- 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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- Enzyme-assisted cyclization of chalcones to flavanones
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Enzyme catalyzed synthesis is an eco-friendly technique in organic synthesis, having several benefits over conventional methods. In the present work, we describe a simple process of laccase and chloroperoxidase assisted cyclization of chalcones, leading to the formation of flavanones. The reaction proceeds in a mixture of phosphate buffer and ethanol, under oxygen atmosphere at room temperature, yielding the corresponding flavanone in good to moderate yield. The relative configuration of the products at C2 is tentatively assigned as S*-flavanone based on the coupling constants with the methylenic protons H3α,β. In comparison to the chemical methods, we describe a process which can be achieved efficiently under mild conditions using oxygen as oxidant.
- Alonso, Mariana Macías,Boluda, Carlos José,Barajas, Gabriela Díaz,Sánchez, Nallely Caldera,Córdova-Guerrero, Iván,Marrero, Joaquín González
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p. 926 - 931
(2020/12/23)
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- Synthesis and cytotoxicity of novel (E)-2-phenylchroman-4-one-O-((1-substituted-1H-1,2,3-triazol-4-yl)methyl) oxime derivatives
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A series of new flavanone-triazole hybrids (7a–m) were synthesized from flavanone oximes (6a–c) via multistep synthetic strategy, involving Cu (I) catalyzed azide, alkyne 1,3-dipolar cycloaddition by Click reaction. All the synthesized compounds were tested for their cytotoxicity against HCT-15, HeLa, NCI-H522, and HEK-293 (normal cell line) cell lines. Compounds 6a, 7a, 7b, 7d, 7e, 7j, and 7m showed the significant cytotoxicity, wherein compound 7b showed potential cytotoxicity against NCI-H522 cell line and compounds 6a and 7a were offensive with HEK-293 in their toxicity profile.
- Gutam, Madhu,Mokenapelli, Sudhakar,Yerrabelli, Jayaprakash Rao,Banerjee, Somesh,Roy, Partha,Chitneni, Prasad Rao
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p. 1883 - 1891
(2020/05/13)
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- Organocatalytic Approach for Assembling Flavanones via a Cascade 1,4-Conjugate Addition/oxa-Michael Addition between Propargylamines with Water
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A DBU-catalyzed one-pot cascade reaction of propargylamines and water for the synthesis of flavanones has been developed. This process proceeds via a sequence of 1,4-conjugate addition of water to alkynyl o-quinone methide (o-AQM), followed by the alkyne-allene isomerization and subsequent intramolecular oxa-Michael addition. This strategy provides a convenient method for accessing a broad range of flavanones in good to excellent yields with good functional-group tolerance, in particular, the reactive halo functional groups.
- He, Xinwei,He, Xinwei,Xie, Mengqing,Li, Ruxue,Choy, Pui Ying,Tang, Qiang,Shang, Yongjia,Kwong, Fuk Yee
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p. 4306 - 4310
(2020/06/05)
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- Discovery of a Prenylated Flavonol Derivative as a Pin1 Inhibitor to Suppress Hepatocellular Carcinoma by Modulating MicroRNA Biogenesis
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Peptidyl-prolyl cis-trans isomerase Pin1 plays a crucial role in the development of human cancers. Recently, we have disclosed that Pin1 regulates the biogenesis of miRNA, which is aberrantly expressed in HCC and promotes HCC progression, indicating the therapeutic role of Pin1 in HCC therapy. Here, 7-(benzyloxy)-3,5-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one (AF-39) was identified as a novel Pin1 inhibitor. Biochemical tests indicate that AF-39 potently inhibits Pin1 activity with an IC50 values of 1.008 μm, and also displays high selectivity for Pin1 among peptidyl prolyl isomerases. Furthermore, AF-39 significantly suppresses cell proliferation of HCC cells in a dose- and time-dependent manner. Mechanistically, AF-39 regulates the subcellular distribution of XPO5 and increases miRNAs biogenesis in HCC cells. This work provides a promising lead compound for HCC treatment, highlighting the therapeutic potential of miRNA-based therapy against human cancer.
- Zheng, Yuanyuan,Pu, Wenchen,Li, Jiao,Shen, Xianyan,Zhou, Qiang,Fan, Xin,Yang, Sheng-Yong,Yu, Yamei,Chen, Qiang,Wang, Chun,Wu, Xin,Peng, Yong
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supporting information
p. 130 - 134
(2018/11/30)
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- Synthesis of Flavanones via Palladium(II)-Catalyzed One-Pot β-Arylation of Chromanones with Arylboronic Acids
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A total of 47 flavanones were expediently synthesized via one-pot β-arylation of chromanones, a class of simple ketones possessing chemically unactivated β sites, with arylboronic acids via tandem palladium(II) catalysis. This reaction provides a novel route to various flavanones, including natural products such as naringenin trimethyl ether, in yields up to 92percent.
- Cho, Yang Yil,Jang, Hyu Jeong,Kim, Dong Hwan,Kim, Nam Yong,Kim, Nam-Jung,Kim, Young Min,Lee, Soo Jin,Lee, Yong Sup,Park, Boyoung Y.,Son, Seung Hwan,Yoo, Hyung-Seok
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p. 10012 - 10023
(2019/08/30)
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- Palladium-Catalyzed [3+3] Annulation of Vinyl Chromium(0) Carbene Complexes through Carbene Migratory Insertion/Tsuji–Trost Reaction
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Vinyl chromium(0) Fischer carbene complexes were employed as the source of π-allylic palladium species for catalytic [3+3] annulation under palladium catalysis. Mechanistically, this transformation is proposed to involve carbene migratory insertion and intramolecular Tsuji–Trost reaction as the key steps. Substituted six-membered heterocyclic flavonones and quinolines are obtained, depending on the nucleophilic functional group on the coupling partners.
- Wang, Kang,Ping, Yifan,Chang, Taiwei,Wang, Jianbo
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supporting information
p. 13140 - 13144
(2017/10/11)
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- Ecofriendly synthesis of halogenated flavonoids and evaluation of their antifungal activity
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Brominated and chlorinated flavonoids belonging to different classes (flavanones, flavones and catechins) were prepared from the corresponding flavonoids by a simple and ecofriendly procedure based on the use of sodium halides, aqueous hydrogen peroxide and acetic acid. Pure samples of substrates and products were tested against Trichoderma koningii, Fusarium oxysporum and Cladosporium cladosporioides, common saprotrophic soil and seed fungi, potential pathogens for humans and their activity was expressed as linear mycelial growth inhibition (%). Among them, 8-chloro-5,7,3′,4′-tetramethoxyepicatechin 29, a novel catechin derivative, exhibited a remarkable effect against all tested fungi also at low concentrations.
- Bernini, Roberta,Pasqualetti, Marcella,Provenzano, Gianfranco,Tempesta, Sabrina
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p. 2980 - 2987
(2015/04/22)
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- Rhodium/chiral diene-catalyzed asymmetric 1,4-addition of arylboronic acids to chromones: A highly enantioselective pathway for accessing chiral flavanones
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Chromone has been noted to be one of the most challenging substrates in the asymmetric 1,4-addi-tion of α,β-unsaturated carbonyl compounds. By employing the rhodium complex associated with a chiral diene ligand, (R,R)-Ph-bod, the 1,4-addition of a variety of aryl-boronic acids was realized to give high yields of the corresponding flavanones with excellent enantioselectivities (≥97% ee, 99% ee for most substrates). Ring-opening side products, which would lead to erosion of product enantioselectivity, were not observed under the stated reaction conditions.
- He, Qijie,Wang, Jun,So, Chau Ming,Hayashi, Tamio,Bian, Zhaoxiang
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supporting information
p. 540 - 543
(2015/05/05)
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- Ferrocenyl flavonoid-induced morphological modifications of endothelial cells and cytotoxicity against B16 murine melanoma cells
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With the aim of improving the cytotoxic and vascular disrupting activities of flavonoids, several classes of ferrocenyl-modified flavonoids were prepared and tested on cancer and endothelial cells. Three ten-member series of ferrocenyl flavonoids: chalcones ((E)-1-(R-2′-hydroxyphenyl)-3- ferrocenylprop-2-en-1-ones), aurones ((Z)-R-2-(ferrocenylidene)benzofuran-3- ones) and flavones (R-2-ferrocenyl-chromen-4-ones) were synthesized by recently reported methods. Three ferrocenyl flavonols (R-3-hydroxy-2-ferrocenyl-chromen- 4-ones) and four ferrocenyl flavanones (3-ferrocenylmethylidenyl-R-2- phenylchroman-4-ones) were also obtained. All compounds were evaluated for their cytotoxic effects on a cancer cell line (B16 murine melanoma) and for their morphological effects on endothelial cells (EAhy 926). Some interesting structure-activity relationships were disclosed: of all the compounds, the halogen-substituted aurones showed the best cytotoxic activity, with IC 50 values ranging between 12 and 18 μM. Ferrocenyl flavonols and ferrocenyl flavanones with substitution in the 3-position (-OH and C-Fc respectively) were not active against cancer or endothelial cells. Some of the ferrocenyl flavones caused the endothelial cells to adopt a round shape ("rounding up") at submicromolar concentrations, which can be predictive of vascular disrupting activity. The most morphologically active flavones showed only moderate cytotoxicity against cancer cells, indicating that they may primarily act as antivascular agents.
- Monserrat, Jean-Philippe,Tiwari, Keshri Nath,Quentin, Lionel,Pigeon, Pascal,Jaouen, Gérard,Vessières, Anne,Chabot, Guy G.,Hillard, Elizabeth A.
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- Synthesis of 5-aryl-2-piperidino-5H-chromeno[3,4-c]pyridine-1-carbonitriles
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4-Chloro-2-aryl-2H-3-chromenecarbaldehydes 3a-g on reaction with malononitrile in ethanol in the presence of piperidine gave 5-aryl-2-piperidino- 5H-chromeno[3,4-c]pyridine-1-carbonitriles 4a-g in good yields. ARKAT-USA, Inc.
- Venkati,Reddy, S. Satyanarayana,Swamy,Ravikumar,Krupadanam, G. L. David
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scheme or table
p. 355 - 364
(2012/06/29)
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- Simple and efficient one step synthesis of functionalized flavanones and chalcones
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A facile and highly efficient microwave-assisted synthesis of functionalized chalcones and flavanones based on the Claisen-Schmidt condensation reaction is reported. The method describes the synthesis of flavanones in single step with excellent yield and it was revealed that position and number of substituents on acetophenones and aromatic aldehydes played a very crucial and key role in the construction of flavanone derivatives. Among the thirty two synthesized compounds, five chalcones and one flavanone were novel compounds.
- Albogami, Abdullah Saad,Karama, Usama,Mousa, Ahmed Amine,Khan,Al-Mazroa, Sara Abdullah,Alkhathlan, Hamad Z.
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p. 619 - 626
(2012/10/30)
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- Iodine catalyzed one-pot synthesis of flavanone and tetrahydropyrimidine derivatives via Mannich type reaction
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A variety of functionalized flavanone derivatives and tetrahydropyrimidine derivatives were achieved under remarkably mild conditions. The combination of good to excellent yields, a simple work-up, and the high compatibility of functional groups makes this an attractive synthetic approach to access flavanone and tetrahydropyrimidine derivatives.
- Kavala, Veerababurao,Lin, Chunchi,Kuo, Chun-Wei,Fang, Hulin,Yao, Ching-Fa
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experimental part
p. 1321 - 1329
(2012/02/13)
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- Synthetic approach to flavanones and flavones via ligand-free palladium(ii)-catalyzed conjugate addition of arylboronic acids to chromones
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The remarkable catalytic effects of Fe(OTf)3 in the context of the Pd(ii)-catalyzed conjugate addition of arylboronic acids to chromones were observed to yield a variety of flavanones under mild conditions. The addition of catalytic amounts of DDQ and KNO2 to the reactions exclusively yielded flavone analogs. The reaction scope for the transformation was fairly broad, affording good yields of a wide range of flavanones and flavones, which are privileged structures in many biologically active compounds.
- Kim, Donghee,Ham, Kyungrok,Hong, Sungwoo
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experimental part
p. 7305 - 7312
(2012/09/22)
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- Solution phase photocyclisation reaction of 2-hydroxychalcones to 4-flavanones
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The photochemical cyclisation of 2-hydroxychalcones leading to the synthesis of 4-flavanones in solution phase has been investigated. The formation of photoproducts has been explained on the basis of excited state intramolecular proton transfer (ESIPT) and the cyclisation efficiency of the chalcones has been found to depend upon the electron density on the phenolic oxygen as well as on the carbonyl group. This synthesis of flavanones by photoirradiation is an eco-friendly route with comparative yield to those of thermal methods. Although the molecular skeletons of these substrates is amenable to cis-trans isomerisations and cycloadditions but no photoproducts corresponding to these reactions have been realized.
- Kamboj, Ramesh C.,Berar, Surinder,Berar, Urmila,Gupta, Satish C.
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experimental part
p. 879 - 885
(2012/04/04)
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- Synthesis and cytotoxic activity of 4-aryl-4H-chromeno[4,3-d] [1,2,3] selenadiazoles
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Fourteen 4-Aryl-4H-chromeno[4,3-d][1,2,3] selenadiazole derivatives were synthesized by the reaction of fla-vonone-4-semicarbazones with SeO2. The structures of the target compounds 1a-n were elucidated by 1H NMR, IR spectra, ESI-MS and elemental analyses. The preliminary cytotoxic activities of 1a-n against K562, KB, A549, SMC-7721 and SGC-7901 cell lines were evaluated by MTT method, indicating that most compounds displayed moderate to good antiproliferative activities against K562 and KB cell lines. Compounds 1m and 1n, the most potent ones, were promising template for development of novel potent antitumor agents.
- Yin, Hong,Huang, Yueyan,Song, Guojie
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p. 721 - 725
(2013/01/09)
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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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- [3+2] Cycloaddition of phenyliodonium bis(arylsulfonyl)methylides with α,β-enones
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The [3+2] cycloaddition of phenyliodonium bis(arylsulfonyl)methylides to α,β-enones affords exclusively trans,trans-configured 1-(arylsulfonyl)-2-aroyl-3-arylindanes. The initial electrophilic attack of the iodonium ylide on the alkenyl double bond of the chalcone, followed by cyclization of the dipolar species, and subsequent ejection of iodobenzene and sulfur dioxide, stereoselectively affords the indane cycloadduct. Georg Thieme Verlag Stuttgart.
- Adam, Waldemar,Gogonas, Efstathios P.,Nyxas, Ioannis A.,Hadjiarapoglou, Lazaros P.
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p. 3211 - 3218
(2008/09/16)
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- Selective halogenation of flavanones
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A mild, efficient and regioselective method for the selective halogenation of flavonoids is presented. Halogenated flavanones and flavones are considered potential benzodiazepine receptor ligands and with DMD/NaX or oxone/acetone/water/NaX systems they can be synthesised in preparative amounts.
- Bovicelli, Paolo,Bernini, Roberta,Antonioletti, Roberto,Mincione, Enrico
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p. 5563 - 5567
(2007/10/03)
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- An improved method for the synthesis of flavanones
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An isomerization of 2′-hydroxychalcones into the corresponding flavanones in ethanol in the presence of triethylamine is described.
- Aitmambetov,Kubzheterova
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p. 165 - 166
(2007/10/03)
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- Synthetic analogs of natural flavolignans. XV. Isomerization of 2′-hydroxychalcones into flavanones using triethylamine
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A simple and effective method for preparing synthetic analogs of natural flavanones via isomerization of 2′-hydroxychalcones with triethylamine was proposed.
- Aitmambetov,Dalimov,Kubzheterova
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p. 421 - 423
(2007/10/03)
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- A facile synthesis of ethyl-2-methyl-5-aryl-5H-chromeno-[3,4-c]pyridine-1-carboxylates
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Flav-4-ones on reaction with DMF/POCl3 gave 4-chloro-2-aryl-2H-chromene-3-carbaldehydes which on reaction with ethyl-3-aminocrotonate give under Hantszch reaction conditions ethyl-2-methyl-5-aryl-5H-chromeno[3,4-c]pyridine-1-carboxylates in good yields.
- Venkati,Krupadanam
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p. 2589 - 2598
(2007/10/03)
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- Highly diastereoselective Michael reaction under solvent-free conditions using microwaves: Conjugate addition of flavanone to its chalcone precursor
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Microwave-assisted reaction of 2′-hydroxychalcones in the presence of DBU resulted in the formation of hitherto unknown dimers by conjugate addition of the intermediate cyclic ketone to the starting enone.
- Patonay, Tamás,Varma, Rajender S.,Vass, András,Lévai, Albert,Dudás, József
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p. 1403 - 1406
(2007/10/03)
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- Synthesis of 1,5-benzothiazepines: Part XIX - Syntheses of 10-substituted benzopyranobenzothiazepines as prospective cardiovascular agents
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10-Substituted-2-chloro-6a,7-dihydro-6H-7-(4-substituted phenyl)-6-phenyl-[1]benzopyrano[3,4-c][1,5]benzothiazepines (3a-l) have been synthesized by reacting (E)-6-chloro-3-(4-chloro/methoxybenzylidene)flavanones (2a,b) with 5-substituted-2-aminobenzenethiols (1a-f) by reflux heating in dry toluene containing piperidine (1:1). The products have been tested for purity by TLC and microestimation of nitrogen. IR and 1H NMR and mass spectral studies have enabled the assignment of structures. Bioassay screening of 3e,f,h and i shows mild analgesic and anticonvulsant activity.
- Upreti, Mani,Pant, Seema,Dandia, Anshu,Pant, Umesh C.,Goel, Anil K.,Patnaik, Gyanendra K.
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p. 1185 - 1188
(2007/10/03)
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- Oxidative Cleavage of 4-Oximinoflavans Using Iodobenzene Diacetate
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Oxidation of 4-oximinoflavans (Ia-g) using iodobenzene diacetate leads to cleavage with the formation of corresponding flavanones (IIa-g) under neutral conditions in 60-80percent yields.
- Prakash, O. M.,Pahuja, Saroj,Sawhney, S. N.
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- DDQ Oxidation of Flavan-4-ols - A New Method for Synthesis of Flavones
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Flavan-4-ols on oxidation with two mol of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) in benzene afford flavones as the major products and flavanones as the minor products.
- Jyotsna, D.,Rao, A. V. Subba
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p. 877 - 878
(2007/10/02)
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