204703-68-4

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 490-78-8 2,5-Dihydroxyacetophenone 

Downstream Products

• 571165-86-1 (E)-1-[2,5-bis(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)phenyl]-3-phenyl-2-propen-1-one 
• 204703-69-5 2',5'-bis(tetrahydropyran-2-yloxy)-4-chlorochalcone 
• 1027656-40-1 (E)-1-[2,5-Bis-(tetrahydro-pyran-2-yloxy)-phenyl]-3-naphthalen-2-yl-propenone 
• 752222-72-3 2',5'-bis(tetrahydropyran-2-yloxy)-3,4-dichlorochalcone 
• 1026233-48-6 (E)-1-[2,5-Bis-(tetrahydro-pyran-2-yloxy)-phenyl]-3-pyridin-3-yl-propenone 
• 1027525-42-3 (E)-1-[2,5-Bis-(tetrahydro-pyran-2-yloxy)-phenyl]-3-(2,5-dihydroxy-phenyl)-propenone 
• 1028296-17-4 (E)-1-[2,5-Bis-(tetrahydro-pyran-2-yloxy)-phenyl]-3-pentafluorophenyl-propenone 
• 1028310-65-7 (E)-1-[2,5-Bis-(tetrahydro-pyran-2-yloxy)-phenyl]-3-(2-bromo-5-hydroxy-phenyl)-propenone 
• 1026835-17-5 (E)-1-[2,5-Bis-(tetrahydro-pyran-2-yloxy)-phenyl]-3-(2-bromo-5-methoxy-phenyl)-propenone 
• 1027499-30-4 (E)-1-[2,5-Bis-(tetrahydro-pyran-2-yloxy)-phenyl]-3-(2-chloro-phenyl)-propenone 
• 1026981-46-3 (E)-1-[2,5-Bis-(tetrahydro-pyran-2-yloxy)-phenyl]-3-(3,4,5-trimethoxy-phenyl)-propenone 
• 1027425-25-7 (E)-1-[2,5-Bis-(tetrahydro-pyran-2-yloxy)-phenyl]-3-(5-bromo-2-methoxy-phenyl)-propenone 

Relevant academic research and scientific papers

2',5'-Dihydroxychalcone as a potent chemical mediator and cyclooxygenase inhibitor

Eleven chalcone derivatives have been tested for their inhibitory effects on platelet aggregation in rabbit platelet suspension and the activation of mast cells and neutrophils. Arachidonic acid-induced platelet aggregation was potently inhibited by almost all the compounds and some also had a potent inhibitory effect on collagen-induced platelet aggregation and cyclooxygenase. Some hydroxychalcone derivatives showed strong inhibitory effects on the release of β-glucuronidase and lysozyme, and on superoxide formation by rat neutrophils stimulated with the peptide fMet-Leu-Phe (fMLP). We found that the anti-inflammatory effect of 2',5'-dihydroxychalcone was greater than that of trifluoperazine. 2',5'-Dihydroxy and 2',3,4,4'-tetrahydroxyl chalcones, even at low concentration (50 μM), tested in platelet-rich plasma from man almost completely inhibited secondary aggregation induced by adrenaline. These results suggest that the anti-platelet effects of the chalcones are mainly a result of inhibition of thromboxane formation.

Nitrogen-containing flavonoid and their analogs with diverse B-ring in acetylcholinesterase and butyrylcholinesterase inhibition

In this study, a series of new flavones (2-phenyl-chromone), 2-naphthyl chromone, 2-anthryl-chromone, or 2-biphenyl-chromone derivatives containing 6 or 7-substituted tertiary amine side chain were designed, synthesized, and evaluated in acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibition. The results indicated that the alteration of aromatic ring connecting to chromone scaffold brings about a significant impact on biological activity. Compared with flavones, the inhibitory activity of 2-naphthyl chromone, 2-anthryl-chromone derivatives against AChE significantly decreased, while that of 2-biphenyl chromone derivatives with 7-substituted tertiary amine side chain is better than relative flavones derivatives. For all new synthesized compounds, the position of tertiary amine side chain obviously influenced the activity of inhibiting AChE. The results above provide great worthy information for the further development of new AChE inhibitors. Among the newly synthesized compounds, compound 5a is potent in AChE inhibition (IC50 = 1.29 ± 0.10 μmol/L) with high selectivity for AChE over BChE (selectivity ratio: 27.96). An enzyme kinetic study of compound 5a suggests that it produces a mixed-type inhibitory effect against AChE.

Synthesis and cytotoxic, anti-inflammatory, and anti-oxidant activities of 2′,5′-dialkoxylchalcones as cancer chemopreventive agents

In an effort to develop novel anti-tumor, or cancer chemopreventive agents, a series of 2′,5′-dialkoxylchalcones were prepared by Claisen-Schmidt condensation of appropriate acetophenones with suitable aromatic aldehyde. In vitro screening revealed low mi

Synthetic chalcones as potential anti-inflammatory and cancer chemopreventive agents

In an effort to develop potent anti-inflammatory and cancer chemopreventive agents, a series of chalcones were prepared by Claisen-Schmidt condensation of appropriate acetophenones with suitable aromatic aldehyde or prepared with appropriate dihydrochalco

Novel chalcone derivatives and pharmaceutical compositions comprising the same

Disclosed herein are novel chalcone derivatives of formulas (I), (II) and (III): wherein each of the substituents is given the definition as set forth in the Specification and Claims. These compounds are demonstrated to have anti-inflammatory activities a

Structure-activity relationship studies on chalcone derivatives: The potent inhibition of chemical mediators release

Some chalcones exert potent anti-inflammatory activities. 2′,5′-Dialkoxychalcones and 2′,5′-dihydroxy-4-chloro-dihydrochalcone inhibited nitric oxide (NO) production in lipopolysaccharide (LPS)/interferon-γ (IFN-γ)-activated N9 microglial cells and in LPS-activated RAW 264.7 macrophage-like cells have been demonstrated in our previous reports. These compounds also suppressed the inducible NO synthase (iNOS) expression and cyclooxygenase-2 (COX-2) activity in RAW 264.7 cells. In an effort to continually develop potent anti-inflammatory agent, a series of chalcones were prepared by Claisen-Schmidt condensation of appropriate acetophenones with appropriate aromatic aldehyde and then evaluated their inhibitory effects on the activation of mast cells, neutrophils, macrophages, and microglial cells. Most of the 2′,5′-dihydroxychaclone derivatives exhibited potent inhibitory effects on the release of β-glucuronidase and lysozyme from rat neutrophils stimulated with formyl-Met-Leu-Phe (fMLP)/cytochalasin B (CB). Some chalcones showed potent inhibitory effects on superoxide anion generation in rat neutrophils in response to fMLP/CB. Compounds 1 and 5 exhibited potent inhibitory effects on NO production in macrophages and microglial cells. Compound 11 showed inhibitory effect on NO production and iNOS protein expression in RAW 264.7 cells. The present results demonstrated that most of the 2′,5′-dihydroxychaclones have anti-inflammatory effects. The potent inhibitory effect of 2′,5′-dihydroxy-dihydrochaclones on NO production in LPS-activated macrophage, probably through the suppression of iNOS protein expression, is proposed to be useful for the relief of septic shock.

Cytotoxic 2',5'-dihydroxychalcones with unexpected antiangiogenic activity.

A series of 2',5'-dihydroxychalcones were synthesized and evaluated for cytotoxicity against tumor cell lines and human umbilical venous endothelial cells (HUVEC). It was found that chalcones with electron-withdrawing substituents on the B ring exhibited potent cytotoxicity against a variety of tumor cell lines while compounds with electron-releasing groups were less potent in general. Those compounds with B ring replaced by extended or heteroaromatic rings exhibited significant bioactivity. Several compounds were shown to have marked cytotoxic selectivity towards HUVECs. Especially, among the synthesized compounds, 2-chloro-2',5'-dihydroxychalcone (2-3) showed the highest selectivity index up to 66 in comparison to HCT116 cells. This compound also exhibited strong inhibitory effects on the HUVEC tube formation in an in vitro model. When administered into BDF1 mice bearing Lewis lung carcinoma cells at 50 mg kg(-1) day(-1), 2-3 was found to inhibit the growth of tumor mass by 60.5%.

Synthesis and anti-inflammatory effect of chalcones and related compounds

Purpose. Mast cell and neutrophil degranulations are the important players in inflammatory disorders. Combined with potent inhibition of chemical mediators released from mast cells and neutrophil degranulations, it could be a promising anti-inflammatory agent. 2',5'-Dihydroxychalcone has been reported as a potent chemical mediator and cyclooxygenase inhibitor. In an effort to continually develop potent anti-inflammatory agents, a novel series of chalcone, 2'- and 3'-hydroxychalcones, 2',5'-dihydroxychalcones and flavones were continually synthesized to evaluate their inhibitory effects on the activation of mast cells and neutrophils and the inhibitory effect on phlogist-induced hind-paw edema in mice. Methods. A series of chalcones and related compounds were prepared by Claisen-Schmidt condensation of appropriate acetophones with appropriate aromatic aldehyde and the anti-inflammatory activities of these synthetic compounds were studied on inhibitory effects on the activation of mast cells and neutrophils. Results. Some chalcones showed strong inhibitory effects on the release of β-glucuronidase and histamine from rat periteonal mast cells stimulated with compound 48/80. Almost all chalcones and 4'-hydroxyflavone exhibited potent inhibitory effects on the release of β-glucuronidase and lysozyme from rat neutrophils stimulated with formyl-Met-Leu-Phe (fMLP). Some chalcones showed potent inhibitory effects on superoxide formation of rat neutrophils stimulated with fMLP/cytochalasin B (CB) or phorbol myristate acetate (PMA). 2',3-Dihydroxy-, 2'5'-dihydroxy-4-chloro-, and 2'5'-dihydroxychalcone showed remarkable inhibitory effects on hind-paw edema induced by polymyxin B in normal as well as in adrenalectomized mice. Conclusions. These results indicated that the anti-inflammatory effects of these compounds were mediated, at least partly, through the suppression of chemical mediators released from mast cells and neutrophils.

3,4-Dihydroxychalcones as potent 5-lipoxygenase and cyclooxygenase inhibitors

A novel series of 3,4-dihydroxychalcones was synthesized to evaluate their effects against 5-lipoxygenase and cyclooxygenase. Almost all compounds exhibited potent inhibitory effects on 5-lipoxygenase with antioxidative effects, and some also inhibited cyclooxygenase. The 2',5'-disubstituted 3,4- dihydroxychalcones with hydroxy or alkoxy groups exhibited optimal inhibition of cyclooxygenase. We found that 2',5'-dimethoxy-3,4-dihydroxychalcone (37; HX-0836) inhibited cyclooxygenase to the same degree as flufenamic acid and 5-lipoxygenase, more than quercetin. Finally, these active inhibitors of 5- lipoxygenase inhibited arachidonic acid-induced mouse ear edema more than phenidone.