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

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

Uses

Used in Pharmaceutical Industry:
Methanesulfonamide, N-[4-[2-(formylamino)acetyl]-5-hydroxy-2-phenoxyphenyl]is used as a pharmaceutical intermediate for the development of drugs targeting various diseases. Its unique chemical structure, including the formylamino and hydroxy groups, may contribute to its bioactivity and potential therapeutic effects.
Used in Biochemical Research:
In the field of biochemical research, Methanesulfonamide, N-[4-[2-(formylamino)acetyl]-5-hydroxy-2-phenoxyphenyl]serves as a valuable compound for studying the interactions between small molecules and biological systems. Its hydrophobic and aromatic properties, conferred by the phenoxyphenyl group, may be utilized to investigate its binding affinity to specific biological targets or its role in cellular processes.
Used in Drug Design and Development:
Methanesulfonamide, N-[4-[2-(formylamino)acetyl]-5-hydroxy-2-phenoxyphenyl]is employed in drug design and development to create novel therapeutic agents. Its structural features, such as the formylamino and hydroxy groups, can be modified to enhance its pharmacological properties, including potency, selectivity, and bioavailability.
Used in Chemical Synthesis:
In the realm of chemical synthesis, Methanesulfonamide, N-[4-[2-(formylamino)acetyl]-5-hydroxy-2-phenoxyphenyl]is utilized as a key building block for the synthesis of more complex molecules with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science.
Overall, the diverse applications of Methanesulfonamide, N-[4-[2-(formylamino)acetyl]-5-hydroxy-2-phenoxyphenyl]highlight its versatility and importance in scientific research and development. Its unique chemical properties and potential biological activity make it a promising candidate for further exploration and utilization in various fields.

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.

Crystalline morphology of Iguratimod intermediate VI

The invention belongs to the technical field of pharmaceutical chemical engineering, and relates to a crystalline morphology of an Iguratimod intermediate VI (alpha-formamido-2-hydroxy-4-methanesulfonamide-5-phenoxyacetophenone). In addition, the invention further relates to a preparation method for two types of crystalline morphologies of Iguratimod intermediates VI. The two different types of crystalline morphologies of Iguratimod intermediates VI provided by the invention have good melting point and quality, the yield by weight is 90 to 95 percent, and the purity is 99.0 to 99.9 percent.

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.