1105056-24-3

Upstream product

• 27740-01-8 scutellarin 
• 2051-90-3 Dichlorodiphenylmethane 
• 529-53-3 scutellarein 

Downstream Products

• 1402607-40-2 9-hydroxy-2,2-diphenyl-6-[4-(phenylmethoxy)phenyl]-8H-1,3-dioxolo[4,5-g][1]benzopyran-8-one 
• 1447-88-7 hispidulin 
• 1351585-69-7 5,6,7-trihydroxy-2-[4-(phenylmethoxy)phenyl]-4H-1-benzopyran-4-one 
• 62252-32-8 7-(benzyloxy)-2-(4-(benzyloxy)phenyl)-5,6-dihydroxy-4H-chromen-4-one 
• 28736-83-6 7-(benzyloxy)-2-(4-(benzyloxy)phenyl)-5-hydroxy-6-methoxy-4H-chromen-4-one 
• 1436402-36-6 C₃₄H₂₉NO₇ 
• 1619254-61-3 5-hydroxy-6,7-bis(methoxymethoxy)-2-[4-(phenylmethoxy)phenyl]-4H-1-benzopyran-4-one 
• 1619254-63-5 5-hydroxy-2-(4-hydroxyphenyl)-6,7-bis(methoxymethoxy)-4H-1-benzopyran-4-one 
• 1619254-65-7 5-hydroxy-6,7-bis(methoxymethoxy)-2-[4-[2-(4-morpholinyl)ethoxy]phenyl]-4H-1-benzopyran-4-one 
• 529-53-3 scutellarein 
• 1436398-09-2 5,6,7-trihydroxy-2-[4-[2-(4-morpholinyl)ethoxy]phenyl]-4H-1-benzopyran-4-one 

Relevant academic research and scientific papers

Synthesis of scutellarein derivatives with antiproliferative activity and selectivity through the intrinsic pathway

To explore antitumor agents with potent efficacy and low toxicity, scutellarein derivatives with benzoic acid mustard (10a?c, 11a?c and 13a?c) were designed and synthesized. The antiproliferative activities of the target derivatives against A549, MCF-7 and Bel-7402 cancer cell lines were tested. Compound 10a showed the strongest potency with an IC50 value of 1.50 μM against MCF-7 cell line, and displayed low toxicity against human liver L-O2 normal cells (IC50 > 50 μM), showing specificity between normal and malignant cells. The mechanism studies revealed that 10a could induce apoptosis in MCF-7 cells, arrest MCF-7 cell cycle at the G1 phase and cause mitochondrial dysfunction in a concentration-dependant manner. Furthermore, the enhanced expression of the pro-apoptotic proteins caspase-9, caspase-3, Bax and cytochrome c, and the reduced expression of the anti-apoptotic protein Bcl-2 confirmed that 10a induced the intrinsic apoptosis pathway in MCF-7 cells. The potent antiproliferative activity and good selectivity guaranteed 10a a lead compound for the further development into anticancer therapeutics, especially for breast cancer.

Design, Synthesis, and Biological Evaluation of Scutellarein Carbamate Derivatives as Potential Multifunctional Agents for the Treatment of Alzheimer's Disease

A series of scutellarein carbamate derivatives were designed and synthesized based on the multitarget-directed drug design strategy for treatment of Alzheimer's disease. Their acetylcholinesterase and butyrylcholinesterase inhibitory activities, antioxida

Concise synthesis and antidiabetic activity of natural flavonoid glycosides, oroxins C and D, isolated from the seeds of Oroxylum indium

The first concise synthesis of natural flavonoid glycosides, oroxins C (1) and D (2), which were isolated from the seeds of Oroxylum indicum, was efficiently achieved by a convergent strategy. The synthesized natural products 1 and 2 were evaluated for th

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.

Scutellarin aglycone nitrogen mustard derivative and preparation method and application thereof

The invention belongs to the field of natural medicine and medicinal chemistry and relates to a scutellarin aglycone nitrogen mustard derivative and a preparation method and application thereof, in particular to a scutellarin aglycone nitrogen mustard derivative of which 4'-OH is combined with benzoic acid nitrogen mustard and a preparation method and antitumor activity thereof. The structure of the scutellarin aglycone nitrogen mustard derivative and pharmaceutically acceptable salt thereof is as shown in the general formula I, wherein R and n are as described in claims and the specification.The formula I is shown in the description.

Permeability of novel 4′-N-substituted (aminomethyl) benzoate-7-substituted nicotinic acid ester derivatives of scutellarein in Caco-2 cells and in an in vitro model of the blood-brain barrier

A series of 4′-N-substituted (aminomethyl) benzoate-7-substituted nicotinic acid ester derivatives of scutellarein was designed and synthesized. Evaluation of physiochemical properties showed that the newly designed compounds had greater chemical stability and aqueous solubility than scutellarin or scutellarein. The permeabilities (Papp AP to BL) of compounds 7b and 7e in Caco-2 cells were 5.9-fold and 3.7-fold higher than that of scutellarin, and 3.7-fold and 2.4-fold higher than that of scutellarein. The permeabilities (Papp AP to BL) of compounds 7b and 7e in an in vitro model of the blood–brain barrier were 9.7-fold and 5.9-fold higher than that of scutellarin, and 9.2-fold and 5.6-fold higher than that of scutellarein.

Application of N-substituted (aminomethyl)benzoate strategy in design of scutellarein derivatives with improved Caco-2 cell permeability and in vitro antioxidative activity

A series of 4′-N-substituted (aminomethyl)benzoate derivatives of scutellarein were designed and synthesized. Evaluation of their physiochemical properties showed that the designed target compounds 5a-e exhibit higher chemical stability and aqueous solubility than scutellarin and scutellarein. The permeability (Papp AP to BL) of 5c-e in Caco-2 cells were 2.8, 8.1, and 12.6 times higher than that of scutellarin and 1.3, 4.1, and 6.0 times higher than that of scutellarein; especially, 5e had the highest Papp AP to BL value (7.19 ± 0.31 × 10-6 cm/s) and the lowest ER (Papp BL to AP/Papp AP to BL) value of 0.17. In vitro antioxidative evaluation results revealed that 5e could protect against H2O2-induced PC12 cells' oxidative damage by attenuating mitochondrial membrane potential loss and decreasing H2O2-induced reactive oxygen species (ROS) production.

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.

Synthesis of scutellarein derivatives to increase biological activity and water solubility

In order to improve the biological activity and water solubility of scutellarin (1), some derivatives of its main metabolite (scutellarein) were designed and synthesized. All the compounds were tested for their thrombin inhibition activity through the analyzation of thrombin time (TT), activated partial thromboplastin time (APTT), prothrombin time (PT) 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, their water solubility were also assessed by ultraviolet (UV) spectrophotometer. The results showed that compound 8b demonstrated stronger anticoagulant and antioxidant activity, better water solubility compared with scutellarein (2), which warrants it as a promising agent for the treatment of ischemic cerebrovascular disease.

Efficient chemical synthesis of a scutellarein derivative containing morpholine ring

Scutellarin (1) [5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7- yl β-D-glucopyranosiduronic acid] is very effective in the clinical treatment of cerebral infarction and coronary heart disease in China. Pharmacokinetic studies showed that scutellarin (1) is readily metabolized to scutellarein (2) [5,6,7-trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one] in the intestine by β-glucuronide enzyme prior to absorption. In order to improve the biological activity of scutellarin (1), our group has previously synthesized many scutellarin derivatives based on their in vivo metabolic mechanism. The results showed that morpholine ring substituted at C-7 or C-8 position induced better antioxidant activity, water solubility and anticoagulant activity compared to scutellarin (1). In this paper, an efficient synthetic method for the construction of 5,6,7-trihydroxy-2-[4-[2-(4-morpholinyl)ethoxy] phenyl]-4H-1-benzopyran-4-one (5) is reported. This synthetic route will facilitate the synthesis of scutellarein derivatives containing an amine side chain at the C-4′ position.