- Molecular characterization, biological activity, and in silico study of 2-(3,4-dimethoxyphenyl)-3-(4-fluorophenyl)-6-methoxy-4H-chromen-4-one as a novel selective COX-2 inhibitor
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The present study aimed to characterize and investigate 2-(3,4-dimethoxyphenyl)-3-(4-fluorophenyl)-6-methoxy-4H-chromen-4-one (22) as a novel selective COX-2 inhibitor. The data collected from the single X-ray crystallographic analysis and in silico study
- Rullah, Kamal,Mohd Aluwi, Mohd Fadhlizil Fasihi,Yamin, Bohari M.,Baharuddin, Mohd Syukri,Ismail, Nor Hadiani,Teruna, Hilwan Yuda,Bukhari, Syed Nasir Abbas,Jantan, Ibrahim,Jalil, Juriyati,Husain, Khairana,Wai, Lam Kok
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- Divergent synthesis of flavones and flavanones from 2′-hydroxydihydrochalconesviapalladium(ii)-catalyzed oxidative cyclization
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Divergent and versatile synthetic routes to flavones and flavanonesviaefficient Pd(ii) catalysis are disclosed. These Pd(ii) catalyses expediently provide a variety of flavones and flavanones from 2′-hydroxydihydrochalcones as common intermediates, depending on oxidants and additives,viadiscriminate oxidative cyclization sequences involving dehydrogenation, respectively, in a highly atom-economic manner.
- Son, Seung Hwan,Cho, Yang Yil,Yoo, Hyung-Seok,Lee, Soo Jin,Kim, Young Min,Jang, Hyu Jeong,Kim, Dong Hwan,Shin, Jeong-Won,Kim, Nam-Jung
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p. 14000 - 14006
(2021/04/22)
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- A novel one-pot synthesis of flavones
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In this paper, a one-pot facile route for the BiCl3/RuCl3-mediated synthesis of functionalized flavones is described, including: (i) intermolecularortho-acylation of substituted phenols with cinnamoyl chlorides, and (ii) intramolecular cyclodehydrogenation of the resultingo-hydroxychalcones. The reaction conditions are discussed herein.
- Chang, Meng-Yang,Tsai, Min-Chen,Lin, Chun-Yi
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p. 11655 - 11662
(2021/03/31)
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- Unraveling the anti-influenza effect of flavonoids: Experimental validation of luteolin and its congeners as potent influenza endonuclease inhibitors
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The biological effects of flavonoids on mammal cells are diverse, ranging from scavenging free radicals and anti-cancer activity to anti-influenza activity. Despite appreciable effort to understand the anti-influenza activity of flavonoids, there is no clear consensus about their precise mode-of-action at a cellular level. Here, we report the development and validation of a screening assay based on AlphaScreen technology and illustrate its application for determination of the inhibitory potency of a large set of polyols against PA N-terminal domain (PA-Nter) of influenza RNA-dependent RNA polymerase featuring endonuclease activity. The most potent inhibitors we identified were luteolin with an IC50 of 72 ± 2 nM and its 8-C-glucoside orientin with an IC50 of 43 ± 2 nM. Submicromolar inhibitors were also evaluated by an in vitro endonuclease activity assay using single-stranded DNA, and the results were in full agreement with data from the competitive AlphaScreen assay. Using X-ray crystallography, we analyzed structures of the PA-Nter in complex with luteolin at 2.0 ? resolution and quambalarine B at 2.5 ? resolution, which clearly revealed the binding pose of these polyols coordinated to two manganese ions in the endonuclease active site. Using two distinct assays along with the structural work, we have presumably identified and characterized the molecular mode-of-action of flavonoids in influenza-infected cells.
- Albi?ana, Carlos Berenguer,Brynda, Ji?í,Fanfrlík, Jind?ich,Flieger, Miroslav,Hodek, Jan,Karlukova, Elena,Ko?í?ek, Milan,Konvalinka, Jan,Machara, Ale?,Majer, Pavel,Radilová, Kate?ina,Weber, Jan,Zima, Václav
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- Inhibitory effect of flavonoids on human glutaminyl cyclase
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Glutaminyl cyclase (QC) plays an important role in the pathogenesis of Alzheimer's disease (AD) and can be a potential target for the development of novel anti-AD agents. However, the study of QC inhibitors are still less. Here, phenol-4′ (R1-), C5-OH (R2-) and C7-OH (R3-) modified apigenin derivatives were synthesized as a new class of human QC (hQC) inhibitors. The efficacy investigation of these compounds was performed by spectrophotometric assessment and the structure-activity relationship (SAR) was evaluated. Molecular docking was also carried out to analyze the binding mode of the synthesized flavonoid to the active site of hQC.
- Li, Manman,Dong, Yao,Yu, Xi,Zou, Yongdong,Zheng, Yizhi,Bu, Xianzhang,Quan, Junmin,He, Zhendan,Wu, Haiqiang
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p. 2280 - 2286
(2016/04/26)
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- Regioselective synthesis of flavone derivatives via DMAP-catalyzed cyclization of o-alkynoylphenols
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A catalytic amount of DMAP promoted cyclization of o-alkynoylphenols via a 6-endo cyclization mode leading to flavone derivatives in high yields without forming 5-exo cyclized aurone derivatives. Utilizing this method, methoxy substituted flavone and alkyl substituted γ-benzopyranone derivatives were synthesized.
- Yoshida, Masahito,Fujino, Yuta,Saito, Koya,Doi, Takayuki
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experimental part
p. 9993 - 9997
(2012/02/06)
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- Synthesis of γ-benzopyranone by TfOH-promoted regioselective cyclization of o-alkynoylphenols
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Regioselective cyclization of o-alkynoylphenols forming γ-benzopyranones has been demonstrated. Trifluoromethanesulfonic acid (TfOH) induced 6-endo cyclization of o-alkynoylphenols without forming 5-exo cyclized benzofuranone derivatives to provide the corresponding γ-benzopyranones in high yields.
- Yoshida, Masahito,Fujino, Yuta,Doi, Takayuki
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supporting information; experimental part
p. 4526 - 4529
(2011/10/09)
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- An efficient conversion of 2'-hydroxychalcones into flavanones: Use of tetra-n-butylammonium iodide
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2'-Hydroxychalcones 1 possessing different substitution patterns in rings A and B, have been found to undergo efficient isomerization to the corresponding flavanones 2 when heated in ethanol with hydrochloric acid and tetra-n-butylammonium iodide.
- Dhawan, Deepika,Grover, S. K.
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- Hypervalent iodine oxidation of 2'-hydroxychalcones: Synthesis of cis-3-hydroxyflavanones
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Oxidation of 2'-hydroxychalcones (1a-h) using C6H5I(OAC)2-KOH/MeOH leads to the formation of cis-3-hydroxyflavanone dimethylacetals (2a-h).Mild acid hydrolysis (50percent AcOH) of 2a-h affords cis-3-hydroxyflavanones (3a-h) in good yields.Oxidation of cha
- Prakash, Om,Pahuja, Saroj,Sawhney, Shanti N
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p. 1023 - 1027
(2007/10/02)
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- Photochemical Deoxygenation of an α-Ketol: The Dihydroflavonol-Flavanone Conversion
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Irradiation of optically pure 2,3-trans-3-hydroxyflavanones in anhydrous ethyl acetate leads directly to free phenolic flavanone analogues with complete retention of configuration at C(2).Similarly their methyl ethers give the corresponding flavanones and flavones.The reaction represents the photochemical equivalent of a reduction under Clemmensen conditions.
- Westhuizen, Jan H. van der,Ferreira, Daneel,Roux, David G.
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p. 1003 - 1006
(2007/10/02)
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