22245-89-2

Usage

Uses

Used in Pharmaceutical Industry:
1,3,4,5-TETRAHYDRO-7-METHOXY-2H-1-BENZAZEPIN-2-ONE is used as a CNS depressant for its potential calming effects on the central nervous system. It is also being explored as an antidepressant due to its potential to alleviate symptoms of depression.
1,3,4,5-TETRAHYDRO-7-METHOXY-2H-1-BENZAZEPIN-2-ONE's specific applications are still under investigation, and it is not yet widely used in clinical practice. However, its unique chemical structure and potential pharmacological effects make it a valuable subject for ongoing research and development in the field of neuropharmacology. As more is learned about its mechanism of action and therapeutic potential, 1,3,4,5-TETRAHYDRO-7-METHOXY-2H-1-BENZAZEPIN-2-ONE may find broader applications in the treatment of various neurological and psychiatric disorders.

InChI:InChI=1/C11H13NO2/c1-14-9-5-6-10-8(7-9)3-2-4-11(13)12-10/h5-7H,2-4H2,1H3,(H,12,13)

Upstream product

• 1078-19-9 6-methoxy-3,4-dihydro-1(2H)-naphthalenone 
• 201230-82-2 carbon monoxide 
• 68267-68-5 2-allyl-4-methoxyaniline 
• 54951-36-9 6-methoxy-1-tetralone oxime 
• 436155-91-8 1-amino-7-methoxy-1,3,4,5-tetrahydrobenzo[b]azepin-2-one 
• 22245-90-5 1,3,4,5-tetrahydro-7-hydroxy-2H-1-benzazepin-2-one 
• 90817-92-8 C₁₈H₁₉NO₄S 
• 32338-02-6 2-bromo-4-methoxyaniline 
• 1536478-81-5 N-(2-bromo-4-methoxyphenyl)formamide 
• 214279-40-0 3-iodo-4-nitroanisol 
• 54951-36-9 (1E)-6-methoxy-3,4-dihydronaphthalen-1(2H)-one oxime 
• 436155-78-1 phenyl (7-methoxy-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepin-1-yl)carbamate 
• 436155-56-5 phenyl 2-[4-(3-methoxyphenyl)butanoyl]hydrazinecarboxylate 
• 952007-72-6 4-(3-methoxyphenyl)butanoyl chloride 

Downstream Products

• 1427309-66-7 1-phenyl-4,5-dihydro-1H-benzo[b]azepin-2(3H)-one 
• 211761-53-4 [3-(3-azido-7-methoxy-2-oxo-2,3,4,5-tetrahydro-benzo[b]azepin-1-ylmethyl)-phenyl]-carbamic acid tert-butyl ester 
• 213664-70-1 3-amino-1-N-(3-(N'-(tert-butoxycarbonyl)amino)benzyl)-7-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one 
• 250131-90-9 (3-benzyloxycarbonylamino-7-methoxy-2-oxo-2,3,4,5-tetrahydro-benzo[b]azepin-1-yl)-acetic acid tert-butyl ester 
• 46180-98-7 7-methoxy-2,3,4,5-tetrahydro-1H-benzo[b]azepine 

Relevant academic research and scientific papers

Design, synthesis, and opioid receptor binding of some novel benzazepine constrained leucine enkephalin mimetics

An N-substituted 2-benzazepine, previously reported to possess morphine-like analgesic activity in vivo, was adapted for use as a constrained mimic of the N-terminal residues of leucine enkephalin. Molecular modeling was used to evaluate the suitability o

Oxidation of Nonactivated Anilines to Generate N-Aryl Nitrenoids

A low-temperature, protecting-group-free oxidation of 2-substituted anilines has been developed to generate an electrophilic N-aryl nitrenoid intermediate that can engage in C-NAr bond formation to construct functionalized N-heterocycles. The exposure of 2-substituted anilines to PIFA and trifluoroacetic acid or 10 mol percent Sc(OTf)3 triggers nitrenoid formation, followed by productive and selective C-NAr and C-C bond formation to yield spirocyclic- or bicyclic 3H-indoles or benzazepinones. Our experiments demonstrate the breadth of these oxidative processes, uncover underlying fundamental elements that control selectivity, and demonstrate how the distinct reactivity patterns embedded in N-aryl nitrenoid reactive intermediates can enable access to functionalized 3H-indoles or benzazepinones.

Rh2(II)-Catalyzed Ring Expansion of Cyclobutanol-Substituted Aryl Azides to Access Medium-Sized N-Heterocycles

A new reactivity pattern of Rh2(II)-N-arylnitrenes was discovered that facilitates the synthesis of medium-sized N-heterocycles from ortho-cyclobutanol-substituted aryl azides. The key ring-expansion step of the catalytic cycle is both chemosel

Optimization of 4-(N-cycloamino)phenylquinazolines as a novel class of tubulin-polymerization inhibitors targeting the colchicine site

The 6-methoxy-1,2,3,4-tetrahydroquinoline moiety in prior leads 2-chloro- and 2-methyl-4-(6-methoxy-3,4-dihydroquinolin-1(2H)-yl)quinazoline (1a and 1b) was modified to produce 4-(N-cycloamino)quinazolines (4a-c and 5a-m). The new compounds were evaluated in cytotoxicity and tubulin inhibition assays, resulting in the discovery of new tubulin-polymerization inhibitors. 7-Methoxy-4-(2-methylquinazolin-4-yl)-3,4-dihydroquinoxalin-2(1H)-one (5f), the most potent compound, exhibited high in vitro cytotoxic activity (GI 50 1.9-3.2 nM), significant potency against tubulin assembly (IC 50 0.77 μM), and substantial inhibition of colchicine binding (99% at 5 μM). In mechanism studies, 5f caused cell arrest in G2/M phase, disrupted microtubule formation, and competed mostly at the colchicine site on tubulin. Compound 5f and N-methylated analogue 5g were evaluated in nude mouse MCF7 xenograft models to validate their antitumor activity. Compound 5g displayed significant in vivo activity (tumor inhibitory rate 51%) at a dose of 4 mg/kg without obvious toxicity, whereas 5f unexpectedly resulted in toxicity and death at the same dose.

High-yield method for the preparation of 1,3,4,5-tetrahydro-7-methoxy-2 H-1-benzazepin-2-one with excellent regio-and stereoselectivity

We have surveyed the effects of different acid catalysts, reaction times, and temperatures on the yield, regioselectivity, and stereoselectivity and calculated the ketoxime isomerization and activation energy of the title compound. A facile synthetic proc

Mild and efficient synthesis of benzo-fused seven- and eight-membered ring lactams: A convenient approach to biologically interesting chemotypes

A general and efficient method for the synthesis of benzo-fused 7- and 8-membered ring lactams via the Beckmann rearrangement of cyclic oximes is presented. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file. Copyright Taylor & Francis Group, LLC.

Synthesis and anticonvulsant activity of 8-alkoxy-5,6-dihydro-4Hbenzo[f][1, 2,4]triazolo[4,3-a]azepine derivatives

A novel series of 8-alkoxy-5,6-dihydro-4Hbenzo[ f][1,2,4]triazolo[4,3-a] azepine derivatives were synthesized and characterized by IR, 1H NMR, 13C NMR, mass spectroscopy, and elemental analysis. The newly synthesized compounds were s

Beckmann rearrangement of ketoximes induced by phenyl dichlorophosphate at ambient temperature

Upon treatment with phenyl dichlorophosphate (PhOP=OCl2) in acetonitrile at ambient temperature, a variety of ketoximes underwent a Beckmann rearrangement in an effective manner to afford the corresponding amides in moderate to high yields.

The application of the schmidt reaction and beckmann rearrangement to the synthesis of bicyclic lactams: Some mechanistic considerations

The syntheses of some methoxy-substituted bicyclic lactams, of the types 3 and 4, are reported employing two different conditions for the Schmidt reaction of appropriate ketones and employing two different conditions for the Beckmann rearrangement of the corresponding ketoximes. The alkyl to aryl migration ratios of the reactions were determined by high-performance liquid chromatography analysis of the reactions. The mechanisms of the reactions reported are discussed, some limitations of the reported mechanisms identified, and an alternative mechanism proposed in light of the outcomes of the various reactions. Application of the Schmidt reaction and Beckmann rearrangement was used for the synthesis of some chloro bicyclic lactams, of the types 3 and 4. CSIRO 2010.

Targeting the polyamine transport system with benzazepine- and azepine-polyamine conjugates

The polyamine transport system (PTS) whose activity is up-regulated in cancer cells is an attractive target for drug design. Two heterocyclic (azepine and benzazepine) systems were conjugated to various polyamine moieties through an amidine bound to afford 18 compounds which were evaluated for their affinity for the PTS and their ability to use the PTS for cell delivery. Structure-activity relationship studies and lead optimization afforded two attractive PTS targeting compounds. The azepine-spermidine conjugate 14 is a very selective substrate of the PTS that may serve as a vector for radioelements used for diagnoses or therapeutics in nuclear medicine. The nitrobenzazepine-spermine conjugate 28 is a very powerful PTS inhibitor with very low intrinsic cytotoxicity, able to prevent the growth of polyamine depleted cells in presence of exogenous polyamines.