86499-35-6

Basic information

• Product Name: 3-Amino-2,3,4,5-Tetrahydro-1H-1-benzazepin-2-one
• Synonyms: 3-AMINO-2,3,4,5-TETRAHYDRO-1H-1-BENAZEPIN-2-ONE;3-AMINO-2,3,4,5-TETRAHYDRO-1H-1-BENZAZEPIN-2-ONE HYDROCHLORIDE;3-AMINO-1,3,4,5-TETRAHYDRO-2H-1-BENZAZEPIN-2-ONE;3-AMINO-1,3,4,5-TETRAHYDRO-BENZO[B]AZEPIN-2-ONE;3-Amino-2,3,4,5-tetrahydro-2-oxo-2H-1-benzazepine;3-Amino-2,3,4,5-Tetrahydro-1H-1-benzazepin-2-one;Benazepril Intermediate;3-amino-1,3,4,5-tetrahydro-2H-benzaone-2-one
• CAS NO: 86499-35-6
• Molecular Formula: C₁₀H₁₂N₂O
• Molecular Weight: 176.22
• Product Categories: pharmacetical
• Mol File: 86499-35-6.mol

Chemical Properties

• Melting Point: 193-195 °C
• Boiling Point: 377.5 °C at 760 mmHg
• Flash Point: 182.1 °C
• Appearance: /
• Density: 1.143 g/cm³
• Storage Temp.: 2-8°C(protect from light)
• PKA: 14.57±0.40(Predicted)
• CAS DataBase Reference: 3-Amino-2,3,4,5-Tetrahydro-1H-1-benzazepin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-2,3,4,5-Tetrahydro-1H-1-benzazepin-2-one(86499-35-6)
• EPA Substance Registry System: 3-Amino-2,3,4,5-Tetrahydro-1H-1-benzazepin-2-one(86499-35-6)

Safety Data

• Hazardous Substances Data: 86499-35-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 50, p. 3408, 1985 DOI: 10.1021/jo00218a034

InChI:InChI=1/C10H12N2O.ClH/c11-8-6-5-7-3-1-2-4-9(7)12-10(8)13;/h1-4,8H,5-6,11H2,(H,12,13);1H

Upstream product

• 4424-80-0 2,3,4,5-tetrahydro-1H-1-benzo[b]azepin-2-one 
• 19832-98-5 4-methyl-3,4-dihydro-2H-naphthalen-1-one 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 7440-44-0 pyrographite 
• 97278-68-7 3-azido-2,3,4,5-tetrahydro-2-oxo-1 H-1-benzazepine 
• 88372-41-2 (+/-)-2-amino-4-(2-amino-phenyl)-butyric acid 
• 86499-96-9 3-bromo-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one 
• 7772-99-8 stannous chloride 
• 68253-36-1 1-tetralone oxime 
• 140700-64-7 3-iodo-1,3,4,5-tetrahydro-2H-1-benzazepin-2-one 

Downstream Products

• 86499-69-6 1,1-dimethylethyl (2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-3-yl)carbamate 
• 145485-06-9 2(R)-t-Butoxycarbonylamino-3-phenyl-N-[2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-3(R)-yl]-propanamide 
• 145455-90-9 2(R)-Amino-4-phenyl-N-[2,3,4,5-tetrahydro-2-oxo-1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1H-1-benzazepin-3(R)-yl]-butanamide, mono(trifluoroacetate) 
• 145485-23-0 1-t-Butoxycarbonylamino-N-[2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-3-yl]-cyclohexanecarboxamide 
• 145554-02-5 3-benzyloxycarbonylamino-3-methyl-N-[2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-3(R)-yl]-butanamide 
• 86499-26-5 3-amino-1-benzyloxycarbonylmethyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one 
• 86499-51-6 3-benzyloxycarbonylamino-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one 
• 1414963-26-0 N-(3-(3-fluorophenyl)-1-((R)-1-isopropyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylamino)-1-oxopropan-2-yl)-2-trimethylstannanylbenzamide 
• 950509-59-8 (R)-3-tritylamino-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one 
• 959845-01-3 (R)-3-tritylamino-1-isopropyl-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one 
• 1414963-22-6 C₂₇H₃₄FN₃O₄ 
• 1414963-23-7 2-amino-3-(2-fluorophenyl)-N-((R)-1-isopropyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-yl)propanamide 
• 1414963-24-8 N-(3-(3-fluorophenyl)-1-((R)-1-isopropyl-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-3-ylamino)-1-oxopropan-2-yl)-2-iodobenzamide 
• 97278-68-7 3-azido-2,3,4,5-tetrahydro-2-oxo-1 H-1-benzazepine 

Relevant articles and documents

HETEROCYCLIC AMIDES AS KINASE INHIBITORS

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Evaluation of a 125I-labelled benzazepinone derived voltage-gated sodium channel blocker for imaging with SPECT

Voltage-gated sodium channels (VGSCs) are a family of transmembrane proteins that mediate fast neurotransmission, and are integral to sustain physiological conditions and higher cognitive functions. Imaging of VGSCs in vivo holds promise as a tool to elucidate operational functions in the brain and to aid the treatment of a wide range of neurological diseases. To assess the suitability of 1-benzazepin-2-one derived VGSC blockers for imaging, we have prepared a 125I-labelled analogue of BNZA and evaluated the tracer in vivo. In an automated patch-clamp assay, a diastereomeric mixture of the non-radioactive compound blocked the Nav1.2 and Nav1.7 VGSC isoforms with IC50 values of 4.1 ± 1.5 μM and 0.25 ± 0.07 μM, respectively. [3H]BTX displacement studies revealed a three-fold difference in affinity between the two diastereomers. Iodo-destannylation of a tin precursor with iodine-125 afforded the two diastereomerically pure tracers, which were used to assess binding to VGSCs in vivo by comparing their tissue distributions in mice. Whilst the results point to a lack of VGSC binding in vivo, SPECT imaging revealed highly localized uptake in the interscapular region, an area typically associated with brown adipose tissue, which in addition to high metabolic stability of the iodinated tracer, demonstrate the potential of 1-benzazepin-2-ones for in vivo imaging.

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A novel class of potent and selective non-peptide neuropeptide Y (NPY) Y1 receptor antagonists, having benzazepine nuclei, have been designed, synthesized, and evaluated for activity. Through a blind screening we found the compound 1-N-(3-(N' -(tert-butoxycarbonyl)amino)benzyl)-7-methoxy-3-(3)-methylureido)-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (9: IC50 =1.6 μM). Chemical modifications of 9 gave a potent NPY Y1 antagonist 3-(N-(4-hydroxyphenyl)-N0 -methylguanidino)-1-N-(3-(N'-(tert- butoxycarbonyl)amino)benzyl)-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (14c: IC50 =43 nM), which had no affnity for NPY Y2 and Y5 receptors. (C) 1999 Elsevier Science Ltd. All rights reserved.