21957-62-0

Basic information

• Product Name: TOS-MET-OH
• Synonyms: TOSYL-L-METHIONINE;TOS-MET-OH;N-(4-Toluenesulfonyl)-L-methionine
• CAS NO: 21957-62-0
• Molecular Formula: C₁₂H₁₇NO₄S₂
• Molecular Weight: 303.4
• Mol File: 21957-62-0.mol

Chemical Properties

• Melting Point: 81-83 °C
• Boiling Point: 510.7±60.0 °C(Predicted)
• Appearance: /
• Density: 1.311±0.06 g/cm3(Predicted)
• PKA: 3.27±0.10(Predicted)
• CAS DataBase Reference: TOS-MET-OH(CAS DataBase Reference)
• NIST Chemistry Reference: TOS-MET-OH(21957-62-0)
• EPA Substance Registry System: TOS-MET-OH(21957-62-0)

Safety Data

• Hazardous Substances Data: 21957-62-0(Hazardous Substances Data)

Upstream product

• 63-68-3 L-methionine 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 108585-00-8 Tos-L-Met-Gly-OMe 
• 108585-06-4 Tos-L-Met-L-Met-OMe 
• 27067-02-3 N-Boc-(S)-methionine ethyl ester p-toluenesulphonic acid salt 
• 952525-18-7 (2S)-4-(methylsulfanyl)-2-[[(4-methylphenyl)sulfonyl]amino]butanoic acid hydrazide 
• 209850-51-1 (R)-5-Methylsulfanyl-3-(toluene-4-sulfonylamino)-pentanoic acid 
• 209850-64-6 (R)-5-Methylsulfanyl-3-(toluene-4-sulfonylamino)-pentanoic acid methyl ester 
• 209850-53-3 N-[(S)-3-Diazo-1-(2-methylsulfanyl-ethyl)-2-oxo-propyl]-4-methyl-benzenesulfonamide 
• 209850-59-9 N-[(R)-4-Diazo-1-(2-methylsulfanyl-ethyl)-3-oxo-butyl]-4-methyl-benzenesulfonamide 
• 108585-11-1 Tos-L-Met-Gly-N₂H₃ 

Relevant articles and documents

Synthesis and Structure-Activity Relationships of Arylsulfonamides as AIMP2-DX2 Inhibitors for the Development of a Novel Anticancer Therapy

AIMP2-DX2, a splicing variant of AIMP2, is up-regulated in lung cancer, possesses oncogenic activity, and results in tumorigenesis. Specifically inhibiting the interaction between AIMP2-DX2 and HSP70 to suppress AIMP2-DX2-dependent cancers with small molecules is considered a promising avenue for cancer therapeutics. Optimization of hit BC-DXI-04 (IC50 = 40.1 μM) provided new potent sulfonamide based AIMP2-DX2 inhibitors. Among these, BC-DXI-843 showed improved inhibition against AIMP2-DX2 (IC50 = 0.92 μM) with more than 100-fold selectivity over AIMP2 in a luciferase assay. Several binding assays indicated that this compound effectively induces cancer cell apoptosis by specifically interrupting the interaction between DX2 and HSP70, which leads to the degradation of DX2 via Siah1-mediated ubiquitination. More importantly, BC-DXI-843 demonstrated in vivo efficacy in a tumor xenograft mouse model (H460 cells) at a dosage of 50 mg/kg, suggesting it as a promising lead for development of novel therapeutics targeting AIMP2-DX2 in lung cancer.

New carboxamides bearing benzenesulphonamides: Synthesis, molecular docking and pharmacological properties

Ten new derivatives of benzenesulphonamide bearing carboxamide functionality were synthesized and investigated for their in vitro antimicrobial, antioxidant and in vivo anti-inflammatory activities. Compound 9d inhibited carrageenan induced rat-paw oedema

Synthesis and physical chemical properties of 2-amino-4-(trifluoromethoxy)butanoic acid-a CF3O-containing analogue of natural lipophilic amino acids

2-Amino-2-(trifluoromethoxy)butanoic acid (O-trifluoromethyl homoserine) was synthesized as a racemate and in both enantiomeric forms. The measured pKa and log D values establish the compound as a promising analogue of natural aliphatic amino acids.

Direct Synthesis of 2-Formylpyrrolidines, 2-Pyrrolidinones and 2-Dihydrofuranones via Aerobic Copper-Catalyzed Aminooxygenation and Dioxygenation of 4-Pentenylsulfonamides and 4-Pentenylalcohols

A new method for the direct conversion of 4-pentenylsulfonamides to 2-formylpyrrolidines and a 2-ketopyrrolidine has been developed. This transformation occurs via aerobic copper-catalyzed alkene aminooxygenation where molecular oxygen serves as both oxidant and oxygen source. The 2-formylpyrrolidines can further undergo oxidative carbon-carbon bond cleavage in situ upon addition of DABCO, providing 2-pyrrolidinones. These transformations have been demonstrated for a range of 4-pentenylsulfonamides. 4-Pentenylalcohols also undergo oxidative cyclization to form γ-lactones predominantly. The reaction is chemoselective, oxidizing one alkene in the presence of others, and is compatible with several functional groups. Application of these reactions to the formal syntheses of baclofen and (+)-monomorine was demonstrated.

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.

INTERMEDIATES OF SITAGLIPTIN AND PREPARATION PROCESS THEREOF

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INTERMEDIATES OF SITAGLIPTIN AND PREPARATION PROCESS THEREOF

Disclosed are intermediates of Sitagliptin, a preparation process thereof, and a process for synthesizing Sitagliptin using these intermediates. Sitagliptin is synthesized by using chiral amino compounds as a raw material, without having to build a chiral center with a chiral asymmetric catalytic hydrogenation, and high-pressure hydrogenation is avoided.

1,5-rhodium shift in rearrangement of N -arenesulfonylazetidin-3-ols into benzosultams

Benzosultams are synthesized in an enantiopure form starting from α-amino acids through a rhodium-catalyzed rearrangement reaction of N-arenesulfonylazetidin-3-ols. Mechanistically, this reaction involves C-C bond cleavage by β-carbon elimination and C-H bond cleavage by a 1,5-rhodium shift.

Synthesis, anti-HIV, and antifungal activity of new benzensulfonamides bearing the 2,5-disubstituted-1,3,4-oxadiazole moiety

A series of novel chiral and achiral N-[1-(1,3,4-oxadiazol-2ylthio)alkyl]- 4-methyl/chloro/methoxybenzenesulfonamides 5a-l were prepared by the reaction of 4-(4-methyl, chloro, methoxyphenylsulfonamido)alkyl carboxylic acid hydrazides 4a-l with CS2 and KO