1911-69-9

Upstream product

• 108-73-6 3,5-dihydroxyphenol 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 89-98-5 2-chloro-benzaldehyde 

Downstream Products

• 1596356-06-7 8-allyl-2-(2-chlorophenyl)-5,7-dimethoxy-2,3-dihydro-4H-1-benzopyran-4-one 
• 952677-96-2 8-allyl-2-(2-chlorophenyl)-5,7-dimethoxy-4H-1-benzopyran-4-one 
• 952677-99-5 2-(2-chlorophenyl)-5,7-dimethoxy-8-oxiranylmethyl-4H-1-benzopyran-4-one 
• 952678-11-4 2-(2-chlorophenyl)-8-[2-hydroxy-3-(morpholin-4-yl)propy]-5,7-dimethoxy-4H-1-benzopyran-4-one 
• 952678-00-1 2-(2-chlorophenyl)-8-[2-hydroxy-3-(piperidin-1-yl)propyl]-5,7-dimethoxy-4H-1-benzopyran-4-on 
• 952678-01-2 2-(2-chlorophenyl)-8-[2-hydroxy-3-(pyrrolidin-1-yl)propyl]-5,7-dimethoxy-4H-1-benzopyran-4-one 
• 952678-03-4 2-(2-chlorophenyl)-8-(3-diethylamino-2-hydroxypropyl)-5,7-dimethoxy-4H-1-benzopyran-4-one 
• 952678-04-5 2-(2-chlorophenyl)-8-(3-ethylmethylamino-2-hydroxypropyl)-5,7-dimethoxy-4H-1-benzopyran-4-one 
• 952678-05-6 2-(2-chlorophenyl)-8-(3-dimethylamino-2-hydroxypropyl)-5,7-dimethoxy-4H-1-benzopyran-4-one 
• 952677-74-6 2-(2-chlorophenyl)-5-hydroxy-8-[2-hydroxy-3-(morpholin-4-yl)propyl]-7-methoxy-4H-1-benzopyran-4-one 
• 952677-75-7 2-(2-chlorophenyl)-5-hydroxy-8-[2-hydroxy-3-(piperidin-1-yl)propyl]-7-methoxy-4H-1-benzopyran-4-one 
• 952677-76-8 2-(2-chlorophenyl)-5-hydroxy-8-[2-hydroxy-3-(pyrrolidin-1-yl)propyl]-7-methoxy-4H-1-benzopyran-4-one 
• 952677-78-0 2-(2-chlorophenyl)-8-(3-diethylamino-2-hydroxypropyl)-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one 
• 952677-79-1 2-(2-chlorophenyl)-8-(3-ethylmethylamino-2-hydroxypropyl)-5-hydroxy-7-methoxy-4H-1-benzopyran-4-one 

Relevant academic research and scientific papers

Aurones as histone deacetylase inhibitors: Identification of key features

In this study, a total of 22 flavonoids were tested for their HDAC inhibitory activity using fluorimetric and BRET-based assays. Four aurones were found to be active in both assays and showed IC50 values below 20 μM in the enzymatic assay. Molecular modelling revealed that the presence of hydroxyl groups was responsible for good compound orientation within the isoenzyme catalytic site and zinc chelation.

Design, synthesis and cytotoxic activities of novel aliphatic amino-substituted flavonoids

A series of flavonoids 9a-f, 13b, 13d, 13e and 14a-f bearing diverse aliphatic amino moieties were designed, synthesized and evaluated for their cytotoxic activities against the ECA-109, A-549, HL-60, and PC-3 cancer cell lines. Most of the compounds exhibited moderate to good activities. The structure-activity relationships were studied, revealing that the chalcone skeleton is the most preferable for cytotoxic activities. Chalcone 9d was the most promising compound due to its high potency against the examined cancer cell lines (its IC50 values against ECA-109, A549, HL-60 and PC-3 cells were 1.0, 1.5, 0.96 and 3.9 μM, respectively).

A synthetic chalcone as a potent inducer of glutathione biosynthesis

Chalcones continue to attract considerable interest due to their anti-inflammatory and antiangiogenic properties. We recently reported the ability of 2′,5′-dihydroxychalcone (2′,5′-DHC) to induce both breast cancer resistance protein-mediated export of glutathione (GSH) and c-Jun N-terminal kinase-mediated increased intracellular GSH levels. Herein, we report a structure-activity relationship study of a series of 30 synthetic chalcone derivatives with hydroxyl, methoxyl, and halogen (F and Cl) substituents and their ability to increase intracellular GSH levels. This effect was drastically improved with one or two electrowithdrawing groups on phenyl ring B and up to three methoxyl and/or hydroxyl groups on phenyl ring A. The optimal structure, 2-chloro-4′,6′-dimethoxy-2′- hydroxychalcone, induced both a potent NF-E2-related factor 2-mediated transcriptional response and an increased formation of glutamate cysteine ligase holoenzyme, as shown using a human breast cancer cell line stably expressing a luciferase reporter gene driven by antioxidant response elements.