33507-92-5

Upstream product

• 33507-93-6 7-hydroxy-5,6-diacetoxy-2-(4'-acetoxyphenyl)-4H-1-benzopyran-4-one 
• 100-39-0 benzyl bromide 
• 1168-42-9 5,6,7,4'-tetramethoxyflavone 
• 3877-67-6 1-(6-hydroxy-2,3,4-trimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 
• 22248-14-2 6-hydroxy-2,3,4-trimethoxyacetophenone 
• 642-71-7 3,4,5-trimethoxyphenol 
• 1180-46-7 4,5,6,7-tetra-O-acetylflavone 
• 100-44-7 benzyl chloride 
• 529-53-3 scutellarein 
• 27740-01-8 scutellarin 

Downstream Products

• 1401320-18-0 C₂₁H₂₀O₁₁ 
• 33507-93-6 7-hydroxy-5,6-diacetoxy-2-(4'-acetoxyphenyl)-4H-1-benzopyran-4-one 
• 676536-34-8 scutellarein 7-O-glucuronopyranoside 
• 137790-43-3 7-benzyloxy-5,6-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one 
• 29528-35-6 7-methoxy-5,6-diacetoxy-2-(4'-acetoxyphenyl)-4H-1-benzopyran-4-one 
• 23130-22-5 5,6-dihydroxy-2-(4-hydroxy-phenyl)-7-methoxy-chromen-4-one 

Relevant academic research and scientific papers

Synthesis and biological evaluation of scutellarein alkyl derivatives as preventing neurodegenerative agents with improved lipid soluble properties

Background: Exogenous antioxidants are considered as a promising therapeutic approach to treat neurodegenerative diseases since they could prevent and/or minimize the neuronal damage by oxidation. Objective: Three series of lipophilic compounds structurally based on scutellarein (2), which is one metabolite of scutellarin (1) in vivo, have been designed and synthesized. Methods: Their antioxidant activity was evaluated by detecting the 2-thiobarbituric acid reactive substance (TBARS) produced in the ferrous salt/ascorbate-induced autoxidation of lipids, which were present in microsomal membranes of rat hepatocytes. The lipophilicity of these compounds indicated as partition coefficient between n-octanol and buffer was investigated by ultraviolet (UV) spectrophotometer. Results: This study indicated that compound 5e which had a benzyl group substituted at the C4'-OH position showed a potent antioxidant activity and good lipophilicity. Conclusion: 5e could be an effective candidate for preventing or reducing the oxidative status associated with the neurodegenerative processes.

Synthesis and biological evaluation of methylated scutellarein analogs based on metabolic mechanism of scutellarin in vivo

Scutellarin (1) could be hydrolyzed into scutellarein (2) in vivo and then converted into methylated, sulfated and glucuronidated forms. In order to investigate the biological activities of these methylated metabolites, eight methylated analogs of scutellarein (2) were synthesized via semi-synthetic methods. The antithrombotic activities of these compounds were evaluated through the analyzation of prothrombin time (PT), activated partial thromboplastin time (APTT), thrombin time (TT) and fibrinogen (FIB). Their antioxidant activities were assessed by measuring their scavenging capacities toward 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) and the ability to protect PC12 cells against H2O2-induced cytotoxicity. Furthermore, the physicochemical properties of these compounds including aqueous solubility and lipophilicity were also investigated. The results showed that 6-O-methylscutellarein (5) demonstrated potent antithrombotic activity, stronger antioxidant activity and balanced solubility and permeability compared with scutellarin (1), which warrants further development of 5 as a promising lead for the treatment of ischemic cerebrovascular disease.

An improved synthesis of scutellarin-7-O-glucuronid

An eight-step synthesis of scutellarin-7-O-glucuronide via a novel preparation of the intermediate 5,6,7,4′-trimethoxyflavone from a chalcone derivative is described. The conditions of certain steps were studied and optimised to give an overall yield of 20%.

Design, synthesis and biological evaluation of glucose-containing scutellarein derivatives as neuroprotective agents based on metabolic mechanism of scutellarin in vivo

Based on metabolic mechanism of scutellarin in vivo that scutellarin could be hydrolyzed into scutellarein by β-glucuronide enzyme, some glucose-containing scutellarein derivatives were designed and synthesized through the introduction of glucose moiety at C-7 position of scutellarein via a glucosidic bond. Biological activity evaluation showed that these glucose-containing scutellarein derivatives exhibited potent DPPH radical scavenging activities. Furthermore, the improvement of physicochemical properties such as anticoagulant and neuroprotective activities alongside with the water solubility was achieved by introducing glucose. These findings suggest that the introduction of the glucose moiety to scutellarein wattants further development of this kind of compounds as neuroprotective agents.