- Glycolytic inhibition and antidiabetic activity on synthesized flavanone scaffolds with computer aided drug designing tools
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Background: Diabetes mellitus is a challengeable metabolic disorder that leads to a group of complications when the HbA1c level is not maintained. Most of the existing drugs avail-able in the market in long-term use may lead to serious adverse effects. He
- Kiruthiga, Natarajan,Saravanan, Govindaraj,Selvinthanuja, Chellappa,Sivakumar, Thangavel,Srinivasan, Kulandaivel
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p. 574 - 592
(2021/09/30)
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- Convenient synthesis of flavanone derivatives via oxa-Michael addition using catalytic amount of aqueous cesium fluoride
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A total of 36 flavanones, which included polycyclic aromatic and heterocyclic rings, were readily synthesized via oxa-Michael addition from the corresponding hydroxychalcones with a catalytic amount of aqueous cesium fluoride solution under mild conditions. This method could be applied to the scalable synthesis of eriodictyol as a known potent inhibitor of the SARS-CoV-2 spike protein.
- Miura, Motofumi,Shigematsu, Karin,Toriyama, Masaharu,Motohashi, Shigeyasu
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supporting information
(2021/10/25)
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- Synthesis and kinetic investigations for the isomerization process of 2–hydroxy chalcone derivatives
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The wide biological activities of flavanones are mainly depends on their physical and chemical properties, thus a number of substituted 2-Hydroxy chalcones have been synthesized, and their isomerization to their corresponding flavanones was studied. In order to determine the rate constant, kinetic experiments were performed using HPLC technique in (9:1) (CH3CN:H2O) medium at different temperature (298-318) K. The obtained results were interpreted by four steps mechanism, which considered the existence of phenoxide ion as the key intermediate. This study performed with a pseudo first order (reaction in which the rate for the studied compounds follow the sequence 5 > 2 > 1 > 4 > 3, the activation energy have the same sequence for these compounds .The effect of substituents on the rate showed that electronic and steric factors play reasonable role on the stability of the product .
- Shareef, Omar A.,Said, Said A.,Abdulrazaq, Ali Y.
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p. 1046 - 1054
(2020/01/09)
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- Direct α-Arylation/Heteroarylation of 2-Trifluoroboratochromanones via Photoredox/Nickel Dual Catalysis
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Utilizing photoredox/nickel dual catalysis, diverse flavanones have been synthesized by coupling novel 2-trifluoroboratochromanone building blocks with aryl and heteroaryl bromide partners. The newly reported trifluoroboratochromanones can be easily accessed from the corresponding chromones on multigram scale. This represents a general route for accessing natural and unnatural flavanones that were previously formed through a synthetically more restrictive ring closure route from chalcone precursors.
- Matsui, Jennifer K.,Molander, Gary A.
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supporting information
p. 436 - 439
(2017/02/10)
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- An efficient synthesis of flavanones and their docking studies with aldose reductase
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A series of flavanone derivatives have been synthesized from 2-hydroxy acetophenone and benzaldehyde using fused calcium chloride in good to moderate yields, and their in vitro aldose reductase inhibitory activity has been tested on aldose reductase purified enzyme from Bovine lens. Most of the synthesized compounds exhibited potent aldose reductase inhibitory activity, and the obtained results are supported by the docking studies. Among the tested derivatives, 2, 3, 4-methoxy derivative 19 (IC50 5.88 ± 0.03 μM) exhibited the highest inhibitory activity whereas 2-methoxy derivative 12 showed the lowest, and the remaining compounds exhibited moderate activity with IC50 in the range of 6.09–7.89 μM. The spatial configuration of the most active derivative 19 was compared with pharmacophore requirements of the aldose reductase inhibitor site using a molecular modeling system.
- Kondhare,Gyananath,Tamboli, Yasinalli,Kumbhar, Santosh S.,Choudhari, Prafulla B.,Bhatia, Manish S.,Zubaidha
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p. 987 - 998
(2017/04/14)
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- Synthesis, crystal structure and antitumour activity evaluation of 1H-thieno[2,3-c]chromen-4(2H)-one derivatives
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A series of 1H-thieno[2,3-c]chromen-4(2H)-one derivatives were synthesised through Knoevenagel condensation of substituted flavanones with thiazolidine-2,4-dione in ethanol in the presence of piperidine. The mechanism of the reaction was proposed. All synthesised compounds were characterised by IR, 1H NMR, 13C NMR, HRMS, and elemental analysis. The structure of 2-(3-chlorophenyl)-1H-thieno[2,3-c]chromen-4(2H)-one was confirmed by a single crystal X-ray diffraction analysis. A preliminary antitumour screening showed that 2-(2-fluorophenyl)-1H-thieno [2,3-c]chromen-4(2H)-one had moderate to good activity against A549, BGC-823, HCT116 and MDA-MB-453 cancer cell lines, and 2-(3,4-dimethoxyphenyl)-1H-thieno[2,3-c]chromen-4(2H)-one displayed similar activity against these four kinds of cancer cells compared with the reference drug.
- Yu, Huchang,Li, Yan,Feng, Zhiyuan,Jiang, Hongwu,Zhao, Yinglan,Luo, Youfu,Huang, Wencai,Li, Zicheng
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- Facile one-pot synthesis of flavanones using tetramethylguanidinum-based ionic liquids as catalysts
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Several tetramethylguanidinum-based ionic liquids (TMGILs) were prepared, characterized and used as catalysts in one-pot synthesis of flavanones. The results indicated that TMGILs composed of phenolate anion was beneficial for one-pot synthesis of flavanones, and [TMG][4-MeO-PhO] induced the good yields of flavanones owing to the electron-donating effect of methoxy substituent on phenolate anion. Furthermore, [TMG][4-MeO-PhO] was found to be used repetitively at least five times without obvious decrease in activity and quantity.
- Zhou, Yan,Huang, Wei,Chen, Xiang-Shu,Song, Zhi-Bin,Tao, Duan-Jian
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p. 1830 - 1836
(2019/11/28)
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- Nanosilica-supported dual acidic ionic liquid as a heterogeneous and reusable catalyst for the synthesis of flavanones under solvent-free conditions
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[Figure not available: see fulltext.] A nanosilica-supported dual acidic ionic liquid on the basis of 1-methyl-3-(4-sulfobutyl)imidazolium hydrogen sulfate was synthesized and used as an efficient, green, non-corrosive, non-toxic, heterogeneous, and reusable catalyst for the synthesis of some new and known substituted flavanones. The synthesis was done by the condensation of 2'-hydroxyacetophenone with different aldehydes and the subsequent cyclization of the resulting 2'-hydroxychalcone in the presence of the catalyst. High yields of the products, short reaction times, and solvent-free conditions characterize this new method.
- Rostamizadeh, Shahnaz,Zekri, Negar,Tahershamsi, Leili
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p. 526 - 530
(2016/02/16)
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- Fe(HSO4)3/SiO2: An efficient and heterogeneous catalyst for one-pot synthesis of 2-aryl-chromene-4-ones (flavanones)
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Silica ferric hydrogensulphate is an efficient heterogeneous catalyst for cyclisation of 2-hydroxychalcones to their corresponding flavanones (chromanone). This intramolecular oxa-Michael reaction was carried out in high yields in the presence of electron donating and electron withdrawing groups in the chalcone structure. Also, we found that aniline can act as an organic co-catalyst in direct synthesis of flavanones from 2-hydroxyacethophenone and aldehydes in the presence of Fe(HSO4)3/SiO2. Flavanones were prepared in high yields in a new catalytic system with similar substituted effect in the indirect cyclisation method. The catalyst in all the above reactions is reusable without significant decreases in its activity after four times of recycling.
- Eshghi, Hossein,Rahimizadeh, Mohammad,Mousavi, Seyed Mohsen
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supporting information
p. 438 - 443
(2014/04/17)
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- Highly efficient and green synthesis of flavanones and tetrahydroquinolones
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Highly efficient and green catalytic conversion of 2′-hydroxy and 2′-amino chalcones to flavanones and tetrahydroquinolones is reported herein. 2′-Hydroxy and 2′-amino chalcones can be almost completely converted to flavanones and tetrahydroquinolones in just 2 min in the presence of piperidine and KOH under room temperature. Liquiritigenin is also efficiently synthesized under similar conditions.
- Zheng, Xuxu,Jiang, Heyan,Xie, Jingjing,Yin, Zhongyi,Zhang, Haidong
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p. 1023 - 1029
(2013/03/13)
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- Asymmetric ion-pairing catalysis of the reversible cyclization of 2'-hydroxychalcone to flavanone: Asymmetric catalysis of an equilibrating reaction
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The asymmetric catalytic cyclization of the simple 2'-hydroxychalcone (1) to flavanone (2), a model for the chalcone isomerase reaction, has been realized as a catalytic asymmetric ion-pairing process with chiral quaternary ammonium salts (e.g., 9-anthracenylmethlycinchoninium chloride; 9-Am-CN-Cl) and NaH as small-molecule co-catalyst. In toluene/CHCl3 solution, the process reaches an intrinsic enantioselectivity of up to S = 14.4 (er = 93.5:6.5). The reversible reaction proceeds in two steps: A fast initial reaction approaches a quasi-equilibrium with KR/S = 4.5, followed by a second, slow racemization phase approaching Krac = 9. A simple mechanistic model featuring a living ion-pairing catalysis with full reversibility is proposed. Deuterium transfer from co-solvent CDCl3 to product 2 and isolation of a Michael conjugate formed from 2 and 1 demonstrate the intermediacy of flavanone enolate ion pairs. A kinetic model shows good agreement with the experimentally observed, peculiar, time-dependent evolution of the species concentrations and the enantiomeric excess of 2. The reaction is a chemical model of the chalcone isomerase enzymatic reaction. Furthermore, it is an ideal model for studying the characteristic behavior of reversible asymmetric catalyses close to their equilibria.
- Hintermann, Lukas,Dittmer, Claudia
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supporting information
p. 5573 - 5584
(2012/11/13)
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- Halogenated flavanones as potential apoptosis-inducing agents: Synthesis and biological activity evaluation
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A series of halogenated flavanones were synthesized from 2-hydroxychalcones and tested for their cytotoxicity against a panel of human cancer cell lines. Among the synthesized compounds, 3′,7-dichloroflavanone (2d) showed the highest activity against MCF-7, LNCaP, PC3, Hep-G2, KB and SK-N-MC cells. However, 3′,6-dichloroflavanone (2g) with IC50 value of 2.9 ± 0.9 μM was the most potent compound against MDA-MB-231 cells, being approximately 12 times more active than etoposide as reference drug. According to the flow-cytometric analysis, compound 2g can induce apoptosis by 66.19 and 21.37% in PC3 and MDA-MB-231 cells, respectively. The results of acridine orange/ethidium bromide staining and TUNEL assay suggested that the cytotoxic activity of this compound in PC3 and MDA-MB-231 cells occurs via apoptosis.
- Safavi, Maliheh,Esmati, Nasim,Ardestani, Sussan Kabudanian,Emami, Saeed,Ajdari, Soheila,Davoodi, Jamshid,Shafiee, Abbas,Foroumadi, Alireza
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p. 573 - 580
(2013/02/21)
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- Tandem intramolecular oxa-Michael addition/decarboxylation reaction catalyzed by bifunctional cinchona alkaloids: Facile synthesis of chiral flavanone derivatives
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Bifunctional cinchona alkaloids were used to catalyze a tandem intramolecular oxa-Michael addition/decarboxylation reaction of alkylidene β-ketoesters 1, providing a series of flavanone derivatives with up to 97% yield and 93% ee.
- Wang, Hai-Feng,Xiao, Hua,Wang, Xiao-Wei,Zhao, Gang
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supporting information; experimental part
p. 5389 - 5394
(2011/08/06)
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- An efficient catalytic synthesis of flavanones under green conditions
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An efficient and "green" catalytic conversion of 2′-hydroxychalcones to flavanones in 15 min in the presence of a simple amino acid and a base at room temperature is reported. Liquiritigenin was also efficiently synthesised under these conditions.
- Jiang, Heyan,Zheng, Xuxu,Yin, Zhongyi,Xie, Jingjing
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experimental part
p. 220 - 221
(2011/07/29)
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- Catalytic enantioselective synthesis of flavanones and chromanones
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Various chromanone, flavanone and abyssinone compounds as can be prepared enantioselectively using a chiral thiourea catalyst.
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Page/Page column 19
(2009/10/21)
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- Asymmetric intramolecular oxa-Michael addition of activated α,β-unsaturated ketones catalyzed by a chiral N,N′-dioxide nickel(II) complex: Highly enantioselective synthesis of flavanones
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(Chemical Equation Presented) The title reaction provides a promising approach for the synthesis of chiral flavanones with broad substrate scope and is tolerant to air and moisture. Good to excellent enantioselectivities and high yields were achieved for most substrates under mild conditions.
- Wang, Lijia,Liu, Xiaohua,Dong, Zhenhua,Fu, Xuan,Feng, Xiaoming
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supporting information; body text
p. 8670 - 8673
(2009/05/16)
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- Catalytic enantioselective synthesis of flavanones and chromanones
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The enantioselective synthesis of flavanones and chromanones is described. Bifunctional thiourea catalysts promote an asymmetric oxo-conjugate addition to a β-ketoester alkylidene in high yields with excellent enantioselectivity (80-94% ee) for aryl and alkyl substrates. Decarboxylation of the β-ketoester proceeds smoothly in a one-pot procedure to afford the enantioenriched flavanones and chromanones. Copyright
- Biddle, Margaret M.,Lin, Michael,Scheidt, Karl A.
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p. 3830 - 3831
(2008/02/04)
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- Enantioselective acylation of (±)-cis-flavan-4-ols catalyzed by lipase from Candida cylindracea (CCL) and the synthesis of enantiopure flavan-4-ones
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Lipase Candida cylindracea (CCL) catalyzed acylation of (±)-cis-flavan-4-ols using vinyl acetate as the acyldonor in DME-toluene (1:2) gave (-)-(2R,4R)-4-acetoxyflavans 9a-m and (+)-(2S,4S)-flavan-4-ols 10a-m in high enantiomeric excess. (+)-(2S,4S)-Flava
- Ramadas, Sathunuru,Krupadanam, G.L. David
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p. 3381 - 3391
(2007/10/03)
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