6336-05-6

Usage

Uses

Used in Pharmaceutical Industry:
6-chloro-2-(4-chlorophenyl)-2,3-dihydro-4H-1-benzopyran-4-one is used as a pharmaceutical agent for its potential role in the treatment of various diseases, including cancer and inflammatory disorders. Its anti-inflammatory and anti-tumor activities make it a promising candidate for therapeutic applications in drug development.
Used in Medicinal Chemistry Research:
6-chloro-2-(4-chlorophenyl)-2,3-dihydro-4H-1-benzopyran-4-one is utilized in medicinal chemistry research to explore its potential therapeutic applications and optimize its properties for drug development. Its chemical structure and properties are of interest for further investigation and modification to enhance its efficacy and safety in treating various diseases.

InChI:InChI=1/C12H13N3OS2/c1-8-10(18-12(17)15(8)2)14-11(16)13-9-6-4-3-5-7-9/h3-7H,1-2H3,(H2,13,14,16)

Upstream product

• 1450-74-4 5-chloro-2-hydroxyacetophenone 
• 104-88-1 4-chlorobenzaldehyde 
• 36768-48-6 (E)-1-(5-Chloro-2-hydroxy-phenyl)-3-(4-chloro-phenyl)-propenone 
• 123743-12-4 6-Chloro-2-(4-chloro-phenyl)-chroman-4-one oxime 

Downstream Products

• 36768-56-6 6-chloro-2-(4-chlorophenyl)-4H-chromen-4-one 
• 145013-56-5 6-chloro-3-(4-chlorophenyl)-4H-chromen-4-one 

Relevant academic research and scientific papers

Halogenated flavanones as potential apoptosis-inducing agents: Synthesis and biological activity evaluation

A series of halogenated flavanones were synthesized from 2-hydroxychalcones and tested for their cytotoxicity against a panel of human cancer cell lines. Among the synthesized compounds, 3′,7-dichloroflavanone (2d) showed the highest activity against MCF-7, LNCaP, PC3, Hep-G2, KB and SK-N-MC cells. However, 3′,6-dichloroflavanone (2g) with IC50 value of 2.9 ± 0.9 μM was the most potent compound against MDA-MB-231 cells, being approximately 12 times more active than etoposide as reference drug. According to the flow-cytometric analysis, compound 2g can induce apoptosis by 66.19 and 21.37% in PC3 and MDA-MB-231 cells, respectively. The results of acridine orange/ethidium bromide staining and TUNEL assay suggested that the cytotoxic activity of this compound in PC3 and MDA-MB-231 cells occurs via apoptosis.

Simple and efficient one step synthesis of functionalized flavanones and chalcones

A facile and highly efficient microwave-assisted synthesis of functionalized chalcones and flavanones based on the Claisen-Schmidt condensation reaction is reported. The method describes the synthesis of flavanones in single step with excellent yield and it was revealed that position and number of substituents on acetophenones and aromatic aldehydes played a very crucial and key role in the construction of flavanone derivatives. Among the thirty two synthesized compounds, five chalcones and one flavanone were novel compounds.

Synthesis of flavanones by use of anhydrous potassium carbonate as an inexpensive, safe, and efficient basic catalyst

Anhydrous potassium carbonate has been utilized as an inexpensive, safe, and efficient basic catalyst for the synthesis of flavanones starting either from 2′-hydroxychalcones or from 2′-hydroxyacetophenones. In both the cases the favored reaction condition was either refluxing in a solvent with added catalyst or microwave irradiation on the catalyst.

A new synthesis of flavanones

Flavanones 2 were synthesized in good yields from 3-chloro-2,3-dihydro-3-nitro-2-phenyl-4H-1-benzopyran-4-ones 1 using a free radical process involving the tributyltin hydride/2,2'-azobisisobutyronitrile system in refluxing benzene.

Oxidative Cleavage of 4-Oximinoflavans Using Iodobenzene Diacetate

Oxidation of 4-oximinoflavans (Ia-g) using iodobenzene diacetate leads to cleavage with the formation of corresponding flavanones (IIa-g) under neutral conditions in 60-80percent yields.