- Discovery of Novel Dual-Target Inhibitor of Bromodomain-Containing Protein 4/Casein Kinase 2 Inducing Apoptosis and Autophagy-Associated Cell Death for Triple-Negative Breast Cancer Therapy
-
Bromodomain-containing protein 4 (BRD4) is an attractive epigenetic target in human cancers. Inhibiting the phosphorylation of BRD4 by casein kinase 2 (CK2) is a potential strategy to overcome drug resistance in cancer therapy. The present study describes the synthesis of multiple BRD4–CK2 dual inhibitors based on rational drug design, structure–activity relationship, and in vitro and in vivo evaluations, and 44e was identified to possess potent and balanced activities against BRD4 (IC50 = 180 nM) and CK2 (IC50 = 230 nM). In vitro experiments show that 44e could inhibit the proliferation and induce apoptosis and autophagy-associated cell death of MDA-MB-231 and MDA-MB-468 cells. In two in vivo xenograft mouse models, 44e displays potent anticancer activity without obvious toxicities. Taken together, we successfully synthesized the first highly effective BRD4–CK2 dual inhibitor, which is expected to be an attractive therapeutic strategy for triple-negative breast cancer (TNBC).
- Chen, Juncheng,Chiang, Cheng-Ming,He, Gu,Liu, Bo,Liu, Jie,Ouyang, Liang,Tang, Pan,Wang, Guan,Yang, Chengcan,Ye, Tinghong,Zhang, Jifa,Zhang, Jin,Zou, Ling
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p. 18025 - 18053
(2022/01/03)
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- N-Benzylation of 6-aminoflavone by reductive amination and efficient access to some novel anticancer agents via topoisomerase II inhibition
-
Series of novel N-benzyl derivatives of 6-aminoflavone (9a–n) were synthesized and evaluated for anticancer and topoisomerase II enzyme inhibition activity. All the synthesized compounds were screened for in vitro anticancer activity against human breast cancer cell line (MCF-7) and human lung cancer cell line (A-549). Among the synthesized compounds, 9f and 9g were found to be the most potent anticancer agents against human breast cancer cell line (MCF-7) with IC50 values of 9.35?μM and 9.58?μM, respectively. Compounds 9b, 9c and 9n exhibited promising anticancer activity against human lung cancer cell line (A-549) with 43.71%, 46.48% and 44.26% inhibition at the highest concentration of 10?μM, respectively. Compounds 9c, 9f and 9g have ability to inhibit the topoisomerase II enzyme. Compound 9f showed most potent topoisomerase II enzyme inhibition activity with IC50 value of 12.11?μM. Further, these compounds have a high potential to be developed as a promising topoisomerase II inhibitors.
- Thorat, Nitin M.,Sarkate, Aniket P.,Lokwani, Deepak K.,Tiwari, Shailee V.,Azad, Rajaram,Thopate, Shankar R.
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p. 937 - 948
(2020/04/15)
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- Rhodium(III)-catalyzed one-pot synthesis of flavonoids from salicylaldehydes and sulfoxonium ylides
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Rh(III)-catalyzed C–H activation of salicylaldehyde followed by an insertion reaction with sulfoxonium ylides and cyclization is applied to the synthesis of flavonoids. This one-pot strategy exhibits good functional group tolerance and gives flavones in moderate-to-good yields.
- Cheng, Kang,Chen, Jinkang,Jin, Licheng,Zhou, Jian,Jiang, Xinpeng,Yu, Chuanming
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p. 392 - 398
(2019/09/03)
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- Microwave assisted efficient synthesis of flavone using ZnO nanoparticles as promoter under solvent-free conditions
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A simple and highly efficient protocol for synthesis of flavones from 1-(2-hydroxyphenyl)-3-aryl-1,3-propanediones in presence of ZnO nanoparticles as a promoter in thermal as well as microwave irradiation under solvent-free conditions have been demonstrated. The catalyst is inexpensive, stable, can be easily recycled/reused for several cycles with consistent activity and observed almost same yield confirming the stability of the catalyst. It is believed that the present approach will become an alternative route for the conventional reactions. Because in this protocol, yield is quite high, short reaction time, simple work up, catalyst can be recycled as well as it is free of any hazardous by-products formation during workup.
- Unde, Pradip J.,Thorat, Nitin M.,Patil, Limbraj R.
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p. 1133 - 1136
(2019/04/05)
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- A 2 - aryl flavone preparation method
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The invention discloses a 2 - aryl flavone preparation method, including: in the silver catalyst and under the action of the oxidizing agent, ortho-hydroxy aryl formyl formic acid and aryl alkynoic ring reaction in a solvent, after the reaction is finished after treatment to obtain the 2 - aryl flavone. The method of this invention easily obtained and cheap agents, mild reaction conditions, reaction functional group compatibility is good, cheap catalyst, the catalytic system is simple.
- -
-
Paragraph 0034; 0035; 0036; 0037
(2018/07/15)
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- One Pot Synthesis of γ-Benzopyranones via Iron-Catalyzed Aerobic Oxidation and Subsequent 4-Dimethylaminopyridine Catalyzed 6-endo Cyclization
-
One-pot synthesis of γ-benzopyranones was realized in decent yields and excellent regioselectivities via iron-catalyzed aerobic oxidation and 4-dimethylaminopyridine-catalyzed cyclization of related propargylic alcohols. Derivatizations to aromatic substituted γ-benzopyranones and synthesis of naturally occurring 3′,4′-dimethoxyflavone have also been realized. (Figure presented.).
- Zhai, Di,Chen, Lingzhu,Jia, Minqiang,Ma, Shengming
-
supporting information
p. 153 - 160
(2017/11/23)
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- One-pot Synthesis of Aurones through Oxidation-cyclization Tandem Reaction Catalyzed by Copper Nanoparticles Catalyst
-
Aurones were synthesized through an oxidation-cyclization tandem reaction of 2-(1- hydroxyprop-2-ynyl)phenols catalyzed by copper nanoparticles (Cu NPs) with bipyridine as the ligand. In the reaction, oxygen worked as a green and mild oxidant to give the best results. Cu NPs were dually activated by bipyridine ligand and water, and showed highly efficient catalytic activities to the oxygen oxidation and the cylization to give aurones and flavonoids.
- Yu, Min,Liu, Guangxiang,Han, Chengyan,Zhu, Li,Yao, Xiaoquan
-
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- Silver-catalyzed Double Decarboxylative Radical Alkynylation/Annulation of Arylpropiolic Acids with α-keto Acids: Access to Ynones and Flavones under Mild Conditions
-
Ynones are privileged building blocks in various organic syntheses of heterocyclic derivatives due to their multifunctional nature, and flavones are an important class of natural products with a wide range of biological activities. We describe the catalytic double decarboxylative alkynylation of arylpropiolic acids with α-keto acids. With Ag(I)/persulfate as the catalysis system, the valuable ynones bearing various substituents could be easily obtained. The introduction of hydroxyl substituent on ortho-site of α-keto acids make this strategy further applicable to the construction of flavone derivatives via heteroannulation in moderate to good yields with a similar silver-catalyzed system. The reactions proceed under relatively mild reaction conditions and tolerate a wide variety of functional groups. Control experiments indicated that both the reactions undergo radical processes. (Figure presented.).
- Meng, Mengting,Wang, Guofang,Yang, Liangfeng,Cheng, Kai,Qi, Chenze
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supporting information
p. 1218 - 1231
(2018/02/16)
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- One-Pot Allan–Robinson/Friedl?nder Route to Chromen-/Quinolin-4-ones through the Domino Acetylative Cyclisation of 2-Hydroxy-/2-Aminobenzaldehydes
-
The domino synthesis of 2-phenyl-4H-chromen-4-ones and quinolin-4-ones through acetylation of 2-hydroxy-/2-aminobenzaldehydes with α-haloketones followed by intramolecular oxa-/azaheterocyclisation is reported. This method represents a new extension of the Allan–Robinson and Friedl?nder reactions, and uses N-heterocyclic-carbene catalysis to construct the target molecules in good to excellent yields: 86–95 % for the chromen-4-ones, and 83–96 % for the quinolin-4-ones. This approach has the advantages of operational simplicity, ambient reaction conditions, and no by-product formation.
- Rai, Vijai K.,Verma, Fooleswar,Sahu, Ganeshwar P.,Singh, Manorama,Rai, Ankita
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p. 537 - 544
(2018/02/09)
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- Synthesis of Phenols: Organophotoredox/Nickel Dual Catalytic Hydroxylation of Aryl Halides with Water
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A highly effective hydroxylation reaction of aryl halides with water under synergistic organophotoredox and nickel catalysis is reported. The OH group of the resulting phenols originates from water, following deprotonation facilitated by an intramolecular base group on the ligand. Significantly, aryl bromides as well as less reactive aryl chlorides served as effective substrates to afford phenols with a wide range of functional groups. Without the need for a strong inorganic base or an expensive noble-metal catalyst, this process can be applied to the efficient preparation of diverse phenols and enables the hydroxylation of multifunctional pharmaceutically relevant aryl halides.
- Yang, Liu,Huang, Zhiyan,Li, Gang,Zhang, Wei,Cao, Rui,Wang, Chao,Xiao, Jianliang,Xue, Dong
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supporting information
p. 1968 - 1972
(2018/02/06)
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- The five carbonyl iron as CO release source preparation benzopyranone compounds (by machine translation)
-
The invention discloses a five-carbonyl iron as CO release source preparation benzopyranone compound of the method, the method to acetic acid palladium are the catalyst, piperazine is alkali, five carbonyl iron as CO release source, so that the 2 - iodo phenol compound with a terminal alkyne under mild condition coupled reactions, generating benzopyranone compounds. The invention has simple operation, mild reaction conditions, less catalyst levels, low source amount used CO release, toxicity is relatively small, low cost, wide applicability of the substrate, the target substance high yield, natural product can be widely used for the preparation of the benzopyranone compound. (by machine translation)
- -
-
Paragraph 0014; 0051-0054
(2017/07/06)
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- A transition-metal-free fast track to flavones and 3-arylcoumarins
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A highly regioselective and transition-metal free one-pot arylation of chromenones with arylboronic acids has been achieved employing K2S2O8. The procedure consists of a sequence of some reactions including an arylation/decarboxylation cascade and proceeds well in aqueous media to afford biologically interesting flavones and 3-arylcoumarins. This method exhibited excellent selectivity and functional group tolerance under mild conditions. The reaction also showed perfect efficacy for the preparation of styryl coumarins.
- Golshani, Mostafa,Khoobi, Mehdi,Jalalimanesh, Nafiseh,Jafarpour, Farnaz,Ariafard, Alireza
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supporting information
p. 10676 - 10679
(2017/10/06)
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- Method for synthesizing flavonoids compound in one step by virtue of catalysis of 1,3-dialkylimidazolium oxometallate
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The invention discloses a method for synthesizing a flavonoids compound in one step by virtue of catalysis of 1,3-dialkylimidazolium oxometallate. The method is characterized by comprising the following steps: sequentially adding raw material benzaldehyde or benzaldehyde derivatives, raw material 2-hydroxyacetophenone or 2-hydroxyacetophenone derivatives, an ion liquid catalyst and an organic solvent into a reactor, stirring, heating to 50 to 90 DEG C, reacting for 2 to 7 hours at a constant temperature by taking oxygen or air as an oxidant, cooling, distilling under reduced pressure, carrying out the column chromatography, and re-crystallizing and separating to obtain the target product flavonoids compound. The method has the characteristics that the ion liquid is used as the catalyst, the yield of the flavonoids compound synthesized in one step reaches 85 percent or more, therefore, compared with the traditional synthetic method, the reaction flow is shortened, and the synthetic efficiency of the flavonoids compound is remarkably improved. The method has advantages of high product yield, low production cost, simple operation procedures, moderate reaction conditions and the like and is proved to be a novel method for high-efficiently synthesizing the flavonoids compound.
- -
-
Paragraph 0092; 0093; 0094; 0095; 0096
(2016/10/08)
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- Mild and efficient organocatalytic method for the synthesis of flavones
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A convenient and efficient organocatalytic procedure for the selective cyclization of 1,3-diketones to give aromatic substituted 4H-chromen-4-ones under mild reaction conditions using N-triflyl phosphoramide is described. Application of the described conditions is presented in a formal synthesis of (S)-flavanone.
- Stanek, Filip,Stodulski, Maciej
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p. 3841 - 3843
(2016/08/02)
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- A very simple solvent-free method for the synthesis of 2-arylchromones using KHSO4 as a recyclable catalyst
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An efficient and solvent-free procedure for the synthesis of flavones using KHSO4 as a recyclable catalyst is described. The methodology represents an environmentally friendly process in comprehensive consideration compared with other catalytic systems listed in publications. This method provides a clean, simple, solvent-free reaction and useful alternatives to prepare flavones and chromones. The use of KHSO4 catalyst provides excellent yields, also leading to an easy separation and recovery of the catalysts, which allows both low environmental impact and low cost. Other green advantages of the method are the low formation of wastes and the replacement of corrosive, soluble mineral acids.
- Pérez, María,Ruiz, Diego,Autino, Juan,Sathicq, Angel,Romanelli, Gustavo
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p. 551 - 555
(2016/06/01)
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- Pd(OAc)2/S=PPh3 accelerated activation of gem-dichloroalkenes for the construction of 3-arylchromones
-
The Pd-catalyzed regioselective intramolecular nucleophilic substitution of gem-dichloroalkene derivatives with salicylaldehydes leading to the synthesis of 3-arylchromones has been developed. Pd(OAc)2/S=PPh3 could activate gem-dichloroalkenes and undergo nucleophilic substitution by salicylaldehydes with the aid of a base.
- Liu, Jianming,Song, Weiwei,Yue, Yuanyuan,Liu, Ren,Yi, Hong,Zhuo, Kelei,Lei, Aiwen
-
supporting information
p. 17576 - 17579
(2015/12/08)
-
- An efficient synthesis of aurone derivatives by the tributylphosphine-catalyzed regioselective cyclization of o-alkynoylphenols
-
An organocatalytic regioselective synthes is of aurones from o-alkynoylphenols was achieved. A catalytic amount of tributylphosphine select ively induced the 5-exo cyclization of o-alkynoylphenols under ambient conditions leading to aurone derivatives in high to excellent yields.
- Saito, Koya,Yoshida, Masahito,Doi, Takayuki
-
supporting information
p. 141 - 143
(2015/02/19)
-
- 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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-
- Convenient one-pot synthesis of chromone derivatives and their antifungal and antibacterial evaluation
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A one-pot method for the synthesis of chromone derivatives from the reaction of 2-hydroxyacetophenones with aliphatic or aromatic acid chlorides is reported. Esterification and Baker-Venkataraman rearrangement were promoted by t-BuOK, which was followed directly by acid-catalyzed cyclization in one pot. Some of 2-cyclohexyl- and 2-cyclohexylmethyl-substituted chromones displayed activity against plant pathogenic fungal strains. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications1 to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
- Ghani, Sherif B. Abdel,Mugisha, Patrick J.,Wilcox, Juliet C.,Gado, Emad A. M.,Medu, Erere O.,Lamb, Andrew J.,Brown, Richard C. D.
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p. 1549 - 1556
(2013/05/22)
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- Synthesis of chromones through LiOtBu/air-mediated oxidation and regioselective cyclization of o-hydroxyphenyl propargyl carbinols
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A cascade oxidative cyclization reaction for the synthesis of chromone derivatives was developed by using LiOtBu as a mediator and air as an oxidant. The reaction was carried out without the assistance of a transition metal under mild conditions to afford the chromones in good yields with high regioselectivities. A tandem reaction for the synthesis of various chromones was developed. LiOtBu was used as a mediator and air was used as a clean oxidant. The reaction generally showed high regioselectivity under mild conditions. Extensive research showed that dehydrogenative oxidation of the alcohols under strongly basic conditions was the crucial step, and Li+ was also found to play an important role in this process. Copyright
- Zhang, Shuai,Wan, Changfeng,Wang, Qiang,Zhang, Baiqun,Gao, Lingfeng,Zha, Zhenggen,Wang, Zhiyong
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p. 2080 - 2083
(2013/05/09)
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- A new synthesis of novel alkenylated flavones by palladium-catalyzed cross-coupling reactions
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Bromoflavones were treated with various terminal alkynes in palladium-catalyzed cross-coupling reactions under phosphine-free condions to give the expected alkenylated flavones in moderate to good yields. The presence of two different β hydrogens in the t
- Fekete, Szabolcs,Patonay, Tamas,Silva, Artur M. S.,Cavaleiro, Jose A. S.
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p. 210 - 225
(2013/09/24)
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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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- A novel route to synthesis of flavones from salicylaldehyde and acetophenone derivatives
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Convenient, facile, and alternate synthesis of medicinally important flavones is reported. The 2-hydroxychalcones derived from condensation between acetophenones and salicylaldehyde, underwent oxidative cyclization on heating in the presence of catalytic iodine, generating diversified flavones under solvent-free conditions. Eleven compounds have been synthesized in good to excellent yields and their mechanism of formation is described.
- Sashidhara, Koneni V.,Kumar, Manoj,Kumar, Abdhesh
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p. 2355 - 2359
(2012/07/14)
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- A novel one pot route to flavones under dual catalysis, an organo- and a Lewis acid catalyst
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Substituted phenylacetylenes react with various o-hydroxy aromatic aldehydes under dual catalysis of piperidine and FeCl3 in refluxing toluene to yield flavones in good to excellent yield. Atmospheric oxygen acts as stoichiometric oxidant in the process. Some of these compounds had been recently reported to show fair insecticidal activity against Spodoptera frugiperda.
- Maiti, Gourhari,Karmakar, Rajiv,Bhattacharya, Rudraksha N.,Kayal, Utpal
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supporting information; experimental part
p. 5610 - 5612
(2011/11/12)
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- Ionic liquid mediated Cu-catalyzed cascade oxa-Michael-oxidation: Efficient synthesis of flavones under mild reaction conditions
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Flavonoids are a class of natural products, found in a wide range of vascular plants and dietary components. Their low toxicity and extensive biological activities, including anti-cancer and anti-bacterial, have made them attractive candidates to serve as therapeutic agents for many diseases. Herein, we disclose a highly efficient synthetic method of CuI-catalyzed cascade oxa-Michael-oxidation, using chalcones as substrates, mediated by the ionic liquid [bmim][NTf2] at a low temperature. This efficient synthetic method has demonstrated high synthetic utility and can afford flavones in good to high yields (up to 98%).
- Du, Zhiyun,Ng, Huifen,Zhang, Kun,Zeng, Huaqiang,Wang, Jian
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p. 6930 - 6933
(2011/11/04)
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- Wells-Dawson heteropolyacid as reusable catalyst for sustainable synthesis of flavones
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The behavior of Wells-Dawson (H6P2W 18O62·24H2O, WD) acid, both bulk and supported on silica, for the cyclodehydration reaction of 1-(2-hydroxyphenyl)-3- phenyl-1,3-propanedione to obtain flavone was studied in heterogeneous conditions, using toluene as solvent. Catalytic experiences with bulk and supported catalysts with different WD acid loadings and reuse of the catalysts were done. The catalytic activity of supported catalysts was higher than that of the bulk catalyst, and their activity was almost constant after three reaction cycles. The following reaction conditions: reflux toluene and 1% mmol of WD supported on silica (0.4 g WD acid by gram of silica) were used for the preparation of five flavones. Yields above 85% were obtained in 4-5 h.
- Bennardi, Daniel O.,Romanelli, Gustavo P.,Sathicq, ángel G.,Autino, Juan C.,Baronetti, Graciela T.,Thomas, Horacio J.
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experimental part
p. 68 - 73
(2012/02/05)
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- Microwave-assisted synthesis and antimicrobial activities of flavonoid derivatives
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Eleven flavonoid derivatives were synthesised using a modified Baker-Venkataraman rearrangement, and subsequent microwave-assisted closure of the heterocyclic ring. All of the synthetic compounds displayed antifungal activity against Aspergillus niger and
- Abdel Ghani, Sherif B.,Weaver, Louise,Zidan, Zidan H.,Ali, Hussein M.,Keevil, C. William,Brown, Richard C.D.
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p. 518 - 522
(2008/09/17)
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- Synthesis of substituted flavones and arylchromones using P and Si Keggin heteropolyacids as catalysts
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A simple and clean procedure for the preparation of functionalized flavones and chromones using commercial Keggin heteropolyacid in acetonitrile medium is described for the cyclization of 1-(2-hydroxyaryl)-3-aryl-1,3-propanodiones. Sixteen examples are reported, yields ranging in 60-91%; five substituted 2-naphthylchromones are prepared for the first time.
- Bennardi, Daniel O.,Romanelli, Gustavo P.,Jios, Jorge L.,Vazquez, Patricia G.,Caceres, Carmen V.,Autino, Juan C.
-
-
- Efficient synthesis of polyoxygenated flavones from naturally occurring flavanones
-
Flavonoids are constituents of the human diet (they are present in many beverages and food), and in organisms they are responsible for several biological functions, including that of antioxidant. Because of the increasing interest in these molecules, methods for their synthesis and structural modification are of great importance; studies on the biological activities of many of these compounds are insufficient because of their scarcity and/or high cost. We have developed an expeditious synthesis of polyoxygenated flavones, starting from available and inexpensive flavanones, using a bromination- methoxylation procedure. A series of flavonoids that are not otherwise accessible can be prepared using this method. As an example, 3′-demethoxysudachitin, a limited flavone possessing antimicrobial activity against methicillin-resistant Staphylococcus aureus and Helicobacter pylori and acting as a 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenger, was prepared in fairly satisfactory yield.
- Bovicelli, Paolo,D'Angelo, Vittoria,Collalto, Daniela,Verzina, Antonio,D'Antona, Nicola,Lambusta, Daniela
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p. 1697 - 1701
(2008/03/11)
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- Microwave enhanced palladium catalysed coupling reactions: A diversity-oriented synthesis approach to functionalised flavones
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Microwave enhanced diversity-oriented synthesis (MEDOS) using palladium catalysed protocols is introduced as a powerful new strategy for the synthesis of systematically modified small molecules and is highlighted by application to functionalised flavones. The Royal Society of Chemistry 2006.
- Fitzmaurice, Richard J.,Etheridge, Zac C.,Jumel, Emelie,Woolfson, Derek N.,Caddick, Stephen
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p. 4814 - 4816
(2007/10/03)
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- Microwave-assisted synthesis of functionalized flavones and chromones
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A facile microwave synthesis of functionalized flavones and chromones via the cyclization of 1-(2-hydroxyaryl)-3-aryl-1,3-propanedione is described.
- Kabalka, George W.,Mereddy, Arjun R.
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p. 6315 - 6317
(2007/10/03)
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- Synthesis of halogenated/nitrated flavone derivatives and evaluation of their affinity for the central benzodiazepine receptor
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A series of halogenated/nitrated flavone compounds were synthesized. Some of the products were found to be potent central benzodiazepine receptor (BDZ-R) ligands. The structure-activity relationships (SAR) analysis of the new synthetic compounds, together with that of others already described, indicates that substitutions at position 6 or 6 and 3' in the flavone nucleus are the only ones that give rise to high affinity BDZ-R ligands.
- Marder, Mariel,Zinczuk, Juan,Colombo, Maria I.,Wasowski, Cristina,Viola, Haydee,Wolfman, Claudia,Medina, Jorge H.,Ruveda, Edmundo A.,Paladini, Alejandro C.
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p. 2003 - 2008
(2007/10/03)
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- REACTIONS OF 3-ARYL-1--2-PROPYN-1-ONES IN THE PRESENCE OF AMINES. TWO TYPES OF INTRAMOLECULAR CYCLIZATION INVOLVING THE ortho-HYDROXYL GROUP
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Amines react with 3-aryl-1--2-propyn-1-ones in three directions, i.e., with addition of the reagent at the triple bond (and the formation of the β-aminovinyl ketone) and intramolecular cyclization leading to the formation of six-membered (flavones) or five-membered (aurones) heterocycles.The development of these reaction paths is controlled by the nature of the amines.Probable reaction paths are proposed.
- Korshunov, S. P.,Korzhova, N. V.,Kazantseva, V. M.,Krasnov, V. L.,Utekhina, N. V.,Bodrikov, I. V.
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p. 1658 - 1663
(2007/10/02)
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- Reaction of 2'-Hydroxychalcone Dibromides with Me2SO
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2'-Hydroxychalcone dibromides on treatment with Me2SO gave 2'-hydroxychalcone, 2'-hydroxy-3'- or 2'-hydroxy-5'-bromochalcone, flavone, monobrominated flavone, 6,8-dibromoflavone, 3-bromoflavone, and 3-, 6-, or 8-dibromoflavone.
- Reddy, Jagannadha N.,Pawar, Sevak Ram,Sharma, Tarachand
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p. 377 - 379
(2007/10/02)
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