1157-39-7

Usage

Uses

Used in Pharmaceutical Applications:
4',7-Dimethoxyisoflavone is used as an antifungal agent for its ability to inhibit fungal growth, making it a potential candidate for treating fungal infections.
4',7-Dimethoxyisoflavone is used as an anticancer agent for its in vitro demonstrated inhibition of cancer cell proliferation, offering potential therapeutic benefits in cancer treatment.
4',7-Dimethoxyisoflavone is used as an enzyme inhibitor for its capacity to inhibit the activity of a-ring hydroxylase and epoxide hydrolase, which may have implications in various therapeutic applications.
Used in Research and Development:
4',7-Dimethoxyisoflavone is used as a research compound for studying its interactions with cytochrome P450 enzymes and the effects of inhibitors like bosentan on its metabolism and formation rate, contributing to the understanding of its pharmacological properties and potential applications in drug development.

in vitro

4',7-Dimethoxyisoflavone shows antifungal activity against some plant pathogenic fungi tested in vitro, and the sensitivity of different fungi to this chemical varied considerably.

Upstream product

• 15236-11-0 4',7-dimethoxyisoflavanone 
• 25369-54-4 1-(2-Hydroxy-4-methoxy-phenyl)-3,3-dimethoxy-2-(4-methoxy-phenyl)-propan-1-one 
• 2198-19-8 2'-hydroxy-4,4'-dimethoxychalcone 
• 130322-26-8 (-)-(αR,βS)-4,4'-dimethoxy-2'-O-methoxymethylchalcone epoxide 
• 186581-53-3 diazomethane 
• 74-88-4 methyl iodide 
• 25826-69-1 4',7-dimethoxyflavanone 
• 546-67-8 lead(IV) tetraacetate 
• 64-19-7 acetic acid 
• 39604-64-3 1-(2-hydroxy-4-methoxyphenyl)-2-(4-methoxyphenyl)ethanone 
• 109-94-4 formic acid ethyl ester 
• 68-12-2 N,N-dimethyl-formamide 
• 486-66-8 daidzein 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 39604-64-3 1-(2-hydroxy-4-methoxyphenyl)-2-(4-methoxyphenyl)ethanone 
• 486-66-8 daidzein 
• 4308-53-6 7-methoxy-3-(4-methoxyphenyl)-2H-chromene 
• 486-63-5 isoformononetin 
• 4366-35-2 4',7-dimethoxyisoflavan 
• 15236-11-0 4',7-dimethoxyisoflavanone 
• 1179998-12-9 2-(2-hydroxy-4-methoxyphenyl)-3-(4-methoxyphenyl)-pyrimido[1,2-a]benzimidazole 
• 1232561-83-9 6-(4-methoxyphenyl)-7-(2-hydroxy-4-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyrimidine 
• 1232562-04-7 3-hydroxy-6-(4-methoxyphenyl)-7-(2-hydroxy-4-methoxyphenyl)-[1,2,4]triazolo[4,3-a]pyrimidine 
• 1225387-37-0 6-(4-methoxyphenyl)-7-(2-hydroxy-4-methoxyphenyl)pyrazolo[1,5-a]pyrimidine 
• 1357294-43-9 5-(2-hydroxy-4-methoxyphenyl)-6-(4-methoxyphenyl)imidazo[1,2-a]pyrimidine 
• 1456626-71-3 3-cyano-6-(2-hydroxy-4-methoxyphenyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one 
• 117375-28-7 8-bromo-4′,7-dimethoxyisoflavone 
• 75187-63-2 8-hydroxydaidzein 

Relevant academic research and scientific papers

Daidzein as an antioxidant of lipid: Effects of the microenvironment in relation to chemical structure

Isoflavone daidzein (D, pKa1 = 7.47 ± 0.02 and pK a2 = 9.65 ± 0.07) was, through a study of the parent compound and its three methyl anisol derivatives 7-methyldaidzein (7-Me-D, pKa = 9.89 ± 0.05), 4'-methyldaidzein (4'-Me-D, pKa = 7.43 ± 0.03), and 7,4'-dimethyldaidzein (7,4'-diMe-D), found to retard lipid oxidation in liposomal membranes through two mechanisms: (i) radical scavenging for which the 4'-OH was more effective than the 7-OH group in agreement with the oxidation potentials: 0.69 V for 4'-OH and 0.92 V for 7-OH versus Ag/AgCl in acidic solution and 0.44 V for 4'-O- and 0.49 V for 7-O- in alkaline solution and (ii) change in membrane fluidity through incorporation of the isoflavones, in effect hampering radical mobility. The radical scavenging efficiency measured by the rate of the reaction with the ABTS?+ in aqueous solution followed the order D > 7-Me-D > 4'-Me-D > 7,4'-diMe-D, as also found for antioxidant efficiency in liposomes when oxidation was initiated with the water-soluble AAPH radical and monitored as the formation of conjugate dienes. For oxidation initiated by the lipid-soluble AMVN radical, the antioxidant efficiency was ranked as 4'-Me-D > D > 7,4'-diMe-D > 7-Me-D, and change in fluorescence anisotropy of fluorescent probes bound to the membrane surface or inside the lipid bilayer confirmed the effects of isoflavones on the membrane fluidity, especially for 7,4'-diMe-D.

Hydrogen bonds and π-π stacking interaction in 4′, 7-dimethoxylisoflavone and 4′,7-diacetyl-O-isoflavone

4′,7-dimethoxylisoflavone, C17H14O4, (I), is linked into a supramolecular structure by a variety of weak but direction-specific intermolecular forces, the molecules are linked into chains through C-H...O hydrogen bonds, th

ISOFLAVONE O-METHYLTRANSFERASE ACTIVITIES IN ELICITOR-TREATED CELL SUSPENSION CULTURES OF MEDICAGO SATIVA

Treatment of alfalfa cell suspension cultures with elicitor preparations from baker's yeast or from cell walls of Colletotrichum lindemuthianum resulted in a ca 200-fold induction of isoflavone O-methyltransferase (IOMT) activity.The elicited cultures contained O-methyltransferase activity against isoflavone, isoflavan and pterocarpan substrates.These activities could be separated into two distinct fractions by ion-exchange chromatography.The major IOMT activity (IOMT II) was purified to homogeneity by a combination of anion exchange chromatography, hydrophobic interaction chromatography and chromatofocussing.It is a monomeric enzyme of subunit Mr 41000 which could be photoaffinity labelled with tritiated SAM.IOMT II converted the isoflavone daidzein to its 7-O-methyl ether isoformononetin, with Km values of 20 μM for daidzein and 150 μM for SAM and a pH optimum of 8.5.Both IOMT II and the less abundant IOMT species (IOMT I) exhibited greatest activity with 6,7,4'-trihydroxyisoflavone as methyl acceptor.IOMT I, but not IOMT II, also catalysed the A-ring methylation of the pterocarpan phytoalexin medicarpin.Isoflavone 4'-OMT activity, which is believed necessary for the formation of the B-ring methoxy substituent of medicarpin, was present at very low activity in extracts from the cultures and was only weakly induced by elicitor.Key Word Index - Medicago sativa; Leguminosae; isoflavone 7-O-methyltransferase; phytoalexin biosynthesis

Synthesis of isoflavones via base catalysed condensation reaction of deoxybenzoin

Base catalysed condensation reaction of o-hydroxyl-α- phenylacetophenones with formyl reagents affords various substituted isoflavones. Many bases were tested in the condensation reaction and DMAP was found to be the most effective catalysis.

An efficient synthesis of daidzein, dimethyldaidzein, and isoformononetin

Synthesis of the soy isoflavone, daidzein, and its derivatives, isoformononetin and dimethyldaidzein, through utilization of a novel synthetic pathway is reported. This synthesis employs an enamine addition and O-methylation of 2,4-dihydroxyacetophenone, a subsequent ring closure and iodination, followed by a Suzuki coupling with PEG 10000. Demethylation of either isoformononetin or dimethyldaidzein afforded daidzein.

Synthesis of isoflavones from 2′-hydroxychalcones using poly[4-(diacetoxy)iodo]styrene or related hypervalent iodine reagent

Isoflavones are synthesized in an one-pot reaction by treating the hypervalent iodine(III) reagent, [hydroxy(tosyloxy)iodo]benzene (HTIB, Koser's reagent) with 2′-benzoyloxychalcones in MeOH. A combined use of (diacetoxyiodo)benzene (DIB)/p-toluenesulfoni

Enantioselective Synthesis of Isoflavanones and Pterocarpans through a RuII-Catalyzed ATH-DKR of Isoflavones

Noyori-Ikariya RuII complexes promoted the one-pot C=C/C=O bonds reduction of isoflavones using sodium formate as the hydrogen source through Asymmetric Transfer Hydrogenation-Dynamic Kinetic Resolution (ATH-DKR). Due to the neutral conditions employed, isoflavones with different substituents at the 2’-position of B-ring (H, OH, OMe and Br) were successfully reduced. Ten cis-3-phenylchroman-4-ols were selectively obtained (>20 : 1 dr) in good yields (up to 86 %) and excellent enantioselectivities (up to >99 : 1 er). The synthetic applications of these chiral compounds were also demonstrated. Enantioenriched isoflavanones were obtained under mild metal-free oxidation of the cis-3-phenylchroman-4-ols while pterocarpans were synthesized by two strategies: an acid-catalyzed cyclization and a novel approach based on a Pd-catalyzed C?O intramolecular cross-coupling reaction.

Stille coupling for the synthesis of isoflavones by a reusable palladium catalyst in water

Isoflavones were synthesized from the reaction of 3-bromochromone derivatives and aryltributylstannanes via Stille coupling catalyzed by a water-soluble and reusable PdCl2(NH3)2/2,2′-cationic bipyridyl system in aqueous solution. For prototype 3-bromochromone, the coupling reaction was performed at 80°C for 24 hr with 2.5 mol% catalyst in water in the presence of tetrabutylammonium fluoride. After the reaction, the aqueous solution could be reused for several runs, indicating that its activity was only slightly decreased. For substituted 3-bromochromones, the addition of NaHCO3 and a higher reaction temperature (120°C) were required to gain satisfactory outcomes. In addition, naturally occurring products, such as daidzein, could be obtained by this protocol via a one-pot reaction.

Synthetic method of polyhydroxy isoflavone

The invention discloses a synthetic method of polyhydroxy isoflavone. The method comprises the following steps: (1) reacting 4', 7-dimethoxyisoflavone with N-bromosuccinimide, and controlling the molar ratio of 4', 7-dimethoxyisoflavone to N-bromosuccinimide and a reaction temperature to enable one or two hydrogen atoms on a 4', 7-dimethoxyisoflavone carbon ring to be substituted by bromine atomsto generate corresponding bromide; (2), enabling the bromide in the (2) to react with sodium methoxide under the action of cuprous salt to enable bromine atoms on a carbon ring of the bromide to be substituted by methoxy to obtain a methoxylation product; and (3), carrying out a demethylation reaction on the methoxylation product obtained in the (3) under the action of aluminum chloride and dimethyl sulfide to obtain polyhydroxy isoflavone. The method has the advantages of abundant sources of initial raw materials, mild reaction conditions, good selectivity and high yield, and is suitable forindustrial production. The purity of the product is greater than 99.0%, and the product can be used for pharmacological activity research.

Synthesis method of 3 ', 4', 7-trihydroxy isoflavone

The invention discloses a synthesis method of 3', 4', 7-trihydroxy isoflavone. The method comprises the steps that 4', 7-dimethoxyisoflavone and bromine are subjected to a mixed reaction in a dichloromethane medium to obtain 3'-bromo-4 ', 7-dimethoxyisoflavone, wherein the molar ratio of 4', 7-dimethoxyisoflavone to bromine is 1: 1.1-1.5, and the reaction temperature is 20-30 DEG C; the 3'-bromo-4', 7-dimethoxyisoflavone reacts with sodium methoxide under the action of cuprous salt to obtain 3', 4', 7-trimethoxyisoflavone; and the 3', 4', 7-trimethoxyisoflavone is demethylated to obtain the 3', 4', 7-trihydroxy isoflavone. Compared with the prior art, the method has the advantages of abundant sources of initial raw materials, mild reaction conditions, high selectivity and high yield, and is suitable for industrial production.