17422-43-4

Basic information

• Product Name: 8-METHOXY-2,3,4,5-TETRAHYDRO-1H-BENZO[B]AZEPINE HYDROCHLORIDE
• Synonyms: 8-METHOXY-2,3,4,5-TETRAHYDRO-1H-BENZO[B]AZEPINE HYDROCHLORIDE;8-methoxy-2,3,4,5-tetrahydro-1H-benzo[b]azepine
• CAS NO: 17422-43-4
• Molecular Formula: C₁₁H₁₅NO
• Molecular Weight: 213.70384
• Mol File: 17422-43-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 45-47 °C
• Boiling Point: 130-134 °C(Press: 5 Torr)
• Appearance: /
• Density: 1.018±0.06 g/cm3(Predicted)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 4.96±0.20(Predicted)
• CAS DataBase Reference: 8-METHOXY-2,3,4,5-TETRAHYDRO-1H-BENZO[B]AZEPINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 8-METHOXY-2,3,4,5-TETRAHYDRO-1H-BENZO[B]AZEPINE HYDROCHLORIDE(17422-43-4)
• EPA Substance Registry System: 8-METHOXY-2,3,4,5-TETRAHYDRO-1H-BENZO[B]AZEPINE HYDROCHLORIDE(17422-43-4)

Safety Data

• Hazardous Substances Data: 17422-43-4(Hazardous Substances Data)

Upstream product

• 887354-63-4 C₁₈H₁₉NO₃S 
• 99833-87-1 7-methoxy-1-tetralone O-tosyloxime 
• 6836-19-7 7-Methoxy-1-tetralone 
• 20175-97-7 7-methoxy-3,4-dihydronaphthalen-1(2H)-one oxime 
• 22246-83-9 8-methoxy-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one 

Downstream Products

• 1439931-08-4 C₃₂H₃₀Cl₄N₂O₃ 
• 1202503-72-7 1-(2,4-dichlorophenyl)-8-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepine 
• 1202503-76-1 1-(2,4-dichlorophenyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-8-yl trifluoromethanesulfonate 
• 1202503-74-9 1-(2,4-dichlorophenyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-8-ol 
• 200010-61-3 [5-Hydroxy-8-methoxy-4-[(E)-methoxyimino]-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl]-propynoic acid ethyl ester 
• 200010-62-4 3-[5-Hydroxy-8-methoxy-4-[(E)-methoxyimino]-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-5-yl]-propionic acid ethyl ester 
• 200010-72-6 N-[8-Methoxy-5-oxo-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-yl]-propionamide 
• 200010-64-6 N-[8-Methoxy-5-oxo-1-(toluene-4-sulfonyl)-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-yl]-acetamide 

Relevant articles and documents

Design, synthesis and biological evaluation of brain penetrant benzazepine-based histone deacetylase 6 inhibitors for alleviating stroke-induced brain infarction

Histone deacetylase 6 (HDAC6) has become a promising therapeutic target for central nervous system diseases due to its more complex protein structure and biological functions. However, low brain penetration of reported HDAC6 inhibitors limits its clinical application in neurological disorders. Therefore, the benzazepine, a brain-penetrant rigid fragment, was utilized to design a series of selective HDAC6 inhibitors to improve brain bioavailability. Various synthetic strategies were applied to assemble the tetrahydro-benzazepine ring, and 22 compounds were synthesized. Among them, compound 5 showed low nanomolar potency and strong isozyme selectivity for the inhibition of HDAC6 (IC50 = 1.8 nM, 141-fold selectivity over HDAC1) with efficient binding patterns like coordination with the zinc ion and π-π stacking effect. Western blot results showed it could efficiently transport into SH-SY5Y cells and selectively enhance the acetylation level of α-tubulin with a moderate effect on Histone H3. Notably, pharmacokinetic studies demonstrated that compound 5 (brain/plasma ratio of 2.30) had an excellent ability to penetrate the blood-brain barrier of C57 mice. In male rats with transient middle cerebral artery occlusion (MCAO), compound 5 significantly reduced the cerebral infarction from 21.22% to 11.47% and alleviated neurobehavioral deficits in post-ischemic treatment, which provided a strong rationale for pursuing HDAC6-based therapies for ischemic stroke.

Ring-expansion reaction of oximes with aluminum reductants

The ring-expansion reactions of heterocyclic ketoximes and carbocyclic ketoximes with several reductants such as AlHCl2, AlH3 (alane), LiAlH4, LiAlH(OtBu)3, and (MeOCH 2CH2O)2AlH2Na (Red-Al) were examined. Among reductants, AlHCl2 (LiAlH4:AlCl 3 = 1:3) in cyclopentyl methyl ether (CPME) has been found to be a suitable reagent for the reaction, and the rearranged cyclic secondary amines were obtained in good to excellent yields.

Azabenzocycloheptenones. Part 20. Synthesis and utilisation of 4-amino-1,2,3,4-tetrahydro-1(1H)-benzazepines

1,2,3,4-Tetrahydro-6- and -7-methoxy-4-oxo-1-(p-tolylsulfonyl)quinolines 3 (R = tosyl, X = 6- and 7-OMe) and 1-ethoxycarbonylmethyl-1,2,3,4-tetrahydro-7-methoxy-4-oxoquinoline3 (R = CH2CO2Et, X = 7-OMe) have been ring-expanded in two