32087-05-1

Basic information

• Product Name: methyl 3-[(methylsulfonyl)amino]benzoate
• CAS NO: 32087-05-1
• Molecular Formula: C₉H₁₁NO₄S
• Molecular Weight: 229.2529
• Mol File: 32087-05-1.mol

Chemical Properties

• Boiling Point: 362°C at 760 mmHg
• Flash Point: 172.7°C
• Density: 1.366g/cm³
• Vapor Pressure: 1.99E-05mmHg at 25°C
• Refractive Index: 1.568
• CAS DataBase Reference: methyl 3-[(methylsulfonyl)amino]benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-[(methylsulfonyl)amino]benzoate(32087-05-1)
• EPA Substance Registry System: methyl 3-[(methylsulfonyl)amino]benzoate(32087-05-1)

Safety Data

• Hazardous Substances Data: 32087-05-1(Hazardous Substances Data)

Upstream product

• 618-95-1 methyl 3-nitrobenzoate 
• 124-63-0 methanesulfonyl chloride 
• 4518-10-9 Methyl 3-aminobenzoate 
• 3144-09-0 methanesulfonamide 
• 618-91-7 methyl 3-iodo-benzoate 
• 7143-01-3 Methanesulfonic anhydride 

Downstream Products

• 376347-09-0 N-(3-hydroxymethylphenyl)methanesulfonamide 
• 55512-05-5 m-(methylsulfonylamino)benzaldehyde 
• 28547-13-9 3-(methanesulfonamido)benzoic acid 
• 834869-24-8 methyl 3-[methyl(methylsulfonyl)amino]benzoate 
• 32087-06-2 Methyl-3-N-mesylamino-4-nitrobenzoat 

Relevant articles and documents

N'-Alkylaminosulfonyl Analogues of 6-Fluorobenzylideneindolinones with Desirable Physicochemical Profiles and Potent Growth Inhibitory Activities on Hepatocellular Carcinoma

The benzylideneindolinone 6-chloro-3-(3′-trifluoromethylbenzylidene)-1,3-dihydroindol-2-one (4) was reported to exhibit potent and selective growth inhibitory effects on hepatocellular carcinoma (HCC). Corroborative evidence supported multi-receptor tyrosine kinase (RTK) inhibition as a possible mode of action. However, the poor physicochemical properties of 4 limited its furtherance as a lead compound. In this study, the modification of 4 was investigated with the aim of improving its potency and physicochemical profile. The 6-fluorobenzylideneindolinone 3-12 bearing a 3′-N-propylaminosulfonyl substituent was found to be a promising substitute. Compound 3-12 [6-fluoro-3-(3′-N-propylaminosulfonylbenzylidene)-1,3-dihydroindol-2-one] was found to be tenfold more soluble than 4 and to have sub-micromolar growth inhibitory activities on HCC cells. It is apoptogenic and inhibits the phosphorylation of several RTKs in HuH7, of which the inhibition of FGFR4 and HER3 are prominent. Compound 3-12 decreased the tumor load in a physiologically relevant orthotopic HCC xenograft murine model. Structure-activity relationships support pivotal roles for the fluoro and N′-propylaminosulfonyl moieties in enhancing cell-based activity and moderating the physicochemical profile (solubility, permeability) of 3-12.

Design, synthesis, and pharmacological evaluation of highly potent and selective dipeptidyl peptidase-4 inhibitors

The optimization of a series of fused β-homophenylalanine inhibitors of dipeptidyl peptidase-4 (DPP-4) is described. Modification on the P2-binding moiety of 6 (IC50 = 10 nM) led to the discovery of β-homophenylalanine derivatives containing pyrrolidin-2-ylmethyl amides. The introduction of a sulfamine in the meta position of the phenyl ring improved the potency against DPP-4 (6-12-fold increase). Compound 14k showed DPP-4 inhibitory activity with an IC50 value of 0.87 nM. Meanwhile, in vivo experiments exhibited that 14h had an efficiency comparable to sitagliptin at the dose of 10 mg/kg.

HETEROARYL COMPOUNDS, COMPOSITIONS THEREOF, AND USE THEREOF AS PROTEIN KINASE INHIBITORS

Provided herein are Heteroaryl Compounds having the following structure: (I) wherein R1, R2, L, X, Y, Z, Q, A and B are as defined herein, compositions comprising an effective amount of a Heteroaryl Compound and methods for treating or preventing cancer, inflammatory conditions, immunological conditions, metabolic conditions and conditions treatable or preventable by inhibition of a kinase pathway comprising administering an effective amount of a Heteroaryl Compound to a patient in need thereof.

Palladium-catalyzed silane/siloxane reductions in the one-pot conversion of nitro compounds into their amines, hydroxylamines, amides, sulfonamides, and carbamates

A combination of palladium(II) acetate, aqueous potassium fluoride, and polymethylhydrosiloxane (PMHS) facilitates the room-temperature reduction of aromatic nitro compounds to anilines. These reactions tend to be quick (30 min), high-yielding, and tolerate a range of other functional groups. Replacement of PMHS/KF with triethylsilane allows for the reduction of aliphatic nitro compounds to their corresponding hydroxylamines. Depending on the substrate, both conditions can allow for the in situ conversion of the product amines into amides, sulfonamides, and carbamates. Georg Thieme Verlag Stuttgart.

Copper-catalyzed cross-coupling of sulfonamides with aryl iodides and bromides facilitated by amino acid ligands

A highly general, convenient, and inexpensive catalyst system was developed for the N-arylation of sulfonamides with aryl iodides or bromides by using 5-20 mol % of CuI as catalyst, 20 mol % of N-methylglycine (for aryl iodides) or N,N-dimethylglycine (for aryl bromides) as ligand, and K3PO 4 as base.

Substituent effects in infrared spectroscopy-VII. Meta and para substituted methanesulphonanilides

Substituent effects on the NH frequencies of the conformers of methanesulphonanilides, their cyclic dimers and their hydrogen bonded complexes with acetonitrile have been analysed by means of the Hammet equation.An electron-withdrawing substituent may either increase or decrease ν(NH) in the XC6H4NHY series according to the electronic nature of the Y group.This can be explained by the non-monotonic dependence of the NH stretching frequency on the ionic character of the NH bond.