3420-72-2

Usage

Uses

Used in Pharmaceutical Industry:
2'-HYDROXY-4,4',6'-TRIMETHOXYCHALCONE is used as an intermediate compound for the synthesis of other bioactive molecules. It serves as a key building block in the production of various pharmaceutical compounds, such as 2′,2”′-dihydroxy-4,4′,4′′,4”′,6′,6′′′-hexamethoxy[5′,5′′′]bichalcone and 3′-bromo-4,4′,6′-trimethoxy-2′-hydroxychalcone. These synthesized compounds may exhibit various therapeutic properties, making them valuable in the development of new drugs and treatments.
Used in Chemical Industry:
In the chemical industry, 2'-HYDROXY-4,4',6'-TRIMETHOXYCHALCONE can be utilized as a starting material for the synthesis of a wide range of chemical products, including dyes, pigments, and other specialty chemicals. Its unique structural features make it a versatile compound for various chemical reactions and applications.

Upstream product

• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 123-11-5 4-methoxy-benzaldehyde 
• 62014-87-3 helichrysetin 
• 74-88-4 methyl iodide 
• 621-23-8 1,2,3-trimethoxybenzene 
• 34446-64-5 (E)-3-(4-methoxyphenyl)propenoyl chloride 
• 94103-36-3 (2E)-1-(2,4,6-trimethoxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one 
• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 77-78-1 dimethyl sulfate 
• 871878-99-8 1-(2,4-dimethoxyphenyl)-2-hydroxyethanone 
• 108-73-6 3,5-dihydroxyphenol 
• 67-56-1 methanol 
• 100-52-7 benzaldehyde 
• 98-86-2 acetophenone 

Downstream Products

• 95931-35-4 (E)-1-(2-{3,5-Dimethoxy-2-[(E)-3-(4-methoxy-phenyl)-acryloyl]-phenoxymethoxy}-4,6-dimethoxy-phenyl)-3-(4-methoxy-phenyl)-propenone 
• 57290-97-8 2',2'''-dihydroxy-4,4',4'',4''',6',6'''-hexamethoxy<5',5'''>bichalcone 
• 1098-92-6 kaempferol 5,7,4'-trimethyl ether 
• 520-36-5 5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 
• 5128-44-9 5-hydroxy-7-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one 
• 29424-96-2 naringenin-4',7-dimethyl ether 
• 81148-82-5 5-acetoxy-7,4′-dimethoxyflavanone 
• 221257-06-3 7,4'-di-O-methylapigenin 5-O-1-β-xylopyranosyl(1->6)-β-glucopyranoside 
• 66074-95-1 4',5,7-trimethoxyflavanone 
• 95931-34-3 2,5-Dihydro-6,8-dimethoxy-3-(4'-methoxyphenyl)-1-benzoxepin 
• 95931-35-4 Bis(4,4',6'-trimethoxy-2'-chalconoxy)methane 
• 10493-04-6 2-(4'-methoxybenzylidene)-4,6-dimethoxycoumaran-3-one 
• 5631-70-9 4',5,7-trimethoxyflavone 
• 3791-75-1 2'-hydroxy-4,4',6'-trimethoxydihydrochalcone 

Relevant academic research and scientific papers

Practical synthesis of naringenin

Two routes for the synthesis of the flavanone naringenin are described. In the first, 3,5-dimethoxyphenol is converted to 2-hydroxy- 4,6-dimethoxyacetophenone and then by condensation with anisaldehyde to 2′-hydroxy-4,4′,6′-trimethoxychalcone. The chalcone is then cyclised with aqueous hydrochloric acid and demethylated with pyridine hydrochloride to form naringenin in 45% overall yield. The condensation of 2-hydroxy-4,6-dimethoxyacetophenone with anisaldehyde could also directly produce 4′,5,7-trimethoxyflavanone, which was then converted into naringenin in 60% overall yield. In the second route, a single step for the preparation of the chalcone is used in which 1,3,5-trimethoxybenzene is acylated with p-methoxycinnamic acid. Although the synthesis of naringenin is achieved in a lower overall yield of 29%, the process is simpler.

Total synthesis of apigenin

An efficient method for the synthesis of apigenin (4',5,7- trihydroxyflavone, a traditional medicine) from phloroglucinol and anisaldehyde has been developed. This transformation features a green method for hydroxyl protection as methyl ethers and a different way for cyclisation using iodine in DMSO. The overall yield of 40% is satisfactory.

An improved synthesis of apigenin

Two routes for the synthesis of the flavone apigenin are described. In the first, taxicatigenin was converted to 2-hydroxy-4,6- dimethoxyacetophenone and then by condensation with anisaldehyde to 2′-hydroxy-4,4′,6′-trimethoxychalcone. The latter was cyclised with iodine and demethylated with pyridine hydrochloride to form apigenin in 53% overall yield. In the second route, a single step for the preparation of the chalcone was used in which 1,3,5-trimethoxybenzene was acylated with p-methoxycinnamic acid. Although the synthesis of apigenin was achieved in a lower overall yield of 34%, the process was simpler.

Insect antifeedant flavonoids from Gnaphalium affine D. Don

The antifeedant flavonoids, 5-hydroxy-3,6,7,8,4'-pentamethoxyflavone (1), 5-hydroxy-3,6,7,8-tetramethoxyflavone (2), 5,6-dihydroxy-3,7- dimethoxyflavone (3), and 4,4',6'-trihydroxy-2'-methoxychalcone (4), have been isolated from cudweed Gnaphalium affine D. Don (Compositae). Four natural flavonoids showed insect antifeedant activity against the common cutworm (Spodoptera litura F.). These flavonoids were detected in small amounts in the plant by HPLC analysis, but these natural compounds had strong antifeedant activity against the common cutworm. On the other hand, 4 was detected in a large amount in the plant, but this compound had only a slight activity. Therefore, these natural compounds were regarded as one of the plant's defensive systems against phytophagous insects along with the woolly plant surface. As for the structure-activity relationship, it is an advantage for antifeedant activity to have no oxy-substituents on the B-ring of the flavonoid but have an ether linkage such as a pyran in the chemical structure.

Flavokawain a induces apoptosis in MCF-7 and MDA-MB231 and inhibits the metastatic process in vitro

Introduction: The kava-kava plant (Piper methsyticum) is traditionally known as the pacific elixir by the pacific islanders for its role in a wide range of biological activities. The extract of the roots of this plant contains a variety of interesting mol

Application of human PCID2 protein in preparation or screening of anti-tumor drugs and compound with anti-tumor activity

The invention belongs to the technical field of biotechnology and gene therapy, and particularly relates to application of human PCID2 protein in preparation or screening of anti-tumor drugs and an anti-tumor compound. It is found that the PCID2 gene promotes tumor cell proliferation and regulates the cell cycle, is a key molecule for regulating tumor generation and development, and can be used as a target protein for preparing or screening anti-tumor drugs; meanwhile, human PCID2 protein is used as target protein, a class of PCID2 protein targeting antitumor compounds are screened out through a molecular docking technology, and the compounds can significantly inhibit tumor cell proliferation and promote tumor cell apoptosis.

Design, synthesis and biological evaluation of dimethyl cardamonin (DMC) derivatives as P-glycoprotein-mediated multidrug resistance reversal agents

Background: P-glycoprotein (P-gp) has been regarded as an important factor in the multidrug resistance (MDR) of tumor cells within the last decade, which can be solved by inhibiting P-gp to reverse MDR. Thus, it is an effective strategy to develop inhibitor of P-gp. Objective: In this study, the synthesis of a series of derivatives had been carried out by bioisosterism design on the basis of Dimethyl Cardamonin (DMC). Subsequently, we evaluated their reversal activities as potential P-glycoprotein (P-gp)-mediated Multidrug Resistance (MDR) agents. Methods: Dimethyl cardamonin derivatives were synthesized from acetophenones and the corresponding benzaldehydes in the presence of 40% KOH by Claisen-Schmidt reaction. Their cytotoxicity and reversal activities in vitro were assessed with MTT. Moreover, the compound B4 was evaluated by Doxorubicin (DOX) accumulation, Western blot and wound-healing assays deeply. Results and Discussion: The results showed that compounds B2, B4 and B6 had the potency of MDR reversers with little intrinsic cytotoxicity. Meanwhile, these compounds also demonstrated the capability to inhibit MCF-7 and MCF-7/DOX cells migration. Besides, the most compound B4 was selected for further study, which promoted the accumulation of DOX in MCF-7/DOX cells and inhibited the expressionof P-gp at protein levels. Conclusion: The above findings may provide new insights for the research and development of P-gp-mediated MDR reversal agents.

Development of a novel nitric oxide (NO) production inhibitor with potential therapeutic effect on chronic inflammation

Inflammation is a complex biological response to stimuli. Activated macrophages induced excessively release of pro-inflammatory cytokines and mediators such as endogenous radical nitric oxide (NO) play a significant role in the progression of multiple inflammatory diseases. Both natural and synthetic chalcones possess a wide range of bioactivities. In this work, thirty-nine chalcones and three related compounds, including several novel ones, based on bioactive kava chalcones were designed, synthesized and their inhibitory effects on NO production in RAW 264.7 cells were evaluated. The novel compound (E)-1-(2′-hydroxy-4′,6′-dimethoxyphenyl)-3-(3-methoxy-4-(3-morpholinopropoxy)phenyl)prop-2-en-1-one (53) exhibited a better inhibitory activity (84.0%) on NO production at 10 μM (IC50 = 6.4 μM) with the lowest cytotoxicity (IC50 > 80 μM) among the tested compounds. Besides, western blot analysis indicated that compound 53 was a potent down-regulator of inducible nitric oxide synthase (iNOS) protein. Docking study revealed that compound 53 also can dock into the active site of iNOS. Furthermore, at the dose of 10 mg/kg/day, compound 53 could both significantly suppress the progression of inflammation on collagen-induced arthritis (CIA) and adjuvant-induced arthritis (AIA) models. In addition, the structure-activity relationship (SAR) of the kava chalcones based analogs was also depicted.

Synthesis method of isolicoflavonol

The invention provides a synthesis method of isolicoflavonol, which comprises the following steps: carrying out condensation reaction on 2,4-O-R1(protective group, the same below)-6-hydroxyacetophenone and 4-O-R2(protective group, the same below)-benzaldehyde to generate 2',4'-O-R1-6'-hydroxy-4-O-R2-chalcone; oxidizing the chalcone to generate flavonol; carrying out selective protection on 3-OH ofthe flavonol to obtain 3,5,7-O-R1-4'-O-R2-flavonol; removing the protecting group R2 from the 3,5,7-O-R1-4'-O-R2-flavonol to obtain 3,5,7-O-R1-4'-hydroxyflavonol; carrying out 1,1-dimethylpropargyl reaction on the 4,4'-OH site to obtain 3,5,7-O-R1-4'-O-(1',1''-dimethyl propargyl)flavonol; carrying out partial hydrogenation on the alkynyl of the 3,5,7-O-R1-4'-O-(1',1''-dimethyl propargyl)flavonolunder the action of a catalyst to obtain 3,5,7-O-R1-4'-O-(1',1''-dimethylpropenyl)flavonol and carrying out Claisen rearrangement on the 3,5,7-O-R1-4'-O-(1',1''-dimethylpropenyl)flavonol to obtain 3,5,7-O-R1-isolicoflavonol, and removing the protecting group R1 from the 3,5,7-O-R1-isolicoflavonol to obtain the isolicoflavonol.

Attrition-enhanced deracemization and absolute asymmetric synthesis of flavanones from prochiral precursors

Seven racemic 5,7-dimethoxyflavanones afforded conglomerate crystals upon recrystallization from a solvent. Three methodologies were investigated to achieve asymmetric transformation based on dynamic crystallization of the chiral conglomerate system. The first was chiral symmetry breaking of racemic flavanones by attrition-enhanced deracemization. Continuous suspension of racemic flavanones in a small amount of propanol in the presence of a base (1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)) and glass beads promoted chiral symmetry breaking and converted the flavanones to crystals of (+)- or (-)-enantiomers with 78 to 99% ee. The second method involved cyclization of the intermediate aldol product to give optically active flavanone with 90% ee involving a reversible oxa-Michael addition reaction with attrition-enhanced deracemization. The third was a reaction starting from prochiral 2-hydroxy-4,6-dimethoxyacetophenone and 2-naphthaldehyde under basic conditions, which gave the corresponding flavanone in 89% ee.