1255-78-3

Basic information

• Product Name: 2-((4-benzyloxy-3-methoxy)phenyl)-5,7-dimethoxy-4H-benzopyran-4-one
• Synonyms: 2-((4-benzyloxy-3-methoxy)phenyl)-5,7-dimethoxy-4H-benzopyran-4-one
• CAS NO: 1255-78-3
• Molecular Weight: 418.446
• Mol File: 1255-78-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-((4-benzyloxy-3-methoxy)phenyl)-5,7-dimethoxy-4H-benzopyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-((4-benzyloxy-3-methoxy)phenyl)-5,7-dimethoxy-4H-benzopyran-4-one(1255-78-3)
• EPA Substance Registry System: 2-((4-benzyloxy-3-methoxy)phenyl)-5,7-dimethoxy-4H-benzopyran-4-one(1255-78-3)

Safety Data

• Hazardous Substances Data: 1255-78-3(Hazardous Substances Data)

Upstream product

• 114021-61-3 4-Benzyloxy-2'-hydroxy-3,4',6'-trimethoxychalcone 
• 1239-68-5 2‐(4‐hydroxy‐3‐methoxyphenyl)‐5,7‐dimethoxy‐4H‐chromen‐4‐one 
• 100-44-7 benzyl chloride 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 121-33-5 vanillin 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 480-66-0 2,4,6-trihydroxyacetophenone 

Downstream Products

• 1239-68-5 2‐(4‐hydroxy‐3‐methoxyphenyl)‐5,7‐dimethoxy‐4H‐chromen‐4‐one 

Relevant articles and documents

Luteolin from Flos Chrysanthemi and its derivatives: New small molecule Bcl-2 protein inhibitors

Over-expression of the Bcl-2 anti-apoptotic proteins is closely related to tumorigenesis and associated with drug resistance. Here we report that luteolin, a main substance found in Flos Chrysanthemi, directly binds to and shows inhibitory activity against the Bcl-2 protein. We studied the binding mode of luteolin and its derivatives with target proteins, their structure-activity relationship, and their effect on the human leukemia cell line HL-60. The results suggest that luteolin and its derivatives with a benzyl group introduced to the B ring, are new small molecule Bcl-2 protein inhibitors, and their anti-tumor activity is likely related to their effect on the Bcl-2 protein.

Structural modification of luteolin from Flos Chrysanthemi leads to increased tumor cell growth inhibitory activity

The luteolin from Flos Chrysanthemi was found to directly bind to the Bcl-2 protein and inhibit the tumor cell growth in our previous study. However, it has been shown to possess wide and week biological activities. In this study, a series of derivatives of luteolin were designed and synthesized, and their tumor cell growth inhibitory activities were evaluated against human leukemia cell line HL-60. The results showed that compounds 1B-2, 2A-3, and 2B-5, with hydrophobic substituted benzyl groups introduced to B ring and hydrogen or methyl introduced to 7-OH group of luteolin, exhibited the strongest inhibitory activity with the IC50lower than 10?μM, which were significantly more potent than luteolin. The studies presented here offer a good example for modifications of flavones to improve their tumor cell growth inhibitory activities.

Acidic rearrangement of benzyl group in flavone benzyl ethers and its regioselectivity

Abstract The benzyl-substituted flavone compounds are rare in nature, while some of which have interesting biological activities. The total synthesis of benzyl-substituted flavone derivatives via the acidic rearrangement of benzyl groups in flavone benzyl ethers, and the complicated regioselectivity of the rearrangement were reported. The regioselectivity was proposed to be determined by the steric hindrance as well as the ease of electrophilic substitution reaction for benzyl cations at different positions of corresponding debenzylated flavone compounds.