66922-84-7

Upstream product

• 131944-44-0 1-(3,4,5-trimethoxyphenyl)-3-(2,4-dihydroxyphenyl)propane-1,3-dione 
• 755722-84-0 imine 
• 108132-06-5 1-(2,4-dihydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 
• 108-46-3 recorcinol 
• 25015-92-3 2-chloro-1-(2,4-dihydroxyphenyl)ethanone 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 118-41-2 Eudesmic acid 
• 155721-24-7 5-(2,4-dihydroxyphenyl)-3-(3,4,5-trimethoxyphenyl)isoxazole 
• 41046-68-8 4-iodobenzene-1,3-diol 
• 3044-56-2 ethyl trimethoxybenzoyl acetate 
• 4521-61-3 3,4,5-Trimethoxybenzoyl chloride 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 

Downstream Products

• 883242-57-7 7-(2,3-epoxypropoxy)-3',4',5'-trimethoxyflavone 
• 3044-57-3 7-methoxy-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one 
• 883242-81-7 7-(2-bromoethoxy)-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one 
• 883242-82-8 7-(3-bromopropoxy)-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one 

Relevant academic research and scientific papers

Design, synthesis, and preliminary biological evaluation of 3′,4′,5′-trimethoxy flavonoid salicylate derivatives as potential anti-tumor agents

According to the pharmacophore combination principle, a set of new 3′,4′,5′-trimethoxy flavonoid salicylate derivatives were designed, synthesized, and evaluated for biological activity. The cytotoxicity evaluation revealed that compound 10v exhibited higher potency than 5-Fu against HCT-116 cells. Preliminary biological activity studies showed that compound 10v could inhibit the colony formation and migration of HCT-116 cells. Besides, the Hoechst 33258 staining assay and flow cytometry revealed that treatment with compound 10v induced the apoptosis of HCT-116 cells in a concentration-dependent manner, while it had no effect on their cell cycle. The WB analysis suggested that HIF-1α, tubulin, HK-2, and PFK might be the potential pharmacophore targets of compound 10v. Tubulin was a potential drug target for compound 10v, which was explained by analyzing the crystal structure of compound 10v complexed with tubulin. These results indicated that compound 10v might be a promising anti-tumor agent candidate, deserving further optimization and evaluation.

A three-methoxy flavone salicylic acid derivatives and its anti-tumor activity (by machine translation)

The invention discloses a three-methoxy flavone salicylic acid derivatives, can be used as a tumor blood vessel and tumor cell glycolysis double-target inhibitors, in order to block the tumor tissue has generated the blood vessel, in order to block tumor cell nutrient supply, at the same time inhibiting glycolysis process of tumor cells, tumor cells in the absence of nutrition, also cannot use their own glycolysis proliferate, thereby accelerating the death of tumor cells. The design of this invention is of tumor blood vessel with the glycolysis double-target inhibitor has the role of both, but than the combined medication safer and more convenient. (by machine translation)

Design, synthesis and biological evaluation of 3′,4′,5′-trimethoxy flavonoid benzimidazole derivatives as potential anti-tumor agents

A series of 3′,4′,5′-trimethoxy flavonoids with benzimidazole linked by different chain alkanes have been designed and synthesized. The potential activity of these compounds as anti-tumor agents was evaluated by cytotoxicity assay in MGC-803 (human gastri

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.

Flavonoids, 45 . A General and Efficient Synthesis of Hydroxyflavones and -chromones

An efficient and versatile method for the synthesis of flavones hydroxylated in either ring A or B and of chromones hydroxylated in is described.This approach is based on the acidic resin-promoted cyclodehydration and simultaneous deprotection of methoxymethoxylated 1-(2-hydroxyphenyl)propane-1,3-diones easily available by either the Baker-Venkataraman rearrangement or the Claisen condensation. - Key words: Amberlyst 15 / Baker-Venkataraman rearrangement / Claisen condensation / hydroxychromone / hydroxyflavone / methoxymethyl protection

Synthesis of Flavones via Application of the Nitrile Oxide and the Stille Reactions

Hydroxylated and methoxylated benzaldehyde oximes have been chlorinated, dehydrohalogenated and cycloadded to tributylstannylacetylene to give 3-aryl-5-tributylstannylisoxazoles in good to excellent yields.The palladium-catalyzed coupling reaction, the so-called Stille reaction, of hindered and electron-rich 2-iodophenols and a 2-iodo-1,4-benzoquinone with 3-aryl-5-tributylstannyl-isoxazoles gave 3-aryl-5-(2-hydroxyaryl)isoxazoles in moderate to excellent yields.The coupling reaction was studied under various conditions and with various Pd(II) and Pd(0) complexes.Reduction of the 3,5-diarylisoxazoles with H2/Raney-Ni, hydrolysis and acid-catalyzed cyclisation gave flavones.The synthesis of 2-iodo-3,5-dimethoxy-1,4-benzoquinone is described.