42749-49-5

Usage

Uses

Used in Pharmaceutical Industry:
(-)-N-[(4-METHYLPHENYL)SULFONYL]-D-GLUTAMINE is used as a research tool for studying the role of glutamine metabolism in various biological processes, given its ability to selectively inhibit glutamine synthetase.
Used in Cancer Therapy:
(-)-N-[(4-METHYLPHENYL)SULFONYL]-D-GLUTAMINE is used as a potential therapeutic agent for cancer treatment, targeting the overexpression of glutamine synthetase in cancer cells, which may lead to the inhibition of tumor growth and progression.
Used in Drug Development:
(-)-N-[(4-METHYLPHENYL)SULFONYL]-D-GLUTAMINE serves as a lead compound in the development of new drugs targeting glutamine-dependent pathways in cancer cells, potentially enhancing the efficacy of existing cancer therapies and overcoming resistance issues.

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

• 882861-84-9 5-oxo-1-(toluene-4-sulfonyl)-D-proline 
• 21957-65-3 1-(4'-methylbenzenesulfonyl)-5-oxopyrrolidine-2-carboxylic acid 
• 56-85-9 L-glutamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 6970-25-8 1-((4-methylbenzene)sulfonyl)-5-oxopyrrolidine-2-carboxylic acid 
• 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 

Downstream Products

• 132465-73-7 N²-(toluene-4-sulfonyl)-DL-glutamine methyl ester 
• 132465-72-6 N²-(toluene-4-sulfonyl)-D-glutamine methyl ester 
• 5959-95-5 D-Glutamin 
• 70-26-8 D-ornithine 
• 1195614-21-1 N-(toluene-4-sulfonyl)-D-glutamic acid-5-nitrile 
• 100616-51-1 N-(toluene-4-sulfonyl)-D-glutamic acid-1-methyl ester-5-nitrile 
• 132465-74-8 N²-(toluene-4-sulfonyl)-L-glutamine methyl ester 
• 95305-51-4 dimethyl (2S)-2-{[(4-methylphenyl)sulfonyl]amino}pentane-1,5-dioate 
• 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 
• 122804-10-8 N²-(toluene-4-sulfonyl)-L-glutaminyl=>L-isoasparaginyl=>S-benzyl-L-cysteine benzyl ester 
• 56-85-9 L-glutamine 
• 62234-29-1 N2-p-toluenesulfonyl-L-2,4-diaminobutyric acid 
• 70-55-3 toluene-4-sulfonamide 

Relevant academic research and scientific papers

(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.

Development of amino acid conjugated sulfonamides as potent antiulcer agent

A series of 2-{[(4-methylphenyl) sulfonyl] amino}-3-sulfanylpropanoic acid (1a) and its analogs 1b-j have been synthesized. These compounds were screened for their in vivo efficacy in pyloric ligation model. Compounds 1a and 1b with higher antiulcer potential were further screened in other gastric models to explore the mode of antiulcer action. To further understand the mode of action, in vitro inhibition of H+/K+ ATPase activity in gastric microsome isolated from rat stomach was studied. This was rationalized by in silico experiments.

HIV protease inhibitors based on amino acid derivatives

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.

The synthesis of unusual tetrahydropyrimidine amino acids

The synthesis of derivatives of 2-(1-an-aminoalkyl)-4-carboxy-3,4,5,6-tetrahydropyrimidines, unusual amino acids isolated from bacterial siderophores, is described, from condensation of N-protected amino acids imidates or thiomidates with 2,4-diaminobutyrylglycine methyl ester.

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.

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.