- Palladium-Catalyzed Synthesis of α-Methyl Ketones from Allylic Alcohols and Methanol
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One-pot synthesis of α-methyl ketones starting from 1,3-diaryl propenols or 1-aryl propenols and methanol as a C1 source is demonstrated. This one-pot isomerization-methylation is catalyzed by commercially available Pd(OAc)2 with H2O as the only by-product. Mechanistic studies and deuterium labelling experiments indicate the involvement of isomerization of allyl alcohol followed by methylation through a hydrogen-borrowing pathway in these isomerization-methylation reactions.
- Biswal, Priyabrata,Samser, Shaikh,Meher, Sushanta Kumar,Chandrasekhar, Vadapalli,Venkatasubbaiah, Krishnan
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supporting information
p. 413 - 419
(2021/11/01)
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- Ligand-Free Palladium-Catalyzed Carbonylative Suzuki Couplings of Vinyl Iodides with Arylboronic Acids under Substoichiometric Base Conditions
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A ligand-free palladium-catalyzed carbonylation of vinyl iodides with arylboronic acids, permitting the synthesis of chalcones and α-branched enones, has been established. This reaction proceeds smoothly at ambient pressure and temperature, and works well even with a substoichiometric amount of base. Importantly, this mild, efficient, and operationally simple protocol is suitable for the late-stage functionalization of an epiandrosterone-derived complex molecule.
- Yang, Zhiyuan,Gong, Pei-Xue,Chen, Junjie,Zhang, Jie,Gong, Xu,Han, Wei
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supporting information
p. 1207 - 1212
(2021/06/18)
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- Iridium and copper supported on silicon dioxide as chemoselective catalysts for dehydrogenation and borrowing hydrogen reactions
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High active ligand usually plays an important role during catalysis and synthesis chemistry. A new and efficient benzotriazole-pyridinyl-silane ligand (BPS) was designed, and the corresponding iridium and copper catalysts were synthesized and thoroughly characterized by means of EDS, TEM, and XPS. The resulting iridium composite revealed excellent catalytic activity for the reaction of tert-butanesulfinamide with benzyl alcohols, while copper catalyst could realize the synthesis of unsaturated carbonyl compounds through the reaction of benzyl alcohols with ketones. This provided an efficient method for selective synthesis of unsaturated carbonyl compounds from benzyl alcohols and ketones in high yields with good recovery performance.
- Zhu, Guanxin,Duan, Zheng-Chao,Zhu, Haiyan,Qi, Minghui,Wang, Dawei
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- Unsaturated ketone compound as well as preparation method and application thereof
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The present invention relates to a novel GPR52 antagonist. Specifically, the invention relates to an unsaturated ketone compound, a pharmaceutically acceptable salt, a stereoisomer or a prodrug molecule thereof, and a method for preparing a pharmaceutical composition thereof. The invention further relates to the use of the GPR52 antagonist as an orphan G protein coupled receptor GPR52 antagonist,and further relates to the use of the GPR52 antagonist in the preparation of drugs for preventing and treating Huntington's disease.
- -
-
Paragraph 0219-0222; 0268-0270
(2020/10/30)
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- Anti-corrosive property of bioinspired environmental benign imidazole and isoxazoline heterocyclics: A cumulative studies of experimental and DFT methods
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In the present study, four imidazoline (IDZ) and four isoxazolines (ISO) heterocyclics differing in the nature of methoxy (-OCH3) and aromatic (phenyl and naphthyl) moieties are synthesized, characterized and evaluated as corrosion inhibitors for mild steel in acidic solution of 1 M HCl. Results showed that imidazoline based heterocyclic compounds are better corrosion inhibitors than isoxazoline based heterocyclics and both classes of compounds showed inhibition efficiency of more than 85% at 20 mgL?1 concentration. Results further showed that inhibitors containing methoxy, phenyl, and naphthyl moieties showed higher protection efficiency as compared to the inhibitors without these moieties. PDP Study revealed that investigated IDZs and ISOs acted as mixed type inhibitors and their adsorption on the metallic surface followed the Langmuir adsorption isotherm model. All the experimental results were corroborated by density function theory (DFT) based quantum chemical calculations. Numerous DFT based indices calculated for neutral as well as protonated forms of the IDZs and ISOs in order to get better insight about metal-IDZs/ISOs interactions. Outcomes of the DFT analysis showed that protonated (cationic) form of the all the inhibitors are more strongly adsorbed on the metallic surface as compared to their neutral form.
- Ramkumar, Sowmya,Nalini,Quraishi, Mumtaz A.,Ebenso, Eno E.,Verma, Chandrabhan
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supporting information
p. 103 - 119
(2019/12/24)
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- Diversified Transformations of Tetrahydroindolizines to Construct Chiral 3-Arylindolizines and Dicarbofunctionalized 1,5-Diketones
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Enantioselective diverse synthesis of a small-molecule collection with structural and functional similarities or differences in an efficient manner is an appealing but formidable challenge. Asymmetric preparation and branching transformations of tetrahydroindolizines in succession present a useful approach to the construction of N-heterocycle-containing scaffolds with functional group, and stereochemical diversity. Herein, we report a breakthrough toward this end via an initial diastereo- A nd enantioselective [3 + 2] cycloaddition between pyridinium ylides and enones, following diversified sequential transformations. Chiral N,N′-dioxide-earth metal complexes enable the generation of optically active tetrahydroindolizines in situ, across the strong background reaction for racemate-formation. In connection with deliberate sequential transformations, involving convenient rearomatic oxidation, and light-active aza-Norrish II rearrangement, the tetrahydroindolizine intermediates were converted into the final library including 3-arylindolizine derivatives and dicarbofunctionalized 1,5-dicarbonyl compounds. More importantly, the stereochemistry of four-stereogenic centered tetrahydroindolizine intermediates could be efficiently transferred into axial chirality in 3-arylindolizines and vicinal pyridyl and aryl substituted 1,5-diketones. In addition, densely functionalized cyclopropanes and bridged cyclic compounds were also discovered depending on the nature of the pyridinium ylides. Mechanism studies were involved to explain the stereochemistry during the reaction processes.
- Feng, Xiaoming,He, Qianwen,Liu, Xiaohua,Pan, Chenjing,Su, Zhishan,Wu, Zhikun,Zhang, Dong,Zhou, Yuqiao
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supporting information
p. 15975 - 15985
(2020/10/18)
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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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- Metal-Free Cyclopropanol Ring-Opening C(sp3)-C(sp2) Cross-Couplings with Aryl Sulfoxides
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A metal-free method for formal β-arylation/heteroarylation of ketones through efficient cyclopropanol ring-opening cross-couplings with aryl sulfoxides at room temperature has been developed. This protocol shows a broad substrate scope and promising scalability. In addition, the utility of the β-arylated ketones is further demonstrated through a variety of postcoupling transformations and synthetic applications.
- Chen, Dengfeng,Fu, Yuanyuan,Cao, Xiaoji,Luo, Jinyue,Wang, Fei,Huang, Shenlin
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p. 5600 - 5605
(2019/08/01)
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- Copper-Promoted Oxidative Intramolecular C–H Amination of Hydrazones to Synthesize 1H-Indazoles and 1H-Pyrazoles Using a Cleavable Directing Group
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A facile and efficient synthesis of 1H-indazoles and 1H-pyrazoles through a copper-promoted oxidative intramolecular C–H amination of hydrazones using a cleavable directing group was developed. This reaction is characterized by its mild conditions, operational simplicity, readily available reagents, and excellent yields. A tentative mechanism for Cu-mediated C–H oxidative amination was proposed.
- Zhang, Guofu,Fan, Qiankun,Zhao, Yiyong,Ding, Chengrong
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supporting information
p. 5801 - 5806
(2019/08/02)
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- 1-Arylvinyl formats: A New CO Source and Ketone Source in Carbonylative Synthesis of Chalcone Derivatives
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1-Arylvinyl formates as a kind of new CO surrogate have been explored for the first time. Most of the known CO precursors usually produce undesired residuals, which have to be removed. In this strategy, after CO release, the in situ generated acetophenones from 1-arylvinyl formates can be successfully applied as a good ketone source in the synthesis of chalcones with benzaldehydes via a palladium-catalyzed reductive carbonylation reaction. A variety of chalcones were isolated in satisfactory to good yields with good substrates compatibilities under mild conditions.
- Qi, Xinxin,Lai, Ming,Zhu, Min-Jie,Peng, Jin-Bao,Ying, Jun,Wu, Xiao-Feng
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p. 5252 - 5255
(2019/02/25)
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- Chiral Hydroxytetraphenylene-Catalyzed Asymmetric Conjugate Addition of Boronic Acids to Enones
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(S)-2,15-Br2-DHTP-catalyzed asymmetric conjugate addition of boronic acids to β-trifluoromethyl α,β-unsaturated ketones and enones was studied. The reaction afforded the corresponding Michael addition products in moderate to high yields with excellent enantioselectivities (up to 99:1 er). This catalytic system features mild reaction conditions, high efficiency, and tolerance to heteroarylboronic acids.
- Chai, Guo-Li,Sun, A-Qiang,Zhai, Dong,Wang, Juan,Deng, Wei-Qiao,Wong, Henry N.C.,Chang, Junbiao
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supporting information
p. 5040 - 5045
(2019/07/03)
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- Indium(III) triflate-catalyzed reactions of AZA-michael adducts of chalcones with aromatic amines: Retro-michael addition versus quinoline formation
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The indium(III) triflate-catalyzed reaction of aza-Michael adducts of chalcones with aromatic amines has been investigated. The Michael adducts derived from substituted anilines and chalcones underwent retro-Michael addition to give the original starting materials, whereas the adducts derived from 1-naphthylamines and chalcones afforded quinolines. A six-membered cyclic transition state has been proposed to explain the retro-Michael addition, while a Povarov mechanism has been put forward to explain the quinoline formation.
- Selvi, Thangavel,Velmathi, Sivan
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p. 4087 - 4091
(2018/04/14)
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- High pressure-assisted low-loading asymmetric organocatalytic conjugate addition of nitroalkanes to chalcones
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The application of high pressure (up to 9 kbar) allows for relatively fast (1-5 h) and highly enantioselective 1,4-addition of nitromethane and 2-nitropropane to chalcones at room temperature with substantial reduction of catalyst loading (0.2-1 mol% of cinchona alkaloid-based thioureas and squaramides). Various γ-nitroketones were obtained at 9 kbar with high yield and enantioselectivity (up to 98%), whereas in control experiments at atmospheric pressure usually only a small amount (10%) of products were formed after 20 h.
- Cholewiak, Agnieszka,Adamczyk, Kamil,Kopyt, Micha?,Kasztelan, Adrian,Kwiatkowski, Piotr
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supporting information
p. 4365 - 4371
(2018/06/22)
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- Synthesis and structure-activity relationships of chalcone derivatives as inhibitors of ovarian cancer cell growth
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Background: Ovarian cancer remains a disease with a poor five year survival rate. As such, novel therapies are needed. Natural chalcones as well as their synthetic derivatives have shown biological activity in a number of areas including the inhibition of cancer cell growth. Objective: To synthesize a library of chalcone derivatives, including novel structures, and determiner the inhibition of ovarian cancer cell growth and Structure-activity-relationships. Methods: The Claisen-Schmidt condensation reaction between substituted acetophenones and aromatic aldehydes was used to produce a series of novel chalcones in moderate to excellent yields and good purity. Cellular proliferation of CA-OV3 cells was measured with a MTS assay. Results: Out of the thirty-four synthesized compounds, eight are new derivatives. The synthesized compounds were characterized by 1H NMR, 13C NMR, and HRMS. Biological evaluation of these β-phenylacrylophenone derivatives in CA-OV3 cells showed interesting antiproliferative activities providing initial structure – activity information. Conclusion: Fourteen of the thirty-four tested compounds showed significant activity, with several showing near complete inhibition of growth at 100 μM. The structure-activity relationships suggest that modification to the A ring is widely tolerated and that electron-donating modifications to the B ring are beneficial to activity. Electron-withdrawing modifications to the B ring did not show inhibition of cell growth.
- Tucker, Zachary D.,Barrios, Francis J.,Krzysiak, Amanda J.
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p. 1259 - 1266
(2017/11/14)
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- New hybrid bromopyridine-chalcones as in vivo phase II enzyme inducers: potential chemopreventive agents
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Cancer prevention can be achieved by the administration of cancer chemopreventive agents (CCAs) that prevent, delay or reverse the carcinogenic process. CCAs that are able to induce detoxification enzymes, especially monofunctional phase II enzymes, have become an excellent therapeutic strategy. Herein, we report the synthesis of eighteen new potential CCAs, structurally designed to combine (naphtho)chalcone and (bromo)pyridine skeletons. After a selection process involving in vitro phase II induction studies, cytotoxicity against tumoral cells, mutagenicity (the Ames test), and capability for DNA strand breakage (the alkaline comet assay), compound 22, (E)-3-(2-bromopyridin-3-yl)-1-(2-hydroxyphenyl)-2-propen-1-one, was selected for animal studies. The in vivo proof of concept study for derivative 22 demonstrated that it was able to significantly increase the QR and GST activities in the liver, colon and mammary gland without significant induction of the phase I enzyme, CYP. Additionally, we found that for 22 and another in vitro QR activity inducer, (E)-1-(2-hydroxyphenyl)-3-(naphthalen-1-yl)-2-propen-1-one (compound 8), Nrf2 nuclear translocation is operative allowing the exertion of protective effects via the expression of downstream phase II enzymes.
- Cabrera, Mauricio,Cerecetto, Hugo,González, Mercedes
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p. 2395 - 2409
(2016/12/18)
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- A new solid acid catalyst FeCl3/bentonite for aldol condensation under solvent-free condition
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For the first time, a new solid acid catalyst has been used for the synthesis of aryl chalcones under solvent free conditions. A simple method (solid dispersion method) has been adopted for the synthesis of FeCl3/bentonite. The prepared catalyst has been characterized by different characterization techniques. A series of E-1-(substituted phenyl)-3-(1-pyrenyl)-2-propen-1-ones have been synthesized using FeCl3/bentonite under microwave-assisted solvent-free conditions. The yields are in the range from 80 to 88%. All the synthesized chalcones have been characterized by their physical constants, analytical, IR, 1H and 13C NMR spectral data. This catalyst can be reused for further runs (after fifth cycle) without decrease in activity. This catalyst gives excellent yields and is inexpensive and easily recyclable for this reaction.
- Muthuvel,Dineshkumar,Thirumurthy,Rajasri,Thirunarayanan
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p. 252 - 260
(2017/01/18)
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- Synthesis, Structure, and Optical Studies of Donor-Acceptor-Type Near-Infrared (NIR) Aza-Boron-Dipyrromethene (BODIPY) Dyes
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Six donor-acceptor-type near-infrared (NIR) aza-boron-dipyrromethene (BODIPY) dyes and their corresponding aza-dipyrrins were designed and synthesized. The donor moieties at the 1,7-positions of the aza-BODIPY core were varied from naphthyl to N-phenylcarbazole to N-butylcarbazole. The 3,5-positions were also substituted with phenyl or thienyl groups in the aza-BODIPYs. Photophysical, electrochemical, and computational studies were carried out. The absorption and emission spectra of aza-BODIPYs were significantly redshifted (≈100 nm) relative to the parent tetraphenylaza-BODIPY. Fluorescence studies suggested effective energy transfer (up to 93 %) from donor groups to the aza-BODIPY core in all of the compounds under study. Time-dependent (TD)-DFT studies indicated effective electronic interactions between energy donor groups and aza-dipyrrin unit in all the aza-BODIPYs studied. The HOMO-LUMO gap (ΔE) calculated from cyclic voltammetry data was found to be lower for six aza-BODIPYs relative to their corresponding aza-dipyrrins. Donations accepted: Donor-acceptor-type near-infrared aza-BODIPYs were designed and synthesized. The presence of donor groups at the 1,7-position of the aza-BODIPYs caused significant bathochromic shifts in their absorption and emission maxima. Efficient energy transfer from donor moieties to the aza-BODIPY core was observed in all compounds studied.
- Balsukuri, Naresh,Lone, Mohsin Y.,Jha, Prakash C.,Mori, Shigeki,Gupta, Iti
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p. 1572 - 1587
(2016/06/01)
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- Chiral octahedral complexes of Co(iii) as catalysts for asymmetric epoxidation of chalcones under phase transfer conditions
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Stereochemically inert and positively charged chiral complexes of Co(iii) were shown to catalyze the asymmetric epoxidation of chalcones with H2O2 under phase transfer conditions. The reaction products had enantiomeric purities of up to 55%. It was also shown that complex 1a I- catalyzed the coupling reaction of a resulting epoxide with CO2 (conversion 72%).
- Larionov, Vladimir A.,Markelova, Elina P.,Smol'yakov, Alexander F.,Savel'yeva, Tat'yana F.,Maleev, Victor I.,Belokon, Yuri N.
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p. 72764 - 72771
(2015/09/15)
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- Synthesis and pharmacochemistry of new pleiotropic pyrrolyl derivatives
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Within the framework of our attempts to synthesize pleiotropic anti-inflammatory agents, we have synthesized some chalcones and their corresponding 3,4-pyrrolyl derivatives. Chalcones constitute a class of compounds with high biological impact. They are k
- Konstantinidou, Markella,Gkermani, Alice,Hadjipavlou-Litina, Dimitra
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p. 16354 - 16374
(2015/12/01)
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- Sulfonamide derivatives containing dihydropyrazole moieties selectively and potently inhibit MMP-2/MMP-9: Design, synthesis, inhibitory activity and 3D-QSAR analysis
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New series of sulfonamide derivatives containing a dihydropyrazole moieties inhibitors of MMP-2/MMP-9 were discovered using structure-based drug design. Synthesis, antitumor activity, structure-activity relationship and optimization of physicochemical pro
- Yan, Xiao-Qiang,Wang, Zhong-Chang,Li, Zhen,Wang, Peng-Fei,Qiu, Han-Yue,Chen, Long-Wang,Lu, Xiao-Yuan,Lv, Peng-Cheng,Zhu, Hai-Liang
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supporting information
p. 4664 - 4671
(2015/10/12)
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- Copper-catalyzed oxidative transformation of secondary alcohols to 1,5-disubstituted tetrazoles
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A mild and convenient oxidative transformation of secondary alcohols to 1,5-disubstituted tetrazoles is uncovered by employing trimethylsilyl azide (TMSN3) as a nitrogen source in the presence of a catalytic amount of copper(II) perchlorate hexahydrate [Cu(ClO4)2 .6 H2O] (5 mol%) and 2,3-dichloro-5,6-dicyano-para- benzoquinone (DDQ) (1.2 equiv.) as an oxidant. This reaction is performed under ambient conditions and proceeds through C-C bond cleavage.
- Rokade, Balaji V.,Gadde, Karthik,Prabhu, Kandikere Ramaiah
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supporting information
p. 946 - 950
(2014/04/03)
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- Synthesis and biological evaluation of compounds which contain pyrazole, thiazole and naphthalene ring as antitumor agents
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A series of compounds which contain pyrazole, thiazole and naphthalene ring (1a-7a, 1b-7b, 1c-7c, 1d-7d) were firstly synthesized and their anti-proliferative activity, EGFR inhibitory activity, cytotoxicity and inhibition to Hela cell migration were evaluated. Compound 2-(3-(3,4- dimethylphenyl)-5-(naphthalen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4(5H) -one (7d) displayed the most potent inhibitory activity (IC50 = 0.86 μM for Hela and IC50 = 0.12 μM for EGFR). Structure-activity relationship (SAR) analysis showed that the anti-proliferative activity was affected by A-ring-substituent (-OCH3 > -CH3 > -H > -Br > -Cl > -F). Docking simulation of compound 7d into EGFR active site showed that naphthalene ring of 7d with LYS721 formed two p-π bonds, which enhanced antitumor activity. Therefore, compound 7d may be developed as a potential antitumor agent.
- Yuan, Ji-Wen,Wang, She-Feng,Luo, Zhong-Liang,Qiu, Han-Yue,Wang, Peng-Fei,Zhang, Xin,Yang, Yong-An,Yin, Yong,Zhang, Fei,Zhu, Hai-Liang
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p. 2324 - 2328
(2014/05/20)
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- Solvent-free synthesis, spectral correlations and antimicrobial activities of some aryl e 2-propen-1-ones
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Totally 38 aryl E 2-propen-1-ones including nine substituted styryl 4-iodophenyl ketones have been synthesised using solvent-free SiO 2-H3PO4 catalyzed Aldol condensation between respective methyl ketones and substituted benzaldehydes under microwave irradiation. The yields of the ketones are more than 80%. The synthesised chalcones were characterized by their analytical, physical and spectroscopic data. The spectral frequencies of synthesised substituted styryl 4-iodophenyl ketones have been correlated with Hammett substituent constants, F and R parameters using single and multi-linear regression analysis. The antimicrobial activities of 4-iodophenyl chalcones have been studied using Bauer-Kirby method.
- Sathiyamoorthi,Mala,Sakthinathan,Kamalakkannan,Suresh,Vanangamudi,Thirunarayanan
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p. 245 - 256
(2013/11/06)
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- Design, modification and 3D QSAR studies of novel naphthalin-containing pyrazoline derivatives with/without thiourea skeleton as anticancer agents
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Two series of novel naphthalin-containing pyrazoline derivatives C1-C14 and D1-D14 have been synthesized and evaluated for their EGFR/HER-2 inhibitory and anti-proliferation activities. Compound D14 displayed the most potent activity against EGFR and A549
- Yang, Wen,Hu, Yang,Yang, Yu-Shun,Zhang, Fei,Zhang, Yan-Bin,Wang, Xiao-Liang,Tang, Jian-Feng,Zhong, Wei-Qing,Zhu, Hai-Liang
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p. 1050 - 1063
(2013/03/14)
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- Preheated fly-ash catalyzed aldol condensation: Efficient synthesis of chalcones and antimicrobial activities of some 3-thienyl chalcones
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In the present study we have prepared a series of some chalcones using solvent - free Aldol - condensation by microwave irradiation. The yields of the ketones are more than 60%. The synthesised chalcones were characterized by their analytical, physical and spectral data. The antimicrobial activities of substituted styryl 3-thienyl ketones have been studied using Bauer-Kirby method.
- Arulkumaran, Ranganathan,Vijayakumar, Sambandhamoorthy,Sakthinathan, S. Pazhanivel,Kamalakkannan, Dakshnamoorthy,Ranganathan, Kaliyaperumal,Suresh, Ramamoorthy,Sundararajan, Rajasekaran,Vanangamudi, Ganesan,Thirunarayanan, Ganesamoorthy
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p. 1684 - 1690
(2013/09/24)
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- Fly-ash:H2SO4 catalyzed solvent free efficient synthesis of some aryl chalcones under microwave irradiation
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Some 2E aryl chalcones have been synthesized using greener catalyst Fly-ash:H2SO4 assisted solvent free environmentally benign Crossed-Aldol reaction. The yields of chalcones are more than 90%. The synthesized chalcones are characterized by their physical constants and spectral data.
- Thirunarayanan,Mayavel,Thirumurthy
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experimental part
p. 18 - 22
(2012/05/05)
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- A simple and efficient method for the allylation of heteroarenes catalyzed by PdCl2
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The PdCl2-catalyzed allylation of heteroarenes is presented. Various heteroarenes including O-, N-, and S-based ones were allylated efficiently with a rich range of allylic acetates in the presence of only 2 mol % of PdCl2, without the need of bases/acids, additives, and external supporting ligands. In addition, the reactions were carried out under mild and simple conditions just by stirring the two reactants and catalyst in CH 2Cl2 at 60 °C. Moreover, the by-product produced was non-toxic acetic acid. Thus, the method presented in this work provides a general, clean, and operationally simple approach for the functionalization of heteroarenes. Finally, a preliminary mechanistic study suggested that the Pd(II) may be reduced in situ by the heteroarenes to Pd(0), which serves as the active metal center to catalyze the following allylations of heteroarenes via a Tsuji-Trost pathway.
- Yuan, Feng-Quan,Sun, Feng-Yi,Han, Fu-She
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scheme or table
p. 6837 - 6842
(2012/08/28)
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- One-pot consecutive reactions based on the synthesis of conjugated enones by the re-catalysed meyer-schuster rearrangement
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Re catalysis in one-pot reactions: An atom-economical, one-pot strategy that involves alkyne deprotonation and a subsequent rhenium(V)-catalysed Meyer-Schuster rearrangement of the alkynol to provide α,β- unsaturated enones in high yield has been developed (see scheme). Subsequent in situ hydride reduction or Diels-Alder reaction of the enones provided products in good-to-high overall yields. Copyright
- Mattia, Elio,Porta, Alessio,Merlini, Valentina,Zanoni, Giuseppe,Vidari, Giovanni
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supporting information
p. 11894 - 11898
(2012/10/29)
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- Ferrocenyl chalcones versus organic chalcones: A comparative study of their nematocidal activity
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A series of 30 organic chlacones and 33 ferrocenyl (Fc) chalcones were synthesized and characterized by melting point, elemental analysis, spectroscopy (1H NMR and FTIR) and, in two cases, by X-ray crystallography. The biological activity of each compound (10-4 M in DMSO) against the model nematode Caenorhabditis elegans was examined in terms of % mortality (percent nematodes that died) and % fecundity (percent nematodes that reproduced) and compared to that obtained for the control medium (1% DMSO) over a 14-day period. Detailed conformational analyses for two Fc-chalcones (studied also by X-ray crystallography) were performed via molecular modeling studies. In general, the organic chalcones were found to be less polar than their Fc analogs. Some structure-activity relationships (SARs) were determined: (a) The nematocidal activities of the organic chalcones in this series were found to be much greater than those of their ferrocenyl analogs. (b) The position of the carbonyl group played a central role in the biological activity of both classes of chalcones studied. (c) For both classes of chalcones, lipophilicity of a compound seemed to play a significant role in its nematocidal activity. (d) The planarity of a ferrocenyl-chlacone seems to play a role in its activity.
- Attar, Saeed,O'Brien, Zachary,Alhaddad, Hasan,Golden, Melissa L.,Calderón-Urrea, Alejandro
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supporting information; experimental part
p. 2055 - 2073
(2011/04/27)
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- Stereoselective olefination of N-sulfonyl imines with stabilized phosphonium ylides for the synthesis of electron-deficient alkenes
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An unprecedented protocol has been developed for thestereoselective synthesis of structurally diverse electron-deficient alkenes in moderate to excellent yields from readily accessible N-sulfonyl imines and stabilized phosphonium ylides. Significantly, the olefination reaction of N-sulfonylimines with nitrile-stabilized phosphonium ylides affords an array of α,β-unsaturated nitriles with high Z selectivity, and the reactions with ester-, amide-, and ketone-stabilized phosphonium ylides afford α,β-unsaturated esters, amides, and ketones with high E selectivity, respectively. Spectroscopic analysis of the reaction mixtures and trapping of the intermediates allow plausible mechanisms to be proposed. Initialimine/ylide addition leads to the formation of betaines that cyclize to form 1,2-azaphosphetanes that subsequently eliminate iminophosphoranes to yield alkenes. For the synthesis of electron-deficient 1,2-disubstituted alkenes, the presence of an electron-withdrawing group in the betaine allows rapid interconversion between its two diastereomers through proton transfer. The Z/E selectivity for alkene synthesis is determined by the different rates at which the two betaine diastereomers form the corresponding 1,2-azaphosphetane diastereomers. In contrast, the Z/E selectivity for the synthesis of electron-deficient trisubstituted alkenes originates from the diastereoselective addition of stabilized phosphonium ylides to N-sulfonyl imines.
- Fang, Fan,Li, Yuan,Tian, Shi-Kai
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experimental part
p. 1084 - 1091
(2011/04/15)
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- Synthesis, molecular modeling and biological evaluation of chalcone thiosemicarbazide derivatives as novel anticancer agents
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A series of novel chalcone thiosemicarbazide derivatives (4a-4x) have been designed, synthesized, structurally determined, and their biological activities were also evaluated as potential EGFR kinase inhibitors. All the synthesized compounds are first reported. Among the compounds, compound 4r showed the most potent biological activity (IC50 = 0.78 ± 0.05 μM for HepG2 and IC50 = 0.35 μM for EGFR), which is comparable to the positive controls. Docking simulation was also performed to position compound 4r into the EGFR active site to determine the probable binding model. Antiproliferative assay results demonstrated that some of these compounds possessed good antiproliferative activity against HepG2. Compound 4r with potent inhibitory activity in tumor growth inhibition may be a potential anticancer agent.
- Zhang, Hong-Jia,Qian, Yong,Zhu, Di-Di,Yang, Xu-Guang,Zhu, Hai-Liang
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experimental part
p. 4702 - 4708
(2011/10/31)
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- Tetrachlorosilane-zinc chloride as a new potent binary reagent for one-pot, three-component synthesis of mannich-type products
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A combination of tetrachlorosilane and zinc chloride in dichloromethane as an efficient and ambient binary reagent to promote a one-pot amidoalkylation reaction of enolizable ketones, aromatic aldehydes with acetonitriles, or benzonitrile have been develo
- Badawy, Doria S.,Abdel-Galil, Ebrahim,Kandeel, Ezzat M.,Basyouni, Wahid M.,Khatab, Tamer K.
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experimental part
p. 2799 - 2812
(2010/04/03)
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- Synthetic chalcones as efficient inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase PtpA
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In the search for lead compounds for new drugs for tuberculosis, the activity of 38 synthetic chalcones were assayed for their potential inhibitory action towards a protein tyrosine phosphatase from Mycobacterium tuberculosis - PtpA. The compounds were ob
- Chiaradia, Louise Domeneghini,Mascarello, Alessandra,Purificacao, Marcela,Vernal, Javier,Cordeiro, Marlon Norberto Sechini,Zenteno, Maria Emilia,Villarino, Andrea,Nunes, Ricardo Jose,Yunes, Rosendo Augusto,Terenzi, Hernan
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supporting information; experimental part
p. 6227 - 6230
(2009/06/30)
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- Amine-promoted, organocatalytic aziridination of enones
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(Chemical Equation Presented) A novel method is presented using N-N ylides (prepared by in situ amination of a tertiary amine) for the aziridination of a range of enone systems. The amine may be used sub-stoichiometrically, and promising levels of enantioselectivity are observed with quinine as promoter.
- Armstrong, Alan,Baxter, Carl A.,Lamont, Scott G.,Pape, Andrew R.,Wincewicz, Richard
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p. 351 - 353
(2007/10/03)
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- Convenient preparation of chiral α,β-epoxy ketones via claisen-schmidt condensation-epoxidation sequence
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A novel Clasisen-Schmidt condensation-epoxidation sequence of aldehydes and ketones was developed to produce a series of chiral α,β-epoxy ketones under asymmetric phase-transfer catalytic conditions. The organocatalytic method reported here can afford chiral α,β-epoxy ketones under mild conditions with moderate to good yields and up to 96% ee.
- Wang, Yongcan,Ye, Jinxing,Liang, Xinmiao
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p. 1033 - 1036
(2008/09/16)
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- Chalcone and its analogs as agents for the inhibition of angiogenesis and related disease states
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The present invention relates to chalcone and chalcone derivatives and analogs which are useful as angiogenesis inhibitors. The present compounds, which are inexpensive to synthesize, exhibit unexpectedly good activity as angiogenesis inhibitors. The pres
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- 3-Aryl-4-aryloyl-1-(1H-imidazol-5-yl)methylpyrrole, a novel class of farnesyltransferase inhibitors
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Design, synthesis and structure-activity relationship of a class of 3-aryl-4-aryloyl-1-(1H-imidazol-5-yl)methylpyrroles as farnesyltransferase inhibitors are described. Compound 7 inhibits farnesyltransferase with an IC50 value of 4.6 nM.
- Lee, Hyunil,Lee, Jinho,Shin, Youseung,Jung, Wonhee,Kim, Jong-Hyun,Park, Kiwon,Ro, Seonggu,Chung, Hyun-Ho,Koh, Jong Sung
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p. 2963 - 2965
(2007/10/03)
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- A CONVENIENT ROUTE TO 1,2-DIBENYOZL-1-ARZLETHZLENES
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Short and convenient synthesis of 1,2-cis-dibenzoyl-1-arylethylenes 5a-e, 6 and 8a-d from the corresponding aryl ethers and dibenzoyl acetylene have been developed using boron trifluoride-etherate or aluminum chloride as catalyst.
- Maitra, S.,Singh, R.,Sinha, A.,Lahiri, S.
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p. 2363 - 2370
(2007/10/02)
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- Some Reactions of 4-Chlorosulfonyl-&α-naphthylchalcone
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4-Chlorosulfonyl-α-naphthylchalcone (2) has been prepared and characterised as the sulfonamides (3-7).With N,N-dimethylhydrazine, 2 gives the chalconedimethylhydrazide (8); reaction with hydrazine and N-methylhydrazine affords the pyrazolines (9, 17) and
- Cremlyn, R. J.,Swinbourne, F. J.,Mookerjee, E.
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p. 562 - 565
(2007/10/02)
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