98232-51-0

Usage

Uses

Used in Pharmaceutical Industry:
8-Methoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one is used as a key intermediate in the synthesis of various pharmaceutical and medicinal products. It is involved in the production of tropane alkaloids with diverse pharmaceutical uses, such as analgesics, anesthetics, and antiarrhythmics.
Used in Neurological and Psychiatric Disorders Treatment:
8-Methoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one is used as a potential therapeutic agent for the treatment of neurological and psychiatric disorders. Its stimulant and psychoactive properties have been studied for their potential benefits in managing these conditions.

Upstream product

• 41214-27-1 4-(3-methoxy-phenoxy)-butyric acid 
• 651027-16-6 1-cyano-3-(3-methoxyphenoxy)propane 
• 3245-40-7 1-bromo-3-(3-methoxyphenoxy)propane 
• 57052-73-0 ethyl 4-(3-methoxyphenoxy)butanoate 
• 150-19-6 O-methylresorcine 
• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 

Downstream Products

• 113967-21-8 8-methoxy-4-bromo-3,4-dihydro-1-benzoxepin-5(2H)-one 
• 1373132-84-3 C₁₉H₂₀O₅ 
• 1373132-83-2 C₂₁H₂₂O₆ 
• 651027-20-2 4-[(8-methoxy-2,3,4,5-tetrahydrobenzo[b]oxepin-5-yl)methyl]phenol 

Relevant academic research and scientific papers

ESTROGEN RECEPTOR-MODULATING COMPOUNDS

Described herein are compounds that are estrogen receptor modulators of formula I' Also described are pharmaceutical compositions and medicaments that include the compounds described herein, as well as methods of using such estrogen receptor modulators, alone and in combination with other compounds, for treating diseases or conditions that are mediated or dependent upon estrogen receptors.

Lead Optimization of Benzoxepin-Type Selective Estrogen Receptor (ER) Modulators and Downregulators with Subtype-Specific ERα and ERβ Activity

Estrogen receptor α (ERα) is an important target for the design of drugs such as tamoxifen (2a) and fulvestrant (5). Three series of ER-ligands based on the benzoxepin scaffold structure were synthesized: series I containing an acrylic acid, series II with an acrylamide, and series III with a saturated carboxylic acid substituent. These compounds were shown to be high affinity ligands for the ER with nanomolar IC50 binding values. Series I acrylic acid ligands were generally ERα selective. In particular, compound 13e featuring a phenylpenta-2,4-dienoic acid substituent was shown to be antiproliferative and downregulated ERα and ERβ expression in MCF-7 breast cancer cells. Interestingly, from series III, the phenoxybutyric acid derivative compound 22 was not antiproliferative and selectively downregulated ERβ. A docking study of the benzoxepin ligands was undertaken. Compound 13e is a promising lead for development as a clinically relevant SERD, while compound 22 will be a useful experimental probe for helping to elucidate the role of ERβ in cancer cells.

FUSED TETRACYCLE DERIVATIVES AND METHODS OF USE THEREOF FOR THE TREATMENT OF VIRAL DISEASES

The present invention relates to novel Fused Tetracycle Derivatives of Formula (I): and pharmaceutically acceptable salts thereof, wherein A, A', B, G, R1, U, V, W, W', X, X', Y and Y' are as defined herein. The present invention also relates to compositions comprising at least one Fused Tetracycle Derivative, and methods of using the Fused Tetracycle Derivatives for treating or preventing HCV infection in a patient.

Discovery of Lu AA33810: A highly selective and potent NPY5 antagonist with in vivo efficacy in a model of mood disorder

The structure-activity relationship of a series of tricyclic-sulfonamide compounds 11-32 culminating in the discovery of N-[trans-4-(4,5-dihydro-3,6- dithia-1-aza-benzo[e]azulen-2-ylamino)-cyclohexylmethyl]-methanesulfonamide (15, Lu AA33810) is reported. Compound 15 was identified as a selective and high affinity NPY5 antagonist with good oral bioavailability in mice (42%) and rats (92%). Dose dependent inhibition of feeding was observed after i.c.v. injection of the selective NPY5 agonist ([cPP1-7,NPY19-23,Ala 31,Aib32,Gln34]-hPP). In addition, ip administration of Lu AA33810 (10 mg/kg) produced antidepressant-like effects in a rat model of chronic mild stress.

Solvent-free friedel-crafts cyclization with trichloroacetic anhydride

Friedel-Crafts cyclization products were obtained using 1.1 equivalents of environmentally benign trichloroacetic anhydride as sole reagent and solvent. The resulting ketones included benzothiepins, benzothiopyrans, benzoxepins, dibenzothiepins, dibenzoxepins, and tetralones.

Synthesis, biological evaluation, structural-activity relationship, and docking study for a series of benzoxepin-derived estrogen receptor modulators

The estrogen receptors ERα and ERβ are recognized as important pharmaceutical targets for a variety of diseases including osteoporosis and breast cancer. A series of novel benzoxepin-derived compounds are described as potent selective modulators of the human estrogen receptor modulators (SERMs). We report the antiproliferative effects of these compounds on human MCF-7 breast tumor cells. These heterocyclic compounds contain the triarylethylene arrangement as exemplified by tamoxifen, conformationally restrained through the incorporation of the benzoxepin ring system. The compounds demonstrate potency at nanomolar concentrations in antiproliferative assays against an MCF-7 human breast cancer cell line with low cytotoxicity together with low nanomolar binding affinity for the estrogen receptor. The compounds also demonstrate potent antiestrogenic properties in the human uterine Ishikawa cell line. The effect of a number of functional group substitutions on the ER binding properties of the benzoxepin molecular scaffold is examined through a detailed docking and 2D-QSAR computational investigation. The best QSAR model developed for ERαβ selectivity yielded R2 of 0.84 with an RMSE for the training set of 0.30. The predictive quality of the model was Q2 of 0.72 and RMSE of 0.18 for the test set. One particular compound (26b) bearing a 4-fluoro substituent, exhibits 15-fold selectivity for ERβ and both our docking and QSAR studies converge on the correlation between enhanced lipophilicity and enhanced ERβ binding for this benzoxepin ring scaffold.

Cyclization of 2-(2-bromoethoxy)-acetophenones and 5-(ω-haloalkoxy)- 1,5-dihydro-2H-pyrrol-2-ones - Formation of five- to eight-membered oxygen-containing heterocycles via intramolecular alkylation

Under basic conditions (lithium diisopropylamide or sodium hydride in THF) 2-(2-bromoethoxy)-acetophenones were transformed to 3,4-dihydro[1]benzoxepin- 5(2H)-ones (homochromanones) in high yields. The preparation of novel tetrahydropyrano[2,3-b]pyrrol-6(

Structure-based drug design: Synthesis, crystal structure, biological evaluation and docking studies of mono- and bis-benzo[b]oxepines as non-steroidal estrogens

Mono- and bis-benzo[b]oxepine derivatives have been rationally synthesized to meet the molecular requirement for interaction with estrogen receptor. Bis-benzo[b]oxepines (7 and 9) and mono-benzo[b]oxepine (10) acquire geometry with phenolic groups disposed in a fashion to stimulate estrogen receptor. Structure-based investigation, in vivo activity and docking studies have been described and correlated to demonstrate a practical approach for suitable ligand design.

The Preparation of 3,4-Dihydro-1-benzoxepin-5(2H)-ones

Several methods for the preparation of 3,4-dihydro-1-benzoxepin-5(2H)-ones are described.In addition to the desired ketones, a veriety of novel by-products have been isolated.