17775-01-8

Usage

Uses

Used in Pharmaceutical Industry:
2,3,4,5-Tetrahydrobenzo[f][1,4]oxazepine is used as a key intermediate in the synthesis of various pharmaceutical compounds for the treatment of neurological and psychiatric disorders. Its unique structure and pharmacological properties make it a promising candidate for drug development in these therapeutic areas.
Used in Medicinal Chemistry Research:
2,3,4,5-Tetrahydrobenzo[f][1,4]oxazepine serves as a valuable scaffold in medicinal chemistry for the design and optimization of novel drug candidates. Its heterocyclic nature allows for the exploration of various chemical modifications to enhance its pharmacological properties and improve its therapeutic potential.
Used in Drug Discovery Research:
2,3,4,5-Tetrahydrobenzo[f][1,4]oxazepine is utilized in drug discovery research to identify and develop new chemical entities with potential therapeutic applications. Its unique structure and pharmacological properties make it an attractive target for the development of innovative drugs to address unmet medical needs.

InChI:InChI=1/C9H11NO/c1-2-4-9-8(3-1)7-10-5-6-11-9/h1-4,10H,5-7H2

Upstream product

• 34844-80-9 4,5-dihydro-1,4-benzoxazepin-3(2H)-one 
• 703-51-5 2,3-dihydro-1,4-benzoxazepin-5(4H)-one 
• 34844-79-6 methyl 2-(2-cyanophenoxy)ethanoate 
• 5755-05-5 7-bromo-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 251326-32-6 2-((2-bromobenzyl)amino)ethan-1-ol 
• 6630-33-7 ortho-bromobenzaldehyde 
• 90-02-8 salicylaldehyde 

Downstream Products

• 21492-58-0 4-(2,3-dihydro-5H-benzo[f][1,4]oxazepin-4-yl)-1-(4-fluoro-phenyl)-butan-1-one 
• 1426385-50-3 C₁₈H₁₄F₃NO₃ 

Relevant academic research and scientific papers

[1,5]-Hydride shift-cyclization versus C(sp2)-H functionalization in the knoevenagel-cyclization domino reactions of 1,4- And 1,5-Benzoxazepines

Domino cyclization reactions of N-aryl-1,4- and 1,5-benzoxazepine derivatives involving [1,5]-hydride shift or C(sp2)-H functionalization were investigated. Neuroprotective and acetylcholinesterase activities of the products were studied. Domino Knoevenagel-[1,5]-hydride shift-cyclization reaction of N-aryl-1,4-benzoxazepine derivatives with 1,3-dicarbonyl reagents having active methylene group afforded the 1,2,8,9-tetrahydro-7bH-quinolino [1,2-d][1,4]benzoxazepine scaffold with different substitution pattern. The C(sp3)-H activation step of the tertiary amine moiety occurred with complete regioselectivity and the 6-endo cyclization took place in a complete diastereoselective manner. In two cases, the enantiomers of the chiral condensed new 1,4-benzoxazepine systems were separated by chiral HPLC, HPLC-ECD spectra were recorded, and absolute configurations were determined by time-dependent density functional theory- electronic circular dichroism (TDDFT-ECD) calculations. In contrast, the analogue reaction of the regioisomeric N-aryl-1,5-benzoxazepine derivative did not follow the above mechanism but instead the Knoevenagel intermediate reacted in an SEAr reaction [C(sp2)-H functionalization] resulting in a condensed acridane derivative. The AChE inhibitory assays of the new derivatives revealed that the acridane derivative had a 6.98 μM IC50 value.

INHIBITORS OF NOROVIRUS AND CORONAVIRUS REPLICATION

Compounds of Formula (I) and methods of inhibiting the replication of viruses in a biological sample or patient, of reducing the amount of viruses in a biological sample or patient, and of treating a virus infection in a patient, comprising administering to said biological sample or patient an effective amount of a compound represented by Formula (I), a compound of Table A or B or a pharmaceutically acceptable salt thereof.

N-Atom Deletion in Nitrogen Heterocycles

Excising the nitrogen in secondary amines, and coupling the two residual fragments is a skeletal editing strategy that can be used to construct molecules with new skeletons, but which has been largely unexplored. Here we report a versatile method of N-atom excision from N-heterocycles. The process uses readily available N-heterocycles as substrates, and proceeds by N-sulfonylazidonation followed by the rearrangement of sulfamoyl azide intermediates, providing various cyclic products. Examples are provided of deletion of nitrogen from natural products, synthesis of chiral O-heterocycles from commercially available chiral β-amino alcohols, formal inert C?H functionalization through a sequence of N-directed C?H functionalization and N-atom deletion reactions in which the N-atom can serve as a traceless directing group.

Design, synthesis and evaluation of chromone-2-carboxamido-alkylbenzylamines as multifunctional agents for the treatment of Alzheimer's disease

A series of chromone-2-carboxamido-alkylbenzylamines were designed, synthesized and evaluated as multifunctional agents for the treatment of Alzheimer's disease (AD). The results showed that most of these compounds exhibited good multifunctional activities. Among them, compound 49 displayed excellent inhibitory potency toward acetylcholinesterase (AChE), moderate anti-oxidative activity, selective biometal chelating, and possessed good inhibitory effects on self-induced and Cu2+-induced Aβ aggregation. Both kinetic analysis of AChE inhibition and molecular modeling study indicated that 49 was a mixed-type inhibitor, binding simultaneously to the catalytic active site and peripheral anionic site of AChE. These results suggested that 49 might be a potential multifunctional agent for AD treatment.

Process Development and Scale-Up of a Benzoxazepine-Containing Kinase Inhibitor

The benzoxazepine core is present in several kinase inhibitors, including the mTOR inhibitor 1. The process development for a scalable synthesis of 7-bromobenzoxazepine and the telescoped synthesis of 1 are reported. Compound 1 consists of three chemicall

Quinoxaline compounds

Certain amidophenyl-sulfonylamino-quinoxaline compounds are CCK2 modulators useful in the treatment of CCK2 mediated diseases.

Heterocyclic derivatives and their use as antithrombotic agents

The present invention relates to antithrombotic compounds comprising the group Q, Q having formula (I), wherein the substructure (i) is a structure selected from (a, b and c), wherein X is O or S; X′ being independently CH or N; and m is 0, 1, 2 or 3; wherein the group Q is bound through an oxygen atom or an optionally substituted nitrogen or carbon atom, or a pharmaceutically acceptable salt thereof or a prodrug thereof. The compounds of the invention are therapeutically active and in particular are antithrombotic agents.

Effect of ring size or an additional heteroatom on the potency and selectivity of bicyclic benzylamine-type inhibitors of phenylethanolamine N- methyltransferase

In the search for potent and selective inhibitors of the enzyme phenylethanolamine N-methyltransferase (PNMT; EC 2.1.1.28), we examined the effect of ring size or an additional heteroatom in the conformationally- restricted benzylamine-type PNMT inhibitors. Based on semiempirical calculations (MNDO) and molecular modeling studies, PNMT-inhibitory activity of these compounds seemed to be dependent on (a) the torsion angle between the plane of the aromatic ring and the endo N atom lone pair (τ2 angle), with the optimal value of τ2 being about -75°, and (b) the amount of steric bulk about the 3-position of 1,2,3,4-tetrahydroisoquinoline (5, THIQ). 2,3,4,5-Tetrahydro-1H-2-benzazepine (6) was found to have the highest selectivity (PNMT K(i) = 3.34 μM, α2 K(i) = 11 μM, selectivity = 3.2) as compared to other homologues of THIQ (PNMT K(i) = 9.67 μM, α2 K(i) = 0.35 μM, selectivity = 0.036). The higher PNMT-inhibitory activity of 6 was attributed to favorable steric interactions of the puckered methylene groups in the putative bioactive conformation of 6 at the PNMT active site, whereas unfavorable interactions of these puckered methylene groups at the α2- adrenoceptor were thought to be the cause of reduced α2 affinity of 6. No further enhancement of the selectivity of the benzazepine ring system could be obtained via introduction of a second heteroatom (N, O, S) at the 5- position in this ring system.