25972-30-9

Upstream product

• 20034-62-2 2'-Hydroxy-4'-(aethoxy-methoxy)-acetophenon 
• 128837-29-6 2,4-bis(ethoxymethoxy)benzaldehyde 
• 6515-05-5 2',4'-bis(methoxymethoxy)acetophenone 
• 13709-06-3 2,4-bis(methoxymethoxy)benzaldehyde 
• 100-52-7 benzaldehyde 
• 79004-62-9 RL334 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 829-20-9 2',4'-dimethoxyacetophenone 
• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 65490-08-6 2-hydroxy-4-(methoxymethoxy)acetophenone 
• 22877-01-6 2,4-bis(benzyloxy)acetophenone 
• 13246-46-3 2,4-dibenzyloxybenzaldehyde 

Downstream Products

• 76472-88-3 morachalcone A 
• 128837-33-2 7,2′,4′–trihydroxyflavanone 

Relevant academic research and scientific papers

Chitosan grafted butein: A metal-free transducer for electrochemical genosensing of exosomal CD24

Metal-free cost-efficient biocompatible molecules are beneficial for opto-electrochemical bioassays. Herein, chitosan (CS) conjugated butein is prepared via graft polymerization. Structural integrity between radical active sites of CS and its probable conjugation routes with reactive OH group of butein during grafting were comprehensively studied using optical absorbance/emission property, NMR, FT-IR and XPS analysis. Fluorescence emission of CS-conjugated butein (CSB) was studied in dried flaky state as well as in drop casted form. Cyclic voltammetric study of CSB modified glassy carbon electrode exhibits 2e?/2H+ transfer reaction in phosphate buffered saline electrolyte following a surface-confined process with a correlation coefficient of 0.99. Unlike pristine butein, CSB modified electrode display a highly reversible redox behavior under various pH ranging from 4 to 9. For the proof-of-concept CSB-modified flexible screen printed electrodes were processed for electrochemical biosensing of exosomal CD24 specific nucleic acid at an ultralow sample concentration, promising for ovarian cancer diagnosis.

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.

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).

Preparation of tyrosinase inhibitors and antibrowning agents using green technology

Chalcones and their derivatives have attracted great interests in recent years for their comprehensive biological activities. In this study, 2,4,2′,4′-tetrahydroxychalcone and its two derivatives, 1,3,5-tris-(2,4-dihydroxy-phenyl)pentane-1,5-dione (new co

Enantioselective biomimetic total syntheses of kuwanons i and J and brosimones A and B

The first enantioselective total syntheses of prenylflavonoid Diels-Alder natural products (-)-kuwanonI, (+)-kuwanonJ, (-)-brosimoneA, and (-)-brosimoneB have been accomplished from a common intermediate based on a concise synthetic strategy. Key elements of the synthesis include a biosynthesis-inspired asymmetric Diels-Alder cycloaddition mediated by a chiral ligand/boron Lewis acid, as well as a process involving regioselective Schenck ene reaction, reduction, and dehydration to realize a biomimetic dehydrogenation for generation of the required diene precursor. Furthermore, a remarkable tandem inter-/intramolecular asymmetric Diels-Alder cycloaddition process was applied for the synthesis of (-)-brosimoneA. Four in a row: The first enantioselective total syntheses of the prenylflavonoid natural products (-)-kuwanonI, (+)-kuwanonJ, (-)-brosimoneA, and (-)-brosimoneB have been accomplished based on a concise synthetic strategy. Key elements of the synthesis include a biosynthesis-inspired asymmetric Diels-Alder cycloaddition mediated by a chiral ligand/boron Lewis acid, as well as a process involving regioselective Schenck ene reaction, reduction, and dehydration.

Aspergillus niger catalyzes the synthesis of flavonoids from chalcones

Flavonoids, which have many biological activities and have been widely used in nature, can be artificially synthesized. However, regioselective cyclization of chalcones is difficult by chemical methods. In this study, we demonstrated that Aspergillus nige

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).

Electron transfer-initiated Diels-Alder cycloadditions of 2′-hydroxychalcones

An efficient approach to cyclohexenyl chalcones employing highly electron rich 2′-hydroxychalcone dienophiles via electron transfer-initiated Diels-Alder cycloaddition is described. Using the methodology, the total synthesis of nicolaiodesin C has been accomplished. Copyright

Synthesis and evaluation of 2′,4′,6′-trihydroxychalcones as a new class of tyrosinase inhibitors

In this study, we synthesized a series of hydroxychalcones and examined their tyrosinase inhibitory activity. The results showed that 2′,4′,6′-trihydroxychalcone (1), 2,2′,3,4′,6′-pentahydroxychalcone (4), 2′,3,4,4′,5,6′-hexahydroxychalcone (5), 2′,4′,6′-trihydroxy- 3,4-dimethoxychalcone (9) and 2,2′,4,4′,6′-pentahydroxychalcone (15) exhibited high inhibitory effects on tyrosinase with respect to l-tyrosine as a substrate. By the structure-activity relationship study, it was suggested that the 2′,4′,6′-trihydroxyl substructure in the chalcone skeleton were efficacious for the inhibition of tyrosinase activity. And also, the catechol structure on B-ring of chalcones was not advantageous for the inhibitory potency. Furthermore, 15 (IC50 = 1 μM) was found to show the highest activity out of a set of 15 hydroxychalcones, even better than both 2,2′,4,4′-tetrahydroxychalcone (13, IC50 = 5 μM) and kojic acid (16, IC50 = 12 μM), which were known as potent tyrosinase inhibitors. Kinetic study revealed that 15 acts as a competitive inhibitor of tyrosinase with Ki value of 3.1 μM.

Synthesis and PPAR-γ ligand-binding activity of the new series of 2′-hydroxychalcone and thiazolidinedione derivatives

Fifteen chalcones and three thiazolidinedione (TZD) chalcones were prepared to evaluate their peroxisome proliferator-activated receptor-γ (PPAR-γ) ligand-binding activities. Among the three TZDs, one compound possessed PPAR-γ transactivation potential, while the others showed antagonistic activity against PPAR-γ transactivation. Among the chalcones, compound 5 was the most potent, and structure-activity relationship studies indicated that a methoxyl group in position C-4 and hydroxyl group in position C-4′ or 5′ in chalcone plays a key role in determining the potency of PPAR-γ activation.