139256-08-9

Upstream product

• 860369-03-5 4',7-dimethoxy-8-methylisoflavone 
• 93434-89-0 1-(2,4-dihydroxy-3-methylphenyl)-2-(4-methoxyphenyl)ethanone 
• 39604-65-4 4,4'-dimethoxy-2-hydroxy-3-methyldeoxybenzoin 
• 853927-76-1 7-hydroxy-3-(4-methoxyphenyl)-4-oxo-4H-1-benzopyran-8-carboxaldehyde 
• 104-47-2 p-methoxybenzylnitrile 
• 14191-95-8 4-cyanomethylphenol 
• 139256-03-4 2,4,4'-trihydroxy-3-methyldeoxybenzoin 
• 68-12-2 N,N-dimethyl-formamide 
• 156-38-7 4-hydroxyphenylacetate 
• 608-25-3 2-methylbenzene-1,3-diol 
• 139256-04-5 2,4,4'-trihydroxy-6-methyldeoxybenzoin 
• 116718-51-5 7-hydroxy-3-(4-methoxyphenyl)-8-methyl-4H-chromen-4-one 

Downstream Products

• 288266-76-2 7-acetoxy-3-(4-acetoxy-phenyl)-8-methyl-chromen-4-one 

Relevant academic research and scientific papers

Enzymatic studies of isoflavonoids as selective and potent inhibitors of human leukocyte 5-lipo-oxygenase

Continuing our search to find more potent and selective 5-LOX inhibitors, we present now the enzymatic evaluation of seventeen isoflavones (IR) and nine isoflavans (HIR), and their in vitro and in cellulo potency against human leukocyte 5-LOX. Of the 26 compounds tested, 10 isoflavones and 9 isoflavans possessed micromolar potency, but only three were selective against 5-LOX (IR-2, HIR-303, and HIR-309), with IC50 values at least 10 times lower than those of 12-LOX, 15-LOX-1, and 15-LOX-2. Of these three, IR-2 (6,7-dihydroxy-4-methoxy-isoflavone, known as texasin) was the most selective 5-LOX inhibitor, with over 80-fold potency difference compared with other isozymes; Steered Molecular Dynamics (SMD) studies supported these findings. The presence of the catechol group on ring A (6,7-dihydroxy versus 7,8-dihydroxy) correlated with their biological activity, but the reduction of ring C, converting the isoflavones to isoflavans, and the substituent positions on ring B did not affect their potency against 5-LOX. Two of the most potent/selective inhibitors (HIR-303 and HIR-309) were reductive inhibitors and were potent against 5-LOX in human whole blood, indicating that isoflavans can be potent and selective inhibitors against human leukocyte 5-LOX in vitro and in cellulo. Of the 26 compounds tested, 10 isoflavones and 9 isoflavans possessed micromolar potency, but only three were selective against 5-LOX (IR-2, HIR-303, and HIR-309), with IC50 values at least 10 times lower than those of 12-LOX, 15-LOX-1, and 15-LOX-2. Docking and steered molecular dynamics were performed to determinate the structure-activity relationship.

Development of 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) from natural isoflavones, a new class of fluorescent scaffolds for biological imaging

Starting from 7-hydroxyisoflavones, we developed a new class of fluorescent scaffolds, 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs, MW ～ 205.19, λab ～ 350 nm, λem ～ 450 nm) via a trial and error process. AMHCs have the advantages of being a small molecular moiety, having strong fluorescence in basic buffers, reasonable solubility and stability, non-toxicity, and are conveniently linked to pharmacophores. AMHCs were successfully used in fluorescence microscopy imaging of cells and tissues. This journal is

In vitro study of isoflavones and isoflavans as potent inhibitors of human 12- and 15-lipoxygenases

In this study, we have investigated 16 isoflavone and isoflavan derivatives as potential inhibitors of human lipoxygenase (platelet 12-lipoxygenase, reticulocyte 15-lipoxygenase-1, and epithelial 15-lipoxygenase-2). The flavonoid baicalein, a known lipoxygenase inhibitor, was used as positive control. Four compounds, 6,7-dihydroxy-3′-chloroisoflavone (1c), 7-hydroxy-8-methyl-4′-chloroisoflavan (5a), 7,8-dihydroxy-4′-methylisoflavan (5b), and 7,8-dihydroxy-3′-methylisoflavan (5c), were effective inhibitors of 12-lipoxygenases and 15-lipoxygenase-1 with IC50's i values in the range of 0.3-3 μm.

SUBSTITUTED CHROMAN DERIVATIVES, MEDICAMENTS AND USE IN THERAPY

Novel substituted chroman derivatives and intermediate compounds, compositions containing same, methods for their preparation and uses thereof as therapeutic agents particularly as anti-cancer and chemotherapeutic selective agents are described.

Expedient Synthesis of Polyhydroxyisoflavones

A general and direct synthesis of polyhydroxy isoflavones (3-phenyl-4H-1-benzopyran-4-ones) starting from the corresponding unprotected phenols and arylacetic acids is described.The aryl rings may carry additional alkyl, methoxy and/or halogeno groups.Intermediate polyhydroxydeoxybenzoins (1,2-diphenylethanones) can also be isolated in good yields.