67858-30-4

Usage

InChI:InChI=1/C18H16O5/c1-20-16-8-11(9-17(21-2)18(16)22-3)15-10-13(19)12-6-4-5-7-14(12)23-15/h4-10H,1-3H3

Upstream product

• 67858-32-6 1-(2-hydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)propane-1,3-dione 
• 126432-36-8 2-(3′,4′,5′-trihydroxyphenyl)chromen-4-one (3′,4′,5′-trihydroxyflavone) 
• 77-78-1 dimethyl sulfate 
• 132018-03-2 3-(methoxycarbonyl)-2-(3,4,5-trimethoxyphenyl)-4H-benzopyran-4-one 
• 1413850-22-2 C₁₈H₁₈O₄ 
• 77295-62-6 1,1-Dibromo-2-(3',4',5'-trimethoxyphenyl)ethene 
• 90-02-8 salicylaldehyde 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 214360-67-5 4,4,5,5-tetramethyl-2-(3,4,5-trimethoxyphenyl)-1,3,2-dioxaborolane 
• 155721-23-6 5-(2-hydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)isoxazole 
• 533-58-4 2-Iodophenol 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 454482-66-7 3-bromo-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one 
• 5720-07-0 4-methoxyphenylboronic acid 

Downstream Products

• 155721-23-6 5-(2-hydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)isoxazole 
• 143468-23-9 3-Nitro-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one 
• 126432-36-8 2-(3′,4′,5′-trihydroxyphenyl)chromen-4-one (3′,4′,5′-trihydroxyflavone) 
• 1370734-52-3 3-(2-(biphenyl-4-yl)-2-oxoethyl)-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one 
• 1370734-47-6 3-(2-(4-chlorophenyl)-2-oxoethyl)-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one 
• 1370734-41-0 ethyl 2?(4?oxo?2?(3,4,5?trimethoxyphenyl)?4H?chromen?3?yl)acetate 
• 454482-66-7 3-bromo-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one 

Relevant academic research and scientific papers

Synthesis, biological evaluation, and NMR studies of 3-fluorinated derivatives of 3′,4′,5′-trihydroxyflavone and 3′,4′,5′-trimethoxyflavone

Flavones are valuable scaffolds in medicinal chemistry, especially as they display activity as antioxidants and neuroprotective agents. The need to incorporate a fluorine atom on flavones has driven much of the recent synthetic work in this area. We now r

A novel one-pot synthesis of flavones

In this paper, a one-pot facile route for the BiCl3/RuCl3-mediated synthesis of functionalized flavones is described, including: (i) intermolecularortho-acylation of substituted phenols with cinnamoyl chlorides, and (ii) intramolecular cyclodehydrogenation of the resultingo-hydroxychalcones. The reaction conditions are discussed herein.

Divergent synthesis of flavones and flavanones from 2′-hydroxydihydrochalconesviapalladium(ii)-catalyzed oxidative cyclization

Divergent and versatile synthetic routes to flavones and flavanonesviaefficient Pd(ii) catalysis are disclosed. These Pd(ii) catalyses expediently provide a variety of flavones and flavanones from 2′-hydroxydihydrochalcones as common intermediates, depending on oxidants and additives,viadiscriminate oxidative cyclization sequences involving dehydrogenation, respectively, in a highly atom-economic manner.

Identification of 3′,4′,5′-trihydroxyflavone as an mammalian target of rapamycin inhibitor and its suppressive effects on dextran sulfate sodium-induced ulcerative colitis

Flavone derivatives have been shown to possess anti-inflammatory properties in various inflammation model systems; however, their underlying molecular mechanisms remain elusive. In this study, a flavone derivative 3′,4′,5′-trihydroxyflavone (THF; NJK16003) was synthesized, and its anti-inflammatory effects and molecular targets were investigated using in vitro systems and an in vivo colitis model. NJK16003 showed potent anti-inflammatory activities in cell-based assays using macrophages. In vitro enzyme activity assays using various inflammation-related kinases revealed the mammalian target of rapamycin (mTOR) as a possible molecular target. Treatment of RAW264.7 cells with NJK16003 resulted in an increase in light chain 3B protein lipidation and a decrease in p62 protein levels and ribosomal S6 kinase phosphorylation, indicating that NJK16003 induces autophagy through mTOR inhibition. NJK16003 treatment resulted in significant induction of autophagy and suppression of inflammatory responses in intestinal epithelial cells. Autophagy induction has been shown to alleviate colitis by suppressing inflammatory responses and apoptotic cell death of intestinal epithelial cells. Indeed, inflammatory responses and intestinal epithelial cell death in our DSS-induced colitis mouse model were significantly suppressed by NJK16003 treatment. Our results indicate that NJK16003 could suppress inflammation by inducing autophagy through its mTOR inhibitory activity. These results suggest that NJK16003 could be a possible therapeutic agent for the treatment of inflammatory bowel diseases including colitis.

Rh-Catalyzed aldehydic C-H alkynylation and annulation

Novel Rh-catalyzed aldehydic C-H bond alkynylation and annulation for the in situ synthesis of chromones and aurones are described. It involves the sequential aldehyde C-H bond alkynylation of salicylaldehyde with in situ generated 1-bromoalkyne from 1,1-

Water-mediated phosphorylative cyclodehydrogenation: An efficient preparation of flavones and flavanones

A new synthetic strategy utilizing POCl3-water for the conversion of 2′-hydroxychalcones to flavanones and flavones has been developed. The reagent efficiently promoted one-pot conversion of 2′-hydroxychalcones to flavones through flavanones involving cyclization and oxidative dehydrogenation. By changing the stoichiometery of the reagents, the reaction can be tuned to generate either flavanone or flavone. The developed protocol was found to be applicable for a variety of 2′-hydroxychalcones.

Regioselective hydrodehalogenation of aromatic α-and β-halo carbonyl compounds by cui in isopropanol

An operationally efficient and regioselective hydrodehalogenation methodology of aromatic α-and β-halo carbonyl compounds has been developed using CuI in isopropanol at 90 °C under basic condition. The catalytic system effectively dehalogenates chloride, bromide, and iodide groups and af-forded high yield (up to 97 %) as carbonyl compounds. The methodology is environmentally friendly and demonstrates excellent tolerance to a broad range of electronically rich and poor substituents.

Design, synthesis and biological evaluation of 2-Phenyl-4H-chromen-4-one derivatives as polyfunctional compounds against Alzheimer’s disease

Polyfunctional compounds comprise a novel class of therapeutic agents for the treatment of multi-factorial diseases. A series of 2-Phenyl-4H-chromen-4-one and its derivatives (5a–n) were designed, synthesized, and evaluated for their poly-functionality against acetylcholinestrase (AChE) and advanced glycation end products (AGEs) formation inhibitors against Alzheimer’s disease (AD). The screening results showed that most of them exhibited a significant ability to inhibit AChE AGEs formation with additional radical scavenging activity. Especially, 5m, 5b, and 5j displayed the greatest ability to inhibit AChE (IC50 = 8.0, 8.2, and 11.8 nM, respectively) and AGEs formation (IC50 = 55, 79, and 54 μM, respectively) with good antioxidant activity. Molecular docking studies explored the detailed interaction pattern with active, peripheral, and mid-gorge sites of AChE. These compounds, exhibiting such multiple pharmacological activities, can be further taken a lead for the development of potent drugs for the treatment of Alzheimer’s disease.

Novel and Efficient Access to Flavones under Mild Conditions: Aqueous HI-Mediated Cascade Cyclization/Oxidative Radical Reaction of 2-Propynolphenols

Herein we disclose a metal-free and efficient method for the direct conversion of 2-propynolphenols to biologically important flavones using aqueous HI as the promoter. This transformation was proved via 4-iodo-2H-chromenes intermediate, which was simultaneously conversed to corresponding flavones by a Csp2?I bond cleavage and a C–O bond formation under air.

Synthesis, antiproliferative and pro-apoptotic effects of nitrostyrenes and related compounds in Burkitt’s lymphoma

Background: Cancers of the lymphatic cells (lymphomas) account for approximately 12% of malignant diseases worldwide. The nitrostyrene scaffold is identified as a lead target structure for the development of particularly effective compounds targeting Burkitt’s lymphoma (BL). Objectives: The aims of the curent study were to synthesise a panel of nitrostyrene compounds and to evaluate their activity in Burkitt’s lymphoma (BL). Methods: A panel of structurally varied compounds were designed and synthesised using Henry Knoevenagel condensation reactions. Single crystal X-Ray analysis confirmed the E configuration for six examples of these novel structures. A number of nitrostyrene-related compounds were also investigated including 1,3-bis(aryl)-2-nitropropenes together with heterocyclic scaffolds containing the nitrovinyl pharmacophore such as 3-nitro-2-phenyl-2H-chromenes. The antiproliferative activities of the compounds were evaluated using the BL cell lines EBV- MUTU-1 and EBV+ DG-75 (chemoresistant) to establish preliminary structure-activity relationships. Results: Lead compounds with optimized nitrostyrene scaffolds and 3-nitro-2-phenyl-2Hchromene structures were successfully established with typical IC50 values of 0.45 μM and 0.47 μM in MUTU-1 cells and 1.41 μM and 1.92 μM, respectively, in DG-75 cells. The mechanism of cell death was identified as apoptotic and the lead compound was found to elicit comparable apoptotic effects to Taxol in Burkitt’s lymphoma cell lines MUTU-1 and DG-75. Conclusion: This class of pharmaceutically active compounds with potential for the treatment of Burkitt’s lymphoma suggest a potential role for nitrostyrene based agents in chemotherapy.