7516-60-1

Usage

Uses

Used in Pharmaceutical Industry:
4-(chlorosulphonyl)benzoyl chloride is used as a building block for the synthesis of various pharmaceutical compounds. Its ability to introduce the chlorosulfonyl group into organic molecules makes it a valuable reagent in the production of drugs.
Used in Agrochemical Industry:
4-(chlorosulphonyl)benzoyl chloride is used as a reagent in the synthesis of agrochemicals, contributing to the development of effective pesticides and other agricultural products.
Used in Dye Industry:
4-(chlorosulphonyl)benzoyl chloride is used as a building block in the production of dyes, enabling the creation of a wide range of colorants for various applications.
Due to the reactivity and potential hazards of 4-(chlorosulphonyl)benzoyl chloride, proper safety measures and handling procedures must be followed when working with this chemical compound.

InChI:InChI=1/C7H4Cl2O3S/c8-7(10)5-1-3-6(4-2-5)13(9,11)12/h1-4H

Upstream product

• 636-78-2 4-sulphobenzoic acid 
• 5399-63-3 potassium p-carboxybenzenesulfonate 
• 22959-32-6 p-sulfobenzoic acid potassium salt 
• 104-15-4 toluene-4-sulfonic acid 
• 10130-89-9 p-carboxyphenylsulfonyl chloride 
• 75-44-5 phosgene 

Downstream Products

• 69812-51-7 4-chlorosulfonyl-benzoic acid methyl ester 
• 26737-96-2 N-phenyl-4-(N-phenylsulfamoyl)benzamide 
• 152278-01-8 4-[2-(4-Dimethylamino-phenyl)-2-oxo-ethylcarbamoyl]-benzenesulfonyl chloride 
• 120133-60-0 4-(5-Phenyl-oxazol-2-yl)-benzenesulfonyl chloride 
• 120133-62-2 4-[5-(4-Methoxy-phenyl)-oxazol-2-yl]-benzenesulfonyl chloride 
• 120133-61-1 4-(5-Biphenyl-4-yl-oxazol-2-yl)-benzenesulfonyl chloride 
• 455-26-5 4-carboxybenzenesulfonyl fluoride 
• 138219-55-3 dapoxylsulfonyl chloride 
• 71901-99-0 N,N-diethyl-1,3-dihydro-1-oxo-3,3-diphenyl-5-isobenzofuransulfonamide 
• 1160839-55-3 isobutyl 4-(isobutoxysulfonyl)benzoate 
• 26933-74-4 4-(phenylcarbamoyl)benzenesulfonyl chloride 
• 1192139-91-5 4-(methyl(prop-2-ynyl)carbamoyl)benzene-1-sulfonyl chloride 
• 1119833-11-2 methyl 4-(N-(4-fluorobenzyl)-N-(4-methoxybenzyl)sulfamoyl)benzoate 
• 1119833-13-4 methyl 4-(N-(4-methoxybenzyl)sulfamoyl)benzoate 

Relevant academic research and scientific papers

A structurally guided dissection-then-evolution strategy for ligand optimization of smoothened receptor

We present herein a novel dissection-then-evolution strategy for ligand optimization. Using the co-crystal structure of the smoothened receptor (SMO) as a guide, we studied the modular contribution of LY2940680 by systematically silencing the specific interaction between the individual residue(s) and the fragment in the ligand. Following evolution by focusing on the benzoyl part finally yielded an improved ligand 21.

Chemoselective reaction of bifunctional carboxysulfonic acid systems: Preparation of useful intermediates for chemiluminescent, fluorescent and UV absorbing bifunctional linkers

Heterobifunctional compounds are of considerable interest in convergent synthesis strategies as well as in the labeling/tagging of biological molecules. Herein is described a synthetic strategy to functionalize sulfonic acids in the presence of carboxylic acids without the need for protection/deprotection steps. Bifunctional carboxysulfonic acids are transformed under mild conditions to the corresponding carboxysulfonyl fluorides which are reacted with the amine of choice to provide sulfonamides. The carboxylic acid remains free and is available for subsequent activation and further chemical elaboration. The generality of this approach is demonstrated herein, and an example of utility is outlined in which carboxysulfonyl-containing chemiluminescent reagents are transformed into unique red-shifted chemiluminescent reagents.

NON-CHROMATOGRAPHIC PURIFICATION OF MACROCYCLIC PEPTIDES BY A RESIN CATCH AND RELEASE

The disclosure is directed to compounds and methods for preparing purified macrocyclic peptide using "catch-release" methods. These methods comprise reacting a free amino group of a resin-bound linear peptide with an azide- or alkyne-functionalized cap to form a resin-bound capped linear peptide having an azide- or alkyne-functionalized cap; cleaving said capped linear peptide from the resin to form a free capped linear peptide having an azide- or alkyne-functionalized cap; reacting the free capped linear peptide having an azide-functionalized cap with an alkyne-functionalized catch resin, or reacting the free capped linear peptide having an akynyl-functionalized cap with an azide functionalized catch resin, to form a catch-resin bound capped linear peptide; reacting the catch-resin bound capped linear peptide under conditions sufficient to effect macrocyclization of the linear peptide and release of the macrocyclic peptide from the catch resin.

FLUORINATED SULFONATE ESTERS OF ARYL KETONES FOR NON-IONIC PHOTO-ACID GENERATORS

Non-ionic photo-acid generating (PAG) compounds were prepared that contain an aryl ketone group having a perfluorinated substituent alpha to the ketone carbonyl. The non-polymeric PAGs release a sulfonic acid when exposed to high energy radiation such as deep UV or extreme UV light. The photo-generated sulfonic acid has a low diffusion rate in an exposed resist layer subjected to a post-exposure bake (PEB) at 100° C. to 150° C., resulting in formation of good line patterns after development. At higher temperatures, the PAGs can also undergo a thermal reaction to form a sulfonic acid. The perfluorinated substituent provides improved thermal stability and hydrolytic/nucleophilic stability.

Leveraging a "catch-Release" Logic Gate Process for the Synthesis and Nonchromatographic Purification of Thioether- or Amine-Bridged Macrocyclic Peptides

Macrocyclic peptides containing N-alkylated amino acids have emerged as a promising therapeutic modality, capable of modulating protein-protein interactions and an intracellular delivery of hydrophilic payloads. While multichannel automated solid-phase peptide synthesis (SPPS) is a practical approach for peptide synthesis, the requirement for slow and inefficient chromatographic purification of the product peptides is a significant limitation to exploring these novel compounds. Herein, we invent a "catch-release" strategy for the nonchromatographic purification of macrocyclic peptides. A traceless catch process is enabled by the invention of a dual-functionalized N-terminal acetate analogue, which serves as a handle for capture onto a purification resin and as a leaving group for macrocyclization. Displacement by a C-terminal nucleophilic side chain thus releases the desired macrocycle from the purification resin. By design, this catch/release process is a logic test for the presence of the key components required for cyclization, thus removing impurities which lack the required functionality, such as common classes of peptide impurities, including hydrolysis fragments and truncated sequences. The method was shown to be highly effective with three libraries of macrocyclic peptides, containing macrocycles of 5-20 amino acids, with either thioether- or amine-based macrocyclic linkages; in this latter class, the reported method represents an enabling technology. In all cases, the catch-release protocol afforded significant enrichment of the target peptides purity, in many cases completely obviating the need for chromatography. Importantly, we have adapted this process for automation on a standard multichannel peptide synthesizer, achieving an efficient and completely integrated synthesis and purification platform for the preparation of these important molecules.

Modeling, Synthesis, and Biological Evaluation of Potential Retinoid X Receptor (RXR)-Selective Agonists: Analogues of 4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic Acid (Bexarotene) and 6-(Ethyl(5,5,8,8-tetrahydronaphthalen-2-yl)amino)nicotinic Acid (NEt-TMN)

Sulfonic acid analogues of 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic acid (bexarotene, 1) as well as seven novel and two reported analogues of 6-(ethyl(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)amino)nicotinic acid (NEt-TMN) were synthesized and assessed for selective retinoid X receptor (RXR) agonism. Compound 1 is FDA-approved for treatment of cutaneous T-cell lymphoma (CTCL); however, 1 can provoke side effects by impacting RXR-dependent receptor pathways. All of the analogues in this study were evaluated for their potential to bind RXR through modeling and then assayed in an RXR-RXR mammalian-2-hybrid (M2H) system and in RXR-responsive element (RXRE)-mediated transcriptional experiments. The EC50 profiles for these unique analogues and their analogous effectiveness to inhibit proliferation in CTCL cells relative to 1 suggest that these compounds possess similar or even enhanced therapeutic potential. Several compounds also displayed more selective RXR activation with minimal cross-signaling of the retinoic acid receptor. These results suggest that modifications of potent RXR agonists such as NEt-TMN can lead to improved biological selectivity and potency compared with the known therapeutic.

Identification of human T2R receptors that respond to bitter compounds that elicit the bitter taste in compositions, and the use thereof in assays to identify compounds that inhibit (block) bitter taste in compositions and use thereof

The present invention relates to the discovery that specific human taste receptors in the T2R taste receptor family respond to particular bitter compounds present in, e.g., coffee. Also, the invention relates to the discovery of specific compounds and compositions containing that function as bitter taste blockers and the use thereof as bitter taste blockers or flavor modulators in, e.g., coffee and coffee flavored foods, beverages and medicaments. Also, the present invention relates to the discovery of a compound that antagonizes numerous different human T2Rs and the use thereof in assays and as a bitter taste blocker in compositions for ingestion by humans and animals.

THERAPEUTIC COMPOUNDS

The invention provides compounds and compositions that are useful for treating conditions including Alzheimer's disease, Parkinson's disease, diabetes, cancer, and psychotic disorders such as schizophrenia.

Fluorescent non-peptidic RGD mimetics with high selectivity for αvβ3 vs αiIbβ3 integrin receptor: Novel probes for in vivo optical imaging

Integrins are heterodimeric transmembrane protein receptors consisting of different α and β subunits. αvβ3 integrins are overexpressed on many tumor cells and tumor-associated angiogenic vessels, whereas αIIbβ3 is a receptor for, e.g., fibrinogen and mediates platelet aggregation. In this study, a near-infrared fluorescent imaging probe has been designed and synthesized by conjugating fluorescent dyes to a non-peptidic, pharmacophore-based ligand, based on a molecular modeling design approach. Affinity values were determined, and in vitro cell binding assays and preliminary in vivo xenograft studies in nude mice were performed to evaluate target binding. Competition assays revealed excellent binding and selectivity to αvβ3 compared to that for αIIbβ3. In vitro, the probe showed high target binding on αvβ3-positive M-21 cells and negligible binding to αvβ3-negative MCF-7 cells. In vivo, the tracer is able to image target expression in U-87 xenografts with a maximum signal-to-noise ratio (SNR) of 2.5:1 at 24 h after injection.

LABELLED COMPOUNDS THAT BIND TO ALPHA-V-BETA-3 INTEGRIN

The present invention concerns in vivo imaging and in particular a novel in vivo imaging agent of formula (I). Also provided by the present invention is a method for the preparation of the in vivo imaging agent of the invention, and precursor compounds useful in said method. The in vivo imaging agent of the invention is useful in the diagnosis of conditions where there is a deviation from normal in the expression of integrin αvβ3.