139149-21-6

Basic information

• Product Name: 6-(benzyloxy)benzofuran-3(2H)-one
• Synonyms: 6-(benzyloxy)benzofuran-3(2H)-one;6-phenylmethoxy-1-benzofuran-3-one;6-(benzyloxy)-1-benzofuran-3(2H)-one
• CAS NO: 139149-21-6
• Molecular Formula: C₁₅H₁₂O₃
• Molecular Weight: 240.25398
• Mol File: 139149-21-6.mol

Chemical Properties

• Melting Point: 99-101 °C(Solv: cyclohexane (110-82-7))
• Boiling Point: 423.5±44.0 °C(Predicted)
• Appearance: /
• Density: 1.259±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 6-(benzyloxy)benzofuran-3(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(benzyloxy)benzofuran-3(2H)-one(139149-21-6)
• EPA Substance Registry System: 6-(benzyloxy)benzofuran-3(2H)-one(139149-21-6)

Safety Data

• Hazardous Substances Data: 139149-21-6(Hazardous Substances Data)

Upstream product

• 6272-26-0 6-hydroxybenzofuran-3-one 
• 29682-12-0 1-[4-(benzyloxy)-2-hydroxyphenyl]ethanone 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 

Downstream Products

• 1027419-07-3 6-benzyloxy-2-(4-chloro-phenyl)-benzofuran-3-one 
• 1026285-38-0 (6-benzyloxy-2-bromo-benzofuran-3-yloxy)-tert-butyl-dimethyl-silane 
• 857062-28-3 3-tert.-butyldimethylsilyloxy-6-benzyloxy-2-(4-chlorophenyl)-benzofurane 
• 1034926-59-4 (R)-6-benzyloxy-2,3-dihydrobenzofuran-3-ol 
• 1350933-39-9 methyl 6-(benzyloxy)-1-benzofuran-3-carboxylate 
• 1373243-56-1 6-(benzyloxy)-3H-spiro[benzofuran-2,1'-cyclopropane] 
• 1373243-62-9 C₃₂H₂₅NO₃ 
• 1373243-61-8 1-benzhydryl-3-(6-hydroxy-3H-spiro[benzofuran-2,1'-cyclopropan]-5-yl)indolin-2-one 
• 1373243-60-7 1-benzhydryl-3-hydroxy-3-(6-hydroxy-3H-spiro[benzofuran-2,1'-cyclopropan]-5-yl)indolin-2-one 
• 1373243-55-0 6-(benzyloxy)-3H-spiro[benzofuran-2,1'-cyclopropan]-3-one 
• 652983-14-7 ethyl [6-(benzyloxy)-1-benzofuran-3-yl]acetate 
• 912669-09-1 6-(benzyloxy)-2,2-dimethylbenzofuran-3(2H)-one 
• 139149-23-8 N-[6-Benzyloxy-2,3-dihydrobenzofuran-3-yl]-hydroxylamine 
• 857062-43-2 2-bromo-6-benzyloxy-benzofuran-3(2H)-one 

Relevant articles and documents

3-coumaranone derivatives as inhibitors of monoamine oxidase

The present study examines the monoamine oxidase (MAO) inhibitory properties of a series of 20 3-coumaranone [benzofuran-3(2H)-one] derivatives. The 3-coumaranone derivatives are structurally related to series of α-tetralone and 1-indanone derivatives, which have recently been shown to potently inhibit MAO, with selectivity for MAO-B (in preference to the MAO-A isoform). 3-Coumaranones are similarly found to selectively inhibit human MAO-B with half-maximal inhibitory concentration (IC50) values of 0.004–1.05 μM. Nine compounds exhibited IC5050values ranged from 0.586 to >100 μM, with only one compound possessing an IC501 μM. For selected 3-coumaranone derivatives, it is established that MAO-A and MAO-B inhibition are reversible since dialysis of enzyme–inhibitor mixtures almost completely restores enzyme activity. On the basis of the selectivity profiles and potent action, it may be concluded that the 3-coumaranone derivatives are suitable leads for the development of selective MAO-B inhibitors as potential treatment for disorders such as Parkinson’s disease and Alzheimer’s disease.

Exploration of 7-azaindole-coumaranone hybrids and their analogues as protein kinase inhibitors

7-Azaindole has been labelled a privileged scaffold for the design of new potent inhibitors of protein kinases. In this paper, we determined the inhibition profiles of novel mono- and disubstituted derivatives of 7-azaindole-coumaranone hybrids on various disease-related protein kinases. Eight hit compounds were identified, including a potent Haspin inhibitor with an IC50 value of 0.15 μM. An interesting observation was that all active monosubstituted compounds displayed dual inhibition for Haspin and GSK-3β, while disubstituted derivatives inhibited GSK-3β and LmCK1 from Leishmania major parasite. Analyses of structure activity relationships (SARs) also revealed that mono-substitution with para-fluorobenzyloxy ring produced an equipotent inhibition of Haspin and GSK-3β. Haspin and GSK-3β are relevant targets for developing new anticancer agents while LmCK1 is an innovative target for leishmanicidal drugs. Novel compounds reported in this paper constitute promising starting points for the development of new anticancer and leishmanicidal drugs.

Carboxylated aurone derivatives as potent inhibitors of xanthine oxidase

Xanthine oxidase is a potential target for treatment of hyperuricemia and gout. In this study, a number of A- and B-ring carboxylated aurone derivatives were synthesized and evaluated for their ability to inhibit xanthine oxidase in vitro. According to the results obtained, two different ranges of inhibitory activity were observed. The aurones with carboxylic acid group at the 4′-position of B-ring were found to be potent inhibitors of the enzyme with IC50 values in the low micromolar range. The effects of these compounds were about 50 fold higher than of A-ring modified aurones with carboxymethoxy group at the 6-position. The binding modes of the carboxylated aurones in the active site of xanthine oxidase were explained using molecular docking calculations.

Chromanones: selective and reversible monoamine oxidase B inhibitors with nanomolar potency

A new series of C7-substituted chromanones has been designed, synthesized and evaluated for hMAO-B inhibitory activity in vitro. Most of the studied compounds were remarkably potent and selective MAO-B inhibitors and showed weak or no inhibition of MAO-A. Especially, compound 4f (IC50 = 8.62 nM) was the best MAO-B inhibitor and exhibited the highest selectivity for MAO-B (SI > 11 627.9-fold). In addition, the structure-activity relationships for MAO-B inhibition indicated that substitutions at the C7 of the chromanone moiety, particularly with the halogen substituted benzyloxy, were more favorable for MAO-B inhibition. Molecular docking studies have been performed to explore the interaction modes of C7-substituted chromanones with MAO-B. Furthermore, the representative compounds 4f and 5d showed low neurotoxicity in SH-SY5Y cells in vitro. So the C7-substituted chromanones could be used to develop promising drug candidates for the therapy of neurodegenerative diseases.

SPIROCYCLIC COMPOUNDS AS VOLTAGE-GATED SODIUM CHANNEL MODULATORS

The present invention relates to compounds of Formula (I) along with processes for their preparation that are useful for treating, preventing and/or managing the diseases, disorders, syndromes or conditions modulated by VGSCs. The invention further relates to methods of treating, preventing managing and/or lessening the diseases, disorders, syndromes or conditions by modulators of VGSC of Formula (I).

Asymmetric synthesis of N-substituted N-hydroxyureas

Asymmetric synthesis of (S)-N-(1-arylethyl)-N-hydroxyureas, (S)-N-(6-methoxy)- and (S)-N-(6-benzyloxy-2,3-dihydrobenzofuran-3-yl)-N-hydroxyurea- lipoxygenase inhibitor, is described. Three approaches to the formation of the N-hydroxyurea moiety at the stereogenic center have been used. The first one, via the reaction of (R)-6-benzyloxy-2,3-dihydrobenzofuran-3-ol with N,O-bis(phenoxycarbonyl)hydroxylamine under Mitsunobu conditions, leads to a partially racemized product. Alternatively, the enantioselective reduction of oximes O-benzyl ethers of acetophenone, 4-methoxy- and 4-benzyloxyacetophenone, 6-methoxy- and 6-benzyloxy-2,3-dihydrobenzofuran-3-one with borane/oxazaborolidines can be controlled to produce either the corresponding hydroxylamine O-benzyl ethers or primary amines which have been transformed into N-substituted N-hydroxyureas in 57% to 99% ee.

ANTIDIABETIC BICYCLIC COMPOUNDS

Biaryl ethers in which one of the aromatic πngs is fused to a cycloalkyl or heterocyclic πng, which is attached to a thiazohdinedione or oxazohdmedione πng, including pharmaceutically acceptable salts and prodrugs thereof, are agonists of G-protein coupled receptor 40 (GPR40) and are useful as therapeutic compounds, particularly in the treatment of Type 2 diabetes melhtus, and of conditions that often occur with type 2 diabetes, including insulin resistance, obesity, and lipid disorders.

ANTIDIABETIC BICYCLIC COMPOUNDS

Diaryl ethers in which one of the aryl groups is a phenyl fused to a cycloalkyl or heterocyclic ring, to which is attached an acetic acid group, are agonists of G-protein coupled receptor 40 (GPR40) and are useful as therapeutic compounds, particularly in the treatment of Type 2 diabetes mellitus, and of conditions that often accompany this disease, including insulin resistance, obesity and lipid disorders.

ANTIDIABETIC BICYCLIC COMPOUNDS

Bicyclic compounds containing a phenyl or pyridyl ring fused to a cycloalkyl or heterocyclic ring, to which is attached a 5-membered heterocyclic ring, including pharmaceutically acceptable salts and prodrugs thereof, are agonists of G-protein coupled receptor 40 (GPR40) and are useful as therapeutic compounds, particularly in the treatment of Type 2 diabetes mellitus, and of conditions that are often associated with this disease, including obesity and lipid disorders, such as mixed or diabetic dyslipidemia, hyperlipidemia, hypercholesterolemia, and hypertriglyceridemia.

NOVEL CYLOPENTA[B]BENZOFURAN DERIVATIVES AND THE UTILIZATION THEREOF

The invention relates to novel cyclopenta[b]benzofuran derivatives, to a method for the production thereof and to their utilization for the production of medicaments, especially for the prophylaxis and/or therapy of acute or chronic diseases which are cha