1322574-14-0

Basic information

• Product Name: AKOS BBS-00006130
• Synonyms: AKOS BBS-00006130;(2Z)-2-(3,4-Dimethoxybenzylidene)-6-hydroxy-1-benzofuran-3(2H)-one;(2Z)-2-(3,4-dimethoxybenzylidene)-6-hydroxy-benzofuran-3-one;(2Z)-2-[(3,4-dimethoxyphenyl)methylene]-6-hydroxy-3-benzofuranone;(2Z)-2-[(3,4-dimethoxyphenyl)methylene]-6-hydroxy-benzofuran-3-one;(2Z)-2-[(3,4-dimethoxyphenyl)methylidene]-6-hydroxy-1-benzofuran-3-one;2-(3,4-dimethoxybenzylidene)-6-hydroxy-benzofuran-3-one;2-[(3,4-dimethoxyphenyl)methylene]-6-hydroxy-3-benzofuranone
• CAS NO: 1322574-14-0
• Molecular Formula: C17H14O5
• Molecular Weight: 298.29006
• Mol File: 1322574-14-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: AKOS BBS-00006130(CAS DataBase Reference)
• NIST Chemistry Reference: AKOS BBS-00006130(1322574-14-0)
• EPA Substance Registry System: AKOS BBS-00006130(1322574-14-0)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 1322574-14-0(Hazardous Substances Data)

Upstream product

• 6272-26-0 6-hydroxybenzofuran-3-one 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 25015-92-3 2-chloro-1-(2,4-dihydroxyphenyl)ethanone 
• 108-46-3 recorcinol 
• 104236-80-8 2′,4′-dihydroxy-3,4-dimethoxychalcone 

Downstream Products

• 1005324-89-9 2-(3,4-dihydroxybenzyl)-6-hydroxybenzofuran-3(2H)-one 

Relevant articles and documents

Efficient synthesis of aurone Mannich bases and evaluation of their antineoplastic activity in PC-3 prostate cancer cells

Abstract: An efficient method for regioselective synthesis of C-7 Mannich bases of 6-hydroxyaurones was accomplished by the N,N-dialkylaminomethylation using aminals prepared from dimethylamine, dipropylamine, bis(2-methoxyethyl)amine, N-methylbutylamine, N-methylbenzylamine, morpholine, piperidine, and 1-methylpiperazine. Further transformation of 7-(N,N-dialkylamino)methyl group in these aurones led to formation of C-7 acetoxymethyl and methoxymethyl derivatives of 6-hydroxyaurones, some of which showed promising inhibition of PC-3 prostate cancer cell proliferation in the high nanomolar to low micromolar range that exceeded that of cisplatin. Graphical abstract: Compound 12c (R3 = Ac, Ar = 3,4-OMePh) displays 75% inhibition of PC-3 prostate cancer cells proliferation at 300 nM concentration.[Figure not available: see fulltext.]

Drug design, synthesis and in vitro evaluation of substituted benzofurans as hsp90 inhibitors

Background: Heat shock protein 90 is a molecular chaperone required for the stability and function of several client proteins that promote cancer cell growth and/or survival. Discovery of Hsp90 inhibitors has emerged as an attractive target of research in cancer therapeutics. Natural products like geldanamycin and radicicol are established Hsp90 inhibitors, but face limitations with toxicity and inactivity, by in vivo studies respectively. However, they lay the logical starting point for the design of novel synthetic or semi-synthetic congeners as Hsp90 inhibitors. Objective: In this article, the structure based drug design of substituted 2-aryl/heteroarylidene-6- hydroxybenzofuran-3(2H)-one analogues to optimize and mimic the pharmacophoric interactions of the valid Hsp90 inhibitor radicicolis focused. Method: In silico docking study was performed by Surflex dock-Geom (SYBYL- X 1.2 drug discovery suite) and the designed ligands were chemically synthesized by conventional method using resorcinol and chlororesorcinol as starting materials. Two dimensional chemical similarity search was carried out to identify the chemical space of 'SY' series in comparison with reported Hsp90 inhibitors. The in vitro cell proliferation assay (resazurin reduction method) and proteomic investigation (DARTS) was carried out on whole cell lysate to evaluate anticancer activity. Results: The chemical structures of all the synthesized compounds were confirmed by IR, 1H-NMR and Mass spectral analysis. The results of chemical similarity search show that SY series fit it in the chemical space defined by existing Hsp90 inhibitors. In vitro cell proliferation assay, against human melanoma and breast cancer cell lines, identified 'SY3' as the promising anticancer agent amongst the series. Conclusion: Docking studies, 2D chemical similarity search, resazurin reduction assay and qualitative proteomic analysis identify 'SY3'as a promising Hsp90 inhibitor amongst the series.

Synthesis of Flavonoid Derivatives of Cytisine. 5. Aminomethylation of 6-Hydroxyaurones

Aminomethylation of 6-hydroxy- and 6-hydroxy-7-methylaurones by the alkaloid cytisine was studied. It was shown that the aminomethylation of the 6-hydroxyaurones occurred at the 7-position of the benzofuran ring and at the 5-position if the 7-position was occupied.

Synthesis of 6-hydroxyaurone analogues and evaluation of their α-glucosidase inhibitory and glucose consumption-promoting activity: Development of highly active 5,6-disubstituted derivatives

A series of 6-hydroxyaurones and their analogues have been synthesized and evaluated for their in vitro α-glucosidase inhibitory and glucose consumption-promoting activity. These compounds exhibited varying degrees of α-glucosidase inhibitory activity, 11 of them showing higher potency than that of the control standard acarbose (IC50?=?50.30?μM). Surprisingly, analogues devoid of a substituent at C-2 but having an aryl group at C-5 were found to be highly active (e.g., 7f, IC50?=?9.88?μM). Docking analysis substantiated these findings. The kinetic analysis of compound 7f, the most potent α-glucosidase inhibitor of this study, revealed that it inhibited α-glucosidase in an irreversible and mixed competitive mode. In addition, compounds 7f and 10c exhibited significant glucose consumption promoting activity at 1?μM.

Synthesis and properties of 2-benzylidene-8,9-dihydro-7H-furo[2,3-f][1,3]benzoxazin-3(2H)-one derivatives

[Figure not available: see fulltext.] Aminomethylation of 6-hydroxyaurones with primary amines was used to synthesize 2-benzylidene-8,9-dihydro-7H-furo[2,3-f][1,3]-benzoxazin-3(2H)-one derivatives, while opening of 1,3-oxazine ring in the presence of acid gave secondary amines containing a 6-hydroxyaurone moiety. Acetylation of 2-benzylidene-8,9-dihydro-7H-furo[2,3-f][1,3]benzoxazin-3(2H)-ones was also accompanied by opening of 1,3-oxazine ring.

6-aryloxyacetic acetoxy orange ketones compound and the application of the pesticides

The invention relates to a 6-aryloxy acetoxy aurone compound and an application thereof on a pesticide, and belongs to the technical field of herbicides. The general formula of the 6-aryloxy acetoxy aurone compound is as shown in the specification, wherein R1 is hydrogen, halogen, C1-C4 haloalkyl, C1-C4 alkyl, C1-C4 alkoxy and C1-C4 alkylamino, and R2 is the hydrogen and the C1-C4 alkyl. The invention provides a lot of novel chemical structures and novel compounds. A biological activity measurement result indicates that the compound I has very high weeding activity.

Synthesis of aminoalkyl-substituted aurone derivatives as acetylcholinesterase inhibitors

Alzheimer's disease (AD), a progressive and neurodegenerative disorder of the brain, is the most common cause of dementia among elderly people. To date, the successful therapeutic strategy to treat AD is maintaining the levels of acetylcholine by inhibiting acetylcholinesterase (AChE). In the present study, aurone derivatives were designed and synthesized as AChE inhibitors based on the lead structure of sulfuretin. Of those synthesized, compound 10d showed ca. 1700-fold and 6-fold higher AChE inhibitory activity than sulfuretin and galantamine, respectively. This compound also ameliorated scopolamine-induced memory deficit in mice when administered orally at the dose of 1 and 2 mg/kg.

Synthesis, docking studies and antioxidant activity of some chalcone and aurone derivatives

Chalcones and aurones are found to possess high antioxidant activity. They are known to inhibit tyrosinase enzyme involved in synthesis of melanin. A series of substituted chalcones and aurones have been synthesized and tested for their antioxidant activi

Synthesis of aurones and their inhibitory effects on nitric oxide and PGE2 productions in LPS-induced RAW 264.7 cells

Sulfuretin is one of major constituents of Rhus verniciflua that exerts anti-inflammatory activities. Some of aurones were synthesized as sulfuretin derivatives and evaluated for their abilities to inhibit NO and PGE2 production in LPS-induced RAW 264.7 cells in order to reveal the relationship. Of the aurones synthesized in the present study, 2h and 2i, which possess C-6 hydroxyl group in A-ring and methoxy substituents in B-ring, more potently inhibited NO and PGE2 production and were less cytotoxic than sulfuretin.

Benzofuranone derivatives and a method for producing them

PCT No. PCT/JP98/00090 Sec. 371 Date Dec. 7, 1998 Sec. 102(e) Date Dec. 7, 1998 PCT Filed Jan. 13, 1998 PCT Pub. No. WO98/30556 PCT Pub. Date Jul. 16, 1998The present invention provides new benzofuranone derivatives and a method for producing the derivatives useful for a therapeutic agent for preventing and/or treating hormone dependent diseases. The present invention is a new benzofuranone derivative represented by a particular general formula (I). In the production, a particular benzofuranone compound and a particular benzaldehyde are reacted.