136258-01-0Relevant articles and documents
Nitrogen-containing flavonoid and their analogs with diverse B-ring in acetylcholinesterase and butyrylcholinesterase inhibition
Lu, Qiao-Qiao,Chen, Ya-Ming,Liu, Hao-Ran,Yan, Jian-Ye,Cui, Pei-Wu,Zhang, Qian-Fan,Gao, Xiao-Hui,Feng, Xing,Liu, Ying-Zi
, p. 1037 - 1047 (2020/08/06)
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.
Antimalarial alkoxylated and hydroxylated chalones: Structure-activity relationship analysis
Liu,Wilairat,Go
, p. 4443 - 4452 (2007/10/03)
Chalcones with 2′,3′,4′-trimethoxy, 2′,4′-dimethoxy, 4′-methoxy, 4′-ethoxy, 2′,4′-dihydroxy, and 4′-hydroxy groups on ring B were synthesized and evaluated in vitro against Plasmodium falciparum (K1) in a [3H] hypoxanthine uptake assay. The other ring A was quinoline, pyridine, naphthalene, or phenyl rings with electron-donating or electron-withdrawing substituents of varying lipophilicities. Trimethoxy 6 and 27, dimethoxy 7, 8, 29, and methoxy 31 analogues had good in vitro activities (IC50 5μM). 3-Quinolinyl ring A derivatives were well represented among the active compounds. Hydroxylated chalcones were less active than the corresponding alkoxylated analogues. When evaluated in vivo, 8 and 208 were comparable to chloroquine in extending the lifespan of infected mice. Multivariate data analysis showed that in vitro activity was mainly determined by the properties of ring B. Quantitative structure - activity relationship models with satisfactory predictive ability were obtained for various B ring chalcones using projections to latent structures. A model with good predictability was proposed for 19 active chalcones. Size and hydrophobicity were identified as critical parameters.
2',5'-Dihydroxychalcone as a potent chemical mediator and cyclooxygenase inhibitor
Lin, Chun-Nan,Lee, Tai-Hua,Hsu, Mei-Feng,Wang, Jih-Pyang,Ko, Feng-Nien,Teng, Che-Ming
, p. 530 - 536 (2007/10/03)
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.
3,4-Dihydroxychalcones as potent 5-lipoxygenase and cyclooxygenase inhibitors
Sogawa,Nihro,Ueda,Izumi,Miki,Matsumoto,Satoh
, p. 3904 - 3909 (2007/10/02)
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.
Synthesis of 2'-hydroxychalcone epoxides
Adams,Main
, p. 4959 - 4978 (2007/10/05)
Various preparations of some 2'-tetrahydropyran-2-yloxychalcone epoxides and removal of their tetrahydropyranyl (THP) protective groups in slightly aqueous acidic dioxane are described. So synthesised were 2'-hydroxy-6'-isopropoxy- and 2'-hydroxy-6'-methoxychalcone epoxide, as well as the 2-CF3, 4-Cl and 4-NO2 analogues of the latter. 2',4'-dihydroxy-6'-methoxychalcone epoxide was similarly prepared. In some other 6'-methoxy cases protective group removal was accompanied by epoxide solvolysis and the corresponding α,β-dihydroxydihydrochalcone was the only isolable product [2-OMe, 4-OMe, 3,4,5-(OMe)3 cases] or a byproduct [4-Me case]. Similarly prepared by THP removal were 2'-hydroxy-4'-methoxychalcone epoxide and 2',4'-dihydroxychalcone epoxide, whereas an attempt to convert 2',6'-ditetrahydropyranyloxychalcone epoxide into 2',6'-dihydroxychalcone epoxide gave the product of cyclisation of the latter, 3,5-dihydroxyflavanone.
