42220-83-7

Upstream product

• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 100-83-4 meta-hydroxybenzaldehyde 
• 111841-07-7 2-hydroxy-4-(tetrahydropyran-2-yloxy)acetophenone 
• 5706-85-4 2-hydroxy-1-(4-hydroxyphenyl)ethan-1-one 
• 829-20-9 2',4'-dimethoxyacetophenone 
• 6515-05-5 2',4'-bis(methoxymethoxy)acetophenone 
• 13709-05-2 3-methoxymethoxybenzaldehyde 
• 1700-37-4 3-Benzyloxybenzaldehyde 
• 22877-01-6 2,4-bis(benzyloxy)acetophenone 
• 34716-73-9 3-(tetrahydro-2H-2-pyranyloxy)benzaldehyde 
• 220430-86-4 (E)-1-[2-Hydroxy-4-(tetrahydro-pyran-2-yloxy)-phenyl]-3-[3-(tetrahydro-pyran-2-yloxy)-phenyl]-propenone 

Downstream Products

• 1428324-97-3 C₁₅H₁₄N₂O₃ 
• 55370-71-3 C₁₇H₁₆N₂O₄ 
• 151698-64-5 3,7-dihydroxy-2-(3-hydroxyphenyl)-4H-chromen-4-one 

Relevant academic research and scientific papers

Synthesis and biological evaluation of isoliquiritigenin derivatives as a neuroprotective agent against glutamate mediated neurotoxicity in HT22 cells

Glutamate-induced neurotoxicity is characterized by cellular Ca2+ uptake, which is upstream of reactive oxygen species (ROS)-induced apoptosis signaling and MAPKs activation. In the present study, we synthesized isoliquiritigenin analogs with electron-donating and electron-withdrawing functional groups. These analogs were evaluated for neuroprotective effect against glutamate-induced neurotoxicity in HT22 cells. Among these analogs, compound BS11 was selected as a potent neuroprotective agent. Cellular Ca2+ concentration, ROS level, MAPKs activation and AIF translocation to the nucleus were increased upon treatment with 5 mM glutamate. In contrast, we identified that compound BS11 reduced the cellular Ca2+ concentration and ROS level upon glutamate exposure. Western blot analysis showed that MAPK activation was decreased by treatment with compound BS11. We further identified that cotreatment of compound BS11 and glutamate inhibited translocation of AIF to the nucleus.

Natural product-based design, synthesis and biological evaluation of 2′,3,4,4′-tetrahydrochalcone analogues as antivitiligo agents

A bioactive component, 2′,3,4,4′-tetrahydrochalcone (RY3-a) was first isolated from Vernohia anthelmintica (L.) willd seeds, and a set of its analogs, RY3-a-1–RY3-a-15 and RY3-c were designed and synthesized. Biological activity assays showed that RY3-c exhibited better melanogenesis and antioxidant activity and lower toxicity in comparison with RY3-a and butin. Further study tests showed that RY3-c exhibited better melanogenesis activity compared with the positive control 8-methoxypsoralan (8-MOP) in a vitiligo mouse model, suggesting that RY3-c is a good candidate antivitiligo agent. Mechanistic studies showed that RY3-c could repair cell damage induced by excessive oxidative stress and may exert melanin synthesis activity in the mouse melanoma B16F10 cell line by activating the mitogen-activated protein kinase (MAPK) pathway and the upregulation of c-kit.

Analogues of xanthones——Chalcones and bis-chalcones as α-glucosidase inhibitors and anti-diabetes candidates

Two series of compounds (chalcones and bis-chalcones) were designed, synthesized, and evaluated as α-glucosidase inhibitors (AGIs) with 1-deoxynojirimycin as positive control in vitro. Most of the compounds with two or four hydroxyl groups showed better inhibitory activities than 1-deoxynojirimycin towards α-glucosidase with noncompetitive mechanism. Moreover, most of the hydroxy bis-chalcones exhibit good α-glucosidase inhibitory activities in enzyme test. Inspiringly, bis-chalcones 2g (at 1 μM concentration) has stronger effect than 1-deoxynojirimycin on reducing the glucose level in HepG-2 cells (human liver cancer cell line).

Synthesis and evaluation of hydroxychalcones as multifunctional non-purine xanthine oxidase inhibitors for the treatment of hyperuricemia

A series of hydroxychalcone derivatives have been designed, synthesized and evaluated for human xanthine oxidase (XO) inhibitory activity. Most of the tested compounds acted moderate XO inhibition with IC50 values in the micromolar rang. Molecular docking and kinetic studies have been performed to explain the binding modes of XO with the selected compounds. In addition, in vitro antioxidant screening results indicated that some of the hydroxychalcones possessed good anti-free radical activities. Furthermore, the preferred compounds 16 and 18 were able to significantly inhibit hepatic xanthine oxidase activity and reduced serum uric acid level of hyperuricemic mice in vivo. In summary, compounds 16 and 18 with balanced activities of antioxidant, XO inhibition and serum uric acid reduction, which are promising candidates for the treatment of hyperuricemia and gout.

Hydroxylated chalcones with dual properties: Xanthine oxidase inhibitors and radical scavengers

In this study, we evaluated the abilities of a series of chalcones to inhibit the activity of the enzyme xanthine oxidase (XO) and to scavenge radicals. 20 mono- and polyhydroxylated chalcone derivatives were synthesized by Claisen-Schmidt condensation reactions and then tested for inhibitory potency against XO, a known generator of reactive oxygen species (ROS). In parallel, the ability of the synthesized chalcones to scavenge a stable radical was determined. Structure-activity relationship analysis in conjunction with molecular docking indicated that the most active XO inhibitors carried a minimum of three hydroxyl groups. Moreover, the most effective radical scavengers had two neighboring hydroxyl groups on at least one of the two phenyl rings. Since it has been proposed previously that XO inhibition and radical scavenging could be useful properties for reduction of ROS-levels in tissue, we determined the chalcones' effects to rescue neurons subjected to ROS-induced stress created by the addition of β-amyloid peptide. Best protection was provided by chalcones that combined good inhibitory potency with high radical scavenging ability in a single molecule, an observation that points to a potential therapeutic value of this compound class.

Chalcones as analytical reagents of aluminum: Stability, thermodynamic and kinetic study

Chalcones, a group of polyphenolic compounds, has been studied for a long time due to their biological properties and their ability as analytical reagents. In this work the stability and thermodynamic parameters concerning the fotmation in ethanolic medium of two chalcone-aluminium complexes (2′,3- dihydroxychalcone-Al(III) and 2′,4′,3-trihydroxychalcone-Al(III)) were studied and a kinetic study of the formation reaction was aslo performed. Both systems showed 1 : 1 L :M stoichiometry and stability constants at four temperatures were determined. Thermodynamic parameters indicate that both formation reactions are endothermic and driving force is entropic. Kinetic study revealed that 2′,4′,3-trihydroxychalcone-Al(III) formation is faster than 2′,3-dihydroxyclacone- Al(III), a factorwhich can be interestingwhen proposingnewanalytical reagents.

Calcium hydroxide is an efficient catalyst for synthesis of polyhydroxy chalcones

Calcium hydroxide was found to be an efficient catalyst for synthesis of polyhydroxy chalcones. This method has been employed to synthesize various 2′,4′-dihydroxychalcones having various substituents on the B ring. The merits of this method include shorter reaction time, inexpensive and easily available catalyst, high yield, and easy workup compared to other reported methods. Copyright Taylor and Francis Group, LLC.

Design and synthesis of 3,5-diaryl-4,5-dihydro-1H-pyrazoles as new tyrosinase inhibitors

In this study, twenty 3,5-diaryl-4,5-dihydro-1H-pyrazole derivatives with hydroxyl(s) (1a-1p, 2a-2d) were synthesized and their inhibitory activity on mushroom tyrosinase was examined. The results showed that among these compounds, 1-(5-(3,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl) ethanone 1d was found to be the most potent tyrosinase inhibitor with IC 50 value of 0.301 μM. Kinetic study revealed that these compounds were competitive inhibitors of tyrosinase and their structure-activity relationships were investigated in this article.

Design, synthesis and SAR study of hydroxychalcone inhibitors of human β-secretase (BACE1)

According to the structural characteristics of isoliquiritigenin from Glycyrrhiza uralensis, a series of hydroxychalcones has been designed, synthesized and evaluated for their in vitro inhibitory activities of β-secretase (BACE1). Structure-activity relationship study suggested that inhibitory activity against BACE1 was governed to a greater extent by the hydroxyl substituent on A-and B-ring of the chalcone, and the most active compound was substituted with four hydroxyl group (17, IC50=0.27 μM).

Novel synthesis of 3,3′-dihydroxyflavone and apparent formation constants of flavonoid-Ga(III) Complexes

Flavonoids are a wide variety of polyphenolic compounds. They have many biological properties. They also exhibit a metallic ion complexation capacity, which is important since it has been found that biological properties these ligands present can be enhan