- Crystal structure of a chalcone derivative
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The crystal and molecular structure of 1-(4-methoxyphenyl)-3-(phenyl)-2-propen-1-one derivative is determined by X-ray diffraction method. The compound, C16H14O2, crystallises in the orthorhombic space group Pbca with a = 10.921(2) A, b = 30.583(1) A, c = 7.535(3) A, V = 2516.7(9) A3, Z = 4, Dcalc = 1.242 Mg/m3, μ = 0.327 mm-1, F000 = 504, λ(MoKα) = 0.71069 A and the structure was refined to R = 0.044.
- Devarajegowda,Sridhar,Prasad, J. Shashidhara,Indira,Sooryanarayanarao,Karat, Prakash P.
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- Method using Ti (III) complex catalytic alkyne selective hydrogenation reduction to prepare chalcone compounds
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The invention discloses a method for preparing chalcone compounds through selective hydrogenation of Ti (III) complexes to prepare chalcone compounds, wherein zinc powder is used as a catalyst, zinc powder is a reducing agent, triethylamine hydrochloride is a proton source, and an alkyne and triethylamine hydrochloride are subjected to radical selective addition reaction under the protection of inert gas to generate chalcone compounds. The reaction condition is mild, the operation is simple, the reaction time is short, the reaction product is single, the atom economy is high, and only the product needs to be separated by simple column chromatography after the reaction is finished. The chalcone compound has wide biological activity and medicinal value.
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Paragraph 0014; 0015; 0016; 0017; 0018
(2021/09/26)
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- Alkene Synthesis by Photo-Wolff-Kischner Reaction of Sulfur Ylides and N-Tosylhydrazones
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A visible-light-driven and room temperature photo-Wolff-Kischner reaction of sulfur ylides and N-tosylhydrazones has been developed for the first time to provide modular access to alkene synthesis. The high functional group tolerance and broad substrate scope were demonstrated by more than 60 examples. Both E- and Z-olefinic stereochemistry in the products could be controlled with excellent stereoselectivity. A series of mechanistic studies support that the reaction should proceed through a radical-carbanion crossover pathway, specifically involving addition of photo-generated sulfur ylide radical cations to N-tosylhydrazones to form carbanions and subsequent Wolff-Kischner process.
- Gao, Pan-Pan,Yan, Dong-Mei,Bi, Ming-Hang,Jiang, Min,Xiao, Wen-Jing,Chen, Jia-Rong
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supporting information
p. 14195 - 14201
(2021/09/20)
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- Iron-Catalyzed ?±,?-Dehydrogenation of Carbonyl Compounds
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An iron-catalyzed α,β-dehydrogenation of carbonyl compounds was developed. A broad spectrum of carbonyls or analogues, such as aldehyde, ketone, lactone, lactam, amine, and alcohol, could be converted to their α,β-unsaturated counterparts in a simple one-step reaction with high yields.
- Zhang, Xiao-Wei,Jiang, Guo-Qing,Lei, Shu-Hui,Shan, Xiang-Huan,Qu, Jian-Ping,Kang, Yan-Biao
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supporting information
p. 1611 - 1615
(2021/03/03)
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- Recyclable Copper Nanoparticles-Catalyzed Hydroboration of Alkenes and β-Borylation of α,β-Unsaturated Carbonyl Compounds with Bis(Pinacolato)Diboron
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Nano-ferrite-supported Cu nanoparticles (Fe-dopamine-Cu NPs) catalyzed anti-Markovnikov-selective hydroboration of alkenes with B2pin2 is reported under mild reaction conditions. This protocol can be applied to a broad range of substrates with high functional group compatibility. In addition, we demonstrated the use of Fe-dopamine-Cu NPs as a catalyst for the β-borylation of α,β-unsaturated ketones and ester, providing alkylboronate esters in up to 98% yield. Reuse of the magnetically recyclable catalyst resulted in no significant loss of activity in up to five reaction runs for both systems. (Figure presented.).
- Shegavi, Mahadev L.,Saini, Suresh,Bhawar, Ramesh,Vishwantha, Meghana Desai,Bose, Shubhankar Kumar
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supporting information
p. 2408 - 2416
(2021/03/16)
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- Asymmetric transfer hydrogenation of unsaturated ketones; factors influencing 1,4- vs 1,2- regio- and enantioselectivity, and alkene vs alkyne directing effects
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A detailed study has been completed on the asymmetric transfer hydrogenation (ATH) of a series of enones using Ru(II) catalysts. Electron-rich rings adjacent to the C[dbnd]O group reduce the level of C[dbnd]O reduction compared to C[dbnd]C. The ATH reaction can readily discriminate between double and triple bonds adjacent to ketones, reducing the double bond but leaving a triple bond intact in the major product.
- Hall, Thomas H.,Adams, Hannah,Vyas, Vijyesh K.,Michael Chu,Wills, Martin
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- A new method for the synthesis of chalcone derivatives promoted by PPh3/I2under non-alkaline conditions
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A straightforward and general method has been developed for the synthesis of chalcone derivatives by a Claisen-Schmidt reaction in the presence of PPh3/I2 in 1,4-dioxane under reflux temperatures. With the condensation of the aromatic ketone and aldehyde occurring at non-strongly alkaline conditions, our proposed method significantly expands the range of applicable substrates, especially for groups that are unstable under alkaline conditions.
- Xue, Kangsheng,Sun, Guoxiang,Zhang, Yanzhi,Chen, Xubing,Zhou, Yang,Hou, Jinjun,Long, Huali,Zhang, Zijia,Lei, Min,Wu, Wanying
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supporting information
p. 625 - 634
(2020/11/23)
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- Combined 3D-QSAR and docking analysis for the design and synthesis of chalcones as potent and selective monoamine oxidase B inhibitors
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Monoamine oxidases (MAOs) are important targets in medicinal chemistry, as their inhibition may change the levels of different neurotransmitters in the brain, and also the production of oxidative stress species. New chemical entities able to interact selectively with one of the MAO isoforms are being extensively studied, and chalcones proved to be promising molecules. In the current work, we focused our attention on the understanding of theoretical models that may predict the MAO-B activity and selectivity of new chalcones. 3D-QSAR models, in particular CoMFA and CoMSIA, and docking simulations analysis have been carried out, and their successful implementation was corroborated by studying twenty-three synthetized chalcones (151–173) based on the generated information. All the synthetized molecules proved to inhibit MAO-B, being ten out of them MAO-B potent and selective inhibitors, with IC50 against this isoform in the nanomolar range, being (E)-3-(4-hydroxyphenyl)-1-(2,2-dimethylchroman-6-yl)prop-2-en-1-one (152) the best MAO-B inhibitor (IC50 of 170 nM). Docking simulations on both MAO-A and MAO-B binding pockets, using compound 152, were carried out. Calculated affinity energy for the MAO-A was +2.3 Kcal/mol, and for the MAO-B was ?10.3 Kcal/mol, justifying the MAO-B high selectivity of these compounds. Both theoretical and experimental structure–activity relationship studies were performed, and substitution patterns were established to increase MAO-B selectivity and inhibitory efficacy. Therefore, we proved that both 3D-QSAR models and molecular docking approaches enhance the probability of finding new potent and selective MAO-B inhibitors, avoiding time-consuming and costly synthesis and biological evaluations.
- Mellado, Marco,González, César,Mella, Jaime,Aguilar, Luis F.,Vi?a, Dolores,Uriarte, Eugenio,Cuellar, Mauricio,Matos, Maria J.
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- Mechanochemical Syntheses of N-Containing Heterocycles with TosMIC
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A mechanochemical van Leusen pyrrole synthesis with a base leads to 3,4-disubstitued pyrroles in moderate to excellent yields. The developed protocol is compatible with a range of electron-withdrawing groups and can also be applied to the synthesis of oxazoles. Attempts to mechanochemically convert the resulting pyrroles into porphyrins proved to be difficult.
- Bolm, Carsten,Molitor, Claude,Rissanen, Kari,Schumacher, Christian,Smid, Sabrina,Truong, Khai-Nghi
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p. 14213 - 14222
(2021/09/07)
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- Reaction rate differences between organotrifluoroborates and boronic acids in BINOL-catalyzed conjugate addition to enones
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Enantioselective organocatalysis has been successfully employed in combination with trifluoroborate reagents for novel organic transformations over the last decade. However, no experimental rate studies of these reactions have been reported. Herein we report Hammett plot analysis of the organocatalyzed enantioselective conjugate addition of alkenyl, aryl, and heteroaryl trifluoroborate salts to chalcone derivatives with substitution at both the β-aryl and keto-aryl positions. The rate trend for keto-aryl substitution diverges from that of boronic acid nucleophiles in that the keto-aryl substituent for trifluoroborate salts does not measurably impact reaction rate in a manner consistent with charge stabilization. In addition, variable temperature NMR in combination with quantitative thin-layer chromatography (TLC) analysis suggests that the reaction is impacted by the low solubility of the trifluoroborate salts, so particle size and stirring speed affect reaction rates.
- Brooks, Bailey,Hiller, Noemi,May, Jeremy A.
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supporting information
(2021/09/28)
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- C3 amino-substituted chalcone derivative with selective adenosine rA1 receptor affinity in the micromolar range
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Abstract: To identify novel adenosine receptor (AR) ligands based on the chalcone scaffold, herein the synthesis, characterization and in vitro and in silico evaluation of 33 chalcones (15–36 and 37–41) and structurally related compounds (42–47) are reported. These compounds were characterized by radioligand binding and GTP shift assays to determine the degree and type of binding affinity, respectively, against rat (r) A1 and A2A ARs. The chalcone derivatives 24, 29, 37 and 38 possessed selective A1 affinity below 10?μM, and thus, are the most active compounds of the present series; compound 38 was the most potent selective A1 AR antagonist (Ki (r) = 1.6?μM). The structure–affinity relationships (SAR) revealed that the NH2-group at position C3 of ring A of the chalcone scaffold played a key role in affinity, and also, the Br-atom at position C3′ on benzylidene ring B. Upon in vitro and in silico evaluation, the novel C3 amino-substituted chalcone derivative 38—that contains an α,?-unsaturated carbonyl system and easily allows structural modification—may possibly be a synthon in future drug discovery. Graphic abstract: C3 amino-substituted chalcone derivative (38) with C3′ Br substitution on benzylidene ring B possesses selective adenosine rA1 receptor affinity in micromolar range.[Figure not available: see fulltext.]
- Janse van Rensburg, Helena D.,Legoabe, Lesetja J.,Terre’Blanche, Gisella
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p. 1581 - 1605
(2020/11/20)
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- Modular access to 1,2-allenyl ketones based on a photoredox-catalysed radical-polar crossover process
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Herein, a new protocol dealing with the preparation of 1,2-allenyl ketones has been successfully developedviathe reactions of enynes with radicals enabled by dual photoredox/copper catalysis. Based on the results of a deuteration experiment and the competition reaction between cyclopropanation and allenation, the mechanism based on a photoredox-neutral-catalysed radical-polar crossover process has been proposed. Synthetic applications of allenes have also been demonstrated.
- Du, Chan,Fang, Jianghua,Fang, Yewen,Lei, Wan,Li, Yan,Liu, Yongjun
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supporting information
p. 8502 - 8506
(2021/10/20)
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- Synthesis of Ketones by C?H Functionalization of Aldehydes with Boronic Acids under Transition-Metal-Free Conditions
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A method for the synthesis of ketones from aldehydes and boronic acids via a transition-metal-free C?H functionalization reaction is reported. The method employs nitrosobenzene as a reagent to drive the simultaneous activation of the boronic acid as a boronate and the activation of the C?H bond of the aldehyde as an iminium species that triggers the key C?C bond-forming step via an intramolecular migration from boron to carbon. These findings constitute a practical, scalable, and operationally straightforward method for the synthesis of ketones.
- Roscales, Silvia,Csáky, Aurelio G.
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supporting information
p. 8728 - 8732
(2021/03/16)
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- Green method for high-selectivity synthesis of chalcone compounds
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Under the condition of air, the water-soluble inorganic weak base is used as a catalyst to catalyze the hydrogen transfer reaction of the propargyl alcohol compound, so that the green synthesis of the high-trans selective chalcone compound is realized. Reaction temperature: 80 - 120 °C and reaction time 12 - 48 hours. To the technical scheme, any transition metal catalyst and ligand do not need to be used, inert gas protection is not needed, no other byproducts are generated, the atom economy 100%, green and environment friendliness are avoided, and the product is a high-selectivity (E)-type product. The reaction conditions are relatively low in requirement. Compared with the prior art, the alkali catalyst is obvious in advantages, and has a certain application prospect in the fields of organic synthesis, biochemistry, medicine and the like.
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Paragraph 0039-0042
(2021/10/02)
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- Iodine-catalyzed α,β-dehydrogenation of ketones and aldehydes generating conjugated enones and enals
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A transition metal-free α,β-dehydrogenation of ketones and aldehydes was developed. This reaction was conducted in a facile I2/KI/DMSO system to produce the corresponding unsaturated compounds in good to high yields. The gram-scale experiment also indicated the potential synthetic value of this new reaction in organic synthesis. In the reaction, DMSO acted as both solvent and mild oxidant.
- Cao, Yuanjie,Chen, Tieqiao,Huang, Tianzeng,Liu, Long
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supporting information
p. 8697 - 8701
(2020/06/08)
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- Computational modeling and target synthesis of monomethoxy-substituted o-diphenylisoxazoles with unexpectedly high antimitotic microtubule destabilizing activity
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The ability of monomethoxy-substituted o-diphenylisoxazoles 2a-d to interact with the colchicine site of tubulin was predicted using computational modeling, docking studies, and calculation of binding affinity. The respective molecules were synthesized in high yields by three steps reaction using easily available benzaldehydes, acetophenones, and arylnitromethanes as starting material. The calculated antitubulin effect was confirmed in vivo in a sea urchin embryo model. Compounds 2a and 2c showed high antimitotic microtubule destabilizing activity compared to that of CA4. Isoxazole 2a also exhibited significant cytotoxicity against human cancer cells in NCI60 screen. For the first time, isoxazole-linked CA4 derivatives 2a and 2c with only one methoxy substituent were identified as potent antimitotic microtubule destabilizing agents. These molecules could be considered as promising structures for further optimization.
- Stroylov, Victor S.,Svitanko, Igor V.,Maksimenko, Anna S.,Kislyi, Victor P.,Semenova, Marina N.,Semenov, Victor V.
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supporting information
(2020/10/21)
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- Polarity-sensitive triphenyl pyridinium fluorescent probe as well as preparation and application thereof
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The invention discloses a polarity-sensitive triphenyl pyridinium salt fluorescent probe and preparation and application thereof. The structural general formula of the fluorescent probe is shown in the specification, and R1 is H, a halogen atom or a methoxy group; and R2 is alkyl or substituted alkyl. The pyridinium salt part in the fluorescent probe with the structure is used as an electron acceptor (Acceptor, A) and has very strong electron withdrawing capability, and meanwhile, the three benzene ring parts in the fluorescent probe are used as an electron donor (Donor, D) and can provide proper electron donating capability; the fluorescent probe with a D-A structure formed in this way has certain fluorescence capability and atypical AIE properties; the solid fluorescence quantum yield is20% or above; in a certain polarity range, along with the enhancement of the solvent polarity, the luminescence red shift in the solvent is realized, the fluorescence intensity is weakened, and the quantum yield is reduced.
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Paragraph 0045-0047
(2020/12/08)
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- Synthesis of 3-fluoro-2,5-disubstituted furans through ring expansion ofgem-difluorocyclopropyl ketones
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The synthesis of 3-fluoro-2,5-disubstituted furans fromgem-difluorocyclopropyl ketones was accomplished using trifluoromethanesulfonic acid (CF3SO3H) through ring expansion owing to the activation of the carbonyl group in the starting material. The present synthesis of 3-fluorofurans tolerates substrates designed for products with aromatic substituents at the C-2 and C-5 positions.
- Amii, Hideki,Matsumura, Chihori,Sugiishi, Tsuyuka
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supporting information
p. 3459 - 3462
(2020/05/25)
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- Methoxychalcones: Effect of methoxyl group on the antifungal, antibac-terial and antiproliferative activities
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Background: Chalcones substituted by methoxyl groups have presented a broad spec-trum of bioactivities, including antifungal, antibacterial and antiproliferative effects. However, a clear and unambiguous investigation about the relevance of this substituent on the chalcone framework has not been described. Objective: The purpose of this work is to assess the antibacterial, antifungal and antiproliferative activities of the two series of seventeen synthesized regioisomeric methoxychalcones. Series I and II were constituted by chalcones substituted by methoxyl groups on rings A (5–12) and B (13–21), respectively. In addition, the library of methoxychalcones was submitted to in silico drug-likeness and pharmacokinetics properties predictions. Methods: Methoxychalcones were synthesized and their structures were confirmed by NMR spectral data analyses. Evaluations of antimicrobial activity were performed against five species of Candida, two Gram-negative and five Gram-positive species. For antiproliferative activity, methoxychalcones were evaluated against four human tumorigenic cell lines, as well as human non-tumorigenic keratinocytes. Drug-likeness and pharmacokinetics properties were predicted using Molinspiration and PreADMET toolkits. Results: In general, chalcones of series I are the most potent antifungal, antibacterial and antipro-liferative agents. 3’, 4’, 5’-Trimethoxychalcone (12) demonstrated potent antifungal activity against Candida krusei (MIC = 3.9 μg/mL), eight times more potent than fluconazole (reference antifungal drug). 3’-Methoxychalcone (6) displayed anti-Pseudomonas activity (MIC = 7.8 μg/mL). 2’,5’-Dimethoxychalcone (9) displayed potent antiproliferative effect against C-33A (cervix), A-431 (skin) and MCF-7 (breast), with IC50 values ranging from 7.7 to 9.2 μM. Its potency was superior to curcumin (reference antiproliferative compound), which exhibited IC50 values ranging from 10.4 to 19.0 μM. Conclusion: Our studies corroborated the relevance of methoxychalcones as antifungal, antibacte-rial and antiproliferative agents. In addition, we elucidated influence of the position and number of methoxyl groups toward bioactivity. In silico predictions indicated good drug-likeness and phar-macokinetics properties to the library of methoxychalcones.
- Marques, Beatriz C.,Santos, Mariana B.,Anselmo, Daiane B.,Monteiro, Diego A.,Gomes, Eleni,Saiki, Marilia F. C.,Rahal, Paula,Rosalen, Pedro L.,Sardi, Janaina C. O.,Regasini, Luis O.
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p. 881 - 891
(2020/08/19)
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- Antiproliferative effects of chalcones on T cell acute lymphoblastic leukemia-derived cells: Role of PKCβ
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In this study, a series of 20 chalcone derivatives was synthesized, and their antiproliferative activity was tested against the human T cell acute lymphoblastic leukemia-derived cell line, CCRF-CEM. On the basis of the structural features of the most active compounds, a new library of chalcone derivatives, according to the structure–activity relationship design, was synthesized, and their antiproliferative activity was tested against the same cancer cell line. Furthermore, four of these derivatives (compounds 3, 4, 8, 28), based on lower IC50 values (between 6.1 and 8.9 μM), were selected for further investigation regarding the modulation of the protein expression of RACK1 (receptor for activated C kinase), protein kinase C (PKC)α and PKCβ, and their action on the cell cycle level. The cell cycle analysis indicated a block in the G0/G1 phase for all four compounds, with a statistically significant decrease in the percentage of cells in the S phase, with no indication of apoptosis (sub-G0/G1 phase). Compounds 4 and 8 showed a statistically significant reduction in the expression of PKCα and an increase in PKCβ, which together with the demonstration of an antiproliferative role of PKCβ, as assessed by treating cells with a selective PKCβ activator, indicated that the observed antiproliferative effect is likely to be mediated through PKCβ induction.
- Corsini, Emanuela,Facchetti, Giorgio,Esposito, Sara,Maddalon, Ambra,Rimoldi, Isabella,Christodoulou, Michael S.
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- Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones Using Amide-Based Cinchona Alkaloids as Hybrid Phase-Transfer Catalysts
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A series of 20 one chiral epoxides were obtained with excellent yields (up to 99%) and enantioselectivities (up to >99% ee) using hybrid amide-based Cinchona alkaloids. Our method is characterized by low catalyst loading (0.5 mol %) and short reaction times. Moreover, the epoxidation process can be carried out in 10 cycles, without further catalyst addition to the reaction mixture. This methodology significantly enhance the scale of the process using very low catalyst loading.
- Jurczak, Janusz,Majdecki, Maciej,Tyszka-Gumkowska, Agata
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supporting information
(2020/11/13)
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- DBU-Catalyzed Rearrangement of Secondary Propargylic Alcohols: An Efficient and Cost-Effective Route to Chalcone Derivatives
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A 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-catalyzed rearrangement of diarylated secondary propargylic alcohols to give α,β-unsaturated carbonyl compounds has been developed. The typical 1,3-transposition of oxy functionality, characteristic of Mayer-Schuster rearrangements, is not observed in this case. A broad substrate scope, functional-group tolerance, operational simplicity, complete atom economy, and excellent yields are among the prominent features of the reaction. Additionally, the photophysical properties and crystal-structure-packing behavior of selected compounds were investigated and found to be of interest.
- De, Rimpa,Savarimuthu, Antony,Ballav, Tamal,Singh, Pijush,Nanda, Jayanta,Hasija, Avantika,Chopra, Deepak,Bera, Mrinal K.
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supporting information
p. 1587 - 1592
(2020/08/28)
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- Studies of NMR Chemical Shifts of Chalcone Derivatives of Five-membered Monoheterocycles and Determination of Aromaticity Indices
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A series of the chalcone derivatives of the five-membered monoheterocyclic compounds, (E)-1-aryl-3-heteroarylpropen-1-ones, were prepared by aldol condensation of the corresponding aldehydes of thiophene, pyrrole, and furan with m- and p-substituted acetophenones. Similar condensation of the acetyl compounds of the heterocycles with m- and p-substituted benzaldehydes gave another series of the chalcone derivatives, (E)-1-heteroaryl-3-arylpropen-1-ones. The 13C chemical shift values (δC) of the chalcone derivatives were determined in order to find if they correlated with the Hammett σ values. A good correlation, especially for the β-C for both series, was found for the 13C chemical shift values (δC) of the chalcone derivatives with the Hammett σ values. The chemical shift values of the β-C of the heterocyclic compounds were plotted against those of the benzene derivatives. The resulting slopes were found to be close to the values of the aromaticity indices.
- Jeong, Eun Jeong,Lee, In-Sook Han
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p. 668 - 673
(2019/07/12)
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- Organocatalytic asymmetric vinylogous 1,4-addition of α,α-Dicyanoolefins to chalcones under a bio-based reaction media: Discovery of new Michael adducts with antiplasmodial activity
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The organocatalysed asymmetric vinylogous Michael addition of α,α-dicyanoolefins to α,β-unsaturated aldehydes and ketones have been reported in the last decade, however, chalcones have been poorly explored. Moreover, a considerable part of the publications in this theme still employs undesirable solvents, such as toluene and THF, with concerns related to health and environmental safety. We report herein the use of a bifunctional catalyst derived from a Cinchona alkaloid to perform the enantio- and diastereoselective Michael addition of α,α-dicyanoolefins to chalcones using 2-MeTHF as solvent. The Michael adducts were obtained in moderate to good yields and were evaluated for their antiplasmodial and cytotoxic activity.
- Martelli, Lorena S.R.,Vieira, Lucas C.C.,Paix?o, Márcio W.,Zukerman-Schpector, Julio,de Souza, Juliana O.,Aguiar, Anna Caroline C.,Oliva, Glaucius,Guido, Rafael V.C.,Corrêa, Arlene G.
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supporting information
p. 3530 - 3542
(2019/05/24)
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- LANTHANIDE COMPLEXES BASED ON TRIETHYLENETETRAMINE-N,N,N',N'',N''',N'''-HEXAACETIC ACID DERIVATIVES
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The present invention relates to a complex comprising at least one lanthanide (Ln) and at least one compound (C) comprising a unit of formula (I) below: said unit of formula (I) being covalently connected to at least one antenna which absorbs at a wavelength ranging from 500 nm to 900 nm.
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Paragraph 0185-0187
(2019/11/11)
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- LANTHANIDE COMPLEXES COMPRISING DENDRIMERS
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The present invention relates to a complex comprising at least one dendrimer and at least one lanthanide, wherein the dendrimer comprises a unit of formula (I) below: in which: C1 is a valence group 4 of formula >N—CH2—CH2—N1, A2 and A3 are groups of formula —(CH2)2—C(O)—NH—(CH2)2—; the unit of formula (I) being connected covalently to at least one antenna which absorbs at a wavelength ranging from 500 nm to 900 nm.
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Paragraph 0149; 0150; 0151
(2019/12/01)
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- Intermolecular Multiple Dehydrogenative Cross-Couplings of Ketones with Boronic Acids and Amines via Copper Catalysis
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An efficient and versatile oxidative coupling reaction was developed for the synthesis of valuable β-functionalized unsaturated ketones and meta-substituted phenols. In the case of intramolecular reactions, achieving rapid molecular complexity through multiple dehydrogenative couplings is already a well-established strategy. Herein, we report an intermolecular multiple dehydrogenative coupling between ketones and nucleophilic amines or boronic acids using inexpensive copper(I) oxide as a catalyst. This method provides a facile access to highly desirable chemical products such as α,β-unsaturated ketones, enaminones, and synthetically relevant meta-substituted phenols. (Figure presented.).
- Wang, Tianzhang,Chen, Guowei,Lu, Yu-Jing,Chen, Qian,Huo, Yanping,Li, Xianwei
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supporting information
p. 3886 - 3892
(2019/07/19)
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- Alpha, beta unsaturated ketone compound and preparation method and application thereof
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The invention belongs to the technical field of organic synthesis, and in particular relates to an alpha, beta unsaturated ketone compound and a preparation method and application thereof. The methodcomprises the following steps: dissolving a compound of
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Paragraph 0075-0081
(2019/09/10)
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- Basic Anion-Exchange Resin-Catalyzed Aldol Condensation of Aromatic Ketones with Aldehydes in Continuous Flow
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A general method for the aldol condensation of aromatic ketones with aldehydes was developed under continuous-flow conditions using a commercially available, strongly basic anion-exchange resin (A26) as catalyst. This procedure, in addition to exhibiting a wide substrate scope, promoted carbon-carbon bond formation under mild conditions using a quasi-stoichiometric ratio of starting reagents with good to excellent yields, thereby forming a limited amount of waste and allowing the process to be applied to sequential-flow systems. A proof of concept was developed in the first fully heterogeneously catalyzed two-step flow synthesis of donepezil, which is a blockbuster commercial anti-Alzheimer's drug.
- Laroche, Benjamin,Saito, Yuki,Ishitani, Haruro,Kobayashi, Shū
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supporting information
p. 961 - 967
(2019/05/02)
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- Phosphine-mediated partial reduction of alkynes to form both (E)- and (Z)-alkenes
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A mild, phosphine-mediated partial reduction of alkynyl carbonyls to the corresponding alkenes was developed. Tuning of the reaction conditions led to either the (E)- or (Z)-diastereomer with high selectivity. A range of alkynyl esters, amides, and ketones were reduced to form alkenes in good to high yields and with excellent functional group tolerance.
- Pierce, Brett M.,Simpson, Brittany F.,Ferguson, Kane H.,Whittaker, Rachel E.
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supporting information
p. 6659 - 6662
(2018/09/29)
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- Chalcone derivatives enhance ATP-binding cassette transporters A1 in human THP-1 macrophages
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Atherosclerosis is a process of imbalanced lipid metabolism in the vascular walls. The underlying pathology mainly involves the deposition of oxidized lipids in the endothelium and the accumulation of cholesterol in macrophages. Macrophages export excessive cholesterol (cholesterol efflux) through ATP-binding cassette transporter A1 (ABCA1) to counter the progression of atherosclerosis. We synthesized novel chalcone derivatives and assessed their effects and the underlying mechanisms on ABCA1 expression in macrophages. Human THP-1 macrophages were treated with synthetic chalcone derivatives for 24 h. In Western blot and flow cytometry analyses, a chalcone derivative, (E)-1-(3,4-diisopropoxyphenyl)-3-(4-isopropoxy-3-methoxyphenyl)prop- 2-en-1-one (1m), was observed to significantly enhance ABCA1 protein expression in THP-1 cells (10 μM, 24 h). Levels of mRNA of ABCA1 and liver X receptor alpha (LXRα) were quantified using a real-time quantitative polymerase chain reaction technique and were found to be significantly increased after treatment with the novel chalcone derivative 1m. Several microRNAs, including miR155, miR758, miR10b, miR145, miR33, and miR106b, which functionally inhibit ABCA1 expression were suppressed after treatment with 1m. Collectively, 1m increases ABCA1 expression in human THP-1 macrophages. The mechanisms involve the activation of the LXRα-ABCA1 pathway and suppression of certain microRNAs that regulate ABCA1 expression.
- Teng, I-Jou,Tsai, Min-Chien,Shih, Shao-Fu,Tsuei, Bi-Feng,Chang, Hsin,Chuang, Yi-Ping,Lin, Chin-Sheng,Chern, Ching-Yuh,Chen, Sy-Jou
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- A Ratiometric Acoustogenic Probe for in Vivo Imaging of Endogenous Nitric Oxide
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Photoacoustic (PA) imaging is an emerging imaging modality that utilizes optical excitation and acoustic detection to enable high resolution at centimeter depths. The development of activatable PA probes can expand the utility of this technology to allow for detection of specific stimuli within live-animal models. Herein, we report the design, development, and evaluation of a series of Acoustogenic Probe(s) for Nitric Oxide (APNO) for the ratiometric, analyte-specific detection of nitric oxide (NO) in vivo. The best probe in the series, APNO-5, rapidly responds to NO to form an N-nitroso product with a concomitant 91 nm hypsochromic shift. This property enables ratiometric PA imaging upon selective irradiation of APNO-5 and the corresponding product, tAPNO-5. Moreover, APNO-5 displays the requisite photophysical characteristics for in vivo PA imaging (e.g., high absorptivity, low quantum yield) as well as high biocompatibility, stability, and selectivity for NO over a variety of biologically relevant analytes. APNO-5 was successfully applied to the detection of endogenous NO in a murine lipopolysaccharide-induced inflammation model. Our studies show a 1.9-fold increase in PA signal at 680 nm and a 1.3-fold ratiometric turn-on relative to a saline control.
- Reinhardt, Christopher J.,Zhou, Effie Y.,Jorgensen, Michael D.,Partipilo, Gina,Chan, Jefferson
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supporting information
p. 1011 - 1018
(2018/02/07)
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- Chalcone and cinnamate synthesis via one-pot enol silane formation-Mukaiyama aldol reactions of ketones and acetate esters
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Aryl alkyl ketones, acetate esters, and acetamides undergo facile one-pot enol silane formation, Mukaiyama aldol addition, and dehydrosilyloxylation in the presence of an amine base and excess trimethylsilyl trifluoromethanesulfonate. The chalcone and cinnamate products are generally recovered in high yield. The relative stoichiometry of the trimethylsilyl trifluoromethanesulfonate and amine base reagents determines whether the reaction yields the β-silyloxy carbonyl product or the α,β-unsaturated carbonyl.
- Downey, C. Wade,Glist, Hadleigh M.,Takashima, Anna,Bottum, Samuel R.,Dixon, Grant J.
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supporting information
p. 3080 - 3083
(2018/07/06)
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- Visible Light-Induced Aerobic Epoxidation of α,β-Unsaturated Ketones Mediated by Amidines
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An aerobic photoepoxidation of α,β-unsaturated ketones driven by visible light in the presence of tetramethylguanidine (3b), tetraphenylporphine (H2TPP), and molecular oxygen under mild conditions was revealed. The corresponding α,β-epoxy ketones were obtained in yields of up to 94% in 96 h. The reaction time was shortened to 4.6 h by flow synthesis. The mechanism related to singlet oxygen was supported by experiments and density functional theory (DFT) calculations.
- Wu, Yufeng,Zhou, Guangli,Meng, Qingwei,Tang, Xiaofei,Liu, Guangzhi,Yin, Hang,Zhao, Jingnan,Yang, Fan,Yu, Zongyi,Luo, Yi
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p. 13051 - 13062
(2018/10/25)
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- Hansch’s analysis application to chalcone synthesis by Claisen–Schmidt reaction based in DFT methodology
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Chalcones are bioactive compounds obtained from either natural sources or synthetic procedures and widely used due to their several biological properties. The most common experimental methodology in obtaining these compounds is Claisen–Schmidt reaction, which is a particular type of aldolic condensation. In this work, we have synthesized 23 chalcones and by density functional theory (DFT) calculation, we have studied the difference in reactivity of the several benzaldehydes and their effects on the yield of this reaction. From molecular orbital descriptors were obtained two quantitative structure–reactivity relationship (QSRR) models based on Hansch’s analysis. The results of this study showed that, for the most benzaldehydes (15 of 23 compounds), their reactivity was correlated with LUMO energy and global Electrophilicity Index (ω) values, which are determined in the first step of Claisen–Schmidt condensation mechanism (nucleophilic addition). Likewise, for the smallest group of benzaldehydes, their reactivity was related to their HOMO and ΔL???H (LUMO???HOMO) energies, which were determined in the second step of the mechanism (trans-elimination). This is the first report of a QSRR model analyzing the yield of chalcone synthesis based on DFT methodology.
- Mellado, Marco,Madrid, Alejandro,Martínez, úrsula,Mella, Jaime,Salas, Cristian O.,Cuellar, Mauricio
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p. 703 - 709
(2018/02/28)
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- The synthesis of chalcones as anticancer prodrugs and their bioactivation in CYP1 expressing breast cancer cells
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Background: Although the expression levels of many P450s differ between tumour and corresponding normal tissue, CYP1B1 is one of the few CYP subfamilies which is significantly and consistently overexpressed in tumours. CYP1B1 has been shown to be active within tumours and is capable of metabolising a structurally diverse range of anticancer drugs. Because of this, and its role in the activation of procarcinogens, CYP1B1 is seen as an important target for anticancer drug development. Objective: To synthesise a series of chalcone derivatives based on the chemopreventative agent DMU-135 and investigate their antiproliferative activities in human breast cancer cell lines which express CYP1B1 and CYP1A1. Method: A series of chalcones were synthesised in yields of 43-94% using the Claisen-Schmidt condensation reaction. These were screened using a MTT assay against a panel of breast cancer cell lines which have been characterised for CYP1 expression. Result: A number of derivatives showed promising antiproliferative activities in human breast cancer cell lines which express CYP1B1 and CYP1A1, while showing significantly lower toxicity towards a non-tumour breast cell line with no CYP expression. Experiments using the CYP1 inhibitors acacetin and α-naphthoflavone provided supporting evidence for the involvement of CYP1 enzymes in the bioactivation of these compounds. Conclusion: Chalcones show promise as anticancer agents with evidence suggesting that CYP1 activation of these compounds may be involved.
- Ruparelia, Ketan C.,Zeka, Keti,Ijaz, Taeeba,Ankrett, Dyan N.,Wilsher, Nicola E.,Butler, Paul C.,Tan, Hoon L.,Lodhi, Sabahat,Bhambra, Avninder S.,Potter, Gerard A.,Arroo, Randolph R.J.,Beresford, Kenneth J.M.
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p. 322 - 332
(2018/06/26)
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- An improved, efficient and microwave assisted synthetic method for the synthesis of chalcone oximes: An experimental and computational study
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Chalcone oximes are important molecules in organic chemistry. Extant literature contains several methods for conversion of chalcones to their oxime forms but rapid and efficient new methods need to be developed. In this study; we have investigated a new, microwave assisted synthetic method for conversion of chalcones to their oxime forms. For this purpose, a series of known chalcones were synthesized and converted to their oxime forms employing the method being examined. The results show that the proposed method is efficient, providing time and energy savings. In the second part of our study, DFT calculations with B3LYP method have been performed on the synthesized molecules and computational results have been compared with the experimentally obtained data. All DFT calculations were performed at the B3LYP/6-31G(d), B3LYP/6-311G(d, p) and B3LYP/6-311+G(2d, p) levels of theory. NMR calculations were carried out using GIAO and CSGT methods. Additionally, MEP maps, FMOs, some global reactivity descriptors and Mulliken atomic charges for the synthesized compounds were computationally determined with the same basis sets.
- Erdogan, Taner,Erdogan, Fatma Oguz
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- Synthesis and evaluation of central antinociceptive activity of ring substituted chalcones; molecular docking studies with monoacylglycerol lipase (MAGL) enzyme
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Chalcones possess Michael acceptor property due to the presence of α,β-unsaturated enone moiety in their structure. In the present study, molecular docking was performed to predict binding affinity of ring substituted chalcones with Monoacylglycerol lipase (MAGL), a serine hydrolase enzyme which can inhibited by Michael acceptors such as maleimide derivatives. 3, 4-Dimethoxy derivative, 3 h with -44.45 kJmol-1 of interaction energy, exhibited highest binding affinity and formed Pi-Sulphur interactions with methionine-123 residue of MAGL enzyme. As MAGL is an emerging target for antinociceptive drug development, ring substituted chalcones were synthesized and evaluated for their central antinociceptive activity using tail immersion and hot plate methods. The results revealed that compound 3 h chalcone bearing methoxy groups at 3rd and 4th positions of phenyl ring exhibited good antinociceptive activity in both the models. Good correlation was observed between antinociceptive activity and binding affinity toward MAGL in case of compound 3 hour.
- Begum, Shaheen,Begum, Arifa,Koganti, Bharathi
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p. 1890 - 1897
(2018/09/18)
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- Three-Component Synthesis of a Library of m-Terphenyl Derivatives with Embedded β-Aminoester Moieties
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The three-component reaction between alkyl- or arylamines, β-ketoesters and chalcones in refluxing ethanol containing a catalytic amount of Ce(IV) ammonium nitrate allowed the construction of a large library of highly substituted dihydro-m-terphenyl derivatives containing β-alkylamino- or β-arylamino ester moieties. This process generates three new bonds and one ring and proceeds in high atom economy, having two molecules of water as the only side product. Another domino process, in which the original MCR was telescoped with a subsequent aza Michael/retro-aza Michael sequence, allowed the one-pot preparation of a library of compounds with a N-unsubstituted β-aminoester fragment. Finally, to extend the structural diversity of these libraries, we also examined the aromatization of the central ring of our compounds in the presence of dichlorodicyanoquinone. This reaction sequence did not affect the integrity of a stereogenic center belonging to the amino component.
- Rocchi, Damiano,González, Juan F.,Gómez-Carpintero, Jorge,González-Ruiz, Víctor,Martín, M. Antonia,Sridharan, Vellaisamy,Menéndez, J. Carlos
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p. 722 - 731
(2018/10/20)
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- Intermolecular [2+2] photocycloaddition of chalcones with 2,3-dimethyl-1,3-butadiene under neat reaction conditions
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The intermolecular [2 + 2] photocycloaddition of chalcones with 2,3-dimethyl-1,3-butadiene under visible-light irradiation for the synthesis of cyclobutane derivatives has been developed. Without using any photosensitizer, metallic catalyst and solvent, the reaction proceeded with high regioselectivity and moderate to high stereoselectivity. Mild reaction conditions and no additives make the reaction easy to operate. Control experiments and density functional theory (DFT) computations demonstrated that the reaction takes place via visible-light activation of chalcones, which is different from the previously reported [2 + 2] cycloaddition of chalcones.
- Tang, Fang,Tang, Li,Guan, Zhi,He, Yan-Hong
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supporting information
p. 6694 - 6703
(2018/10/15)
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- Transition-Metal-Free Catalytic Formal Hydroacylation of Terminal Alkynes
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Although hydroacylation is a very useful reaction for producing ketones from aldehydes with 100% atom efficiency, classical Rh-catalyzed hydroacylation presents several problems, including the need for transition metal catalysts, unwanted decarbonylation of aldehydes, and difficulty in regioselectivity control. However, formal hydroacylation utilizing the nucleophilicity of terminal alkynes can avoid these problems. In this work, we have achieved transition-metal-free formal hydroacylation of terminal alkynes using an Mg3Al-CO3-layered double hydroxide as a heterogeneous catalyst. This system was applicable to the efficient synthesis of α,β-unsaturated ketones with various substituents, and the catalyst can be reused without a significant loss of catalytic performance.
- Yatabe, Takafumi,Mizuno, Noritaka,Yamaguchi, Kazuya
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p. 11564 - 11569
(2018/11/23)
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- Bifunctional Thiourea-Catalyzed Stereoablative Retro-Sulfa-Michael Reaction: Concise and Diastereoselective Access to Chiral 2,4-Diarylthietanes
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Owing to the chiral recognition capacity of bifunctional thioureas, a stereoablative retro-sulfa-Michael reaction has been developed. Utilization of a biphasic system enabled us to render the process catalytic. The usefulness of this methodology was further illustrated by the diastereoselective synthesis of all possible stereoisomers of 2,4-diarylthiethanes.
- Bacsó, András,Szigeti, Mariann,Varga, Szilárd,Soós, Tibor
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p. 429 - 439
(2016/12/24)
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- CBr4 as a Halogen Bond Donor Catalyst for the Selective Activation of Benzaldehydes to Synthesize α,β-Unsaturated Ketones
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CBr4 has been employed as a halogen bond donor catalyst for the selective activation of aldehyde, to achieve an efficient solvent- and metal-free CC bond forming reaction in the presence of strong acid sensitive groups such as methoxy, cyanide, ester, and ketal for the synthesis of α,β-unsaturated ketones. This unique capability of CBr4 to act as a halogen bond donor has been explored and established using UV-vis as well as IR spectroscopy. Moreover, this unprecedented methodology enables the synthesis of the pharmaceutically important molecule licochalcone A.
- Kazi, Imran,Guha, Somraj,Sekar, Govindasamy
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supporting information
p. 1244 - 1247
(2017/03/14)
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- Synthesis and evaluation of modified chalcone based p53 stabilizing agents
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Tumor suppressor protein p53 induces cell cycle arrest and apoptotic cell death in response to various cellular stresses thereby preventing cancer development. Activation and stabilization of p53 through small organic molecules is, therefore, an attractive approach for the treatment of cancers retaining wild-type p53. In this context, a series of nineteen chalcones with various substitution patterns of functional groups including chloro, fluoro, methoxy, nitro, benzyloxy, 4-methyl benzyloxy was prepared using Claisen-Schmidt condensation. The compounds were characterized using NMR, HRMS, IR and melting points. Evaluation of synthesized compounds against human colorectal (HCT116) and breast (CAL-51) cancer cell lines revealed potent antiproliferative activities. Nine compounds displayed GI50 values in the low micromolar to submicromolar range; for example (E)-1-phenyl-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (SSE14108) showed GI50 of 0.473 ± 0.043 μM against HCT116 cells. Further analysis of these compounds revealed that (E)-3-(4-chlorophenyl)-1-phenylprop-2-en-1-one (SSE14105) and (E)-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one (SSE14106) caused rapid (4 and 8-h post-treatment) accumulation of p53 in HCT116 cells similar to its induction by positive control, Nutlin-3. Such activities were absent in 3-(4-methoxyphenyl)propiophenone (SSE14106H2) demonstrating the importance of conjugated ketone for antiproliferative and p53 stabilizing activity of the chalcones. We further evaluated p53 levels in the presence of cycloheximide (CHX) and the results showed that the p53 stabilization was regulated at post-translational level through blockage of its degradation. These chalcones can, therefore, act as fragment leads for further structure optimization to obtain more potent p53 stabilizing agents with enhanced anti-proliferative activities.
- Iftikhar, Sunniya,Khan, Sardraz,Bilal, Aishah,Manzoor, Safia,Abdullah, Muhammad,Emwas, Abdel-Hamid,Sioud, Salim,Gao, Xin,Chotana, Ghayoor Abbas,Faisal, Amir,Saleem, Rahman Shah Zaib
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supporting information
p. 4101 - 4106
(2017/08/22)
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- Asymmetric synthesis of new γ-butenolides: Via organocatalyzed epoxidation of chalcones
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γ-Butenolides have been recognized as an important structural framework in a number of natural products and medicinally important agents. In this work we describe a new metal-free sequential strategy for the asymmetric synthesis of substituted γ-butenolides having epoxychalcones as the advanced intermediate. Using the optimized reaction conditions, we were able to carry out the three-step sequence, epoxidation, olefination and hydrolysis, with only one single chromatographic purification of the final product, furnishing new enantiomerically enriched γ-butenolides in moderate overall yield and good enantiomeric excess.
- Vieira, Lucas C. C.,Matsuo, Bianca T.,Martelli, Lorena S. R.,Gall, Mayara,Paix?o, Marcio W.,Corrêa, Arlene G.
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supporting information
p. 6098 - 6103
(2017/08/02)
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- Facile epoxidation of α, β-unsaturated ketones with urea-2,2-dihydroperoxypropane as a new oxidant
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Abstract: Various aromatic α, β-unsaturated ketones were successfully transformed into their corresponding epoxides using urea-2,2-dihydroperoxypropane as the oxygen source for the first time. The reactions were carried out under mild alkaline conditions at room temperature in high yields and short reaction times. Graphical Abstract: [Figure not available: see fulltext.]
- Khosravi, Kaveh,Naserifar, Shirin
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p. 323 - 328
(2017/01/10)
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- Metal-Free and Efficient Epoxidation of α,β-Unsaturated Ketones with 1,1,2,2-Tetrahydroperoxy-1,2-Diphenylethane as a Powerful Solid Oxidant
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1,1,2,2-Tetrahydroperoxy-1,2-diphenylethane was used for the efficient and metal-free epoxidation of various α,β-unsaturated ketones, carried out under mild alkaline conditions at room temperature.
- Khosravi, Kaveh,Naserifar, Shirin,Mahmoudi, Boshra
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p. 683 - 689
(2017/06/19)
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- Photoredox-Catalyzed Cyclopropanation of Michael Acceptors
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A new protocol for the catalytic cyclopropanation of α,β-unsaturated carbonyl compounds with diiodomethane by means of photoredox catalysis has been successfully developed. The transformation is characterized by its mild conditions, functional-group compatibility, and excellent selectivity profile.
- del Hoyo, Ana M.,García Suero, Marcos
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supporting information
p. 2122 - 2125
(2017/04/24)
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- Monoamine oxidase inhibitory activity of methoxy-substituted chalcones
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The MAO-B inhibitory activity of chalcone (1, 3- diphenyl-2-propen-1-one) based compounds arise from its structural similarity with 1, 4-diphenyl-2-butene, a known MAO-B inhibitor. Based on our previous report, the methoxy-substituted with fluorine containing chalcones are promising reversible MAO-B inhibitors, while in the present study, a series of methoxylated chalcones (C1-C9) bearing substitution on the para position of ring B was synthesized and evaluated for their human monoamine oxidase inhibitory activity. With the exception of (2E)-1-(4-methoxyphenyl)-3-(4-nitrophenyl) prop-2-en-1-one (C7), which is a nonselective inhibitor, the chalcones exhibited competitive, selective, and reversible inhibition of hMAO-B. The most potent compound, (2E)-3-[4-(dimethylamino) phenyl]-1-(4-methoxyphenyl) prop-2-en-1-one (C5), showed the best inhibitory activity towards hMAO-B (IC50 = 0.29 ± 0.011 μM; Ki = 0.14 ± 0.001 μM). The reversibility of MAO-B inhibition by compound C5 was demonstrated by the recovery of enzyme activity after dialysis of mixtures containing enzyme and inhibitor. The reversiblity of C5 was 25.38 ± 1.40 and 92.00 ± 3.87% before and after dialysis, respectively. PAMPA was carried out to evaluate the blood-brain barrier effects of the designated compounds. Moreover, the most potent MAO-B inhibitor, C5, was found to be nontoxic towards cultured hepatic cells at 5 and 25 μM, with 97 and 90% viability. Molecular docking study was performed against hMAO-B to observe the binding site interactions of the lead compound.
- Mathew, Bijo,Mathew, Githa Elizabeth,Ucar, Gulberk,Joy, Monu,Nafna,Lohidakshan, Krishnakumar K.,Suresh, Jerad
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p. 1321 - 1329
(2017/09/05)
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- Ag(i)/persulfate-catalyzed decarboxylative coupling of α-oxocarboxylates with organotrifluoroborates in water under room temperature
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The decarboxylative coupling reaction of α-oxocarboxylates and organotrifluoroborates was carried out smoothly in the presence of catalytic AgNO3 using K2S2O8 as oxidant to generate diarylketone products in high
- Chang, Sheng,Wang, Jian Feng,Dong, Lin Lin,Wang, Dan,Feng, Bo,Shi, Yuan Tai
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p. 51928 - 51934
(2017/11/22)
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- Carbon-carbon bond formation in acid deep eutectic solvent: Chalcones synthesis: Via Claisen-Schmidt reaction
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One of the most studied properties of novel organic solvents is represented by their use as media for many chemical reactions. In this field Ionic Liquids (ILs) and more recently Deep Eutectic Solvents (DESs) have been playing significant roles for their smart properties. DESs are increasing their relevance thanks to their low toxicity, and because of their simple and cheap preparation that can be carried out by simply mixing two compounds. In this work we present the studies of the use of an acid DES obtained from 3-(cyclohexyldimethylammonio)propane-1-sulfonate and (1S)-(+)-10-camphorsulfonic acid (SB3-Cy/CSA) as reaction media and catalyst for carbon-carbon bond formation reaction via Claisen-Schmidt condensation. This powerful and widely used aldol condensation was performed without the use of any catalysts that are usually needed in this reaction, because of the presence of acid CSA in the DES components. We synthesised fourteen substituted chalcones from benzaldehydes and substituted benzaldehydes in combination with acetophenone and substituted acetophenones as probe reactions. The advantages of the use of this DES in this relevant reaction are represented by: the green properties of the media and its low toxicity; the absence of harmful acids to catalyse the aldol condensation because of the camphorsulfonic acid composing the DES mixture; the recycling and the re-use of the DES in subsequent reaction cycles; the mild conditions and the excellent conversions and yields observed.
- Tiecco, Matteo,Germani, Raimondo,Cardellini, Fabio
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p. 43740 - 43747
(2016/05/24)
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