38412-59-8

Upstream product

• 104-47-2 p-methoxybenzylnitrile 
• 104-01-8 4-Methoxyphenylacetic acid 
• 87-66-1 2-hydroxyresorcinol 

Downstream Products

• 37816-19-6 retusin 
• 1241384-58-6 1-(2,3-dihydroxy-4-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethoxy)phenyl)-2-(4-methoxyphenyl)ethanone 
• 116703-43-6 3,4-Bisethoxymethoxy-2-hydroxy-α-hydroxymethyl-4'-methoxydesoxybenzoin 
• 116703-46-9 7,8-Bisethoxymethoxy-4'-methoxyisoflavanone 
• 97165-42-9 7,8-methylenedioxy-4'-methoxyisoflavone 
• 116703-49-2 7,8-Dihydroxy-4'-methoxyisoflavanone 

Relevant academic research and scientific papers

A mild and efficient protocol to synthesize chromones, isoflavones, and homoisoflavones using the complex 2,4,6-trichloro-1,3,5-triazine/ dimethylformamide

A mild and efficient one-flask method has been developed for the synthesis of chromones, isoflavones, and homoisoflavones from 2-hydroxyacetophenones, deoxybenzoins, and dihydrochalcones, respectively, via one-carbon extension using the complex 2,4,6-trichloro-1,3,5-triazine/dimethylformamide. Deoxybenzoins and dihydrochalcones were prepared in situ by the reaction of readily available substituted phenols with phenylacetic acids and 3-phenylpropanoic acids, respectively. This method allows the synthesis of a wide range of compounds with multiple phenolic hydroxyls and other substituents. The methodology has been applied to the synthesis of three naturally occurring isoflavones such as formononetin (9c), daidzein (9d), and retusin (9h).

Metronidazole-deoxybenzoin derivatives as anti-Helicobacter pylori agents with potent inhibitory activity against HPE-induced interleukin-8

A series of new metronidazole-deoxybenzoin derivatives were synthesized and evaluated for their antimicrobial activity against Helicobacter pylori. Highly selective anti-H. pylori activity was also observed in synthesized compounds. Compound 34 exhibited

Synthesis and structure-activity relationship study of deoxybenzoins on relaxing effects of porcine coronary artery

Deoxybenzoins are potent antioxidants and tyrosinase inhibitors with potential to be developed as food preservatives and cosmetic ingredients. To explore the potential in cardiovascular protection, 25 polyphenolic deoxybenzoins were synthesized and evaluated for inhibitory effects on KCl-induced porcine coronary arterial contraction. The results revealed deoxybenzoins are significant inhibitors of KCl-induced arterial contraction. Among those synthesized, two-thirds of the deoxybenzoins exhibited moderate to good efficacy on relaxing contracted artery including 2,4-dihydroxydeoxybenzoin with EC50 = 3.30 μM (Emax = 100%, n = 7) and 2,4-dihydroxy-4′-methoxydeoxybenzoin EC50 = 3.70 μM (E max = 100%, n = 5). Deoxybenzoins displayed an endothelium-dependent relaxing manner on the contracted artery; the contractile responses of neither endothelium denuded nor L-NAME deactivated rings were inhibited. The structure-activity relationships of deoxybenzoin on arterial relaxing effects concluded that the 2,4-dihydroxylated deoxybenzoins presented a potential vascular relaxing pharmacophore, with favoring substitution on ring B in the order of H ≤ p-OMe > p-OH > o-OMe > m,p-diOMe ≤ m-OMe.

Potential antioxidants and tyrosinase inhibitors from synthetic polyphenolic deoxybenzoins

Deoxybenzoins (DOBs) are one-pot synthetic precursors of isoflavones with feature analogous to those beneficial polyphenols such as resveratrol (stilbene) and phloretin (dihydrochalcone). In this study, seventeen polyphenolic DOBs were synthesized and evaluated by various antioxidant assays and tyrosinase inhibitory effect in vitro. Results displayed that these DOBs are powerful antioxidants; for example, 2,3,4-trihydroxy-3′,4′-dimethoxydeoxybenzoin possesses an excellent anti-lipid peroxidation activity (IC50 = 0.72 ± 0.16 μM), whilst 2,4,4′,5-tetrahydroxydeoxybenzoin showed good DPPH radical scavenging activity (IC50 = 0.69 ± 0.04 μM), which were better than Trolox and vitamin C. Besides exhibiting a weak metal chelating effect, these DOBs were effective in scavenging ABTS{radical dot}+ and superoxide anion (O2{radical dot} -) radicals. DOBs also exhibited potent mushroom tyrosinase inhibitory activity; for example 2,3,4′-trihydroxy-4-methoxydeoxybenzoin displayed stable and significant inhibitory effect on tyrosinase activity, with IC50 values 43.37, 43.10 and 46.10 μM at incubation intervals of 0.5, 1.5, and 2.5 h, respectively. These results suggest that, with the advantage of being readily synthesizable small molecules, DOBs can be potentially developed into clinical and industrial antioxidants. Crown Copyright

Discovery of novel 2′,3′,4′-trihydroxy-2- phenylacetophenone derivatives as anti-gram-positive antibacterial agents

A number of 2′,3′,4′-trihydroxy-2-phenylacetophenone derivatives were synthesized and examined for growth inhibition of several kinds of bacteria. 2′,3′,4′-Trihydroxy-2-phenylacetophenone itself exhibited no antibacterial activity, but some of its derivat

Polyphenols based on isoflavones as inhibitors of Helicobacter pylori urease

Twenty polyphenols were synthesized and evaluated for their effect on Helicobacter pylori urease. Among these compounds, 4-(p-hydroxyphenethyl)pyrogallol (15) (IC50 = 0.03 mM) and 7,8,4′-trihydroxyisoflavone (19) (IC50 = 0.14 mM) showed potent inhibitory activities, and inhibited Helicobacter pylori urease in a time-dependent manner. The structure-activity relationship of these polyphenols revealed: the two ortho hydroxyl groups were essential for inhibitory activity of polyphenol. When the C-ring of isoflavone was broken, the inhibitory activity markedly decreased. As for deoxybenzoin, the carboxyl group was clearly detrimental.

The preparation of new isoflavones

The synthesis of ten new isoflavones in good yield is described. The method, involving intermediate 2-hydroxybenzyl ketones, did not require protection of the hydroxyl groups of the starting polyphenols.