17724-38-8

Basic information

• Product Name: 8-METHOXY-1,2,4,5-TETRAHYDROBENZO[C]AZEPIN-3-ONE
• Synonyms: 8-METHOXY-1,2,4,5-TETRAHYDROBENZO[C]AZEPIN-3-ONE;2,3,4,5-tetrahydro-1h-2-benzazepin-3-one;1,2,4,5-tetrahydro-3H-2-benzazepin-3-one
• CAS NO: 17724-38-8
• Molecular Formula: C₁₀H₁₁NO
• Molecular Weight: 191.23
• Product Categories: pharmacetical
• Mol File: 17724-38-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 417.7°C at 760 mmHg
• Flash Point: 206.4°C
• Appearance: /
• Density: 1.121g/cm³
• Vapor Pressure: 3.48E-07mmHg at 25°C
• Refractive Index: 1.536
• CAS DataBase Reference: 8-METHOXY-1,2,4,5-TETRAHYDROBENZO[C]AZEPIN-3-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 8-METHOXY-1,2,4,5-TETRAHYDROBENZO[C]AZEPIN-3-ONE(17724-38-8)
• EPA Substance Registry System: 8-METHOXY-1,2,4,5-TETRAHYDROBENZO[C]AZEPIN-3-ONE(17724-38-8)

Safety Data

• Hazardous Substances Data: 17724-38-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H13NO2/c1-14-10-4-2-8-3-5-11(13)12-7-9(8)6-10/h2,4,6H,3,5,7H2,1H3,(H,12,13)

Upstream product

• 530-93-8 1,2,3,4-tetrahydronaphthalen-2-one 
• 79815-19-3 methyl (3S)-1,2,3,4-tetrahydro-3-isoquinolinecarboxylate 

Downstream Products

• 7216-22-0 2,3,4,5-tetrahydro-1H-benzo[c]azepine 

Relevant articles and documents

Discovery of tetrahydroquinolines and benzomorpholines as novel potent RORγt agonists

The retinoic acid receptor-related orphan receptor γt (RORγt) is an important nuclear receptor that regulates the differentiation of Th17 cells and production of interleukin 17(IL-17). RORγt agonists increase basal activity of RORγt and could provide a potential approach to cancer immunotherapy. Herein, hit compound 1 was identified as a weak RORγt agonist during in-house library screening. Changes in LHS core of 1 led to the identification of tetrahydroquinoline compound 6 as a partial RORγt agonist (max. act. = 39.3%). Detailed structure-activity relationship on substituent of the LHS core, amide linker and RHS arylsulfonyl moiety was explored and a novel series of tetrahydroquinolines and benzomorpholines was discovered as potent RORγt agonists. Tetrahydroquinoline compound 8g (EC50 = 8.9 ± 0.4 nM, max. act. = 104.5%) and benzomorpholine compound 9g (EC50 = 7.5 ± 0.6 nM, max. act. = 105.8%) were representative compounds with high RORγt agonistic activity in dual FRET assay, and they showed good activity in cell-based Gal4 reporter gene assay and Th17 cell differentiation assay (104.5% activation at 300 nM of 8g; 59.4% activation at 300 nM of 9g). The binding modes of 8g and 9g as well as the two RORγt inverse agonists accidentally discovered were also discussed.

Further studies on a samarium diiodide-promoted reductive carbon-nitrogen bond cleavage rection: Synthesis of (+)-aphanorphine

Samarium diiodide-promoted carbon-nitrogen bond cleavage reaction was applied to the 1,2,3,4-tetrahydroisoquinoline derivatives bearing an ester group at the 1- or 3-position to give the corresponding benzazepinones. Synthesis of (+)-aphanorphine was esta