10465-91-5

Usage

Uses

Used in Pharmaceutical Industry:
3-(4-chlorophenyl)chromen-2-one is used as a pharmaceutical candidate for its anti-inflammatory properties, which can help in the treatment of various inflammatory conditions. Its antioxidant activity also makes it a potential candidate for the development of drugs targeting oxidative stress-related disorders.
Used in Anticancer Applications:
In the field of oncology, 3-(4-chlorophenyl)chromen-2-one is used as an anticancer agent. Its potential to modulate various oncological signaling pathways makes it a promising compound for the development of new cancer therapies. It may be particularly effective against a range of solid malignancies, and its combination with conventional chemotherapeutic drugs could enhance chemo-sensitivity and efficacy in resistant cases.
Used in Drug Development:
3-(4-chlorophenyl)chromen-2-one is used as a key component in the development of new drugs for various medical conditions. Its unique structure and pharmacological properties make it a valuable compound for the creation of innovative therapeutic agents that can address unmet medical needs.

InChI:InChI=1/C15H9ClO2/c16-12-7-5-10(6-8-12)13-9-11-3-1-2-4-14(11)18-15(13)17/h1-9H

Upstream product

• 2028-74-2 p-chlorobenzenediazonium chloride 
• 91-64-5 coumarin 
• 1878-66-6 4-chlorophenylacetic Acid 
• 90-02-8 salicylaldehyde 
• 92-45-5 3-chloro-2H-chromen-2-one 
• 1679-18-1 4-Chlorophenylboronic acid 
• 939-18-4 3-bromo-2H-chromen-2-one 
• 637-87-6 1-Chloro-4-iodobenzene 
• 100-52-7 benzaldehyde 
• 73720-02-2 Z-α-p-chlorophenyl-β-phenylacrylic acid 
• 4998-15-6 4-chlorophenylglyoxal 
• 33491-03-1 1-(bromoethynyl)-4-chlorobenzene 
• 1333483-16-1 N-((4-chlorophenyl)ethynyl)-N-methylmethanesulfonamide 
• 50978-45-5 3-oxobenzo[d]isothiazole-2(3H)-carbaldehyde 1,1-dioxide 

Downstream Products

• 69976-31-4 3-(2,4-dichlorophenyl)-2H-chromen-2-one 

Relevant academic research and scientific papers

A convenient synthesis of 3-arylcoumarins from arylacetonitriles

The condensation of salicylaldehydes with various arylacetonitriles catalyzed by anion-exchange resins such as Amberlite IRA 900, leads to the corresponding 3-arylcoumarins in good yields and selectivity.

Photophysical investigation of 3-substituted 4-alkyl and/or 7-acetoxy coumarin derivatives-A study of the effect of substituents on fluorescence

In the present work an array of novel substituted 2H-chromen-2-one (coumarin) derivatives has been subjected to photophysical analysis. Though the influence of the electron-donating groups such as amino, substituted amino, hydroxyl, alkoxy groups, etc. at position 7 of the coumarin ring system has been extensively studied, the luminescent properties of the coumarin moieties with an acetoxy substituent have not been explored. Herein it is attempted to study the variation of fluorescence behavior of substituted coumarin derivatives with change of nature and position of the substituents on the 2H-chromen-2-one skeleton. Effect of a methyl substituent at position 4 which imposes abnormal photophysical behavior to the chromenone unit has also been briefly described.

Dual Role of Oxoaldehydes: Divergent Synthesis of 3-Aryl- and 3-Aroylcoumarins

A facile and efficient synthetic approach to various valuable 3-aryl- and 3-aroylcoumarins by the direct arylation and aroylation of coumarins with glyoxals in a metal-free manner is presented. The aryl glyoxal is for the first time recognized to serve as an aryl surrogate in addition to its role as an aroyl transfer reagent via a simple switch in reaction conditions. The approach accommodates a broad substrate scope and high yields of the two types of cross-coupling reactions starting from identical starting materials.

Combatting AMR: A molecular approach to the discovery of potent and non-toxic rhenium complexes active against C. albicans-MRSA co-infection

Antimicrobial resistance (AMR) is a major emerging threat to public health, causing serious issues in the successful prevention and treatment of persistent diseases. While the problem escalates, lack of financial incentive has lead major pharmaceutical co

Visible-light promoted oxidative cyclization of cinnamic acid derivatives using xanthone as the photocatalyst

We have developed an efficient photocatalytic synthesis of coumarin derivativesviaa tandem double bond isomerization/oxidative cyclization of cinnamic acids. Inexpensive and stable xanthone was used as the photocatalyst, and readily available Selectfluor was used as the oxidant. This method tolerates a wide range of functional groups and offers excellent chemical yields in general. Besides, the photocatalytic oxidative cyclization of cinnamic acid esters gives dimerized lignan-type products.

Zn(II)-Catalyzed One-Pot Synthesis of Coumarins from Ynamides and Salicylaldehydes

A highly efficient and straightforward synthesis of diversely substituted coumarins from ynamides and salicylaldehydes in the presence of Zn(II) catalyst has been developed. The sulfonamide moiety of ynamides was successfully recycled in this process, serving as an effective traceless directing group for high regioselectivity in the bond-forming event. The advantages of this protocol are good functional group tolerance, broad substrate scope, simple and high-yielding reaction, recovery/reuse of the sulfonamides, low catalyst loading of inexpensive catalyst, and, by these merits, a more cost-effective and greener process.

Pd-catalysed carbonylative annulation of salicylaldehydes with benzyl chlorides using N-formylsaccharin as a CO surrogate

A convenient and highly efficient Pd-catalysed carbonylative annulation of salicylaldehydes with benzyl chlorides to afford the corresponding 3-arylcoumarins in good to excellent yields has been developed. Importantly, the protocol utilizes a commercially available, low cost, solid and easy to handle N-formylsaccharin as an alternative to the highly toxic CO gas.

KMnO4/AcOH-mediated C3-selective direct arylation of coumarins with arylboronic acids

An efficient protocol for KMnO4/AcOH-mediated dehydrogenative direct radical arylation of coumarins with arylboronic acids to afford 3-arylcoumarin derivatives is described. A similar reaction system is also applicable to the 3-arylation of quinolinone derivatives. These KMnO4/AcOH-mediated coupling reactions occur regioselectively at the C3 position of coumarins and quinolinones. Some notable features of this method are high efficiency, moderate to good yield, and a broad group tolerance.

Synthesis and Evaluation of Coumarin-Resveratrol Hybrids as 15-Lipoxygenaze Inhibitors

A series of coumarin-resveratrol hybrids, 3-arylcoumarin derivatives 3a-u, were synthesized through the intermolecular condensation reaction of various salicylaldehydes and phenylacetic acids in the presence of 1,4-diazabicyclo[2.2.2]octane under solvent-free conditions. All the synthesized compounds were screened for their inhibitory potency against soybean 15-lipoxygenase. Among them, three compounds (3c, 3j, and 3q) showed good enzyme-inhibitory activities. GRAPHICAL ABSTRACT.

Regioselective α-arylation of coumarins and 2-pyridones with phenylhydrazines under transition-metal-free conditions

A facile regioselective metal-free direct α-arylation of coumarins and 2-pyridones is achieved by the reaction of coumarins and 2-pyridones with phenylhydrazine in good yields. The reaction proceeds at room temperature under mild conditions using inexpensive reagents and without the need for step intensive activating groups. The methodology is operationally simple, practically viable and also allows the coupling of similar nitrogen heterocycle aza-coumarins without prerequisite N-protection.