1138-56-3

Usage

Uses

Used in Pharmaceutical Research:
4-(N-BUTOXY)BENZENESULFONYL CHLORIDE is used as a synthetic intermediate for the development of bis-aryl sulfonamides, which are compounds that exhibit immune-stimulating properties. The study of structure-activity relationships in these compounds is crucial for identifying affinity probes that can prolong immune stimuli, potentially leading to the development of new therapeutic agents for various diseases.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4-(N-BUTOXY)BENZENESULFONYL CHLORIDE serves as a versatile building block for the creation of a wide range of chemical compounds. Its reactivity allows for the formation of various derivatives, which can be further utilized in different applications, such as the development of new materials, dyes, and pharmaceuticals.
Used in Material Science:
4-(N-BUTOXY)BENZENESULFONYL CHLORIDE can be employed in the development of novel materials with specific properties, such as improved thermal stability, chemical resistance, or optical characteristics. By incorporating 4-(N-BUTOXY)BENZENESULFONYL CHLORIDE into the molecular structure of these materials, researchers can tailor their properties for various applications, including electronics, aerospace, and automotive industries.

InChI:InChI=1/C10H13ClO3S/c1-2-3-8-14-9-4-6-10(7-5-9)15(11,12)13/h4-7H,2-3,8H2,1H3

Upstream product

• 1126-79-0 n-butyl phenyl ether 
• 139-02-6 sodium phenoxide 
• 352209-87-1 sodium 4-butoxybenzenesulfonate 
• 825-90-1 sodium p-hydroxybenzenesulfonate 
• 108-95-2 phenol 
• 7790-94-5 chlorosulfonic acid 

Downstream Products

• 101108-67-2 1-(4-butoxy-benzenesulfonyl)-piperidine 
• 105411-89-0 1-(4-Butoxy-benzenesulfonyl)-5-fluoro-1H-pyrimidine-2,4-dione 
• 105411-94-7 5-Bromo-1-(4-butoxy-benzenesulfonyl)-1H-pyrimidine-2,4-dione 
• 1138-58-5 4-n-butoxybenzenesulfonamide 
• 203994-92-7 (2R,4R)-1-(4-Butoxy-benzenesulfonyl)-4-hydroxy-pyrrolidine-2-carboxylic acid 
• 1054625-30-7 (2R,4S)-1-(4-Butoxy-benzenesulfonyl)-4-(1,1-dioxo-1λ⁶-isothiazolidin-2-yl)-pyrrolidine-2-carboxylic acid methyl ester 
• 392231-80-0 1-(4-butoxy-benzenesulfonyl)-piperidin-4-one 
• 392231-63-9 4-butoxy-benzenesulfonic acid 1-(4-butoxy-benzenesulfonyl)-azetidin-3-yl ester 
• 202750-96-7 N-(2-hydroxy-1R-methylethyl)-4-(n-butoxy)benzenesulfonamide 

Relevant academic research and scientific papers

N-ARYL SULFONAMIDE DERIVATIVES AS VACCINE ADJUVANT

Bis-aryl sulfonamide compounds and methods of using those compounds, e.g., in a method of enhancing or prolonging an immune response, are provided. For example, the compounds may be employed with a vaccine and optionally at least one other adjuvant and/or one or more TLR ligands, at least one MAP kinase inhibitor, or any combination thereof.

Structure-Activity Relationship Studies to Identify Affinity Probes in Bis-aryl Sulfonamides That Prolong Immune Stimuli

Agents that safely induce, enhance, or sustain multiple innate immune signaling pathways could be developed as potent vaccine adjuvants or coadjuvants. Using high-throughput screens with cell-based nuclear factor κB (NF-κB) and interferon stimulating response element (ISRE) reporter assays, we identified a bis-aryl sulfonamide bearing compound 1 that demonstrated sustained NF-κB and ISRE activation after a primary stimulus with lipopolysaccharide or interferon-α, respectively. Here, we present systematic structure-activity relationship (SAR) studies on the two phenyl rings and amide nitrogen of the sulfonamide group of compound 1 focused toward identification of affinity probes. The murine vaccination studies showed that compounds 1 and 33 when used as coadjuvants with monophosphoryl lipid A (MPLA) showed significant enhancement in antigen ovalbumin-specific immunoglobulin responses compared to MPLA alone. SAR studies pointed to the sites on the scaffold that can tolerate the introduction of aryl azide, biotin, and fluorescent rhodamine substituents to obtain several affinity and photoaffinity probes which will be utilized in concert for future target identification and mechanism of action studies.

CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme ceramide galactosyltransferase (CGT), such as, for example, lysosomal storage diseases. Examples of lysosomal storage diseases include, for example, Krabbe disease and Metachromatic Leukodystrophy.

N-[4-(alkoxyl)-benzenesulfonyl]-5-aryl-oxazole-2-thioketone neuraminidase inhibitor

The invention discloses an N-[4-(alkoxyl)-benzenesulfonyl]-5-aryl-oxazole-2-thioketone neuraminidase inhibitor. A preparation method specifically comprises the following steps: (1) performing a reaction on aromatic aldehyde ArCHO, lithium perchlorate and

Characterization of a selective inverse agonist for estrogen related receptor α as a potential agent for breast cancer

The estrogen-related receptor α (ERRα) is an orphan nuclear receptor that plays a primary role in the regulation of cellular energy homeostasis and osteogenesis. It is reported that ERRα is widely expressed in a range of tissues and accumulating evidence has supported that the high expression of ERRα correlates with poor prognosis of various human malignancies, including breast, endometrium, colon, prostate and ovary cancers. Herein is described the discovery of a novel selective inverse agonist (HSP1604) of ERRα, but not of ERRβ and ERRγ, as determined using transient transfection luciferase reporter assay and a time-resolved fluorescence resonance energy transfer (TR-FRET) co-activator assay. HSP1604 potently inhibits ERRα transcriptional activity with IC50=1.47±0.17?μM in cell-based luciferase reporter assay and also decreases the protein level of ERRα and the mRNA levels of its downstream target genes such as pyruvate dehydrogenase kinase 4 (PDK4), pS2 and osteopontin. HSP1604 has also suppressed the proliferation of different human cancer cell lines and the migration of breast cancer cells with high expression of ERRα. Representative in vivo results show that HSP1604 suppresses the growth of human breast cancer xenograft in nude mice as doses at 30?mg/kg or 100?mg/kg administered every other day during 28-day period. HSP1604 thus has the potential both as a new agent to inhibit the growth of tumors and as a chemical probe of ERRα biology.

Novel, potent, selective and cellular active ABC type PTP1B inhibitors containing (methanesulfonyl-phenyl-amino)-acetic acid methyl ester phosphotyrosine mimetic

Protein tyrosine phosphatase 1B (PTP1B) which plays an important role in the negative regulation of insulin and leptin pathway has emerged as a novel promising therapeutic target for the treatment of type 2 diabetes mellitus and obesity. Upon careful study, a series of novel scaffold and simple synthesis method inhibitors were discovered based on the analysis of X-ray crystal structures of PTP1B/inhibitor complexes and docking simulations. Among them, compound P7 exhibited high inhibitory activity (IC50 = 222 nM) with moderate selectivity (8-fold) over T-cell PTPase (TCPTP) through interacting with the A, B and C binding sites of PTP1B enzyme. Further studies on cellular activities revealed that compound P7 could enhance insulin-mediated IRβ phosphorylation and insulin-stimulated glucose uptake.

Design and bio-evaluation of indole derivatives as potent Kv1.5 inhibitors

Atrial fibrillation (AF) is one of the common arrhythmias that threaten human health. Kv1.5 potassium channel is reported as an efficacious and safe target for the treatment of AF. In this paper, we designed and synthesized three series of compounds through modifying the lead compound RH01617 that was screened out by the pharmacophore model we reported earlier. All of the compounds were evaluated by the whole-patch lamp technology and most of them possessed potent inhibitory activities against Kv1.5. Compounds IIIi and IIIl were evaluated for the target selectivity as well as the pharmacodynamic effects in an isolated rat model. Due to the promising pharmacological behavior, compound IIIl deserves further pharmacodynamic and pharmacokinetic evaluations.

NOVEL SEMI-SYNTHETIC GLYCOPEPTIDES AS ANTIBACTERIAL AGENTS

Semi-synthetic glycopeptides having antibacterial activity are described, in particular, the semi-synthetic glycopeptides described herein are made by chemical modification of the a glycopeptide (Compound A, Compound B, Compound H or Compound C) or the monosaccharide made by hydrolyzing the disaccharide moiety of the amino acid-4 of the parent glycopeptide in acidic medium to give the amino acid-4 monosaccharide; conversion of the monosaccharide to the amino-sugar derivative; acylation of the amino substituent on the amino acid-4 amino-substituted sugar moiety on these scaffolds with certain acyl groups; conversion of the amide group in amino acid-3 on these scaffolds to various acylamide, acylsulfonamide, acylsulfonylurea derivatives; aminomethylation with substituent containing sulfonamide or acylsulfonamide group on amino acid-7 through Mannich reaction; and conversion of the acid moiety on the macrocyclic ring of these scaffolds to certain substituted amides. Also provided are methods for the synthesis of the compounds, pharmaceutical compositions containing the compounds, and methods of use of the compounds for the treatment and/or prophylaxis of diseases, especially bacterial infections.

Method for preparing alpha-sulfonyl hydroxamic acid derivatives

Compounds of the formula: that can be important as matrix metalloproteinase (MMP) and TNF-alpha converting enzyme (TACE) inhibitors, phosphodiesterase inhibitors, renin inhibitors, antithrombotics, and 5-lipoxygenase inhibitors are prepared by novel methods of the present invention.