33513-36-9

Usage

Occurrence

Naturally occurring in citrus fruits such as oranges and tangerines

Chemical class

Flavonoid

+ Antioxidant

Sinensetin has been shown to possess antioxidant properties, which may help protect cells from damage caused by free radicals.

+ Anti-inflammatory

Sinensetin has been shown to possess anti-inflammatory properties, which may help reduce inflammation in the body.

+ Protective effects

Due to its antioxidant and anti-inflammatory properties, sinensetin may have potential protective effects against certain diseases.

+ Neurodegenerative disorders

Sinensetin has been investigated for its potential use in the treatment of neurodegenerative disorders.

InChI:InChI=1/C17H14O5/c1-20-14-6-3-10(7-17(14)21-2)15-9-13(19)12-5-4-11(18)8-16(12)22-15/h3-9,18H,1-2H3

Upstream product

• 854651-91-5 1-(3,4-dimethoxy-phenyl)-3-(2-hydroxy-4-veratroyloxy-phenyl)-propane-1,3-dione 
• 127-09-3 sodium acetate 
• 64-19-7 acetic acid 
• 3535-37-3 3,4-dimethoxybenzoic acid chloride 
• 755722-84-0 imine 
• 93-07-2 Veratric acid 
• 108-46-3 recorcinol 
• 25015-92-3 2-chloro-1-(2,4-dihydroxyphenyl)ethanone 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 3943-77-9 ethyl veratrate 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 99474-24-5 1-(3,4-dimethoxyphenyl)-3-(2,4-dihydroxyphenyl)propane-1,3-dione 

Downstream Products

• 883242-59-9 3',4'-dimethoxy-7-(2,3-epoxypropoxy)flavone 
• 22395-24-0 3',4',7-trimethoxyflavone 
• 883242-84-0 7-(3-bromopropoxy)-2-(3,4-dimethoxyphenyl)-4H-chromen-4-one 
• 113495-06-0 C₂₇H₂₅N₃O₇S 
• 113495-05-9 C₂₆H₂₂ClN₃O₆S 
• 113495-04-8 C₂₇H₂₅N₃O₆S 
• 113512-82-6 C₂₆H₂₃N₃O₆S 
• 113494-97-6 [2-(3,4-Dimethoxy-phenyl)-4-oxo-4H-chromen-7-yloxy]-acetic acid hydrazide 
• 2150-11-0 3',4',7-trihydroxyflavone 
• 113494-94-3 [2-(3,4-Dimethoxy-phenyl)-4-oxo-4H-chromen-7-yloxy]-acetic acid methyl ester 

Relevant academic research and scientific papers

Design, synthesis and apoptosis inducing activity of nonsteroidal flavone-methanesulfonate derivatives on MCF-7 cell line as potential sulfatase inhibitor

In recent years, focusing on new potent anticancer agents with selective activity is one of the greatest challenges in cancer therapy. Breast cancer is the most common cancer and the main cause of cancer deaths in women. The sulfatase enzyme plays an important role in converting the sulfated steroids into non-sulfate steroid hormones, which increases the growth and development of many hormone-dependent cancers, such as breast cancer. In this regard, structure-based optimization was conducted to design novel flavone-sulfonates pharmacophore as a new steroid sulfatase inhibitor. In the present work, the conventional methods for the synthesis of 4-oxo-2-phenyl-4H-chromen-7-yl methanesulfonate derivatives were reported. Their cytotoxicity was evaluated with MTT assay against a breast cancer cell line (MCF-7). The apoptosis inducing activity of the most cytotoxic compound 3c with an IC50 value of 0.615 μM was evaluated in comparison to docetaxel in the presence of estradiol which is a crucial growth factor to survive the cancerous cells. The results of double staining Annexin V-FITC/PI analysis suggested that the cytotoxic activity of this compound 3c in MCF-7 cells occurs via apoptosis. Molecular docking studies were conducted to clarify the inhibition mode of the most promising compound (3c) over the sulfatase (1P49) binding site. The analysis revealed the role of hydrogen bond interaction with Gly181 and hydrophobic interactions through the 1P49 active site in the ligand-receptor complex as significant descriptors to rationalize the potential inhibition activity. [Figure not available: see fulltext.]

Exploration of multi-target potential of chromen-4-one based compounds in Alzheimer's disease: Design, synthesis and biological evaluations

A novel series of flavonoid based compounds were designed, synthesized and biologically evaluated for Acetylcholinesterase (AChE) inhibitory activity integrated with advanced glycation end products (AGEs) inhibitory and antioxidant potential. Most of the derivatives inhibited AChE in nanomolar IC50 range along with good AGEs inhibitory and radical scavenging activity. Among them, 7m, strongly inhibited AChE (IC50 = 5.87 nM) and found to be potent as compared to the reference drug donepezil (IC50 = 12.7 nM). Its potent inhibitory activity has been justified by docking analysis that revealed its dual binding characteristic with both CAS (catalytic active site) and PAS (peripheral anionic site) of AChE, simultaneously. Additionally, this compound also displayed ability to prevent advanced glycation end products formation (IC50 = 23.0 μM) with additional radical scavenging property (IC50 = 37.12 nM). It (7m) also ameliorated scopolamine induced memory deficit in mice employing Morris water maze test. Thus, flavonoids might be the promising lead compounds as potential polyfunctional anti-Alzheimer's agents.

Inhibitory effect of flavonoids on human glutaminyl cyclase

Glutaminyl cyclase (QC) plays an important role in the pathogenesis of Alzheimer's disease (AD) and can be a potential target for the development of novel anti-AD agents. However, the study of QC inhibitors are still less. Here, phenol-4′ (R1-), C5-OH (R2-) and C7-OH (R3-) modified apigenin derivatives were synthesized as a new class of human QC (hQC) inhibitors. The efficacy investigation of these compounds was performed by spectrophotometric assessment and the structure-activity relationship (SAR) was evaluated. Molecular docking was also carried out to analyze the binding mode of the synthesized flavonoid to the active site of hQC.

Design, synthesis and evaluation of novel 7-aminoalkyl-substituted flavonoid derivatives with improved cholinesterase inhibitory activities

A novel series of 7-aminoalkyl-substituted flavonoid derivatives 5a-5r were designed, synthesized and evaluated as potential cholinesterase inhibitors. The results showed that most of the synthesized compounds exhibited potent acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities at the micromolar range. Compound 2-(naphthalen-1-yl)-7-(8-(pyrrolidin-1-yl)octyloxy)-4H-chromen-4-one (5q) showed the best inhibitory activity (IC50, 0.64 μM for AChE and 0.42 μM for BChE) which were better than our previously reported compounds and the commercially available cholinergic agent Rivastigmine. The results from a Lineweaver-Burk plot indicated a mixed-type inhibition for compound 5q with AChE and BChE. Furthermore, molecular modeling study showed that 5q targeted both the catalytic active site (CAS) and the peripheral anionic site (PAS) of AChE. Besides, these compounds (5a-5r) did not affect PC12 and HepG2 cell viability at the concentration of 10 μM. Consequently, these flavonoid derivatives should be further investigated as multipotent agents for the treatment of Alzheimer's disease.

Flavone-based novel antidiabetic and antidyslipidemic agents

The hybrid congeners 62-90 of 6- and 7-hydroxyflavones with aminopropanol have been synthesized and evaluated for their antidiabetic activity in sucrose-challenged low-dosed streptozotocin (STZ)-induced diabetic rats and db/db mice. The optical enantiomers 70a, 70b, 90a, and 90b of two congeners 70 and 90 exhibiting consistent antidiabetic and antidyslipidemic activities were also prepared, and their antidiabetic activity results indicate its association mainly with S isomers. These compounds also lower cholesterol and TG profiles while improving high-density lipoprotein cholesterol to CHOL ratio in db/db mice. The bioavailability of compound 70 and its isomer varies between 27 and 29% whereas that of the more polar compound 90a is poor as determined in rat by oral and intraperitoneal administrations. Published 2012 by the American Chemical Society.

OXY SUBSTITUTED FLAVONES AS ANTIHYPERGLYCEMIC AND ANTIDYSLIPIDEMIC AGENTS

The present invention provides novel substituted flavone derivatives which exhibit anti- hyperglycemic and antidyslipedemic activity. The invention also provides a method for controlling type ii diabetes and associated hyperlipidemic conditions in a mammal by administering compound of the present invention and compositions containing these derivatives.

Process for the preparation of flavone derivatives

The invention relates to a process for the preparation of flavone derivatives in which a 2-hydroxyacetophenone compound is metallated using a lithium compound at low temperatures and subsequently reacted with a keto compound, and where the ratio of the mo