (L) on the aliphatic side chain correlate significantly with the antitumor activity. Resonance factor occupies the major electronic contribution on the aromatic ring system to the activity.

Synthesis and Antineoplastic Activity of 5-N-Alkyl-2-p-substituted-benzenesulphonyl-L-glutamines

5-N-Alkyl-2-p-substituted-benzenesulphonyl-l-glutamines (III) have been synthesised and their antineoplastic potency evaluated in Ehrlich ascites carcinoma (EAC) in Swiss albino mice.A few of the compounds show appreciable activity.An interesting phenomenon of C-N bond cleavage has been observed when 2-p-toluenesulphonyl-L-glutamine (III; X = CH3, R = H) is treated with PPA.