42749-49-5

Basic information

• Product Name: (-)-N-[(4-METHYLPHENYL)SULFONYL]-D-GLUTAMINE
• Synonyms: (R)-4-CARBAMOYL-2-(TOLUENE-4-SULFONYLAMINO)-BUTYRIC ACID;(-)-N-[(4-METHYLPHENYL)SULFONYL]-D-GLUTAMINE;Ts-Gln-OH;(S)-5-AMino-2-(4-MethylphenylsulfonaMido)-5-oxopentanoic acid;L-Glutamine, N2-[(4-methylphenyl)sulfonyl]-
• CAS NO: 42749-49-5
• Molecular Formula: C₁₂H₁₆N₂O₅S
• Molecular Weight: 300.33
• Mol File: 42749-49-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 164-165 °C
• Boiling Point: 607.3°Cat760mmHg
• Flash Point: 321.1°C
• Appearance: /
• Density: 1.376g/cm³
• Vapor Pressure: 1.34E-15mmHg at 25°C
• PKA: 3.28±0.10(Predicted)
• CAS DataBase Reference: (-)-N-[(4-METHYLPHENYL)SULFONYL]-D-GLUTAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-N-[(4-METHYLPHENYL)SULFONYL]-D-GLUTAMINE(42749-49-5)
• EPA Substance Registry System: (-)-N-[(4-METHYLPHENYL)SULFONYL]-D-GLUTAMINE(42749-49-5)

Safety Data

• Hazardous Substances Data: 42749-49-5(Hazardous Substances Data)

Usage

General Description

(-)-N-[(4-METHYLPHENYL)SULFONYL]-D-GLUTAMINE is a chemical compound that belongs to the class of sulfonyl-containing amino acid derivatives. It is a stereoselective inhibitor of the enzyme glutamine synthetase, which plays a key role in the synthesis of glutamine. (-)-N-[(4-METHYLPHENYL)SULFONYL]-D-GLUTAMINE is a potent and selective inhibitor of glutamine synthetase, and it has been studied for its potential application in cancer therapy, as glutamine synthetase is often overexpressed in cancer cells. Its chemical structure consists of a sulfonamide group attached to a D-glutamine backbone, with a 4-methylphenyl group attached to the nitrogen atom. (-)-N-[(4-METHYLPHENYL)SULFONYL]-D-GLUTAMINE has shown promise as a research tool in the study of glutamine metabolism and as a potential therapeutic agent for cancer.

InChI:InChI=1/C12H16N2O5S/c1-8-2-4-9(5-3-8)20(18,19)14-10(12(16)17)6-7-11(13)15/h2-5,10,14H,6-7H2,1H3,(H2,13,15)(H,16,17)/p-1/t10-/m1/s1

Upstream product

• 56-85-9 L-glutamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 56-86-0 L-glutamic acid 
• 4816-80-2 N-tosyl-L-glutamic acid 
• 7664-41-7 ammonia 
• 108541-02-2 5-oxo-1-(toluene-4-sulfonyl)-L-prolyl chloride 
• 21957-65-3 1-(4'-methylbenzenesulfonyl)-5-oxopyrrolidine-2-carboxylic acid 
• 6970-25-8 1-((4-methylbenzene)sulfonyl)-5-oxopyrrolidine-2-carboxylic acid 
• 882861-84-9 5-oxo-1-(toluene-4-sulfonyl)-D-proline 

Downstream Products

• 122804-10-8 N²-(toluene-4-sulfonyl)-L-glutaminyl=>L-isoasparaginyl=>S-benzyl-L-cysteine benzyl ester 
• 100723-63-5 N-(toluene-4-sulfonyl)-L-glutamic acid-1-ethyl ester-5-nitrile 
• 100616-51-1 N-(toluene-4-sulfonyl)-D-glutamic acid-1-methyl ester-5-nitrile 
• 1195614-21-1 N-(toluene-4-sulfonyl)-D-glutamic acid-5-nitrile 
• 70-26-8 D-ornithine 
• 132465-74-8 N²-(toluene-4-sulfonyl)-L-glutamine methyl ester 
• 70-55-3 toluene-4-sulfonamide 
• 62234-29-1 N2-p-toluenesulfonyl-L-2,4-diaminobutyric acid 
• 108478-42-8 N²-(toluene-4-sulfonyl)-L-glutamine ethyl ester 
• 6304-81-0 N-[(4-methylphenyl)sulfonyl]-L-glutamic acid-1,5-diethyl ester 
• 95305-51-4 dimethyl (2S)-2-{[(4-methylphenyl)sulfonyl]amino}pentane-1,5-dioate 
• 132465-73-7 N²-(toluene-4-sulfonyl)-DL-glutamine methyl ester 
• 132465-72-6 N²-(toluene-4-sulfonyl)-D-glutamine methyl ester 
• 56-85-9 L-glutamine 

Relevant articles and documents

(S)-2-methyl-1,4,5,6-tetrahydromethylpyrimidine-4-carboxylic acid synthesis method

The present invention relates to a (S)-2-methyl-1,4,5,6-tetrahydromethylpyrimidine-4-carboxylic acid synthesis method. According to the method, L-glutamine is used as a raw material, the alpha-amino of the L-glutamine is protected with a protection group, a decarbonylating agent is added, a Hofmann degradation reaction is performed to remove the carbonyl group attached to the remaining amino, the protection group is removed to obtain L-2,4-diaminobutyric acid, and finally the prepared L-2,4-diaminobutyric acid and trimethyl orthoacetate are subjected to a ring forming reaction to obtain the (S)-2-methyl-1,4,5,6-tetrahydromethylpyrimidine-4-carboxylic acid. Compared to the method in the prior art, the method of the present invention has the following characteristics that the chemical synthesis route is provided, the steps of the synthesis process are simple, the raw materials are easy to obtain, the product purity is high, and the method is suitable for large-scale industrial production.

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A compound selected from the group consisting of a compound of formula I 1a compound of formula II 2and when the compound of formula I and II comprises an amino group pharmaceutically acceptable ammonium salts thereof, wherein R1, R2, Cx, n, R3, R4, R5, Y are as defined in the specification.

Syntheses and Evaluation as Antifolates of MTX Analogues Derived from 2,ω-Diaminoalkanoic Acids

Methotrexate (MTX) analogues 27a-c bearing 2,ω-diaminoalkanoic acids (ornithine and its two lower homologues) in place of glutamic acid were synthesized by routes proceeding through N2--Nω--2,ω-diaminoalkanoic acids ethyl esters (12a,b) and N2--N5--2,5-diaminopentanoic acid (13) followed by alkylation with 6-(bromomethyl)-2,4-pteridinediamine hydrobromide.Reactions at the terminal amino group of 27-type analogues or of appropriate precursors led to other MTX derivatives whose side chains terminate in ureido (23a,b), methylureido (24), N-methyl-N-nitrosoureido (30), N-(2-chloroethyl)-N-nitrosoureido (31), and 4-chlorobenzamido (28a-c) groups.Also prepared were unsymmetrically disubstituted ureido types resulting from addition of ethyl isocyanatoacetate and diethyl 2-isocyanotoglutarate to the ethyl esters of 27a,b.Of these ureido adducts (32a,b and 33a,b, respectively), only 33a was successfully hydrolyzed to the corresponding pure acid, in this instance the tricarboxylic acid 34, a pseudo-peptide analogue of the MTX metabolite MTX-γ-Glu.Bilogical evaluations of the prepared compounds affirmed previous findings that the γ-carboxyl is not required for tight binding to dihydrofolate reductase (DHFR) but is operative in the carrier-mediated transport of classical antifolates through cell membranes.High tolerance levels observed in studies against L1210 leukemia in mice suggest the reduced potency may be due not only to lower transport efficacy but also to loss of the function of intracellular γ-polyglutamylation.The N-nitrosoureas 30 and 31 showed appreciable activity in vivo vs.L1210, but the activity did not appear to be due to antifolate action as evidenced by their poor inhibition of both L1210 DHFR and cell growth in vitro.