137489-76-0

Usage

Uses

Used in Organic Chemistry:
3-[(3-BROMOBENZYL)OXY]BENZALDEHYDE is used as a building block for the synthesis of various organic compounds, contributing to the development of new chemical entities with diverse applications.
Used in Pharmaceutical Industry:
3-[(3-BROMOBENZYL)OXY]BENZALDEHYDE is utilized as an intermediate in the preparation of various drugs and fine chemicals, facilitating the advancement of pharmaceutical formulations and treatments.
Used in Medicinal Chemistry and Drug Discovery:
Due to its unique structural features and chemical reactivity, 3-[(3-BROMOBENZYL)OXY]BENZALDEHYDE is employed as a potential candidate in medicinal chemistry, aiding in the discovery and development of new drugs with improved therapeutic properties.

InChI:InChI=1/C14H11BrO2/c15-13-5-1-4-12(7-13)10-17-14-6-2-3-11(8-14)9-16/h1-9H,10H2

Upstream product

• 823-78-9 meta-bromobenzyl bromide 
• 100-83-4 meta-hydroxybenzaldehyde 

Relevant academic research and scientific papers

Benzyloxynitrostyrene analogues – A novel class of selective and highly potent inhibitors of monoamine oxidase B

This study examines a series of novel 3-benzyloxy-β-nitrostyrene analogues as a novel class of inhibitors of the monoamine oxidase (MAO) enzymes. MAO inhibitors are considered useful for the treatment of depression and Parkinson's disease, and have recently attracted attention as potential therapeutic agents for a range of disorders including Alzheimer's disease, prostate cancer and certain cardiomyopathies. This study shows that the 3-benzyloxy-β-nitrostyrene analogues are potent inhibitors of the MAO-B isoform with IC50values in the nanomolar range (39–565 nM). Significantly, effectiveness towards MAO-B inhibition seems to be governed by the introduction of a 4″-fluoro-substituent on the benzyloxy ring, with compound 2b exhibiting the highest degree of MAO-B inhibition potency (IC50= 0.039 μM) and selectivity (SI = 166) among the compounds investigated. Since some of the 3-benzyloxy-β-nitrostyrene analogues possess potencies that are comparable to that of the reversible inhibitor, safinamide (IC50= 0.080 μM), it may be concluded that this class may be promising leads for the development of reversible and selective MAO-B inhibitors, that may be useful for the management of Parkinson's disease.

Synthesis and evaluation of small molecules bearing a benzyloxy substituent as novel and potent monoamine oxidase inhibitors

A new series of small molecules bearing a benzyloxy substituent have been designed, synthesized and evaluated for hMAO inhibitory activity in vitro. Most of the compounds were potent and selective MAO-B inhibitors, and were weak inhibitors of MAO-A. In particular, compounds 9e (IC50 = 0.35 μM) and 10e (IC50 = 0.19 μM) were the most potent MAO-B inhibitors, and exhibited the highest selectivity for MAO-B (9e, SI > 285.7-fold and 10e, SI = 146.8-fold). In addition, the structure-activity relationships for MAO-B inhibition indicated that electron-withdrawing groups in the open small molecules were more suitable for MAO-B inhibition, and substitutions at the benzyloxy of the open small molecules, particularly with the halogen substituted benzyloxy, were more favorable for MAO-B inhibition. Molecular docking studies have been done to explain the potent MAO-B inhibition of the open small molecules. Furthermore, the representative compounds 9e and 10e showed low neurotoxicity in SH-SY5Y cells in vitro. So the small molecules bearing the benzyloxy substituent could be used to develop promising drug candidates for the therapy of neurodegenerative diseases.