52206-05-0

Basic information

• Product Name: 1-ACETYL-2,3-DIHYDRO-1H-INDOLE-5-SULFONYL CHLORIDE
• Synonyms: N-ACETYLINDOLINE-5-SULPHONYL CHLORIDE;BUTTPARK 120\07-98;1-ACETYL-5-INDOLINESULFONOYL CHLORIDE;1-ACETYL-5-INDOLINESULFONYL CHLORIDE;1-ACETYLINDOLINE-5-SULFONYL CHLORIDE;1-ACETYL-2,3-DIHYDRO-1H-INDOLE-5-SULFONYL CHLORIDE;N-Acetylindoline-5-sulphonyl chloride 97%;1-acetyl-2,3-dihydroindole-5-sulfonyl chloride
• CAS NO: 52206-05-0
• Molecular Formula: C₁₀H₁₀ClNO₃S
• Molecular Weight: 259.71
• Product Categories: Benzenesulfonyl chloride
• Mol File: 52206-05-0.mol

Chemical Properties

• Melting Point: 172 °C
• Boiling Point: 498.984 °C at 760 mmHg
• Flash Point: 255.577 °C
• Appearance: /
• Density: 1.463g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.602
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -3.49±0.20(Predicted)
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: 1-ACETYL-2,3-DIHYDRO-1H-INDOLE-5-SULFONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ACETYL-2,3-DIHYDRO-1H-INDOLE-5-SULFONYL CHLORIDE(52206-05-0)
• EPA Substance Registry System: 1-ACETYL-2,3-DIHYDRO-1H-INDOLE-5-SULFONYL CHLORIDE(52206-05-0)

Safety Data

• Hazard Codes: C,Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 52206-05-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Chemistry:
1-Acetyl-2,3-dihydro-1H-indole-5-sulfonyl chloride is used as a synthetic intermediate for the production of various pharmaceutical compounds. Its reactive Sulfonyl Chloride functional group allows for the formation of new bonds and the creation of more complex molecules, which can be further utilized in drug development.
Used in Industrial Chemistry:
In the industrial chemistry sector, 1-Acetyl-2,3-dihydro-1H-indole-5-sulfonyl chloride is used as a key component in the synthesis of specialty chemicals. Its reactivity and ability to form new bonds make it a valuable asset in the production of a wide range of industrial products, from dyes to agrochemicals.
Used in Research and Development:
1-Acetyl-2,3-dihydro-1H-indole-5-sulfonyl chloride is employed as a research compound in academic and industrial laboratories. Its unique structure and reactivity make it an interesting subject for studying chemical reactions and exploring new synthetic pathways, potentially leading to the discovery of novel compounds with various applications.

InChI:InChI=1/C10H10ClNO3S/c1-7(13)12-5-4-8-6-9(16(11,14)15)2-3-10(8)12/h2-3,6H,4-5H2,1H3

Upstream product

• 16078-30-1 1-Acetyl-2,3-dihydro-1H-indole 
• 496-15-1 1-indoline 

Downstream Products

• 108583-96-6 (S)-2-(1-Acetyl-2,3-dihydro-1H-indole-5-sulfonylamino)-3-(4-hydroxy-phenyl)-propionic acid 
• 108583-91-1 (S)-2-(1-Acetyl-2,3-dihydro-1H-indole-5-sulfonylamino)-3-methyl-butyric acid 
• 1396964-72-9 (S)-2-(1-Acetyl-2,3-dihydro-1H-indole-5-sulfonylamino)-3-phenyl-propionic acid 
• 841275-85-2 3-[(1-acetyl-2,3-dihydro-1H-indol-5-yl)sulfonyl]propanoic acid 
• 113162-46-2 5-(methylsulfamoyl)indoline 
• 1145658-36-1 1-acetyl-N,N-dibenzylindoline-5-sulfonamide 
• 838887-37-9 1-acetyl-N-(3,4-dimethylphenyl)indoline-5-sulfonamide 
• 1393348-47-4 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl ((2S,3R)-3-hydroxy-4-(N-isobutylindoline-5-sulfonamido)-1-phenylbutan-2-yl)carbamate 
• 1393348-48-5 ((2S,3R)-4-(1-acetyl-N-isobutylindoline-5-sulfonamido)-3-hydroxy-1-phenylbutan-2-yl)carbamate 
• 3074-27-9 1H-indole-5-sulfonamide 
• 3264-38-8 1-acetyl-2,3-dihydro-indole-5-sulfonic acid amide 

Relevant articles and documents

POLYCYCLIC COMPOUNDS AS ROR-GAMMA MODULATORS

The present invention provides compounds which are modulators of RORγ and their use for the treatment of diseases or conditions mediated by RORγ. Further, the present invention relates to processes of preparing such compounds, their tautomeric forms, novel intermediates involved in their synthesis, their pharmaceutically acceptable salts, methods for using such compounds and pharmaceutical compositions containing them.

Phenyl Benzenesulfonylhydrazides Exhibit Selective Indoleamine 2,3-Dioxygenase Inhibition with Potent in Vivo Pharmacodynamic Activity and Antitumor Efficacy

Tryptophan metabolism has been recognized as an important mechanism in immune tolerance. Indoleamine 2,3-dioxygenase plays a key role in local tryptophan metabolism via the kynurenine pathway and has emerged as a therapeutic target for cancer immunotherapy. Our prior study identified phenyl benzenesulfonyl hydrazide 2 as a potent in vitro (though not in vivo) inhibitor of indoleamine 2,3-dioxygenase. Further lead optimization to improve in vitro potencies and pharmacokinetic profiles resulted in N′-(4-bromophenyl)-2-oxo-2,3-dihydro-1H-indole-5-sulfonyl hydrazide 40, which demonstrated 59% oral bioavailability and 73% of tumor growth delay without apparent body weight loss in the murine CT26 syngeneic model, after oral administration of 400 mg/kg. Accordingly, 40, is proposed as a potential drug lead worthy of advanced preclinical evaluation.

Enamino-oxindole HIV protease inhibitors

We have designed and synthesized a series of HIV protease inhibitors (PIs) with enamino-oxindole substituents optimized to interact with the S2′ subsite of the HIV protease binding pocket. Several of these inhibitors have sub-nanomolar Ki and antiviral IC50 in the low nM range against WT HIV and against a panel of multi-drug resistant (MDR) strains.

Identification of inhibitors of NOD1-induced nuclear factor-κB activation

NOD1 (nucleotide-binding oligomerization domain 1) protein is a member of the NLR (NACHT and leucine rich repeat domain containing proteins) protein family, which plays a key role in innate immunity as a sensor of specific microbial components derived from bacterial peptidoglycans and induction of inflammatory responses. Mutations in NOD proteins have been associated with various inflammatory diseases that affect NF-κB (nuclear factor κB) activity, a major signaling pathway involved in apoptosis, inflammation, and immune response. A luciferase-based reporter gene assay was utilized in a high-throughput screening program conducted under the NIH-sponsored Molecular Libraries Probe Production Center Network program to identify the active scaffolds. Herein, we report the chemical synthesis, structure-activity relationship studies, downstream counterscreens, secondary assay data, and pharmacological profiling of the 2-aminobenzimidazole lead (compound 1c, ML130) as a potent and selective inhibitor of NOD1-induced NF-κB activation.

BORON-CONTAINING SMALL MOLECULES

This invention relates to 6-substituted benzoxaborole compounds of the following formula and their use for treating bacterial infections.

PYRIMIDINE DERIVATIVES AS POSH AND POSH-AP INHIBITORS

Pyrimidine derivatives are ubiquitination inhibitors that inhibit the ubiquitin ligase activity, particularly of POSH polypeptides, are useful for the treatment of viral infections and neurological disorders.

6' SUBSTITUTED COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY

The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): wherein R1—R4 A, B, D, E, and G are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.

A convenient synthesis of novel 3-(heterocyclylsulfonyl)propanoic acids and their amide derivatives

A large number of novel 3-(heterocyclylsulfonyl)propanoic acids and their amide derivatives were prepared in good yields and excellent purity starting from the corresponding heterocyclic compounds. At first, chlorosulfonates were generated by reaction of initial heterocycles with various sulfonating and chlorinating agents followed by their conversion into sodium sulfinates. Treatment of sulfinates with acrylic acid smoothly afforded a series of sulfonylpropionates, which were used as convenient reagents for the preparation of a large number of the corresponding carboxamide derivatives.

Sulfonamide inhibitors of aspartyl protease

The present invention relates to a novel class of sulfonamides which are aspartyl protease inhibitors. In one embodiment, this invention relates to a novel class of HIV aspartyl protease inhibitors characterized by specific structural and physicochemical features. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well suited for inhibiting HIV-1 and HIV-2 protease activity and consequently, may be advantageously used as anti-viral agents against the HIV-1 and HIV-2 viruses. This invention also relates to methods for inhibiting the activity of HIV aspartyl protease using the compounds of this invention and methods for screening compounds for anti-HIV activity.

SULFONAMIDE INHIBITORS OF ASPARTYL PROTEASE

The present invention relates to a novel class of sulfonamides which are aspartyl protease inhibitors. In one embodiment, this invention relates to a novel class of HIV aspartyl protease inhibitors characterized by specific structural and physicochemical features. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well suited for inhibiting HIV-1 and HIV-2 protease activity and consequently, may be advantageously used as anti-viral agents against the HIV-1 and HIV-2 viruses. This invention also relates to methods for inhibiting the activity of HIV aspartyl protease using the compounds of this invention and methods for screening compounds for anti-HIV activity.