32274-71-8

Upstream product

• 115123-09-6 (R)-2-(4-β-D-glucopyranosyloxy-phenyl)-7-methoxy-chroman-4-one 
• 63529-06-6 4,2'-dihydroxy-4'-methoxy-trans-chalcone 
• 115123-09-6 (S)-2-(4-β-D-glucopyranosyloxy-phenyl)-7-methoxy-chroman-4-one 
• 23423-35-0 (E)‐3‐(4‐hydroxyphenyl)‐1‐(2,4‐dimethoxyphenyl)prop‐2‐en‐1‐one 
• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 
• 123-08-0 4-hydroxy-benzaldehyde 
• 74189-56-3 4-(tetrahydropyran-2-yloxy)benzaldehyde 
• 6515-21-5 4-methoxymethoxy-benzaldehyde 
• 1314539-19-9 2'-hydroxyl-4'-methoxy-4-methoxymethoxychalcone 
• 551-15-5 liquiritin(sh) 
• 651325-79-0 Acetic acid 4-[(E)-3-(2,4-dimethoxy-phenyl)-3-oxo-propenyl]-phenyl ester 
• 651325-80-3 3-bromo-1-(2,4-dimethoxy-phenyl)-propan-1-one 
• 151-10-0 1,3-Dimethoxybenzene 
• 33527-94-5 4-acetoxyiodobenzene 

Downstream Products

• 109600-77-3 7-methoxy-2-(4-sulfooxy-phenyl)-chroman-4-one 
• 6954-53-6 3,4'-Bis-benzyloxystilben 
• 919112-04-2 4-{4-[bis-(4-methoxy-phenyl)-methylene]-7-methoxy-chroman-2-yl}-phenol 
• 10019-24-6 1,1,2,2-tetrakis(4-methoxyphenyl)ethene 
• 4705-34-4 4,4'-dimethoxystilbene 

Relevant academic research and scientific papers

Design, Synthesis, and Structure–Activity Relationships of Bavachinin Analogues as Peroxisome Proliferator-Activated Receptor γ Agonists

Peroxisome proliferator-activated receptor γ (PPARγ) agonists have been used for the treatment of diabetes with the effect of lowering blood glucose levels and improving insulin sensitivity. Natural compounds such as flavones, flavanones, and isoflavones

Rapid synthesis of 4-benzylidene and 4-[bis-(4-methoxyphenyl)-methylene-2-substituted phenyl-benzopyrans as potential selective estrogen receptor modulators (SERMs) using McMurry coupling reaction

7-Methoxy-4-(4-methoxybenzylidene)-2-substituted phenyl-benzopyrans I and 4-[bis-(4-methoxyphenyl)-methylene-2-substituted phenyl-benzopyrans II carrying different alkylamino residues, designed as estrogen receptor (ER) binding ligands, were successfully synthesized through the McMurry coupling reaction of substituted benzaldehyde/substituted benzophenones and 2-hydroxyphenyl-7-methoxy-chroman-4-one in presence of lithium aluminum hydride and titanium (IV) chloride (LAH-TiCl4). Self-coupling of carbonyl reactants led to the formation of several side products. The prototypes were evaluated for their relative binding affinity (RBA), as well as their estrogenic and antiestrogenic activities. High order of estrogenic activity (>50% gain) observed with compounds 3, 7a, 7b, 7c, 8, and 10a and also their partial estrogen antagonistic activity (≥15%) at the uterine level points toward successful designing of the compounds. Compounds 4, 7a, 7b, 7c, and 10a also possessed significant anticancer activity against human adenocarcinoma cell line (MCF-7 cell line) that may be related to their estrogen-dependent action.

A new synthesis of flavonoids via Heck reaction

Several naturally occuring flavonoids have been synthesised following a new proposed method based on the use of the Heck reaction. The key step involves the coupling of an aryl vinyl ketone with an aryl iodide. This procedure affords the flavonoid moiety in a single step.

Synthesis and aromatase inhibitory activity of flavanones

Purpose. Aromatase inhibitors are known to prevent the conversion of androgens to estrogens and play a significant role in the treatment of estrogen dependent diseases such as breast cancer. Some flavonoids have been reported as potent aromatase inhibitors; therefore, in an effort to develop novel anti breast cancer agents, B ring substituted flavanones with a 7-methoxy group on A ring were synthesized and tested to assess their ability to inhibit aromatase activity and to determine the optimal B ring substitution pattern. Methods. A series of flavanones was prepared by cyclisation of 2′hydroxychalcones previously obtained by Claisen-Schmidt condensation and the aromatase inhibitory activity of these compounds was investigated using human placental microsomes and radiolabeled [1,2,6,7-3H]-androstenedione as substrate. Results. Almost all flavanones exhibited inhibitory effect on the aromatase activity but their potency was dependent on their B ring substitution pattern. Hydroxylation at position 3′ and/or 4′ enhanced the anti-aromatase activity; thus, 3′,4′-dihydroxy-7-methoxyflavanone was found to be twice more potent than aminoglutethimide, the first aromatase inhibitor clinically used. Conclusions. These results indicated that these flavanones could be considered as potential anti breast cancer agents through the inhibition of aromatase activity and allowed us to select some of these compounds as skeleton for the development of flavonoid structurally-related aromatase inhibitors.

Structural requirements of flavonoids and related compounds for aldose reductase inhibitory activity

The methanolic extracts of several natural medicines and medicinal foodstuffs were found to show an inhibitory effect on rat lens aldose reductase. In most cases, flavonoids were isolated as the active constituents by bioassay-guided separation, and among them, quercitrin (IC50=0.15 μM), guaijaverin (0.18 μM), and desmanthin-1 (0.082 μM) exhibited potent inhibitory activity. Desmanthin-1 showed the most potent activity, which was equivalent to that of a commercial synthetic aldose reductase inhibitor, epalrestat (0.072 μM). In order to clarify the structural requirements of flavonoids for aldose reductase inhibitory activity, various flavonoids and related compounds were examined. The results suggested the following structural requirements of flavonoid: 1) the flavones and flavonols having the 7-hydroxyl and/or catechol moiety at the B ring (the 3′,4′-dihydroxyl moiety) exhibit the strong activity; 2) the 5-hydroxyl moiety does not affect the activity; 3) the 3-hydroxyl and 7-O-glucosyl moieties reduce the activity; 4) the 2-3 double bond enhances the activity; 5) the flavones and flavonols having the catechol moiety at the B ring exhibit stronger activity than those having the pyrogallol moiety (the 3′,4′,5′-trihydroxyl moiety).