33924-49-1

Usage

Uses

Used in Pharmaceutical Industry:
5-Chloro-2-methoxy-N-(2-phenylethyl)benzamide is used as a metabolite in the pharmaceutical industry for its potential role in the treatment of diabetes. As a metabolite of Glyburide, it may contribute to the drug's overall efficacy in managing blood sugar levels and could be a subject of interest for further research and development in the field of diabetes treatment.

InChI:InChI=1/C16H16ClNO2/c1-20-15-8-7-13(17)11-14(15)16(19)18-10-9-12-5-3-2-4-6-12/h2-8,11H,9-10H2,1H3,(H,18,19)

Upstream product

• 64-04-0 phenethylamine 
• 29568-33-0 2-methoxy-5-chlorobenzoyl chloride 
• 33924-48-0 methyl 5-chloro-2-methoxybenzoate 
• 3438-16-2 5-chloro-2-methoxybenzoic acid 
• 635-93-8 5-chlorosalicyclaldehyde 
• 7035-09-8 5-chloro-2-methoxybenzaldehyde 

Downstream Products

• 54870-28-9 meglitinide 
• 16673-34-0 5-chloro-2-methoxy-N-(4-sulfamoylphenethyl)benzamide 
• 33924-53-7 4-[2-(5-Chloro-2-methoxy-benzoylamino)-ethyl]-benzenesulfonic acid 
• 33924-54-8 4-(2-[(5-chloro-2-methoxyphenyl)formamido]ethyl)benzene-1-sulfonyl chloride 
• 10238-21-8 Glibenclamid 

Relevant academic research and scientific papers

Structure and absolute configuration of some 5-chloro-2-methoxy-N-phenylbenzamide derivatives

The absolute configuration of 5-chloro-2-methoxy-N-phenylbenzamide single crystal [compound (1)] and the effect of introducing –[CH2]n–, n?=?1,2 group adjacent to the amide group [compounds (2) and (3)], were studied. Furthermore, the replacement of the methoxy group with a hydroxy group [compound (4)] was defined. Proton and carbon-13 NMR spectrometer were used to record the structural information of the prepared compounds. X-ray single crystal diffractometer were used to elucidate the 3D structural configurations. Intensity data for the studied compounds were collected at room temperature. The X-ray data prove that compound (1) is almost planar, with maximum r.m.s. deviations of 0.210(3)?? corresponds to C13. This planarity starts to disturb by adding –[CH2]n–, n?=?1,2 groups between the NH group and the phenyl ring in compounds (2) and (3), respectively. By replacing the OCH3 group by an OH group in compound (4), the plane of the chlorophenyl moiety is nearly perpendicular to that of the phenyl ring. Such new structural configurations were further illustrated by the infrared, and ultraviolet-visible spectroscopy measurements in the frequency range 400–4000?cm??1 and 190–1100?nm, respectively. Spectroscopic analyses were verified with the help of molecular modeling using density functional theory. The estimated total dipole moment for the prepared compounds reflects its ability to interact with its surrounding molecules. The higher dipole moment for a given structures is combined with the higher reactivity for potential use in medicinal applications.

Structural Insights of Benzenesulfonamide Analogues as NLRP3 Inflammasome Inhibitors: Design, Synthesis, and Biological Characterization

NLRP3 inflammasome plays critical roles in a variety of human diseases and represents a promising drug target. In this study, we established the in vivo functional activities of JC124, a previously identified NLRP3 inflammasome inhibitor from our group, in mouse models of Alzheimer's disease and acute myocardial infarction. To understand the chemical space of this lead structure, a series of analogues were designed, synthesized, and biologically characterized. The results revealed the critical roles of the two substituents on the benzamide moiety of JC124. On the other hand, modifications on the sulfonamide moiety of JC124 are well tolerated. Two new lead compounds, 14 and 17, were identified with improved inhibitory potency (IC50 values of 0.55 ± 0.091 and 0.42 ± 0.080 μM, respectively). Further characterization confirmed their selectivity and in vivo target engagement. Collectively, the results strongly encourage further development of more potent analogues based on this chemical scaffold.

Intermolecular C-H Amidation of Alkenes with Carbon Monoxide and Azides via Tandem Palladium Catalysis

An atom- and step-economic intermolecular multi-component palladium-catalyzed C-H amidation of alkenes with carbon monoxide and organic azides has been developed for the synthesis of alkenyl amides. The reaction proceeds efficiently without an ortho -directing group on the alkene substrates. Nontoxic dinitrogen is generated as the sole by-product. Computational studies and control experiments have revealed that the reaction takes place via an unexpected mechanism by tandem palladium catalysis.

Pd-catalyzed amidation of 1,3-diketones with CO and azidesviaa nitrene intermediate

An efficient Pd-catalyzed amidation of 1,3-diketones has been developed using carbon monoxide and organic azides. This reaction provides a step-economic approach to produce β-ketoamides from readily available compounds under mild ligand-, oxidant-, and base-free conditions. The mechanistic studies showed that the reaction occurred through anin situgenerated isocyanate intermediate.

Metal-Free Thermal Activation of Molecular Oxygen Enabled Direct α-CH2-Oxygenation of Free Amines

Direct oxidation of α-CH2 group of free amines is hard to achieve due to the higher reactivity of amine moiety. Therefore, oxidation of amines involves the use of sophisticated metallic reagents/catalyst in the presence or absence of hazardous oxidants under sensitive reaction conditions. A novel method for direct C-H oxygenation of aliphatic amines through a metal-free activation of molecular oxygen has been developed. Both activated and unactivated free amines were oxygenated efficiently to provide a wide variety of amides (primary, secondary) and lactams under operationally simple conditions without the aid of metallic reagents and toxic oxidants. The method has been applied to the synthesis of highly functionalized amide-containing medicinal drugs, such as O-Me-alibendol and -buclosamide.

N-HYDROXY-BENZENE-SULFONAMIDE DERIVATIVES AND THEIR USES THEREOF

Inhibitors with anti-inflammatory agents are provided, as are methods of using the analogs to inhibit inflammation and prevent or treat diseases and conditions associated with inflammation, such as multiple sclerosis and autoinflammatory diseases.

Room temperature C(sp2)-H oxidative chlorination: Via photoredox catalysis

Photoredox catalysis has been developed to achieve oxidative C-H chlorination of aromatic compounds using NaCl as the chlorine source and Na2S2O8 as the oxidant. The reactions occur at room temperature and exhibit exclusive selectivity for C(sp2)-H bonds over C(sp3)-H bonds. The method has been used for the chlorination of a diverse set of substrates, including the expedited synthesis of key intermediates to bioactive compounds and a drug.

Development and Characterization of a Hydroxyl-Sulfonamide Analogue, 5-Chloro-N-[2-(4-hydroxysulfamoyl-phenyl)-ethyl]-2-methoxy-benzamide, as a Novel NLRP3 Inflammasome Inhibitor for Potential Treatment of Multiple Sclerosis

In our efforts to develop novel small-molecule inhibitors for the NOD-like receptor family pyrin-domain-containing 3 (NLRP3) inflammasome as potential disease-modifying agents to treat neurological disorders including multiple sclerosis (MS), a hydroxyl sulfonamide analogue JC-171 has been rationally designed and biologically characterized both in vitro and in vivo. Our studies established that JC-171 dose dependently inhibited LPS/ATP-induced interleukin-1β (IL-1β) release from J774A.1 macrophages with an IC50 of 8.45 ± 1.56 μM. Selective inhibition of the NLRP3 inflammasome induced IL-1β release by this compound was also confirmed using mouse bone-marrow-derived macrophages and LPS-challenged mice in vivo. Furthermore, immunoprecipitation study revealed that JC-171 interfered with NLRP3/ASC interaction induced by LPS/ATP stimulation. More importantly, JC-171 treatment delayed the progression and reduced the severity of experimental autoimmune encephalomyelitis (EAE), a mouse model of MS, in both prophylactic and therapeutic settings. This coincided with blocking of IL-1β production and a pathogenic Th17 response. Collectively, these results suggest that JC-171 is a selective NLRP3 inflammasome inhibitor with biological activity in vivo, thus strongly encouraging further development of this lead compound as a potential therapeutic agent for human MS.

Product-Derived Bimetallic Palladium Complex Catalyzes Direct Carbonylation of Sulfonylazides

A novel product-derived bimetallic palladium complex catalyzes a sulfonylazide-transfer reaction with the σ-donor/π-acceptor ligand CO, and is advantageous given its broad substrate scope, high efficiency, and mild reaction conditions (atmospheric pressure of CO at room temperature). This methodology provides a new approach to sulfonylureas, which are present in both pharmaceuticals and agrochemicals. The synthesis of Glibenclamide on a gram scale further revealed the practical utility of this procedure. Mechanistically, the generation of a bridged bimetallic palladium species derived from the product sulfonylurea is disclosed as the crucial step for this catalytic cycle.

Synthetic process of 4-[2-(5-chloro-2-methoxy benzamide)ethyl]benzsulfamide

The invention discloses a synthetic process of 4-[2-(5-chloro-2-methoxy benzamide)ethyl]benzsulfamide, and belongs to the technical field of medicinal synthesis processes. According to the process, 5-chloro-2-methoxybenzoic acid and phenylethylamine serve as the raw materials, and a target product is obtained through reactions of four steps including acylating chlorination, amidation, chlor amidation osulfonation and sulfanil amination. By means of the synthesis method, low-price industrial chemicals serve as raw materials and reaction reagents, single-solvent systems are adopted, smooth process connection is achieved, reaction yield is increased, process operation is simplified, and production cost is reduced while raw material cost is reduced.