56394-24-2

Usage

Uses

Used in Biomedical Research:
6-Chloro-3-cyano-4-methylcoumarin is used as a fluorescent probe for detecting and measuring the presence of various reactive oxygen and nitrogen species in biological systems. Its ability to fluoresce upon interaction with these species makes it a valuable tool for studying oxidative stress and related biological processes.
Used in Pharmaceutical Development:
6-Chloro-3-cyano-4-methylcoumarin has been studied for its potential use as a fluorescent indicator for the detection of zinc ions. Zinc is an essential trace element involved in numerous biological functions, and its detection is important for understanding its role in health and disease.
Used in Antimicrobial Applications:
6-Chloro-3-cyano-4-methylcoumarin has been investigated for its antimicrobial activities, showing promising results in inhibiting the growth of certain bacteria. This property could be useful in the development of new antibiotics or disinfectants to combat bacterial infections.
Used in Anticancer Applications:
6-Chloro-3-cyano-4-methylcoumarin has also been studied for its potential anticancer activities, with research indicating that it can inhibit the growth of certain cancer cells. Further investigation into its mechanism of action and potential therapeutic applications could lead to the development of new cancer treatments.

Upstream product

• 106-48-9 4-chloro-phenol 
• 876-27-7 4-chlorophenyl acetate 
• 1450-74-4 5-chloro-2-hydroxyacetophenone 
• 105-56-6 ethyl 2-cyanoacetate 

Downstream Products

• 151710-23-5 6-chloro-2-oxo-4-[2-(4-chlorophenyl)ethenyl]-2H-chromene-3-carbonitrile 
• 151710-25-7 4-[(Z)-2-(4-Bromo-phenyl)-vinyl]-6-chloro-2-oxo-2H-chromene-3-carbonitrile 
• 1260430-29-2 C₂₁H₁₅Cl₂NO₃ 
• 1260430-28-1 C₂₂H₁₈ClNO₄ 
• 1260430-27-0 C₂₂H₁₈ClNO₃ 
• 1260430-30-5 C₂₁H₁₅BrClNO₃ 
• 1260430-26-9 C₂₁H₁₆ClNO₃ 
• 1304134-35-7 6-chloro-2-oxo-4-[2-(3-bromophenyl)ethenyl]-2H-chromene-3-carbonitrile 
• 1304134-32-4 6-chloro2-oxo-4-[2-(4-fluorophenyl)ethenyl]-2H-chromene-3-carbonitrile 
• 1304134-33-5 6-chloro-2-oxo-4-[2-(2-chlorophenyl)ethenyl]-2H-chromene-3-carbonitrile 
• 1304134-37-9 6-chloro-2-oxo-4-[2-(3-nitrophenyl)ethenyl]-2H-chromene-3-carbonitrile 
• 1304134-42-6 6-chloro-2-oxo-4-[2-(3,4,5-trimethoxyphenyl)ethenyl]-2H-chromene-3-carbonitrile 
• 1304134-31-3 6-chloro-2-oxo-4-[2-(phenyl)ethenyl]-2H-chromene-3-carbonitrile 
• 1304134-39-1 6-chloro-2-oxo-4-[2-(4-hydroxyphenyl)ethenyl]-2H-chromene-3-carbonitrile 

Relevant academic research and scientific papers

Palladium-Catalyzed Regioselective and Diastereoselective C-Glycosylation by Allyl-Allyl Coupling

A Pd-catalyzed C-glycosylation reaction was developed by allyl-allyl coupling process using Achmatowicz rearrangement products as donors and methylcoumarins as acceptors under mild conditions. This method featured regio- and diastereoselectivities, stereo

Iridium-catalyzed direct asymmetric vinylogous allylic alkylation

The catalytic asymmetric vinylogous allylic alkylation of α,β-unsaturated lactones (including coumarins) was achieved with excellent regio- and enantioselectivity. Transformations of the product were carried out by means of the versatile terminal olefin and lactone moieties. The synthetic application of the present methodology was showcased by the asymmetric synthesis of an advanced synthetic Merck intermediate toward a new drug candidate.

Synthesis and biological evaluation of 4-styrylcoumarin derivatives as inhibitors of TNF-α and IL-6 with anti-tubercular activity

A series of 4-styrylcoumarin have been synthesized by Knoevenagel condensation between substituted 4-methylcoumarin-3-carbonitrile and different heterocyclic or aromatic aldehydes. 4-Methylcoumarin-3-carbonitrile has been synthesized by the base catalyzed reaction between substituted 2-hydroxyacetophenone and ethyl cyanoacetate. The structures of the newly synthesized compounds were confirmed by 1H NMR, IR and mass spectral analysis. All the compounds were evaluated for their anti-inflammatory activity (against TNF-α and IL-6) and anti-tubercular activity. Compounds 6a, 6h and 6j exhibited promising activity against IL-6 with 72-87% inhibition and compound 6v showed potent activity against TNF-α with 73% inhibition at 10 μM concentration. Whereas compounds 6n, 6o, 6r and 6u showed very good anti-tubercular activity against Mycobacterium tuberculosis H37Rv strain at 6.25 μM.

SYNTHESIS AND REACTIONS OF SOME 3-CYANO-4-METHYLCOUMARINS

o-Hydroxy ketones (I) were converted into 3-cyano-4-methylcoumarins (II) via condensation with ethyl cyanoacetate in presence of piperidine or ammonium acetate as catalyst.The behavior of compound (II) towards Grignard and Michael reactions was investigat