25158-68-3

Upstream product

• 97-51-8 5-Nitrosalicylaldehyde 
• 885951-98-4 2-ethynyl-4-nitrophenol 
• 100-17-4 para-methoxynitrobenzene 
• 79-04-9 chloroacetyl chloride 
• 77123-62-7 1-ethynyl-2-methoxy-5-nitrobenzene 
• 5037-70-7 2-bromo-1-(2-hydroxy-5-nitrophenyl)ethanone 
• 53074-73-0 2-(2-chloroacetyl)phenol 

Downstream Products

• 1093451-04-7 C₁₆H₁₁NO₅ 

Relevant academic research and scientific papers

A Hg(OTf)2-Catalyzed Enolate Umpolung Reaction Enables the Synthesis of Coumaran-3-ones and Indolin-3-ones

The potential of mercury catalysis has been extended to the arena of enolate umpolung reactions for the first time by the generation of enolonium species via Hg(OTf)2-catalyzed N-oxide addition to alkynes. The enolonium species formed can undergo intramolecular nucleophilic attack by hydroxyl or amino groups, leading to the synthesis of various coumaran-3-ones and indolin-3-ones.

Catalytic synthesis method of 3-benzofuranone compound

The invention discloses a catalytic synthesis method of a 3-benzofuranone compound. The catalytic synthesis method comprises the following steps: dissolving a 2-acetenyl phenol derivative into a solvent dichloromethane at normal temperature and normal pressure according to a molar volume ratio of the 2-acetenyl phenol derivative to the dichloromethane of 1:5mmol/mL, so as to obtain a dichloromethane solution of the 2-acetenyl phenol derivative; then adding mercury trifluoromethanesulfonate and pyridine-N-oxide into a dichloromethane solution of the 2-ethynylphenol derivative, wherein the molaramounts of mercury trifluoromethanesulfonate and pyridine-N-oxide are respectively 5% and 120% of the molar amount of the 2-ethynylphenol derivative; and then performing stirring for 1 hour at room temperature, and performing reacting to generate the 3-benzofuranone compound. The market price of the catalyst mercury trifluoromethanesulfonate used in the catalytic synthesis method is lower than 30yuan/g, the cost is low, the operation is simple, the reaction time is short, the reaction conditions are mild, the reaction yield is high, and the yield can reach 91.0-96.0%.

Discovery of benzofuran-3(2H)-one derivatives as novel DRAK2 inhibitors that protect islet β-cells from apoptosis

Death-associated protein kinase-related apoptosis-inducing kinase-2 (DRAK2) is a serine/threonine kinase that plays a key role in a wide variety of cell death signaling pathways. Inhibition of DRAK2 was found to efficiently protect islet β-cells from apoptosis and hence DRAK2 inhibitors represent a promising therapeutic strategy for the treatment of diabetes. Only very few chemical entities targeting DRAK2 are currently known. We carried out a high throughput screening and identified compound 4 as a moderate DRAK2 inhibitor with an IC50value of 3.15?μM. Subsequent SAR studies of hit compound 4 led to the development of novel benzofuran-3(2H)-one series of DRAK2 inhibitors with improved potency and favorable selectivity profiles against 26 selected kinases. Importantly, most potent compounds 40 (IC50?=?0.33?μM) and 41 (IC50?=?0.25?μM) were found to protect islet β-cells from apoptosis in dose-dependent manners. These data support the notion that small molecule inhibitors of DRAK2 represents a promising strategy for the treatment of diabetes.

Practical, modular, and general synthesis of 3-coumaranones through gold-catalyzed intermolecular alkyne oxidation strategy

A gold-catalyzed intermolecular alkyne oxidation for the preparation of 3-coumaranones has been developed. Using 8-isopropylquinoline N-oxides as oxidants, the reactions of o-ethynylanisoles afford versatile 3-coumaranones in moderate to good isolated yields. The synthetic utility of this chemistry is also indicated by the synthesis of the natural product sulfuretin.

4-Substituted-7-azaindoles bearing a ureidobenzofuranone moiety as potent and selective, ATP-competitive inhibitors of the mammalian target of rapamycin (mTOR)

A series of 5-ureidobenzofuranones was discovered as potent and selective inhibitors of mTOR with good cellular activity. Molecular modeling studies revealed several hydrogen bond interactions of the ureido group with the enzyme at the ATP-binding site. Furthermore, modeling showed that the ureido group is best situated at C-5 of the benzofuranone. Syntheses of 4-ureido and 5-ureidobenzofuranones are presented.

5-Ureidobenzofuranone indoles as potent and efficacious inhibitors of PI3 kinase-α and mTOR for the treatment of breast cancer

A series of 5-ureidobenzofuran-3-one indoles as potent inhibitors of PI3Kα and mTOR has been developed. The best potency in cells was obtained when the urea group was extended to a 4-[2-(dimethylamino)ethyl]methylamino amidophenyl group. A 7-fluoro group

Regioselective synthesis of tetrasubstituted pyrroles by 1,3-dipolar cycloaddition and spontaneous decarboxylation

We developed a novel regioselective synthesis of tetrasubstituted pyrroles via the classic 1,3-dipolar cycloaddition of α,β-unsaturated benzofuran-3(2H)-one and azlactones (1) followed by spontaneous decarboxylation. The complete regiochemical control of tetrasubstituted pyrroles was confirmed by the orthogonal synthesis of complementary regioisomers (7a and 7b) simply by using different azlactones (1a and 1b, respectively).

[a]-FUSED INDOLE COMPOUNDS, THEIR USE AS mTOR KINASE AND PI3 KINASE INHIBITORS, AND THEIR SYNTHESES

The invention relates to [a]-fused indole compounds of the Formula II, or a pharmaceutically acceptable salt thereof, wherein the constituent variables are as defined herein. The invention also relates to compositions comprising the compounds of Formula II, and methods for making and using the compounds.