- Flavanone compound as well as preparation method and application thereof
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The invention belongs to the technical field of medicines, and particularly relates to a flavanone compound as well as a preparation method and application thereof. Specifically disclosed is a compound represented by formula (I) or a pharmaceutically acceptable salt thereof. The compound shown in the formula (I) can target hURAT1 and/or GLUT9, so that uric acid excretion is promoted, and the effect of reducing uric acid is achieved. The compound can be used for preparing medicines for treating and/or preventing and/or delaying and/or adjunctively treating and/or treating diseases related to hURAT1/GLUT9 activity, and has a good application prospect in preventing or treating diseases (such as gout, gouty arthritis, uric acid kidney stone and the like) related to hyperuricemia.
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Paragraph 0202; 0206-0208
(2021/04/17)
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- Semisynthesis of prunetin, a bioactive O-methylated isoflavone from naringenin, by the sequential deacetylation of chalcone intermediates and oxidative rearrangement
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Prunetin (4′,5-dihydroxy-7-methoxyisoflavone) was semisynthesized in 8 steps from readily available naringenin in 26% total yield. The key reaction was chemoenzymatic sequential deacetylation to 6′-acetoxy-2′,4″-dihydroxy-4′-methoxychalcone, the in situ-formed precursor for thallium(III) nitrate-mediated oxidative rearrangement.
- Hanaya, Kengo,Higashibayashi, Shuhei,Sugai, Takeshi
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p. 143 - 147
(2022/03/18)
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- Synthesis and Evaluation of the Acetylcholinesterase Inhibitory Activities of Some Flavonoids Derived from Naringenin
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Alzheimer's disease (AD) is an irreversible neurodegenerative disease that affects many older people adversely. AD has been putting a huge socioeconomic burden on the healthcare systems of many developed countries with aging populations. The need for new therapies that can halt or reverse the progression of the disease is now extremely great. A research approach in the finding new treatment for AD that has attracted much interest from scientists for a long time is the reestablishment of cholinergic transmission through inhibition of acetylcholinesterase (AChE). Naringenin is a flavonoid with the potential inhibitory activity against AChE. From naringenin, many other flavonoid derivatives, such as flavanones and chalcones, can be synthesized. In this study, by applying the Williamson method, nine flavonoid derivatives were synthesized, including four flavanones and five chalcones. The evaluation of AChE inhibitory activity by the Ellman method showed that there were four substances (2, 4, 5, and 7) with relatively good biological activities (IC50 100 μM), and these biological activities were better than that of naringenin. The molecular docking revealed that strong interactions with amino acid residue Ser200 of the catalytic triad and those of the peripheral region of the enzyme were crucial for strong effects against AChE. Compound 7 had the strongest AChE inhibitory activity (IC50 13.0 ± 1.9 μM). This substance could be used for further studies.
- Cao, Thi-Cam-Nhung,Tran, Thai-Son,Tran, The-Huan,Vo, Thi-Quynh-Nhi,Vo, Thi-Thu-Hien
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- Total synthesis of agalloside, isolated from: Aquilaria agallocha, by the 5-O-glycosylation of flavan
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Agalloside (1) is a neural stem cell differentiation activator isolated from Aquilaria agallocha by our group using Hes1 immobilized beads. We conducted the first total synthesis of agalloside (1) via the 5-O-glycosylation of flavan 25 using glycosyl fluoride 20 in the presence of BF3·Et2O. Subsequent oxidation with DDQ to flavanone 2 and deprotection successively provided agalloside (1). This synthetic strategy holds promise for use in the synthesis of 5-O-glycosylated flavonoids. The synthesized agalloside (1) accelerated neural stem cell differentiation, which is a result comparable to that for the naturally occurring compound 1.
- Arai, Midori A.,Yamaguchi, Yumi,Ishibashi, Masami
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p. 5025 - 5032
(2017/07/10)
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- A Biomimetic Strategy to Access the Silybins: Total Synthesis of (-)-Isosilybin A
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(Figure Presented). We report the first asymmetric, total synthesis of (-)-isosilybin A. A late-stage catalytic biomimetic cyclization of a highly functionalized chalcone is employed to form the characteristic benzopyranone ring. A robust and flexible app
- McDonald, Benjamin R.,Nibbs, Antoinette E.,Scheidt, Karl A.
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- Purification and identification of naringenin 7-O-methyltransferase, a key enzyme in biosynthesis of flavonoid phytoalexin sakuranetin in rice
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Sakuranetin, the major flavonoid phytoalexin in rice, is induced by ultraviolet (UV) irradiation, CuCl2 treatment, jasmonic acid treatment, and infection by phytopathogens. It was recently demonstrated that sakuranetin has anti-inflammatory activity, anti-mutagenic activity, anti-pathogenic activities against Helicobacter pylori, Leishmania, and Trypanosoma and contributes to the maintenance of glucose homeostasis in animals. Thus, sakuranetin is a useful compound as a plant antibiotic and a potential pharmaceutical agent. Sakuranetin is biosynthesized from naringenin by naringenin 7-O-methyl-transferase (NOMT). In previous research, rice NOMT (OsNOMT) was purified to apparent homogeneity from UV-treated wild-type rice leaves, but the purified protein, named OsCOMT1, exhibited caffeic acid O-methyltransferase (COMT) activity and not NOMT activity. In this study, we found that OsCOMT1 does not contribute to sakuranetin production in rice in vivo, and we purified OsNOMT using the oscomt1 mutant. A crude protein preparation from UV-treated oscomt1 leaves was subjected to three sequential purification steps, resulting in a 400-fold purification from the crude enzyme preparation. Using SDS-PAGE, the purest enzyme preparation showed a minor band at an apparent molecular mass of 40 kDa.Two O-methyltransferase-like proteins, encoded by Os04g0175900 and Os12g0240900, were identified from the 40-kDa band by MALDI-TOF/TOF analysis. Recombinant Os12g0240900 protein showed NOMT activity, but the recombinant Os04g0175900 protein did not. Os12g0240900 expression was induced by jasmonic acid treatment in rice leaves prior to sakuranetin accumulation, and the Os12g0240900 protein showed reasonable kinetic properties toOsNOMT.Onthe basis of these results, we conclude that Os12g0240900 encodes an OsNOMT.
- Shimizu, Takafumi,Lin, Fengqiu,Hasegawa, Morifumi,Okada, Kazunori,Nojiri, Hideaki,Yamane, Hisakazu
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experimental part
p. 19315 - 19325
(2012/08/14)
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- Efficient synthesis of scutellarein
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Scutellarein is a component of Scutellaria, recently known as a potent cytotoxic agent on human leukaemia cells. The aim of this study was the synthesis of scutellarein and its methylated derivative. The new features are the innovating method to afford flavones from flavanones and the A-ring regioselective bromination step that lead to the target molecule by a facile and high-yielding pathway.
- Righi, Giuliana,Silvestri, Ilaria Proietti,Barontini, Maurizio,Crisante, Fernanda,Di Manno, Andrea,Pelagalli, Romina,Bovicelli, Paolo
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experimental part
p. 1278 - 1284
(2012/09/25)
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- Efficient one-pot synthesis of hydroxyflavanones by cyclization and O-demethylation of methoxychalcones
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An efficient one-pot method for the synthesis of hydroxyflavanones is described. Methoxychalcones are treated with 36% HBr to afford cyclization and regioselective O-demethylation products (2a-i) while cyclization and complete O-demethylation products (3a
- Liu, Tao,Ying, Huazhou,Lin, Guan,Hu, Yongzhou
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p. 1815 - 1821
(2008/12/20)
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- Total synthesis of flavocommelin, a component of the blue supramolecular pigment from Commelina communis, on the basis of direct 6-C-glycosylation of flavan
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We succeeded in a first total synthesis of flavocommelin (1), a component of the blue supramolecular pigment, commelinin (2), from Commelina communis, by direct 6-C-glycosylation of the flavan 4 using perbenzylglucosyl fluoride 8 in the presence of MS 5 A in CH2Cl2 and a catalytic amount of BF3·Et2O. After 6-C-glycosylation of 4, oxidation with CAN to flavanone 18 and subsequent 4′-O-glycosylation, promoted with a combination of BF3·Et2O and DTBMP, afforded diglucosylflavanone 20. DDQ oxidation of 20 and deprotection successively gave 1.
- Oyama, Kin-Ichi,Kondo, Tadao
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p. 5240 - 5246
(2007/10/03)
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- Regioselective hydroxylation of 2-hydroxychalcones by dimethyldioxirane towards polymethoxylated flavonoids
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The flavone nucleus is part of a large number of natural products and medicinal compounds. In this presentation the novel regioselective hydroxylation of hydroxyarenes with DMD is described. The results showed further that flavonoids with 5-hydroxy group were selectively oxyfunctionalized at the para-position C8 carbon atom by DMD. Finally, according to this methodology, the naturally occurring isosinensetin, tangeretin, sinensetin, nobiletin, natsudaidain, gardenin B, 3,3′,4′,5,6,7,8- heptamethoxyflavone, quercetin and its derivatives were synthesized.
- Chu, Han-Wei,Wu, Huan-Ting,Lee, Yean-Jang
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p. 2647 - 2655
(2007/10/03)
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- Kinetics and Mechanism of the Cyclisation of 2',6'-Dihydroxy-4,4'-dimethoxychalcone; Influence of the 6'-Hydroxy Group on the Rate of Cyclisation under Neutral Conditions
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The pH-rate profile for the cyclisation of the title compound has been established under aqueous conditions and is accounted for in terms of contributions from uncatalysed cyclisation of neutral, monoanionic, and dianionic chalcone species, together with an acid-catalysed cyclisation.At high pH the reaction does not go to completion and a kinetic term representing hydroxide promotion of the reverse ring-opening reaction of the flavanone anion intervenes.Rate coefficients for all contributing reactions and dissociation constants for the chalcone and its monoanion are established.The chalcone monoanion cyclises about 440 times faster than the neutral chalcone and about 3 times faster than the dianion.The known ease of cyclisation under neutral conditions of 2',6'-dihydroxychalcones as compared with other 2'-hydroxychalcones is considered to be associated with two contributing factors: (i) a much larger first dissociation constant of the chalcone which results in a higher proportion of the chalcone being present as the reactive monoanion at neutral pH; (ii) specially high reactivity of the chalcone monoanion associated with intramolecular general acid catalysis by the 6'-OH group.The latter is implicated through the observation of a large kinetic isotope effect for monoanion cyclisation, which is 5.7 times slower in D2O than in H2O.This isotope effect also establishes for the monoanion that the s-cis - s-trans conformational isomerisation of the monoanion must be a pre-equilibrium rather than the rate-determining stage in the cyclisation.
- Miles, Christopher O.,Main, Lyndsay
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p. 1639 - 1642
(2007/10/02)
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