59887-91-1

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 5,7-diMethoxy-
• Synonyms: 4H-1-Benzopyran-4-one, 5,7-diMethoxy-
• CAS NO: 59887-91-1
• Molecular Formula: C₁₁H₁₀O₄
• Molecular Weight: 206.1947
• Mol File: 59887-91-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 5,7-diMethoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 5,7-diMethoxy-(59887-91-1)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 5,7-diMethoxy-(59887-91-1)

Safety Data

• Hazardous Substances Data: 59887-91-1(Hazardous Substances Data)

Upstream product

• 34818-77-4 7-benzyloxy-5-methoxy-chromen-4-one 
• 67-56-1 methanol 
• 54107-66-3 5,7-dimethoxy-4-chromanone 
• 61350-59-2 2.3-Dihydro-2-hydroxy-5.7-dimethoxy-chromon (II) 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 621-23-8 1,2,3-trimethoxybenzene 
• 4672-74-6 propiolic acid anhydride 
• 187877-87-8 3-dimethylamino-1-(2-hydroxy-4,6-dimethoxyphenyl)prop-2-en-1-one 
• 832-58-6 1-(2,4,6-trimethoxyphenyl)ethanone 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 829-20-9 2',4'-dimethoxyacetophenone 
• 109-94-4 formic acid ethyl ester 
• 500-99-2 3,5-dimethoxyphenol 
• 854678-45-8 β-(3,5-dimethoxyphenoxy)propionic acid 

Downstream Products

• 445388-25-0 3,4,5-tris-benzyloxy-benzoic acid 5,7-dimethoxy-chroman-3-yl ester 
• 1277188-85-8 (R)-2,3-dihydro-5,7-dimethoxy-2-phenyl-4H-1-benzopyran-4-one 
• 221385-53-1 5-hydroxy-7-methoxyflavonone 
• 480-37-5 pinostrobin 
• 1036-72-2 Pinocembrin dimethyl ether 
• 54107-66-3 5,7-dimethoxy-4-chromanone 
• 1392217-69-4 5,7-dimethoxy-3-(2′hydro-xybenzyl)-4-chromanone 
• 76672-84-9 3-benzyl-5,7-dimethoxychroman-4-one 
• 246244-10-0 rac-5,7-dimethoxy-3-(4-methoxybenzyl)-chroman-4-one 

Relevant articles and documents

The Antiangiogenic Activity of Naturally Occurring and Synthetic Homoisoflavonoids from the Hyacinthaceae (sensu APGII)

Excessive blood vessel formation in the eye is implicated in wet age-related macular degeneration, proliferative diabetic retinopathy, neovascular glaucoma, and retinopathy of prematurity, which are major causes of blindness. Small molecule antiangiogenic

Asymmetric Synthesis of Sakuranetin-Relevant Flavanones for the Identification of New Chiral Antifungal Leads

Discovery and efficient synthesis of new promising leads have a central role in agrochemical science. Reported herein is the sakuranetin-directed synergistic exploration of an asymmetric synthesis and an antifungal evaluation of chiral flavanones. A new palladium catalytic system with CarOx-type ligands was successfully identified for the highly enantioselective addition of arylboronic acids to chromones. This enabled the facile and programmable construction of a constellation of chiral flavanones (up to 98% yield and 97% ee), in which (R)-pinostrobin was efficiently constructed without laborious protecting/deprotecting operations. Its good performance in asymmetric induction and functional tolerance expanded the chemical space of pharmaceutically important flavanones. The chiral differentiation of flavanones based on antifungal activity and a concise structure-activity relationship model was disclosed and summarized. This synergistic project culminated with acquisition of the naturally unprecedented flavanones with better antifungal potentials than sakuranetin, in which the R-enantiomer of flavanone 54 (EC50 = 0.8 μM) demonstrated better performance than boscalid against Rhizoctonia solani. The novel scaffold and predicted new target compared with the commercial fungicides in the FRAC reinforce the value of further exploration.

The study on structure-activity relationship between chromone derivatives and inhibition of superoxide anion generating from human neutrophils

Over activation of neutrophils has been linked to many inflammatory diseases; one of critical pathologic mechanisms is that generation and exocellular release of superoxide anion from neutrophils results in peripheral tissues damage. Besides, in this study, 2-(3,5-dimethoxyphenoxy)-5,7-dimethoxy-chromen-4-one (4), a 2-phexnoychromone from our compound bank, was demonstrated to have the moderate inhibitory effect on superoxide anion generating. Therefore, serial chromones substituted with phenols or 3-flourothiophenol were designed, synthesized, and examined for suppression of superoxide anion generation. In accordance with the results, the methoxy group at 7 position (R3) of the chromone, as well as a hydrogen bond donor at a meta site of the phenyl ring greatly impacted on the activity. 2-(3-fluorophenyl)sulfanyl-7-methoxy-chromen-4-one (16), a successful example of bioisosteres from a phenol to a thiophenol, exhibited prominent anti-inflammatory effects with the IC50 value against superoxide anion generation of 5.0 ± 1.4 μM.

Synthetic method for portulacanone compounds and their derivatives and anti-inflammatory pharmaceutical compounds containing thereof

The present inventors synthesized described portulacanone derivatives (compound 1: R^1, R^2 = H; and compound 2: R^1, R^2 = H), natural homoisoflavonoids (andplusmn;)-portulacanone A-C (compound 4: R^1 = OMe, R^2 = H; compound 8: R^1, R^2 = OMe; and compound 9: R^1 = OH, R^2 = OMe), and derivatives thereof (compound 3: R^1 = OMe, R^2 = H; compound 5: R^1 = OH, R^2 = H, and compound 7: R^1, R^2 = OMe), and thus evaluated ability to inhibit NO production in LPS-induced RAW 264.7 macrophages as an indicator of anti-inflammatory activity. All tested compounds showed no clear cytotoxicity and inhibited NO production in a concentration dependent manner in RAW 264.7 macrophages. A compound 3 (97.2% inhibition at 10 andmu;M; IC50 = 1.26 andmu;M) shows a significant inhibition effect compared to a compound 1 (91.4% inhibition at 10 andmu;M; IC50 = 1.75 andmu;M) and a compound 7 (83.0% inhibition at 10 andmu;M; IC50 = 2.91 andmu;M). Compounds of the present invention are useful for developing NO producing targeted anti-inflammatory drugs.COPYRIGHT KIPO 2019

Synthetic method for portulacanone D and anti-inflammatory pharmaceutical compounds containing thereof

Inventors of the present invention synthesized natural homoisoflavonoid portulacanone D (compound 6) isolated from Portulaca oleracea L (POL). An ability to inhibit NO production in LPS-induced RAW 264.7 macrophages was assessed as an indicator of anti-inflammatory activity. The tested portulacanone D did not show clear cytotoxicity and inhibited NO production in the RAW 264.7 macrophages in a concentration dependent manner. The portulacanone D exhibits 92.5% of NO production inhibition at 10 andmu;M and has an IC50 value of 2.09 andmu;M. The finding has additional correlation with the suppressed expression of iNOS induced by LPS. According to the information obtained from the study of the present invention, the portulacanone D can be used in the development of anti-inflammatory drugs targeting NO production.COPYRIGHT KIPO 2019

Synthesis and in vitro evaluation of homoisoflavonoids as potent inhibitors of nitric oxide production in RAW-264.7 cells

Syntheses of natural homoisoflavonoids, (±)-portulacanones A–C (4, 8 and 9), portulacanone D (6), isolated from Portulaca oleracea L. (POL) and their derivatives (3, 5 and 7) have been achieved for the first time along with the synthesis of known derivatives (1 and 2) and their in vitro inhibitory effect against NO production in LPS-induced RAW-264.7 macrophages was evaluated as an indicator of anti-inflammatory activity. All the compounds tested had a concentration-dependent inhibitory effect on NO production by RAW-264.7 macrophages without obvious cytotoxicity. Compounds 3 (97.2% at 10 μM; IC50 = 1.26 μM) followed by 6 (portulacanone D) (92.5% at 10 μM; IC50 = 2.09 μM), 1 (91.4% at 10 μM; IC50 = 1.75 μM) and 7 (83.0% at 10 μM; IC50 = 2.91 μM) were the most potent from the series. This finding was further correlated with the suppressed expression of iNOS induced by LPS. Our promising preliminary results may provide the basis for the assessment of compound 3 as a lead structure for a NO production-targeted anti-inflammatory drug development and also could support the usefulness of POL as a folklore medicinal plant in the treatment of inflammatory diseases.

Novel homoisoflavanone derivatives, preparation method thereof, and pharmaceutical composition for use in preventing or treating ischemic brain damage and multiple sclerosis containing the same as an active ingredient

The present invention relates to: a homoisoflavanone compound; a manufacturing method thereof; and a pharmaceutical composition for preventing or treating ischemic brain damage and multiple sclerosis containing the homoisoflavanone compound as an active i

Natural products as sources of new fungicides (V): Design and synthesis of acetophenone derivatives against phytopathogenic fungi in vitro and in vivo

A series of acetophenone derivatives (10a–10i, 11, 12a–12g, 13a–13g, 14a–14d and 15a–15l) were designed, synthesized and evaluated for antifungal activities in vitro and in vivo. The antifungal activities of 53 compounds were tested against several plant pathogens, and their structure–activity relationship was summarized. Compounds 10a–10f displayed better antifungal effects than two reference fungicides. Interestingly, the most potent compound 10d exhibited antifungal properties against Cytospora sp., Botrytis cinerea, Magnaporthe grisea, with IC50 values of 6.0–22.6 μg/mL, especially Cytospora sp. (IC50 = 6.0 μg/mL). In the in vivo antifungal assays, 10d displayed the significant protective efficacy of 55.3% to Botrytis cinerea and 73.1% to Cytospora sp. The findings indicated that 10d may act as a potential pesticide lead compound that merits further investigation.

Highly enantioselective and efficient synthesis of flavanones including pinostrobin through the rhodium-catalyzed asymmetric 1,4-addition

An efficient synthesis of bioactive chiral flavanones (1) was achieved through the αh-catalyzed asymmetric 1,4-addition of arylboronic acid to chromone. The reaction in toluene proceeded smoothly at room temperature in the presence of 0.5% Rh catalyst with electron-poor chiral diphosphine MeO-F 12-BIPHEP. In this reaction, the 1,2-addition to (S)-1 frequently occurred to yield (2S,4α)-2,4-diaryl-4-chromanol as a byproduct, which could be reduced by changing the reaction solvent to CH2C 12 to deactivate the Rh catalyst (3% required).

Synthesis, and cyclization to aurones and flavones, of alkoxy-substituted aryl, arylalkynyl ketones

Acylation of 1,3,5-tribenzyloxybenzene with alkoxy-substituted phenylpropioloyl chlorides provides the corresponding aryl alkoxylarylalkynyl ketones in which one of the benzyl groups has been removed. Cyclization of these phenolic ketones using basic reagents (potassium carbonate in acetone is best) provides the corresponding aurone system. When the phenolic group of the alkynyl ketones is protected as the t-butyldimethylsilyl ether followed by cyclization, using 18-crown-6 and potassium fluoride, mixtures of the corresponding aurones and flavones are produced. A by-product from the formation of the ketones is the corresponding β-chlorochalcone, which can also be cyclized to an aurone product using basic conditions. Similarly, the t-butyldimethylsilyl ethers of the HCl adducts can also be cyclized to a mixture of the corresponding aurones and flavones. CSIRO 2008.