- Pharmacophore hybridization approach to discover novel pyrazoline-based hydantoin analogs with anti-tumor efficacy
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In search for new and safer anti-cancer agents, a structurally guided pharmacophore hybridization strategy of two privileged scaffolds, namely diaryl pyrazolines and imidazolidine-2,4-dione (hydantoin), was adopted resulting in a newfangled series of compounds (H1-H22). Herein, a bio-isosteric replacement of “pyrrolidine-2,5-dione” moiety of our recently reported antitumor hybrid incorporating diaryl pyrazoline and pyrrolidine-2,5-dione scaffolds with “imidazoline-2,4-dione” moiety has been incorporated. Complete biological studies revealed the most potent analog among all i.e. compound H13, which was at-least 10-fold more potent compared to the corresponding pyrrolidine-2,5-dione, in colon and breast cancer cells. In-vitro studies showed activation of caspases, arrest of G0/G1 phase of cell cycle, decrease in the expression of anti-apoptotic protein (Bcl-2) and increased DNA damage. In-vivo assay on HT-29 (human colorectal adenocarcinoma) animal xenograft model unveiled the significant anti-tumor efficacy along with oral bioavailability with maximum TGI 36% (i.p.) and 44% (per os) at 50 mg/kg dose. These findings confirm the suitability of hybridized pyrazoline and imidazolidine-2,4-dione analog H13 for its anti-cancer potential and starting-point for the development of more efficacious analogs.
- Upadhyay, Neha,Tilekar, Kalpana,Loiodice, Fulvio,Anisimova, Natalia Yu.,Spirina, Tatiana S.,Sokolova, Darina V.,Smirnova, Galina B.,Choe, Jun-yong,Meyer-Almes, Franz-Josef,Pokrovsky, Vadim S.,Lavecchia, Antonio,Ramaa
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- Rapid umpolung Michael addition of isatin N, N ′-cyclic azomethine imine 1,3-dipoles with chalcones
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The umpolung Michael addition of isatin N,N′-cyclic azomethine imine 1,3-dipoles with chalcones is reported. The reaction could be finished within a very short time (0.3-2 min), with 3,3-disubstituted oxindole derivatives obtained in moderate to excellent yields with promising dr values. Unusual Michael adducts were obtained in moderate to high yields (26-98%) with low to high diastereoselectivities (0.8: 1 to 8.5: 1 dr). All the synthesized compounds (3, 3′, 4, 5, 5′, 7, 7′, 9 and 9′) were well characterized by FTIR, NMR, and mass spectral analyses and further confirmed by the single-crystal X-ray diffraction analysis of compounds 3aa and 4n.
- Yue, Guizhou,Jiang, Dan,Dou, Zhengjie,Li, Sicheng,Feng, Juhua,Zhang, Li,Chen, Huabao,Yang, Chunping,Yin, Zhongqiong,Song, Xu,Liang, Xiaoxia,Wang, Xianxiang,Lu, Cuifen
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supporting information
p. 11712 - 11718
(2021/07/12)
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- Multi-target weapons: diaryl-pyrazoline thiazolidinediones simultaneously targeting VEGFR-2 and HDAC cancer hallmarks
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In anticancer drug discovery, multi-targeting compounds have been beneficial due to their advantages over single-targeting compounds. For instance, VEGFR-2 has a crucial role in angiogenesis and cancer management, whereas HDACs are well-known regulators o
- C S, Ramaa,Kumar, Alan P.,Meyer-Almes, Franz-Josef,Safuan, Sabreena,Schweipert, Markus,Tilekar, Kalpana,Upadhyay, Neha
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p. 1540 - 1554
(2021/10/26)
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- Double-edged Swords: Diaryl pyrazoline thiazolidinediones synchronously targeting cancer epigenetics and angiogenesis
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In the present study, two novel series of compounds incorporating naphthyl and pyridyl linker were synthesized and biological assays revealed 5-((6-(2-(5-(2-chlorophenyl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-2-oxoethoxy) naphthalene-2-yl)methylene)thiazolidine-2,4-dione (14b) as the most potent dual inhibitors of vascular endothelial growth factors receptor-2 (VEGFR-2) and histone deacetylase 4 (HDAC4). Compounds 13b, 14b, 17f, and 21f were found to stabilize HDAC4; where, pyridyl linker swords were endowed with higher stabilization effects than naphthyl linker. Also, 13b and 14b showed best inhibitory activity on VEGFR-2 as compared to others. Compound 14b was most potent as evident by in-vitro and in-vivo biological assessments. It displayed anti-angiogenic potential by inhibiting endothelial cell proliferation, migration, tube formation and also suppressed new capillary formation in the growing chick chorioallantoic membranes (CAMs). It showed selectivity and potency towards HDAC4 as compared to other HDAC isoforms. Compound 14b (25 mg/kg, i.p.) also indicated exceptional antitumor efficacy on in-vivo animal xenograft model of human colorectal adenocarcinoma (HT-29). The mechanism of action of 14b was also confirmed by western blot.
- Kumar, Alan P.,Meyer-Almes, Franz-Josef,Ramaa, C. S.,Safuan, Sabreena,Schweipert, Markus,Tilekar, Kalpana,Upadhyay, Neha
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- Potassium Base-Promoted Diastereoselective Synthesis of 1,3-Diols from Allylic Alcohols and Aldehydes through a Tandem Allylic-Isomerization/Aldol–Tishchenko Reaction
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This study reports the first base-promoted aldol–Tishchenko reactions of allylic alcohols with aldehydes initiated by allylic isomerization. The reaction enables the diastereoselective synthesis of a variety of 1,3-diols with three contiguous stereogenic centers. Unlike commonly reported systems, our method allows the use of readily available allylic alcohols as nucleophiles instead of enolizable aldehydes and ketones.
- Sai, Masahiro
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supporting information
p. 4053 - 4056
(2021/10/25)
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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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- Synthesis and Biological Evaluation of Pyrazoline and Pyrrolidine-2,5-dione Hybrids as Potential Antitumor Agents
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In search of novel and effective antitumor agents, pyrazoline-substituted pyrrolidine-2,5-dione hybrids were designed, synthesized and evaluated in silico, in vitro and in vivo for anticancer efficacy. All the compounds exhibited remarkable cytotoxic effects in MCF7 and HT29 cells. The excellent antiproliferative activity toward MCF7 (IC50=0.78±0.01 μM), HT29 (IC50=0.92±0.15 μM) and K562 (IC50=47.25±1.24 μM) cell lines, prompted us to further investigate the antitumor effects of the best compound S2 (1-(2-(3-(4-fluorophenyl)-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)-2-oxoethyl)pyrrolidine-2,5-dione). In cell-cycle analysis, S2 was found to disrupt the growth phases with increased cell population in G1/G0 phase and decreased cell population in G2/M phase. The excellent in vitro effects were also supported by inhibition of anti-apoptotic protein Bcl-2. In vivo tumor regression studies of S2 in HT29 xenograft nude mice, exhibited equivalent and promising tumor regression with maximum TGI, 66 % (i. p. route) and 60 % (oral route) at 50 mg kg?1 dose by both the routes, indicating oral bioavailability and antitumor efficacy. These findings advocate that hybridization of pyrazoline and pyrrolidine-2,5-dioes holds promise for the development of more potent and less toxic anticancer agents.
- Anisimova, Natalia Y.,Choe, Jun-yong,Lavecchia, Antonio,Loiodice, Fulvio,Meyer-Almes, Franz-Josef,Pokrovsky, Vadim S.,S Ramaa, C.,Smirnova, Galina B.,Sokolova, Darina V.,Spirina, Tatiana S.,Tilekar, Kalpana,Upadhyay, Neha
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p. 1813 - 1825
(2020/09/07)
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- Synthesis, biological activities, and docking study of novel chalcone-pleuromutilin derivatives
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The issue of antibiotic resistance is becoming progressively serious these days, and the feasible solution to address it is to develop and discover novel antibiotics. The diterpene natural pleuromutilin is a prominent candidate for its special mode of act
- Xie, Chuan,Zhang, Siyu,Zhang, Wei,Wu, Chunxia,Yong, Can,Sun, Yuhao,Zeng, Zhengxing,Zhang, Qian,Huang, Zixin,Chen, Tian,Zhang, Yuanyuan
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p. 836 - 849
(2020/04/30)
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- Tuning the Product Selectivity of the α-Alkylation of Ketones with Primary Alcohols using Oxidized Titanium Nitride Photocatalysts and Visible Light
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The direct α-alkylation of ketones with alcohol to synthesize important α-alkylated ketones and enones is an attractive procedure for C-C bond formation. High reaction temperatures are always needed for heterogeneous catalysis using non-noble metals, and switching product selectivity in one catalysis system remains a great challenge. In the present study, a visible-light-driven procedure for this reaction is proposed, using oxidized TiN photocatalysts under mild conditions, whereby the product selectivity can be well-tuned. Oxidized TiN photocatalysts with tunable surface N/O ratios were successfully synthesized through the facile and flexible thermal oxidation treatment of low-cost TiN nanopowder. The α-alkylation of acetophenone with benzyl alcohol to form the two important compounds chalcone and dihydrochalcone occurred even at room temperature and almost complete conversion was achieved at 100 °C under visible light. The proportion of the two products can be well-tuned by switching the surface N/O ratio of the synthesized photocatalysts. Visible light is demonstrated to affect the surface N/O ratio of the photocatalysts and contribute to tuning the product selectivity. Light intensity and action spectrum study proves that the generation of energetic charge carriers results in the observed activities under visible light, based on interband transitions of TiN or the ligand-to-metal charge transfer (LMCT) effect of the surface complex formed on TiO2. Thermal energy can be coupled with light energy within this photocatalytic system, which will facilitate the full use of solar energy. Different sequential reaction mechanisms on TiN and TiO2 are proposed to be responsible for the tunable product selectivity. The wide reaction scope, the fine conversion at a low light intensity, and the favorable reusability of photocatalysts prove the great application potential of this visible-light-driven procedure for the α-alkylation of ketones with primary alcohols.
- Li, Peifeng,Su, Haijia,Xiao, Gang,Zhao, Yilin
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p. 3640 - 3649
(2020/04/09)
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- Hydroxyl- and Halogen-containing Chalcones for the Inhibition of LPS-stimulated ROS Production in RAW 264.7 Macrophages: Design, Synthesis and Structure–Activity Relationship Study
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Oxidative stress due to overproduction of reactive oxygen species (ROS) plays a major role in inflammation, cancer, and neurodegenerative disorders. In this study, 60 chalcone derivatives with fluorine (F), trifluoromethyl (CF3), trifluoromethoxy (OCF3), chlorine (Cl), and bromine (Br) in ring A and with or without hydroxy (OH) in ring B were designed, synthesized, and screened for inhibitory activity against lipopolysaccharide (LPS)-stimulated ROS production in RAW 264.7 macrophages. Structure–activity relationship study revealed the importance of a hydroxyl moiety in ring B for enhancing inhibitory activity of ROS production. Furthermore, a hydroxyl group at the ortho-position is more essential for inhibition of ROS production followed by meta- and para-positions. Among all, compound 27 that contains para-chlorine moiety in ring A and ortho-hydroxy in ring B displayed the strongest inhibitory activity (IC50 = 3.42 μM) against LPS-stimulated ROS production in RAW264.7 macrophages.
- Shrestha, Aarajana,Shrestha, Aastha,Park, Pil-Hoon,Lee, Eung-Seok
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p. 729 - 734
(2019/07/19)
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- Method for synthesizing chalcone by solvent-free catalysis on basis of alkaline ionic liquid
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The invention relates to a method for preparing chalcone from benzaldehyde and acetophenone as raw materials by solvent-free catalysis on the basis of an alkaline ionic liquid, that is, acetophenone and benzaldehyde in a molar ratio of is 0.5:1-5:1 are mixed in the absence of a solvent, 1wt.%-10wt.% of an alkaline ionic liquid catalyst is added, a reaction is performed at 20-60 DEG C for 2-6 h, and chalcone is prepared, wherein the yield of chalcone can reach 86.7%-96.7%. The synthesis route (one-pot method) is simple, reaction conditions are mild, reaction time is shorter, the product yield is high, selectivity is good, pollution of the ionic liquid is low, the problems that traditional strong alkali catalysts are high in requirement for reaction devices and pollute the environment are solved, and green catalytic synthesis of chalcone is effectively realized.
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-
Paragraph 0045-0046
(2019/09/17)
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- Pleuromutilin derivative as well as preparation method and application thereof
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The invention relates to a pleuromutilin derivative as shown in a general formula (I), as well as stereoisomers, pharmaceutically acceptable salts or crystal forms thereof, or pharmaceutical compositions containing same, as well as preparation methods and
- -
-
Paragraph 0011
(2019/11/21)
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- Application of Polyphosphoric Acid-Mediated Acyl Migration for Regiospecific Synthesis of Diverse 2-Acylpyrroles from Chalcones
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A metal-free approach for the synthesis of 2-acylpyrroles is reported in this paper. Synthesis of the target molecule started from chalcones and was carried out in two steps. Initial step involved the conversion of chalcones to corresponding 4-substituted-3-acylpyrroles by reaction with TosMIC. In the subsequent step, target molecules were obtained in modest to good yields by polyphosphoric acid-mediated acyl rearrangement of 3-acylpyrroles to their 2-acyl congeners. The crucial final step was amenable to diverse substitutions on pyrrole ring. Preliminary experiment for the determination of mechanism indicated the involvement of acylium ion.
- Kumar, Togiti Uday,Thigulla, Yadagiri,Rangan, Krishnan,Bhattacharya, Anupam
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supporting information
p. 1283 - 1290
(2019/03/07)
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- Design, synthesis, and carbonic anhydrase inhibition activity of benzenesulfonamide-linked novel pyrazoline derivatives
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Carbonic anhydrases (CA, EC 4.2.1.1) are Zinc metalloenzymes and are present throughout most living organisms. Among the catalytically active isoforms are the cytosolic CA I and II, and tumor-associated CA IX and CA XII. The carbonic anhydrase (CA) inhibitory activities of newly synthesized pyrazoline-linked benzenesulfonamides 18–33 against human CA (hCA) isoforms I, II, IX, and XII were measured and compared with that of acetazolamide (AAZ), a standard inhibitor. Potent inhibitory activity against hCA I was exerted by compounds 18–25, with inhibition constant (KI) values of 87.8–244.1 nM, which were greater than that of AAZ (KI, 250.0 nM). Compounds 19, 21, 22, 29, 30, and 32 were proven to have inhibitory activities against hCA IX with KI values (5.5–37.0 nM) that were more effective than or nearly equal to that of AAZ (KI, 25.0 nM). Compounds 20–22, and 30 exerted potent inhibitory activities (KIs, 7.1–10.1 nM) against hCA XII, in comparison with AAZ (KI, 5.7 nM).
- Abdel-Aziz, Alaa A.-M.,El-Azab, Adel S.,Bua, Silvia,Nocentini, Alessio,Abu El-Enin, Mohamed A.,Alanazi, Mohammed M.,AlSaif, Nawaf A.,Hefnawy, Mohamed M.,Supuran, Claudiu T.
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p. 425 - 431
(2019/03/27)
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- Electrochemical 1,4-reduction of α,β-unsaturated ketones with methanol and ammonium chloride as hydrogen sources
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A sustainable, chemoselective 1,4-reduction of α,β-unsaturated ketones by means of an electrochemical method is presented, wherein the extremely inexpensive ammonium chloride (NH4Cl) is applied as the only additive. The reaction proceeds smoothly in the air at ambient temperature. Mechanistic studies reveal that both NH4Cl and solvent methanol work as hydrogen donors.
- Huang, Binbin,Li, Yanan,Yang, Chao,Xia, Wujiong
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supporting information
p. 6731 - 6734
(2019/06/17)
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- Reaction condition controlled nickel(ii)-catalyzed C-C cross-coupling of alcohols
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The challenge in the C-C cross-coupling of secondary and primary alcohols using acceptorless dehydrogenation coupling (ADC) is the difficulty in accurately controlling product selectivities. Herein, we report a controlled approach to a diverse range of β-alkylated secondary alcohols, α-alkylated ketones and α,β-unsaturated ketones using the ADC methodology employing a Ni(ii) 4,6-dimethylpyrimidine-2-thiolate cluster catalyst under different reaction conditions. This catalyst could tolerate a wide range of substrates and exhibited a high activity for the annulation reaction of secondary alcohols with 2-aminobenzyl alcohols to yield quinolines. This work is an example of precise chemoselectivity control by careful choice of reaction conditions.
- Zhang, Meng-Juan,Li, Hong-Xi,Young, David J.,Li, Hai-Yan,Lang, Jian-Ping
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supporting information
p. 3567 - 3574
(2019/04/14)
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- MIL-101 supported highly active single-site metal catalysts for tricomponent coupling
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Metal-organic frameworks with regular pore structures provide powerful platforms for the design of single-site metal catalysts for chemical transformation. In this paper, we develop a facile, stable and recyclable MOF-supported Cu(II) catalyst, MIL-101-SO3Cu. It shows extremely high activity for the A3 coupling of alkynes, aldehydes and amines. The turnover frequency can reach 6.8 × 105 h?1 under neat conditions, which is the highest so far reported for the reaction. The high activity is because the specific structure of the MIL-101-SO3 support enables a single-site dispersion and an unhindered open environment for the metal ion. MIL-101-SO3Cu also exhibits high activity for the one-pot cascade reactions combining A3 coupling and 5-endo-dig cyclization.
- Sun, Weng-Jie,Gao, En-Qing
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p. 110 - 116
(2018/11/10)
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- Synthesis of arylated chalcone derivatives via palladium cross-coupling reactions
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A useful protocol for arylation of the olefin double bond of chalcones to afford tri- and tetra-substituted chalcone derivatives is reported. The protocol begins with the Heck reaction between chalcones and aryl iodides providing β-arylchalcones. This reaction tolerates various functional groups on both rings, as well as deactivated aryl iodides. The products are obtained in moderate to excellent yields and the (E)-β-arylchalcones (E:Z > 96:4) can be isolated via precipitation. Competitive Heck reactions pointed to a significant effect of ring one substituents on the reaction rate, while substituents on ring two have a much smaller effect. To access α,β-diarylchalcones, a sequential bromination-Suzuki cross coupling strategy was applied to the β-arylated compounds which afforded double arylated chalcone derivatives in 60–99% yield over two steps.
- da Costa, Rafaela G.M.,Farias, Francisco R.L.,Back, Davi,Limberger, Jones
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supporting information
p. 771 - 775
(2018/01/27)
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- Method of utilizing micro channel reactor to prepare fluorine containing chalcone derivatives
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The invention discloses a method of utilizing a micro channel reactor to prepare fluorine containing chalcone derivatives. The method comprises following steps: individually dissolving a compound represented by a formula I and a compound represented by a
- -
-
Paragraph 0031-0032; 0037-0038
(2020/11/23)
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- A robust multifunctional ligand-controlled palladium-catalyzed carbonylation reaction in water
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A novel, hydrophilic and recyclable methoxypolyethylene glycol (PEG)-modulated s-triazine-based multifunctional Schiff base/N,P-ligand L9 was prepared and used in Pd-catalyzed Heck-type carbonylative coupling reactions, affording diverse chalcone derivatives and 1,4-dicarbonyl esters in good yields.
- Gao, Pei-Sen,Zhang, Kan,Yang, Ming-Ming,Xu, Shan,Sun, Hua-Ming,Zhang, Jin-Lei,Gao, Zi-Wei,Zhang, Wei-Qiang,Xu, Li-Wen
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supporting information
p. 5074 - 5077
(2018/05/26)
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- Kinetic Resolution of β-Hydroxy Carbonyl Compounds via Enantioselective Dehydration Using a Cation-Binding Catalyst: Facile Access to Enantiopure Chiral Aldols
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A practical and highly enantioselective nonenzymatic kinetic resolution of racemic β-hydroxy carbonyl (aldol) compounds through enantioselective dehydration process was developed using a cation-binding Song's oligoethylene glycol (oligoEG) catalyst with p
- Paladhi, Sushovan,Hwang, In-Soo,Yoo, Eun Jeong,Ryu, Do Hyun,Song, Choong Eui
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supporting information
p. 2003 - 2006
(2018/04/16)
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- Bi(OTf)3 catalyzed disproportionation reaction of cinnamyl alcohols
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Bi(OTf)3 catalyzed disproportionation reaction of cinnamyl alcohols provides chalcones and benzyl styrenes. The use of various metal triflates is investigated herein for facile and efficient redox transformation. A plausible mechanism has been proposed.
- Chan, Chieh-Kai,Tsai, Yu-Lin,Chang, Meng-Yang
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p. 3368 - 3376
(2017/05/22)
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- Revisiting the Juliá-Colonna enantioselective epoxidation: Supramolecular catalysis in water
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We describe an efficient epoxidation process leading to chiral epoxyketones using the reusable homo-oligopeptide poly-l-leucine (PLL) in pure water, without any organic co-solvent. A range of substituted epoxyketones can be accessed with good conversions and high enantioselectivities. Based on the experimental results and computational studies, we propose a mechanism that demonstrates the importance of both the α-helical structure and the presence of a hydrophobic groove of the homo-oligopeptide catalyst for reactivity and selectivity.
- Bérubé, Christopher,Barbeau, Xavier,Lagüe, Patrick,Voyer, Normand
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supporting information
p. 5099 - 5102
(2017/07/12)
-
- Synthesis, carbonic anhydrase I and II inhibition studies of the 1,3,5-trisubstituted-pyrazolines
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4-(3-(4-Substituted-phenyl)-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl) benzenesulfonamides (9–16) were successfully synthesized and their chemical structures were confirmed by 1H NMR, 13C NMR, and HRMS spectra. Carbonic anhydrase I and II inhibitory effects of the compounds were investigated. Ki values of the compounds were in the range of 316.7 ± 9.6–533.1 ± 187.8 nM towards hCA I and 412.5 ± 115.4–624.6 ± 168.2 nM towards hCA II isoenzymes. While Ki values of the reference compound Acetazolamide were 278.8 ± 44.3 nM and 293.4 ± 46.4 nM towards hCA I and hCA II izoenzymes, respectively. Compound 14 with bromine and compound 13 with fluorine substituents can be considered as the leader compounds of the series because of the lowest Ki values in series to make further detailed carbonic anhydrase inhibiton studies.
- Gul, Halise Inci,Mete, Ebru,Taslimi, Parham,Gulcin, Ilhami,Supuran, Claudiu T.
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p. 189 - 192
(2017/11/21)
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- Synthesis and biological screening of some new 1,5-benzodiazepine derivatives as promising antibacterial and antitubercular agents
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In this study, various substituted 1,5-benzodiazepines were synthesized by condensing different substituted chalcones with o-phenylenediamine in methanol using piperidine as a base under refluxing conditions and were obtained in good yield after purificat
- Monga, Vikramdeep,Nayak, Surendra Kumar,Singh, Gurpreet
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p. 143 - 149
(2020/07/21)
-
- Imidazole-triazine type compound and preparation method and application thereof
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The invention provides an imidazole-triazine type compound which is shown as the formula 3 in the description and a preparation method and application thereof. The method comprises the steps that a triazine compound and an alpha,beta-unsaturated ketone type compound are mixed and added into a solvent, under the existence of a metal copper catalyst and an oxidizing material, the mixed solution is stirred and reacts 5-20 hours under the temperature of 60-150 DEG C, after the reaction is finished, the reacted solution is subjected to post processing, and the imidazole-triazine type compound which is shown as the formula 3 is obtained; the metal copper catalyst is halogenide of the copper or a copper salt; the oxidizing material is a halogen elementary substance. The imidazole-triazine type compound can be applied to prepare antibacterial drugs or antibacterial agents, and the preferred antibacterial drugs are the drugs which inhibit activity of escherichia coli.
- -
-
Paragraph 0031; 0032; 0033; 0034; 0035; 0037
(2017/10/06)
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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, spectroscopic and computational characterization of the tautomerism of pyrazoline derivatives from chalcones
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In the present study a series of novel pyrazolines derivatives has been synthesized, and their structures assigned on the basis of FT-Raman, 1H and 13C NMR spectral data and computational DFT calculations. A joint computational study using B3LYP/6-311G(2d,2p) density functional theory and FT-Raman investigation on the tautomerism of 3-(4-substituted-phenyl)-4,5-dihydro-5-(4-substituted-phenyl)pyrazole-1-carbothioamide and 3-(4-substituted-phenyl)-4,5-dihydro-5-(4-substituted-phenyl)pyrazole-1-carboxamide are presented. The structures were characterized as a minimum in the potential energy surface using DFT. The calculated Raman and NMR spectra were of such remarkable agreement to the experimental results that the equilibrium between tautomeric forms has been discussed in detail. Our study suggests the existence of tautomers, the carboxamide/carbothioamide group may tautomerize, in the solid state or in solution. Thermodynamic data calculated suggests that the R(CS)NH2 and R(CO)NH2 species are more stable than the R(CNH)SH and R(CNH)OH species. Additionally, results found for the 1H NMR shifting, pointed out to which structure is present.
- Miguel, Fbio Balbino,Dantas, Juliana Arantes,Amorim, Stefany,Andrade, Gustavo F.S.,Costa, Luiz Antnio Sodr,Couri, Mara Rubia Costa
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supporting information
p. 318 - 326
(2015/08/06)
-
- Substituent-Controlled Chemoselective Cleavage of C = C or Csp2 - C(CO) Bond in α,β-Unsaturated Carbonyl Compounds with H-Phosphonates Leading to β-Ketophosphonates
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An unprecedented substituent-controlled chemoselective cleavage of C = C double bond or C(sp2)-C(CO) bond along with aerobic phosphorylation of α,β-unsaturated carbonyl compounds with H-phosphonates through a radical process has been disclosed. The current strategy provides an access to β-ketophosphonates under mild conditions with a wide substrate scope.
- Zhou, Yao,Rao, Changqing,Mai, Shaoyu,Song, Qiuling
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p. 2027 - 2034
(2016/03/15)
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- Synthesis of α,β-unsaturated ketones from alkynes and aldehydes over Hβ zeolite under solvent-free conditions
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A facile Hβ zeolite-catalyzed strategy has been successfully developed for the synthesis of α,β-unsaturated ketones from alkynes and aldehydes under solvent-free conditions. The reaction proceeds via tandem hydration/condensation of alkynes with aldehydes to afford a range of α,β-unsaturated carbonyls in good to excellent yields. This journal is.
- Mameda, Naresh,Peraka, Swamy,Kodumuri, Srujana,Chevella, Durgaiah,Banothu, Rammurthy,Amrutham, Vasu,Nama, Narender
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p. 58137 - 58141
(2016/07/07)
-
- Kinetic Resolution of β-Sulfonyl Ketones through Enantioselective β-Elimination using a Cation-Binding Polyether Catalyst
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Reported herein is the first enantioselective β-elimination reaction catalyzed by a chiral cation-binding polyether. By using this catalytic protocol, a wide range of β-sulfonyl ketones could be effectively resolved with high stereoselectivity (S up to >300). Key to the success of this process is the favorable secondary interactions of the catalyst with the Lewis basic groups on the sulfone substrate. The enone product of this process can be easily converted into the racemic starting material, and allows an effective recycling and overall synthesis of chiral β-sulfonyl ketones in high yield and excellent enantioselectivity.
- Li, Liang,Liu, Yidong,Peng, Yang,Yu, Lei,Wu, Xiaoyan,Yan, Hailong
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supporting information
p. 331 - 335
(2016/01/25)
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- Design, synthesis, and pharmacological evaluation of new pyrazoline derivatives
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In the present investigation, a new series of pyrazoline derivatives has been synthesized by the reaction of chalcones with hydrazine derivatives like hydrazine hydrate and phenyl hydrazines in the presence of different aliphatic acids. The chemical struc
- Sapnakumari, Majal,Narayana, Badiadka,Gurubasavarajswamy, Purawarga Matada,Sarojini, Balladka Kunhanna
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p. 1015 - 1024
(2015/08/06)
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- Synthesis, structure-activity relationship and molecular docking of cyclohexenone based analogous as potent non-nucleoside reverse-transcriptase inhibitors
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The chalcones core in compounds is advantageously chosen effective synthons, which offer exciting perspectives in biological and pharmacological research. The present study reports the successful development of eight new cyclohexenone based anti-reverse t
- Nazar, Muhammad Faizan,Abdullah, Muhammad Imran,Badshah, Amir,Mahmood, Asif,Rana, Usman Ali,Khan, Salah Ud-Din
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- Efficient Protocol for the Synthesis of Novel Spiro[acenaphthylene-1,2′-pyrrolidin]-2-one Compounds
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An efficient catalyst-free synthesis of 3′-benzoyl-4′,5′-diphenyl-2H-spiro[acenaphthylene-1,2′-pyrrolidin]-2-one derivatives via one-pot 1,3-dipolar cycloaddition of acenaphthenequinone, arylmethyl amines, and chalcones with high regioselectivity is described. The structure of the cycloadducts were characterized by infrared, high-resolution mass spectrometry (electrospray ionization), 1H NMR, and 13C NMR spectra, and the structure of 4a was confirmed using x-ray single-crystal structure analysis.
- Lin, Yan,Fu, Zhijie,Shen, Tianhua,Che, Fengfeng,Song, Qingbao
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supporting information
p. 2188 - 2194
(2015/09/22)
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- Synthesis and anticancer activity of 1,3,5-triaryl-1H-pyrazole
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Previous studies demonstrated that some pyrazole derivatives could be considered as potential anticancer agents. A series of 1,3,5-triaryl-1H-pyrazole derivatives were prepared by the reaction of phenylhydrazin and different chalcones. The previous classi
- Ghadbeigi, Sajad,Ostad, Seyed Nasser,Shafiee, Abbas,Amini, Mohsen
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p. 754 - 759
(2015/10/05)
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- Hierarchical flowerlike magnesium oxide hollow spheres with extremely high surface area for adsorption and catalysis
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Three-dimensionally hierarchical flowerlike MgO hollow spheres with an extremely high surface area of 343 m2 g-1 were prepared through a facile and environmentally friendly solvothermal route. The maximum adsorption capacity at natural pH reached 569.7 mg g-1 for the removal of arsenic in water, which is the highest among all of the reported adsorbents. In addition, flowerlike MgO hollow spheres also displayed excellent catalytic activity and stability for the Claisen-Schmidt condensation reaction as a solid base catalyst.
- Yang, Shuliang,Huang, Peipei,Peng, Li,Cao, Changyan,Zhu, Yanan,Wei, Fang,Sun, Yongbin,Song, Weiguo
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p. 400 - 406
(2016/01/15)
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- Synthesis and screening of antimicrobial activity of novel 2,5-dimethylpyrrolyl-pyrazole derivatives
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A new series of 2,5-dimethylpyrrolyl-pyrazole derivatives (5a-g) was synthesized by refluxing a mixture of substituted chalcones in ethanol with 4-(2,5-dimethylpyrrol- 1-yl) benzoic acid hydrazide. Purity of newly synthesized compounds was confirmed by TLC and melting point. The structures of all newly synthesized compounds were confirmed by spectral study such as FTIR, 1H NMR and Mass spectroscopy. The compounds were screened for their antimicrobial and antitubercular activities using broth microdilution and MABA methods respectively.
- Hallikeri,Joshi, Shrinivas D.,Kulkarni
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p. 157 - 160
(2019/01/16)
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- Synthesis of new indazole derivatives as potential antioxidant agents
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New indazole derivatives were synthesized by reacting hydrazine hydrate and its derivatives with cyclohexenone derivatives, which in turn prepared from respective chalcones. The chemical structure of newly synthesized compounds was well characterized by using 1H NMR, 13C NMR, IR and mass spectral data. All the synthesized products were screened for their antioxidant properties. All indazole derivatives exhibited noticeable DPPH radical scavenging activity, reducing power capacity and total antioxidant capacity in comparison with the respective standards. Springer Science+Business Media 2013.
- Sapnakumari, Majal,Narayana, Badiadka,Sarojini, Balladka Kunhanna,Madhu, Leelavathi Narayana
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p. 2368 - 2376
(2014/05/06)
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- Functionalization of the Benzylic C-H Bonds in Azaarenes by Cobalt-Catalyzed 1,4-Addition to Enones
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Functionalization of the C(sp3)-H bonds in azaarenes was catalyzed by CoCl2 as an inexpensive Lewis acid catalyst. Enones were demonstrated to be good C=C electrophilic acceptors for the construction of various azaarene-containing 1,4-addition products in yields of up to 95 %. Functionalization of the C(sp3)-H bonds in azaarenes catalyzed by CoCl2 as an inexpensive Lewis acid catalyst is reported. Enones are demonstrated to be good C=C electrophilic acceptors for the construction of various azaarene-containing 1,4-addition products in yields up to 95 %.
- Jamal, Zaini,Teo, Yong-Chua,Wong, Ling-Keong
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supporting information
p. 7343 - 7346
(2016/02/20)
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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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- Microwave-assisted synthesis and tyrosinase inhibitory activity of chalcone derivatives
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A series of chalcones and their derivatives were synthesized, and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were evaluated. The results showed that some of the synthesized compounds exhibited significant inhibitory activity, and four compounds exhibited more potent tyrosinase inhibitory activity than the reference standard inhibitor kojic acid (5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one). Specifically, 1-(-1-(4-methoxyphen- yl)-3-phenylallylidene)thiosemicarbazide (18) exhibited the most potent tyrosinase inhibitory activity with IC50 value of 0.274 μm. The inhibition mechanism analysis of 1-(-1-(2,4-dihydroxyphenyl)-3-phenylallylidene) thiosemicarbazide (16) and 1-(-1-(4-methoxyphenyl)-3-phenylallylidene) thiosemicarbazide (18) demonstrated that the inhibitory effects of the two compounds on the tyrosinase were irreversible. Preliminary structure activity relationships' analysis suggested that further development of such compounds might be of interest.
- Liu, Jinbing,Chen, Changhong,Wu, Fengyan,Zhao, Liangzhong
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- Biomimetic hydrogenation: A reusable NADH co-enzyme model for hydrogenation of α,β-epoxy ketones and 1,2-diketones
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A biomimetic method has been developed to transform α,β-epoxy ketones or 1,2-diketones into corresponding β-hydroxy ketones or α-hydroxy ketones using a catalytic amount of BNAH or BNA +Br-. The regeneration of BNAH or BNA+Br - is achieved by a mixture of HCOOH/Et3N. A radical mechanism is proposed to explain these observations.
- Huang, Qiang,Wu, Ji-Wei,Xu, Hua-Jian
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supporting information
p. 3877 - 3881
(2013/07/05)
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- Chemoselective transfer hydrogenation of α,β-unsaturated ketones catalyzed by pincer-Pd complexes using alcohol as a hydrogen source
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A pincer-Pd complex was utilized in the chemoselective transfer hydrogenation of α,β-unsaturated ketones using n-BuOH as a hydrogen source and solvent. Good to excellent yields were obtained for various substrates even with reducible groups. Based on deuterium-labeling experiments, the reaction mechanism is proposed to occur via a pincer-Pd-hydride intermediate.
- Ding, Boqiang,Zhang, Zhenfeng,Liu, Yangang,Sugiya, Masashi,Imamoto, Tsuneo,Zhang, Wanbin
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supporting information
p. 3690 - 3693
(2013/08/23)
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- PAA-supported Hantzsch 1,4-dihydropyridine ester: An efficient catalyst for the hydrogenation of α,β-epoxy ketones
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A new type of water-soluble polymer-supported NADH co-enzyme model-PAA (polyacrylic acid)-supported Hantzsch 1,4-dihydropyridine ester (PAA-HEH) was designed and synthesized. Catalytic amount of the supported reagent was used in the hydrogenation of α,β-epoxy ketones to the corresponding β-hydroxy ketones and showed great catalytic efficiency in the reduction reaction. This PAA-HEH was an optimal potential for recycling use.
- Zhou, Xin-Feng,Wang, Peng-Fei,Geng, Ye,Xu, Hua-Jian
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supporting information
p. 5374 - 5377
(2013/09/12)
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- Lithium hydroxide mediated synthesis of 3,4-disubstituted pyrroles
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LiOH·H2O in ethanol was found to be an effective reagent for the synthesis of 3,4-disubstituted pyrrole derivatives by the van Leusen method. In situ formation of chalcones from aromatic aldehydes and enolisable ketones, and their subsequent reaction with tosylmethyl isocyanide resulted in the formation and precipitation of pyrrole derivatives from the reaction medium, in good yields. The solvation effect of the polar medium facilitates the reaction. The Royal Society of Chemistry 2013.
- Sharma, Ratnesh,Kumar, Kapil,Chouhan, Mangilal,Grover, Vikas,Nair, Vipin A.
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p. 14521 - 14527
(2013/09/02)
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- Design, synthesis and biological evaluation of pyrazolyl-thiazolinone derivatives as potential EGFR and HER-2 kinase inhibitors
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A series of pyrazolyl-thiazolinone derivatives (E1-E36) have been designed and synthesized and their biological activities were also evaluated as potential EGFR and HER-2 kinase inhibitors. Thirty-four of the 36 compounds were reported for the first time. Among them, compound 2-(5-(4-bromophenyl)-3-p-tolyl-4,5- dihydro-1H-pyrazol-1-yl)thiazol-4(5H)-one (E28) displayed the most potent inhibitory activity (IC50 = 0.24 μM for EGFR and IC50 = 1.07 μM for HER-2). Antiproliferative assay results indicated that compound E28 owned high antiproliferative activity against MCF-7, B16-F10 and HCT-116 in vitro, with IC50 value of 0.30, 0.54, and 0.70 μM, respectively. Docking simulation was further performed to position compound E28 into the EGFR active site to determine the probable binding model. Based on the preliminary results, compound E28 with potent inhibitory activity in tumor growth would be a potential anticancer agent.
- Qiu, Ke-Ming,Wang, Hai-Hong,Wang, Li-Ming,Luo, Yin,Yang, Xian-Hui,Wang, Xiao-Ming,Zhu, Hai-Liang
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experimental part
p. 2010 - 2018
(2012/05/04)
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- Palladium-catalyzed oxidative carbonylative coupling reactions of arylboronic acids with styrenes to chalcones under mild aerobic conditions
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Do the coupling: A palladium-catalyzed oxidative carbonylative coupling process of arylboronic acid with styrenes to chalcone has been developed. The reactions proceed under mild conditions using air as the terminal oxidant reagent.
- Wu, Xiao-Feng,Neumann, Helfried,Beller, Matthias
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experimental part
p. 282 - 285
(2012/04/18)
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- A straightforward synthesis of pyrazolines and pyrazoles: Palladium-catalyzed carbonylative vinylation-cyclocondensation reactions of aryl halides
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A novel consecutive one-pot synthesis of pyrazolines and pyrazoles starting from simple aryl halides, styrenes, carbon monoxide, and hydrazines has been established. Palladium-catalyzed carbonylative vinylation of aryl halides gave the corresponding chalcones, which are trapped in situ by addition of hydrazines.
- Wu, Xiao-Feng,Neumann, Helfried,Beller, Matthias
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experimental part
p. 4919 - 4924
(2011/10/31)
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- TiO2-SO42- as a novel solid acid catalyst for highly efficient, solvent free and easy synthesis of chalcones under microwave irradiation
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TiO2-SO42- has been prepared by the sol-gel method using H2SO4 and used for the synthesis of chalcones under microwave irradiation. Sulfate loading by H2SO 4 increases the Lewis acidity of TiO2. This catalyst gives an excellent yield with less reaction time and is an inexpensive, easily recyclable catalyst for this reaction.
- Krishnakumar,Velmurugan,Swaminathan
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experimental part
p. 375 - 379
(2011/09/20)
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- Solvent free synthesis of quinoxalines, dipyridophenazines and chalcones under microwave irradiation with sulfated Degussa titania as a novel solid acid catalyst
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Sulfated TiO2-P25 (Degussa titania) has been prepared by sol-gel method using H2SO4 and characterized by FT-IR, XRD, FE-SEM, EDS, HR-TEM, XPS, DRS and BET surface area measurements. Sulfate loading by H2SO4 increases the Lewis acidity of Degussa tiatania. This catalyst gives an excellent yield with less reaction time and is an inexpensive and easily recyclable solid acid catalyst for the synthesis of quinaxalines, dipyridophenazines and chalcones under microwave irradiation.
- Krishnakumar,Swaminathan
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experimental part
p. 16 - 25
(2011/12/14)
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