927869-56-5

Basic information

• Product Name: 2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-7-sulfonyl chloride
• Synonyms: 2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-7-sulfonyl chloride;1H-1-BENZAZEPINE-7-SULFONYL CHLORIDE, 2,3,4,5-TETRAHYDRO-2-OXO-;2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-7-sulfonyl chloride;2-oxo-1,3,4,5-tetrahydro-1-benzazepine-7-sulfonyl chloride
• CAS NO: 927869-56-5
• Molecular Formula: C₁₀H₁₀ClNO₃S
• Molecular Weight: 259.712
• Mol File: 927869-56-5.mol

Chemical Properties

• Boiling Point: 462.2°C at 760 mmHg
• Flash Point: 233.3°C
• Appearance: /
• Density: 1.417g/cm³
• Vapor Pressure: 1E-08mmHg at 25°C
• Refractive Index: 1.576
• CAS DataBase Reference: 2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-7-sulfonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-7-sulfonyl chloride(927869-56-5)
• EPA Substance Registry System: 2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepine-7-sulfonyl chloride(927869-56-5)

Safety Data

• Hazardous Substances Data: 927869-56-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H10ClNO3S/c11-16(14,15)8-4-5-9-7(6-8)2-1-3-10(13)12-9/h4-6H,1-3H2,(H,12,13)

Upstream product

• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 4424-80-0 2,3,4,5-tetrahydro-1H-1-benzo[b]azepin-2-one 

Downstream Products

• 927869-66-7 4-((2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-7-sulfonamido)methyl)cyclohexanecarboxylic acid 
• 1029781-71-2 N-(3,4-dimethylphenyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-7-sulfonamide 
• 1393727-02-0 7-(4-(4-acetylphenyl)piperazin-1-ylsulfonyl)-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one 

Relevant articles and documents

XANTHINE DERIVATIVES AND USES THEREOF AS INHIBITORS OF BROMODOMAINS OF BET PROTEINS

The present invention relates to a compound having the following formula (I): (I) wherein: - R is a (C1-C6)alkyl group;- R'' is preferably H;- Ar is a (C5-C12)arylene radical;- X1 is -C(=O)- or -SO2-; and- R' is chosen from the group consisting of possibly substituted (C1-C6)alkyl, heteroaryl, (C5-C12)aryl, and (hetero)cycloalkyl groups, or a pharmaceutically acceptable salt and/or tautomeric form thereof, or its racemates, diastereomers or enantiomers.

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.

Synthesis of 7-sulfamoyl-substituted 2-oxo-2,3,4,5-tetrahydro-1H-benzo[b] azepines

Sulfochlorination of 2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine led to regioselective formation of the corresponding 7-chlorosulfonyl derivative. Starting from this reagent, a large number of substituted 2-oxo-7-sulfamoyl-2,3, 4,5-tetrahydro-1H-benzo[b]a