4139-73-5

Usage

Uses

Used in Pharmaceutical Industry:
4-hydroxy-3-propionyl-2H-chromen-2-one is used as a potential therapeutic agent for its anti-cancer and anti-diabetic activities. Its antioxidant and anti-inflammatory properties make it a promising candidate for the development of novel pharmaceutical agents.
Used in Drug Delivery Systems:
4-hydroxy-3-propionyl-2H-chromen-2-one is being investigated for its potential as a drug delivery system. Its unique structure and properties may allow for improved delivery and bioavailability of therapeutic agents, enhancing their efficacy and reducing side effects.

InChI:InChI=1/C12H10O4/c1-2-8(13)10-11(14)7-5-3-4-6-9(7)16-12(10)15/h3-6,15H,2H2,1H3

Upstream product

• 20349-86-4 Methyl 3-(2-hydroxy-phenyl)-3-oxopropanoate 
• 123-62-6 propionic acid anhydride 
• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 802294-64-0 propionic acid 
• 36953-85-2 4-propionyloxy-coumarin 

Downstream Products

• 85689-36-7 3-Ethyl-1-phenyl-1H-chromeno[2,3-c]pyrazol-4-one 
• 85689-29-8 (3-Ethyl-5-hydroxy-1-phenyl-1H-pyrazol-4-yl)-(2-hydroxy-phenyl)-methanone 

Relevant academic research and scientific papers

Synthesis and Evaluation of 4-Hydroxycoumarin Imines as Inhibitors of Class II Myosins

Inhibitors of muscle myosin ATPases are needed to treat conditions that could be improved by promoting muscle relaxation. The lead compound for this study ((3-(N-butylethanimidoyl)ethyl)-4-hydroxy-2H-chromen-2-one; BHC) was previously discovered to inhibit skeletal myosin II. BHC and 34 analogues were synthesized to explore structure-activity relationships. The properties of analogues, including solubility, stability, and toxicity, suggest that the BHC scaffold may be useful for developing therapeutics. Inhibition of actin-activated ATPase activity of fast skeletal and cardiac muscle myosin II, inhibition of skeletal muscle contractility ex vivo, and slowing of in vitro actin-sliding velocity were measured. Several analogues with aromatic side arms showed improved potency (half-maximal inhibitory concentration (IC50) 1 μM) and selectivity (≥12-fold) for skeletal myosin versus cardiac myosin compared to BHC. Several analogues blocked neurotransmission, suggesting that they are selective for nonmuscle myosin II over skeletal myosin. Competition and molecular docking studies suggest that BHC and blebbistatin bind to the same site on myosin.

Efficient synthesis of trisubstituted [1]benzopyrano[4,3-b]pyrrol-4(1H)-one derivatives from 4-hydroxycoumarin

Various trisubstituted [1]benzopyrano[4,3-b]pyrrol-4(1H)-one derivatives have been synthesized from 4-hydroxycoumarin with a 30-40% yield over six steps. The key step of the synthesis is a base-promoted intramolecular cyclization of enamines 5, followed by dehydration to generate the fused pyrrole ring.

CONJUGATE ADDITION OF CUPRATE REAGENTS TO CHROMONES: A ROUTE TO 2-SUBSTITUTED CHROMAN-4-ONES

Chromones (4-oxo-4H-1-benzopyrans) activated by electron-withdrawing groups attached to C-3 undergo efficient 1,4-addition of cuprate reagents, producing 2,3-disubstituted chroman-4-ones.The addition products from methyl chromone-3-carboxylates can be converted into 2-substituted chroman-4-ones by treatment with sodium chloride in wet dimethylsulphoxide.