53472-19-8

Usage

Uses

Used in Pharmaceutical Industry:
N-3-Pyridylbenzenesulfonamide is used as a pharmacological agent for the treatment of certain diseases such as glaucoma and epilepsy. Its ability to inhibit carbonic anhydrase makes it a potential candidate for these applications, as this enzyme is implicated in the pathophysiology of these conditions.
Used in Medicinal Chemistry Research:
N-3-Pyridylbenzenesulfonamide is used as an inhibitor of carbonic anhydrase in research settings. Its potential to modulate the activity of this enzyme is of interest to scientists studying the role of carbonic anhydrase in various physiological and pathological processes, which may lead to the development of new therapeutic strategies.
Used in Drug Development:
N-3-Pyridylbenzenesulfonamide is used as a lead compound in drug development efforts. Its chemical properties and known biological activities make it a valuable starting point for the design and synthesis of new drugs targeting carbonic anhydrase and related pathways.

InChI:InChI=1/C11H10N2O2S/c14-16(15,11-6-2-1-3-7-11)13-10-5-4-8-12-9-10/h1-9,13H

Upstream product

• 462-08-8 pyridin-3-ylamine 
• 98-09-9 benzenesulfonyl chloride 
• 2530-26-9 3-nitropyridine 
• 98-80-6 phenylboronic acid 
• 368-43-4 phenylsulfonyl fluoride 
• 873-55-2 sodium benzenesulfonate 
• 98-10-2 benzenesulfonamide 
• 1692-25-7 3-pyridylboronic acid 
• 626-55-1 3-Bromopyridine 

Relevant academic research and scientific papers

Sequential C-S and S-N Coupling Approach to Sulfonamides

A one-pot three-component reaction involving nitroarenes, (hetero)arylboronic acids, and potassium pyrosulfite leading to sulfonamides was described. A broad range of sulfonamides bearing different reactive functional groups were obtained in good to excellent yields through sequential C-S and S-N coupling that does not require metal catalysts.

Method for coupling nitroaromatic compound and boric acid compound to synthesize sulfonamide compound

The invention belongs to the field of organic synthesis, and specifically discloses a method for coupling a nitroaromatic compound and a boric acid compound to synthesize a sulfonamide compound. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound comprises the steps that in an organic solvent, pyrosulfite is used as a source of SO2,and heating is carried out for a coupling reaction, and then after the post-treatment, the sulfonamide compound is obtained. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound is simple in operation, does not require nitrogen protection, and can be carried out under air. The nitroaromatic compound and the boric acid compound are abundant in source, relatively low in price, high in reaction yield, wide in applicability of a substrate and free in metal residual. The method for coupling the nitroaromatic compound and the boric acid compound to synthesize the sulfonamide compound can be used for synthesizing a series of sulfonamide compounds, and the synthesized compounds have wide application value in the fields of pesticidesand medicines.

Sulfonamidation of Aryl and Heteroaryl Halides through Photosensitized Nickel Catalysis

Herein we report a highly efficient method for nickel-catalyzed C?N bond formation between sulfonamides and aryl electrophiles. This technology provides generic access to a broad range of N-aryl and N-heteroaryl sulfonamide motifs, which are widely represented in drug discovery. Initial mechanistic studies suggest an energy-transfer mechanism wherein C?N bond reductive elimination occurs from a triplet excited NiII complex. Late-stage sulfonamidation in the synthesis of a pharmacologically relevant structure is also demonstrated.

Sulfonamide Synthesis via Calcium Triflimide Activation of Sulfonyl Fluorides

A method using calcium triflimide [Ca(NTf2)2] as a Lewis acid to activate sulfonyl fluorides toward nucleophilic addition with amines is described. The reaction converts a wide array of sterically and electronically diverse sulfonyl fluorides and amines into the corresponding sulfonamides in good yield.

Sulfonamide formation from sodium sulfinates and amines or ammonia under metal-free conditions at ambient temperature

A novel, practical and highly efficient method for the construction of a variety of sulfonamides mediated by I2 was demonstrated. The reaction proceeds readily at room temperature using a variety of sodium sulfinates and amines or ammonia in water in a metal-, base-, ligand-, or additive-free protocol. Primary, secondary and tertiary sulfonamides were obtained in good to excellent yields with a broad range of functional group tolerability. This journal is

Copper-catalyzed N-arylation of sulfonamides with boronic acids in water under ligand-free and aerobic conditions

An efficient and novel method for the copper-catalyzed arylation of sulfonamides in water under ligand-free conditions is reported. The significant advantages of this methodology are high yields, simple workup procedure, and elimination of toxic materials

Copper-catalyzed N-arylation of sulfonamides with aryl bromides under mild conditions

This Letter describes a copper catalyzed sulfonamide coupling reaction with aryl bromides to form N-aryl sulfonamides under mild conditions, including the first examples of Cu-catalyzed sulfonamide coupling at room temperature. The reaction protocol tolerates a broad range of substrates including a variety of primary and secondary sulfonamides and challenging heteroaryl bromides such as 2-bromothiazole.

Copper-catalysed N-arylation of arylsulfonamides with aryl bromides and aryl iodides using KF/Al2O3

An efficient synthesis of N-arylsulfonamides with a variety of aryl bromides, aryl iodides and heteroaryl bromides using KF/Al2O 3 as a suitable base, CuI as an inexpensive catalyst and N,N′dimethylethylenediamine (N,N′-DMEDA) as an effective ligand is described. Indian Academy of Sciences.

Second-generation peptidomimetic inhibitors of protein farnesyltransferase demonstrating improved cellular potency and significant in vivo efficacy

The synthesis and evaluation of analogues of previously reported farnesyltransferase inhibitors, pyridyl benzyl ether 3 and pyridylbenzylamine 4, are described. Substitution of 3 at the 5-position of the core awl ring resulted in inhibitors of equator less potency against the enzyme and decreased efficacy in a cellular assay against Ras processing by the enzyme. Substitution of 4 at the benzyl nitrogen yielded 26, which showed improved efficacy and potency and yet presented a poor pharmacokinetic profile. Further modification afforded 30, which demonstrated a dramatically improved pharmacokinetic profile. Compounds 26 and 29 demonstrated significant in vivo efficacy in nude mice inoculated with MiaPaCa-2, a human pancreatic tumor- derived cell line.