405905-26-2

Basic information

• Product Name: 7-[(4-bromobenzyl)oxy]-4-methyl-2H-chromen-2-one
• Synonyms: 7-[(4-bromobenzyl)oxy]-4-methyl-2H-chromen-2-one
• CAS NO: 405905-26-2
• Molecular Formula: C₁₇H₁₃BrO₃
• Molecular Weight: 345.18732
• Mol File: 405905-26-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7-[(4-bromobenzyl)oxy]-4-methyl-2H-chromen-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 7-[(4-bromobenzyl)oxy]-4-methyl-2H-chromen-2-one(405905-26-2)
• EPA Substance Registry System: 7-[(4-bromobenzyl)oxy]-4-methyl-2H-chromen-2-one(405905-26-2)

Safety Data

• Hazardous Substances Data: 405905-26-2(Hazardous Substances Data)

Upstream product

• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 108-46-3 recorcinol 

Relevant articles and documents

Synthesis and evaluation of 7-substituted coumarin derivatives as multimodal monoamine oxidase-B and cholinesterase inhibitors for the treatment of Alzheimer's disease

A series of 7-substituted coumarin derivatives were designed and synthesised to display ChE and MAO-B inhibitory activity. The compounds consisted out of a coumarin structure (MAO-B inhibitor) and benzyl-, piperidine-, N-benzylpiperidine- or p-bromo-N-benzylpiperizine moiety, resembling the N-benzylpiperidine function of donepezil (ChE inhibitor), connected via an alkyl ether linkage at the 7 position. The biological assay results indicated that all the compounds (1–25) displayed selective inhibition to hMAO-B over hMAO-A, with the benzyloxy series (1–8, 10–13) showing nano-molar hMAO-B inhibition (IC50: 0.5–73?nM). Limited ChE inhibitory activity was however observed for the benzyloxy series with the exception of 2 and especially 3 showing selective BuChE inhibition. From this series 3 showed the best multifunctional activity (eqBuChE IC50?=?0.96?μM, hMAO-A IC50?=?2.13?μM, hMAO-B IC50?=?0.0021?μM). Within the N-benzylpiperidine (16–19) and p-bromo-N-benzylpiperizine (21–24) series the compounds in general showed moderate ChE and MAO-B inhibitory activity. Of these compounds 19 was the most potent multifunctional agent showing good eeAChE and eqBuChE inhibition (IC50?=?9.10?μM and 5.90?μM, respectively), and relatively potent and selective hMAO-B inhibition (IC50?=?0.30?μM, SI?= >33). Molecular modeling revealed that 19 was able to bind simultaneously to the CAS, mid-gorge and PAS sites of AChE and BuChE suggesting that it will be able to inhibit AChE induced Aβ aggregation. From this study, compounds that 3 and 19 can be considered as promising multifunctional lead compounds.

Synthesis, spectral characterization and α-chymotrypsin activity of 7-O-substituted derivatives of 7-hydroxy-4-methyl-1-benzopyran-2-one

In this work, a series of O-alkyl/arenyl/acyl substituted derivatives of 7-hydorxy-4-methyl-1-benzenpyran-2-one (3a-l) was synthesized. The parent compound 7-hydroxy-4-methyl-1-benzenpyran-2-one (1) was geared up by the coupling of resorcinol (a) with ethylacetoacetate (b) in the presence of conc. sulphuric acid. Further, O-substituted derivatives of parent compound were prepared by treating with different electrophiles (2a-l) using sodium hydride as base and DMF as a solvent. The structure of these synthesized compounds were characterized by IR, EI-MS and 1H NMR. These derivatives were also screened against α-chymotrypsin enzyme to check their enzyme inhibition activity. All the compounds displayed a-chymotrypsin activity to varying degree.