21957-65-3

Basic information

• Product Name: 5-oxo-1-[(p-tolyl)sulphonyl]-L-proline
• Synonyms: 5-oxo-1-[(p-tolyl)sulphonyl]-L-proline;1-[(4-Methylphenyl)sulfonyl]-5-oxo-L-proline;Nsc163455
• CAS NO: 21957-65-3
• Molecular Formula: C₁₂H₁₃NO₅S
• Molecular Weight: 283.30032
• EINECS: 244-680-9
• Mol File: 21957-65-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 499°Cat760mmHg
• Flash Point: 255.6°C
• Appearance: /
• Density: 1.475g/cm³
• Vapor Pressure: 8.93E-11mmHg at 25°C
• Refractive Index: 1.613
• CAS DataBase Reference: 5-oxo-1-[(p-tolyl)sulphonyl]-L-proline(CAS DataBase Reference)
• NIST Chemistry Reference: 5-oxo-1-[(p-tolyl)sulphonyl]-L-proline(21957-65-3)
• EPA Substance Registry System: 5-oxo-1-[(p-tolyl)sulphonyl]-L-proline(21957-65-3)

Safety Data

• Hazardous Substances Data: 21957-65-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H13NO5S/c1-8-2-4-9(5-3-8)19(17,18)13-10(12(15)16)6-7-11(13)14/h2-5,10H,6-7H2,1H3,(H,15,16)/t10-/m0/s1

Upstream product

• 4816-80-2 N-tosyl-L-glutamic acid 
• 886203-20-9 acetic acid-[5-oxo-1-(toluene-4-sulfonyl)-L-proline]-anhydride 
• 56-86-0 L-glutamic acid 
• 98-59-9 p-toluenesulfonyl chloride 
• 34605-45-3 N-[(4-methylphenyl)sulfonyl] D-glutamic acid 

Downstream Products

• 113752-42-4 N-(toluene-4-sulfonyl)-L-γ-glutamyl=>glycyl=>L-glutamic acid diethyl ester 
• 1071694-87-5 N-[N-(toluene-4-sulfonyl)-L-γ-glutamyl]-L-tyrosine ethyl ester 
• 7460-91-5 NCS 400401 
• 122767-19-5 N-(toluene-4-sulfonyl)-L-glutamic acid-dianilide 
• 83871-04-9 N⁵-benzyl-N²-(toluene-4-sulfonyl)-L-glutamine 
• 42749-49-5 N²-<(4-methylphenyl)sulfonyl>-L-glutamine 
• 6304-79-6 N-(toluene-4-sulfonyl)-L-glutamic acid-5-hydrazide 
• 882861-84-9 5-oxo-1-(toluene-4-sulfonyl)-D-proline 
• 108541-02-2 5-oxo-1-(toluene-4-sulfonyl)-L-prolyl chloride 
• 17669-13-5 N²-(4-Toluolsulfonyl)-N⁵-(3-methylthio-ethyl)-L-glutamin 
• 18304-74-0 N²-(4-Toluolsulfonyl)-N⁵-(3-methylthio-propyl)-L-glutamin 
• 17669-15-7 N,N'-Bis-<γ-(N-p-toluolsulfonyl)-L-glutamyl>-cystamin 
• 5105-80-6 N--γ-L-glutaminyl-γ-Aminobuttersaeure-tert-butylester 
• 17669-14-6 N²-(4-Toluolsulfonyl)-N⁵-(2-hydroxyethyl)-L-glutamin 

Relevant articles and documents

Chemoselective Intramolecular Functionalization of Methyl Groups in Nonconstrained Molecules Promoted by N-Iodosulfonamides

Mechanistic evidence observed in Hofmann-L?ffler-Freytag-type reactions has been crucial to achieve the chemoselective functionalization of methyl groups under mild conditions. Radical-mediated methyl iodination and subsequent oxidative deiodination are the key steps in this functionalization, where iodine chemistry has a pivotal role on the formation of the C-N bond. The concepts of single hydrogen atom transfer (SHAT) and multiple hydrogen atom transfer (MHAT) are introduced to describe the observed chemoselectivity. (Chemical Equation Presented).

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.