20727-61-1

Upstream product

• 6272-26-0 6-hydroxybenzofuran-3-one 
• 123-11-5 4-methoxy-benzaldehyde 
• 4225-35-8 4,6-dimethoxycoumaranone 
• 25015-92-3 2-chloro-1-(2,4-dihydroxyphenyl)ethanone 
• 108-46-3 recorcinol 
• 2491-39-6 2-bromo-2',4'-dihydroxyoacetophenone 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 65490-08-6 2-hydroxy-4-(methoxymethoxy)acetophenone 
• 1311271-71-2 (Z)-2-(4-methoxybenzylidene)-6-(methoxymethoxy)benzo[b]furan-3-one 
• 109471-14-9 2'-hydroxy-4'-(methoxymethoxy)-4-methoxychalcone 

Downstream Products

• 1311271-89-2 (Z)-2-(4-methoxybenzylidene)-3-oxo-2,3-dihydrobenzofuran-6-yl (10E,12Z)-linoleate 
• 1311272-16-8 (Z)-2-(4-methoxybenzylidene)-3-oxo-2,3-dihydrobenzofuran-6-yl 10-undecylenate 
• 1311272-02-2 (Z)-2-(4-methoxybenzylidene)-3-oxo-2,3-dihydrobenzofuran-6-yl stearate 

Relevant academic research and scientific papers

Design, synthesis, and biological evaluation of a novel dual peroxisome proliferator-activated receptor alpha/delta agonist for the treatment of diabetic kidney disease through anti-inflammatory mechanisms

Diabetic kidney disease (DKD) is a major feature of the final stage of nearly all cause types of diabetes mellitus (DM). To date, few safe and effective drugs are available to treat. Peroxisome proliferator-activated receptors (PPARs), comprised of three members: PPAR-α, PPAR-δ and PPAR-γ, play a protective role in the DKD through glycemic control and lipid metabolism, whereas systemic activation of PPAR-γ causes serious side-effects in clinical trials. GFT505 is a dual PPAR-α/δ agonist, and the selectivity against PPAR-γ is still to be improved. Sulfuretin has been shown to suppress the expression of PPAR-γ and improve the pathogenesis of diabetic complications. In this study, by hybridizing the carboxylic acid of GFT505 and the parent nucleus of sulfuretin, we pioneeringly designed and synthetized a series of novel dual PPAR-α/δ agonists, expecting to provide a better benefit/risk ratio for PPARs. Of all the synthesized compounds, compound 12 was identified with highly activity on PPAR-α/δ and higher selectivity against PPAR-γ than that of GFT505 (EC50: hPPAR-α: 0.26 μM vs.0.76 μM; hPPAR-δ: 0.50 μM vs.0.73 μM; hPPAR-γ: 4.22 μM vs.2.79 μM). The molecular docking studies also depicted good binding affinity of compound 12 for PPAR-α and PPAR-δ compared to GFT505. Furthermore, compound 12 exhibited an evidently renoprotective effect on the DKD through inhibiting inflammatory process, which might at least partly via JNK/NF-κB pathways in vivo and in vitro. Overall, compound 12 hold therapeutic promise for DKD.

Structure-Based virtual screening and de novo design of PIM1 inhibitors with anticancer activity from natural products

Background: the proviral insertion site of Moloney murine leukemia (PIM) 1 kinase has served as a therapeutic target for various human cancers due to the enhancement of cell proliferation and the inhibition of apoptosis. Methods: to identify effective PIM1 kinase inhibitors, structurebased virtual screening of natural products of plant origin and de novo design were carried out using the protein-ligand binding free energy function improved by introducing an adequate dehydration energy term. Results: as a consequence of subsequent enzyme inhibition assays, four classes of PIM1 kinase inhibitors were discovered, with the biochemical potency ranging from low-micromolar to sub-micromolar levels. The results of extensive docking simulations showed that the inhibitory activity stemmed from the formation of multiple hydrogen bonds in combination with hydrophobic interactions in the ATP-binding site. Optimization of the biochemical potency by chemical modifications of the 2-benzylidenebenzofuran-3(2H)-one scaffold led to the discovery of several nanomolar inhibitors with antiproliferative activities against human breast cancer cell lines. Conclusions: these new PIM1 kinase inhibitors are anticipated to serve as a new starting point for the development of anticancer medicine.

Synthesis of anabasine-containing aminomethyl derivatives of 6-hydroxyaurones

[Figure not available: see fulltext.] Aminomethylation of aurones was studied by using anabasine. The reaction in the case of 6-hydroxyaurones was shown to selectively provide 7-aminomethyl-6-hydroxyaurones, while 5-aminomethyl-6-hydroxy-7-methylaurones could be obtained by transamination of 5-dimethylaminomethyl derivatives of 6-hydroxy-7-methylaurones in the presence of anabasine.

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.]

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.

THERAPEUTIC AURONES

Substituted aurones were found to have antitrypanosomal, antifungal and immunomodulatory activity. The invention provides novel aurone compounds, pharmaceutical compositions, and methods encompassing medical and veterinary applications.

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 and antiproliferative activity of 2-arylidene 6-(2-aryl-2-oxoethoxy)benzofuran-3-one derivatives

The synthesis of 2-arylidene 6-(2-aryl-2-oxoethoxy)benzofuran-3-one derivatives was reported and selected compounds were determined for their anticancer activity evaluation in National Cancer Institute NCI, USA according to the drug screening protocol of the institute against approximately 60 tumor cell lines derived from nine cancer diseases. Compound 3r, namely 2-(4-chlorobenzylidene)-6-[2-(4-methoxyphenyl)-2-oxoethoxy]benzofuran-3-one exhibited the highest antitumor activity against non-small lung cancer cell lines.

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.

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.