111391-55-0

Upstream product

• 36768-48-6 (E)-1-(5-chloro-2-hydroxyphenyl)-3-(4-chlorophenyl)prop-2-en-1-one 
• 36768-56-6 6-chloro-2-(4-chlorophenyl)-4H-chromen-4-one 
• 36768-48-6 (E)-1-(5-Chloro-2-hydroxy-phenyl)-3-(4-chloro-phenyl)-propenone 
• 1450-74-4 5-chloro-2-hydroxyacetophenone 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 131136-65-7 6-Chloro-2-(4-chloro-phenyl)-3-hydroxy-2,3-dimethoxy-chroman-4-one 
• 111391-74-3 6-Chloro-2-(4-chloro-phenyl)-3-methoxy-chromen-4-one 

Relevant academic research and scientific papers

Synthesis, molecular properties, anti-inflammatory and anticancer activities of novel 3-hydroxyflavone derivatives

A new series of 3-hydroxyflavones (1–46) were synthesized according to the Claisen-Schmidt followed by Algar-Flynn-Oyamada reactions (AFO) in one step. The synthesized flavonoids were characterized by 1H NMR, 13C NMR and DCI-HRMS. All the synthesized compounds were tested in vitro for their 15-lipoxygenase inhibitory and cytotoxic activity against the human cell lines HCT-116 (Human colon carcinoma), IGROV-1 and OVCAR-3 (human ovarian carcinoma). It has been found that the derivatives 25, 37 and 45 were the most actives against HCT-116 (IC50 = 8.0, 9.0 and 9.0 μM, respectively) and against IGROV-1 (IC50 = 2.4, 5.0 and 6.0 μM, respectively). The derivatives 14 and 21 exhibited the higher anti-inflammatory activity at 100 μM with PI values of 76.50 and 72.70%, respectively. Molecule description was performed with DFT calculations, the drug likeness and bioactivity scores. The results exhibted that some compounds are in linear correlation with Lipinski's rule of five showing good drug likeness and bioactivity score for drug targets.

Absorption and fluorescent studies of 3-hydroxychromones

The synthesis and spectral studies of variously substituted 3-hydroxychromones have been carried out. A key relationship between the structural motif of synthesized 3-hydroxychromones (3-HCs) and their fluorescent properties was found. The chromones substituted with electron-donating group at 4′-position expressed the red shift of the N and T band and also exhibited the increased fluorescent intensity ratio while the chromones with electron-withdrawing group showed the blue shift of the N and T band. Therefore, these 3-HCs may behave as the possible fluorescent probes.

C-3 Hydroxylation of flavones using hypervalent iodine oxidation

Hypervalent iodine oxidation of several flavones (1b-g) with iodobenzene diacetate in methanolic potassium hydroxide, followed by acid hydrolysis of the resultant 3-hydroxy-2-methoxyflavonones dimethylacetals (2b-g), offers a general method for 3-hydroxyflavones (3b-g).

4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity

4'-Hydroxy-3-methoxyflavones are natural compounds with known antiviral activities against picornaviruses such as poliomyelitis and rhinoviruses. In order to establish a structure-activity relationship a series of analogues were synthesized, and their antiviral activities and cytotoxicities were compared with those of flavones from natural origin. The 4'-hydroxyl and 3-methoxyl groups, a substitution in the 5 position and a polysubstituted A ring appeared to be essential requirements for a high activity. The most interesting compound was 4',7-dihydroxy-3-methoxy-5,6-dimethylflavone possessing in vitro TI99 values of > 1000 and > 200 against poliovirus type 1 and rhinovirus type 15, respectively. This compound was also active against other rhinovirus serotypes (2, 9, 14, 29, 39, 41, 59, 63, 70, 85, and 89) tested, having MIC50 values ranging from 0.016 to 0.5 μg/mL. Finally in contrast to quercetin it showed to be not mutagenic in concentrations up to 2.5 mg in the Ames test.