3033-90-7

Upstream product

• 32267-16-6 1-(2,5-dimethoxyphenyl)-3-phenyl-prop-2-en-1-one 
• 102-92-1 cinnamoyl chloride 
• 150-78-7 1,4-dimethoxybezene 
• 705-15-7 1-(2-hydroxy-5-methoxyphenyl)ethan-1-one 
• 100-52-7 benzaldehyde 
• 22867-46-5 4'-methoxyphenyl cinnamate 
• 150-76-5 4-methoxy-phenol 
• 3034-04-6 6-methoxyflavanone 
• 67-63-0 isopropyl alcohol 
• 22867-46-5 (E)-4-methoxyphenyl cinnamate 
• 99430-02-1 4-methoxyphenyl 2,3-dibromo-3-phenylpropanoate 
• 102-92-1 Cinnamoyl chloride 
• 85630-18-8 N,N-diethyl-O-(4-methoxyphenyl)carbamate 

Downstream Products

• 26964-24-9 6-methoxyflavone 
• 22956-02-1 2-phenyl-6-methoxy-2H-benzopyran 
• 84963-03-1 6-methoxy-2-phenylchroman-4-one 
• 190831-06-2 6-methoxy-2-phenylchroman-4-one 
• 3034-04-6 6-methoxyflavanone 
• 93176-00-2 3-Hydroxy-6-methoxyflavone 
• 1266399-51-2 C₁₇H₁₇N₃O₃ 
• 1266399-40-9 8-methoxy-4-phenyl-4H-benzopyran[4,3-d][1,2,3]selenadiazole 
• 960505-51-5 (E)-4-methoxy-2-(3-phenylprop-2-enoyl)phenyl nonafluorobutanesulfonate 
• 38216-58-9 (Z)-2-benzylidene-5-methoxybenzofuran-3(2H)-one 
• 36941-04-5 2-(1-phenyl-1-propen-3-yl)-4-methoxyphenol 
• 138580-56-0 3-(2-hydroxy-5-methoxyphenyl)-5-phenylisoxazole 

Relevant academic research and scientific papers

Discovery of polymethoxyflavones as potential cyclooxygenase-2 (COX-2), 5-lipoxygenase (5-LOX) and phosphodiesterase 4B (PDE4B) inhibitors

Non-steroidal anti-inflammatory drugs (NSAIDs) are widely prescribed to treat inflammatory-related diseases, pain and fever. However, the prolong use of traditional NSAIDs leads to undesirable side effects such as gastric, ulceration, and renal toxicity due to lack of selectivity toward respective targets for COX-2, 5-LOX, and PDE4B. Thus, targeting multiple sites can reduce these adverse effects of the drugs and increase its potency. A series of methoxyflavones (F1–F5) were synthesized and investigated for their anti-inflammatory properties through molecular docking and inhibition assays. Among these flavones, only F2 exhibited selectivity toward COX-2 (Selectivity Index, SI: 3.90, COX-2 inhibition: 98.96 ± 1.47%) in comparison with celecoxib (SI: 7.54, COX-2 inhibition: 98.20 ± 2.55%). For PDEs, F3 possessed better selectivity to PDE4B (SI: 4.67) than rolipram (SI: 0.78). F5 had the best 5-LOX inhibitory activity among the flavones (33.65 ± 4.74%) but less than zileuton (90.81 ± 0.19%). Docking analysis indicated that the position of methoxy group and the substitution of halogen play role in determining the bioactivities of flavones. Interestingly, F1–F5 displayed favorable pharmacokinetic profiles and acceptable range of toxicity (IC50>70 μM) in cell lines with the exception for F1 (IC50: 16.02 ± 1.165 μM). This study generated valuable insight in designing new anti-inflammatory drug based on flavone scaffold. The newly synthesized flavones can be further developed as future therapeutic agents against inflammation.

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.

Flavanone-based fluorophores with aggregation-induced emission enhancement characteristics for mitochondria-imaging and zebrafish-imaging

Fluorophores with aggregation-induced emission enhancement (AIEE) characteristics applied in bioimaging have attracted more and more attention in recent years. In this work, a series of flavanone compounds with AIEE characteristics was developed and applied to fluorescence imaging of mitochondria and zebrafish. The compounds were readily prepared by the thermal dehydration of chalcone that was obtained by the reaction of o-hydroxyacetophenone and benzaldehyde. Two of these compounds showed significant AIEE characteristics by fluorescence performance experiments, including optical spectra, fluorescence spectra, fluorescence quantum yield (?F), fluorescence lifetime, and scanning electron microscopy (SEM). Compared with traditional organic fluorescent dyes, these compounds have high fluorescence emission and high fluorescence quantum yield in solid or aggregated state, which overcomes the shortcoming of aggregation-caused quenching (ACQ). More importantly, the two compounds exhibited low cytotoxicity and good cytocompatibility in A549 lung cells at the experimental concentration range and they specifically targeted mitochondria, which make it of great potential use in mitochondria labeling. In addition, they were embryonic membrane permeable and had different affinities for different tissues and organs of zebrafish, but mainly distributed in the digestive system, providing a basis for the application of such compounds in bioimaging. These AIEE compounds with superior properties could be of great potential use in mitochondria imaging and other in vivo studies.

From Carbamate to Chalcone: Consecutive Anionic Fries Rearrangement, Anionic Si → C Alkyl Rearrangement, and Claisen-Schmidt Condensation

A highly efficient one-pot procedure was developed for the synthesis of various 2′-hydroxychalcones from phenyl diethylcarbamate, featuring consecutive Snieckus-Fries rearrangement, anionic Si a?' C alkyl rearrangement, and Claisen-Schmidt condensation in a single operation. The applicability of this protocol was demonstrated by the highly efficient synthesis of the anti-inflammatory natural product lonchocarpin. The mechanism insight is also provided.

Enantioselective Halo-oxy- and Halo-azacyclizations Induced by Chiral Amidophosphate Catalysts and Halo-Lewis Acids

Catalytic enantioselective halocyclization of 2-alkenylphenols and enamides have been achieved through the use of chiral amidophosphate catalysts and halo-Lewis acids. Density functional theory calculations suggested that the Lewis basicity of the catalyst played an important role in the reactivity and enantioselectivity. The resulting chiral halogenated chromans can be transformed to α-Tocopherol, α-Tocotrienol, Daedalin A and Englitazone in short steps. Furthermore, a halogenated product with an unsaturated side chain may provide polycyclic adducts under radical cyclization conditions.

Exploring the anti-breast cancer potential of flavonoid analogs

In the course of our search for new antitumor agents for breast cancer, novel flavone derivatives were synthesized, characterized and examined for their antitumor activities against breast cancer cell lines. In initial screening, analogs 7a [3-(5-amino-1,3,4-thiadiazol-2-yl)methoxy-2-phenyl-4H-chromen-4-one] and 7b [3-(5-amino-1,3,4-thiadiazol-2-yl)methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one] were found to be effective against the estrogen receptor negative cell line (MDA-MB 453), which was followed by their evaluation in five dose assays. In addition, mechanistic studies of 7a and 7b were performed by cytometric analysis and electrophoretic studies and it was observed that apoptosis is a mechanism of cell death, confirmed morphologically by acridine orange/ethidium bromide double staining and TUNEL analysis. Further in vivo evaluation of the anti-tumor activity of compound 7a and 7b by Ehrlich Ascites Carcinoma (EAC) model and related studies confirms the anti-breast cancer potential of flavonoid analogs.

Impact of mono- and disubstitution on the colorimetric dynamic covalent switching chalcone/flavanone scaffold

The effect of aryl substitution on various aspects of the interconversion of ortho-hydroxychalcones and flavanones has been studied using multiple spectroscopic techniques. Derivatization of the core scaffold predictably alters the midpoint pH of this equilibration process suggesting its viability for application as a functional colorimetric molecular switch.

Pharmacophore model of the quercetin binding site of the SIRT6 protein

SIRT6 is a histone deacetylase that has been proposed as a potential therapeutic target for metabolic disorders and the prevention of age-associated diseases. We have previously reported on the identification of quercetin and vitexin as SIRT6 inhibitors,

Copper (II) chloride: A regioselective catalyst for oxidative aromatization of pyrazoline, isoxazoline and 3-methyl flavanones

A new protocol has been reported in which a series of pyrazoline, isoxazoline and 3-methyl flavanone has been conveniently aromatized by using CuCl2.2H2O in DMSO within a short reaction time in excellent yields. The attraction of this new protocol is regioselective aromatization of substrate 3i-j and 5a-e which has been carried out to afford the aromatized product with O-allyl group intact in excellent yield.

Towards a dynamic covalent molecular switch: Substituent effects in chalcone/flavanone isomerism

Chalcone/flavanone interconversion occurs facilely under aqueous alkaline conditions making it a promising scaffold for the development of a covalent molecular switch. In this study, a single methoxy substituent is shown to have a significant impact on the equilibrium dynamics of this reaction; this impact is dependent on the site of substitution. The Royal Society of Chemistry.