149457-03-4

Basic information

• Product Name: MethanesulfonaMide, N-[4-[2-(forMylaMino)acetyl]-5-hydroxy-2-phenoxyphenyl]-
• Synonyms: MethanesulfonaMide, N-[4-[2-(forMylaMino)acetyl]-5-hydroxy-2-phenoxyphenyl]-;ForMaMidoMethyl-2-hydroxy-4-Methanesulfonyl aMino -5-phenoxyphenylethanone;N-[4-[(Formylamino)acetyl]-5-hydroxy-2-phenoxyphenyl]methanesulfonamide;N-{[4-[2-(ForMylaMino)acetyl]-5-hydroxy-2-phenoxyphenyl}MethanesulfonaMide;N-(2-(2-Hydroxy-4-(methylsulfonamido)-5-phenoxyphenyl)-2-oxoethyl)formamide;Iguratimod Impurity 13;N-[2-[2-hydroxy-4-(methanesulfonamido)-5-phenoxyphenyl]-2-oxoethyl]formamide
• CAS NO: 149457-03-4
• Molecular Formula: C₁₆H₁₆N₂O₆S
• Molecular Weight: 378.39962
• EINECS: -0
• Mol File: 149457-03-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 622.4±65.0 °C(Predicted)
• Appearance: /
• Density: 1.439±0.06 g/cm3(Predicted)
• PKA: 6.45±0.10(Predicted)
• CAS DataBase Reference: MethanesulfonaMide, N-[4-[2-(forMylaMino)acetyl]-5-hydroxy-2-phenoxyphenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: MethanesulfonaMide, N-[4-[2-(forMylaMino)acetyl]-5-hydroxy-2-phenoxyphenyl]-(149457-03-4)
• EPA Substance Registry System: MethanesulfonaMide, N-[4-[2-(forMylaMino)acetyl]-5-hydroxy-2-phenoxyphenyl]-(149457-03-4)

Safety Data

• Hazardous Substances Data: 149457-03-4(Hazardous Substances Data)

Usage

General Description

Methanesulfonamide, N-[4-[2-(formylamino)acetyl]-5-hydroxy-2-phenoxyphenyl]- is a compound with a long chemical name that contains a methanesulfonamide group and a substituted phenyl group. This chemical is likely a derivative of N-acetylglucosamine, which is involved in the biosynthesis of glycoproteins and glycolipids. The presence of a formylamino and hydroxy groups suggests potential involvement in biological processes, as these are common functional groups in bioactive compounds. The phenoxyphenyl group indicates that this compound may have aromatic and hydrophobic properties, which could impact its solubility and interaction with biological membranes. Overall, the chemical structure of Methanesulfonamide, N-[4-[2-(formylamino)acetyl]-5-hydroxy-2-phenoxyphenyl]- suggests potential biological activity and relevance in medicinal and biochemical research.

InChI:InChI=1S/C16H16N2O6S/c1-25(22,23)18-13-8-14(20)12(15(21)9-17-10-19)7-16(13)24-11-5-3-2-4-6-11/h2-8,10,18,20H,9H2,1H3,(H,17,19)

Upstream product

• 108-95-2 phenol 
• 149436-41-9 α-amino-2-methoxy-4-methanesulfonamido-5-phenoxyacetophenone hydrochloride 
• 123664-84-6 N-(5-methoxy-2-phenoxyphenyl)methanesulfonamide 
• 10298-80-3 2-chloro-5-methoxynitrobenzene 
• 76838-72-7 5-methoxy-2-phenoxyaniline 
• 84594-95-6 5-methoxy-1-nitro-2-phenoxybenzene 
• 149456-98-4 N-(2-(2-methoxy-4-(methylsulfonamido)-5-phenoxyphenyl)-2-oxoethyl)formamide 

Downstream Products

• 123663-49-0 Iguratimod 

Relevant articles and documents

Preparation method of N-[4-(2-formylaminoacetyl)-5-hydroxy-2-phenoloxyphenyl]methanesulfonamide

The invention discloses a preparation method of N-[4-(2-formylaminoacetyl)-5-hydroxy-2-phenoloxyphenyl]methanesulfonamide. The preparation method comprises the following steps: with N-[4-(2-formylaminoacetyl)-5-methoxy-2-phenoloxyphenyl]methanesulfonamide as a raw material, dissolving the raw material in N,N-dimethylformamide (DMF) by using NaBr, and carrying out a demethylation reaction to obtain N-[4-(2-formylaminoacetyl)-5-hydroxy-2-phenoloxyphenyl]methanesulfonamide. The preparation method of N-[4-(2-formylaminoacetyl)-5-hydroxy-2-phenoloxyphenyl]methanesulfonamide provided by the invention is friendly to environment, simple in process, high in yield and low in cost.

Synthesis and antiinflammatory activity of 7-methanesulfonylamino-6- phenoxychromones. Antiarthritic effect of the 3-formylamino compound (T-614) in chronic inflammatory disease models

A group of derivatives of 7-methanesulfonylamino-6-phenoxychromone (1) at the pyrone and phenoxy rings was synthesized starting with 4-chloro-3- nitroanisole and evaluated against acute and chronic inflammations in oral administration in animals. Significant potency in the rat models of carrageenin-induced edema (CPE) and adjuvant-induced arthritis (AA) was realized with 2'-fluoro and 2',4'-difluoro derivatives (9a and 9d), and 3- formylamino derivative (19a) and its 2'-fluoro and 2',4'-difluoro compounds (22a and 22d), displaying AA therapeutic effect of ED40=2.5-7.1 mg/kg/d for 7 d and AA prophylactic effect of 53-70% inhibition at the dosage of 3 mg/kg/d for 22 d. To identify a candidate for further pharmacological study, the five compounds were subjected to evaluation of their gastro-ulcerogenic liability, leading to selection of the fluorine-free compound 19a which did not cause acute ulceration at 300 mg/kg in oral administration in rats. Compound 19a (ED40=3.6 mg/kg in established AA) possessed good therapeutic efficacy against type II collagen-induced arthritis in DBA/1J mice with doses of 30 and 100 mg/kg, suggesting the development of 19a (designated T-614) as a prospective disease-modifying antirheumatic agent. In addition, a preparative-scale synthetic route to T-614 has been established.