- Effect of cyclodextrin complexation on the photochemistry of the lignin model α-guaiacoxyacetoveratrone
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The photodecomposition of α-guaiacoxyacetoveratrone (GAV) in homogeneous solvents and in aqueous cyclodextrin solutions was studied by following the fluorescence emission of the photoproducts formed. The same qualitative behavior as previously observed for the photodegradation quantum yield measurements was reproduced in the fluorescence studies in dry or wet methanol and acetonitrile. The yield for GAV photodegradation in water is smaller than in the organic solvents. Complexation of GAV to β- and γ-cyclodextrins leads to an increase in the photodecomposition yield, especially during the early part of the photodecomposition kinetics. The transients formed in the photolysis of GAV in water are similar to those observed in acetonitrile, and the lifetime of triplet GAV in water is 130 ns. In addition, solvated electrons were formed when GAV was photolyzed in water. Complexation of GAV to cyclodextrins leads to an increase in the triplet yield compared to the radical yield and a mode rate shortening of the triplet lifetime.
- Okano,Ovans,Zunic,Moorthy,Bohne
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- Using fluorogenic probes for the investigation of selective biomass degradation by fungi
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A library of fifteen commercially purchased and synthetic fluorogenic probes was employed for the investigation of biomass degradation using extracts of white-rot fungi. These probes were selected or designed to mimic the dominant linkages in celluloses, hemicelluloses, and lignin, the three most abundant polymers found in biomass. The results show that white-rot fungi display a high preference for cleaving mannose- and glucose-based probes, which mimic hemicelluloses. Low degrees of cleavages were noted for xylose- and cellobiose-based probes. No cleavages were observed for probes that mimic the linkages in lignin. Overall, these discoveries prove that it is possible to employ fungi for selective degradation or release of hemicelluloses from biomass.
- Zhang, Qian,Peng, Xinrui,Grilley, Michelle,Takemoto, Jon Y.,Chang, Cheng-Wei Tom
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- Synthesis and Fluorescence Properties of Novel indol-3yl-thiazolo[3,2-a][1,3,5]triazines and indole-3-carbaldehyde Schiff Bases
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Novel photoactive 4-(4-chlorophenyl)-2-(1H-indol-3-yl)-6-substituted phenyl-2H-thiazolo[3,2-a][1,3,5]triazines were synthesized by the conjugate addition of ammonia to the indole-3-carbaldehyde Schiff bases followed by the condensation with 4-chlorobenzaldehyde. All the synthesized compounds were characterized by FT-IR, NMR, mass spectra and elemental analyses. Their antioxidant property, electrochemical and photophysical properties in different organic solvents were investigated. Comparative discussion on the photophysical properties of indole-3-carbaldehyde Schiff bases and 4-(4-chlorophenyl)-2-(1H-indol-3-yl)-6-substituted phenyl-2H-thiazolo[3,2-a][1,3,5]triazines has been described. The fluorescence quantum yield of Schiff bases (Φf = 0.66-0.70 in DMSO) found to be interestingly higher. High fluorescence quantum yield, large molar extinction coefficient, high stokes shift and smaller optical band gap positioning these new derivatives as an efficient metal free organic fluorescent and semiconductor material.
- Sravanthi,Manju
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- Design, synthesis, and biological evaluation of acetophenone derivatives as dual binding acetylcholinesterase inhibitors
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As part of a project aimed at developing new agents for potential application in Alzheimer's disease, a new series of acetophenone derivatives which possess alkylamine side chains were designed, synthesized and assayed as acetylcholinesterase (AChE) inhibitors that could simultaneously bind to the peripheral and catalytic sites of the enzyme. The compounds were synthesized, and the inhibitory activities toward AChE and butyrylcholinesterase (BuChE) in vitro were determined using a modified Ellman method. Of the compounds tested, 6 derivatives were found to inhibit AChE in the micromolar range. The best compound, 2e, had an IC50 of 0.13 M. A detailed molecular modeling study was performed to explore the interaction of 2e with AChE.
- Shen, Yanhong,Li, Baoli,Xu, Hu,Zhang, Guoqiang
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- Design, synthesis and biological evaluation of 2-(3,4-dimethoxyphenyl)-6 (1,2,3,6-tetrahydropyridin-4-yl)imidazo[1,2-a]pyridine analogues as antiproliferative agents
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Two series of forty five novel 2-(3,4-dimethoxyphenyl)-6-(1,2,3,6-tetrahydropyridin-4-yl) imidazo[1,2-a]pyridine analogues (IPA 1–22, IPS 1–22 and IP-NH) have been designed, synthesized and structures confirmed by 1H NMR, 13C NMR, mass spectrometry. Furthermore, single crystal was developed for IPS-13. All the final derived conjugates were evaluated for their in vitro antiproliferative activity against a panel of diverse cancer cell lines viz., A549 (lung cancer), HeLa (cervical cancer), B16F10 (melanoma) and found to show potent anticancer activity on the tested cell lines. Many of them showed the IC50 values in the range 2.0–20.0 μM. The most active compounds (IPA 5,6,8,9,12,16,17,19 and IPS 7,8,9,22) from IPA and IPS series were screened to determine their cytotoxicity on HEK-293 (human embryonic kidney) normal cell line and were found to be nontoxic to normal human cells. The molecular interactions of the derivatised conjugates were also supported by molecular docking simulations. These derivatives may serve as lead structures for development of novel potential anticancer drug candidates.
- Chitti, Surendar,Singireddi, SrinivasaRao,Santosh Kumar Reddy, Pochana,Trivedi, Prakruti,Bobde, Yamini,Kumar, Chandan,Rangan, Krishnan,Ghosh, Balaram,Sekhar, Kondapalli Venkata Gowri Chandra
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- Thio-assisted reductive electrolytic cleavage of lignin β-O-4 models and authentic lignin
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Avoiding the use of expensive catalysts and harsh conditions such as elevated temperatures and high pressures is a critical goal in lignin depolymerization and valorization. In this study, we present a thio-assisted electrocatalytic reductive approach using inexpensive reticulated vitreous carbon (RVC) as the working cathode to cleave the β-O-4-type linkages in keto aryl ethers. In the presence of a pre-electrolyzed disulfide (2,2′-dithiodiethanol) and a radical inhibitor (BHT) at room temperature at a current density of 2.5 mA cm-2, cathodic reduction of nonphenolic β-O-4 dimers afforded over 90% of the corresponding monomeric C-O cleavage products in only 1.5 h. Extended to DDQ-oxidized poplar lignin, this combination of electric current and disulfide, applied over 6 h, released 36 wt% of ethyl acetate soluble fragments and 26 wt% of aqueous soluble fragments, leaving only 38 wt% of insoluble residue. These findings represent a significant improvement over the current alone values (24 wt% ethyl acetate soluble; 22 wt% aqueous soluble; 54 wt% insoluble residue) and represent an important next step in our efforts to develop a mild electrochemical method for reductive lignin deconstruction.
- Fang, Zhen,Flynn, Michael G.,Jackson, James E.,Hegg, Eric L.
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p. 412 - 421
(2021/01/28)
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- Alkylation of monomeric, dimeric, and polymeric lignin models through carbon-hydrogen activation using Ru-catalyzed Murai reaction
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In this study, we have assessed directed carbon-hydrogen activation (CHA) for alkylation of monomeric, dimeric, and polymeric lignin models using Murai's catalyst [RuH2(CO)(PPh3)3]. Based on related work from our laboratory showing that isolated organosolv lignin bears benzylic directing groups ideal for CHA reactions, this approach could offer new methodology for the valorization of biorefinery lignin. Monomeric and dimeric models bearing a keto group at the benzylic position undergo Ru-catalyzed alkylation in good to excellent yield. Similarly, models bearing a benzylic OH group also undergo alkylation via a tandem oxidation/alkylation process enabled by the Ru catalyst. Polymeric models show low levels of functionalization as a result of the poor solubility of the starting polymer. With unsymmetrical models, functionalization occurs first at the least sterically hindered ortho-site, but a subsequent alkylation, leading to disubstituted products can occur at the more sterically hindered site, leading to hexasubstituted arenes. The reaction shows sensitivity to free phenolic OH groups, which appears to reduce the yield in some reactions, and is also a contributing factor to the low yields observed with polymeric lignin models. Combining CHA methodology with lignin isolation technology able to introduce appropriate directing groups for catalytic functionalization will form the basis for improved conversion of lignin to high value chemical products.
- Zuleta, Ernesto C.,Bozell, Joseph J.
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- Microwave-assisted multicomponent synthesis of benzo[f]pyrrolo[1,2-a]quinoline derivatives
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We present an efficient one-pot, three component microwave-assisted synthesis of benzo[f]pyrrolo[1,2-a]quinoline derivatives starting from benzo[f]quinoline, 2-bromo-acetophenones or 2-chloro-(N-phenyl)acetamides and electron-deficient alkynes. This synthetic strategy provides a direct and easy access to a range of novel benzo[f]pyrrolo[1,2-a]quinoline derivatives. The method has the advantages of considerable shorter reaction time, reduced solvent consumption, operational simplicity and minimal impact on the environment. Nine new benzo[f]pyrrolo[1,2-a]quinoline derivatives have been synthesized with the new method and they are fully characterized.
- Georgescu, Emilian,Georgescu, Florentina,Dumitrascu, Florea,Draghici, Constantin,Nicolescu, Alina,Marinescu, Daniela,Deleanu, Calin
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- An umpolung oxa-[2,3] sigmatropic rearrangement employing arynes for the synthesis of functionalized enol ethers
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An oxa-[2,3] sigmatropic rearrangement involving arynes is reported featuring the umpolung of ketones, where the C=O bond polarity is reversed. The in situ-generated sulfur ylides from β-keto thioethers and arynes undergo efficient rearrangement allowing the facile and robust synthesis of functionalized enol ethers in high yields and excellent functional group compatibility. Preliminary mechanistic studies rule out the possibility of Pummerer-type rearrangement operating in this case.
- Gaykar, Rahul N.,George, Malini,Guin, Avishek,Bhattacharjee, Subrata,Biju, Akkattu T.
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supporting information
p. 3447 - 3452
(2021/05/04)
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- Nucleus-independent chemical shift (NICS) as a criterion for the design of new antifungal benzofuranones
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The assertion made by Wu et al. that aromaticity may have considerable implications for molecular design motivated us to use nucleus-independent chemical shifts (NICS) as an aromaticity criterion to evaluate the antifungal activity of two series of indol-4-ones. A linear regression analysis of NICS and antifungal activity showed that both tested variables were significantly related (p –1 for Candida glabrata, Candida krusei and Candida guilliermondii with compounds 15-32, 15-15 and 15-1. The MIC for filamentous fungi was 1.95 μg·mL–1 for Aspergillus niger for compounds 15-1, 15-33 and 15-34. The results obtained support the use of NICS in the molecular design of compounds with antifungal activity.
- González-Chávez, Marco Martín,González-Chávez, Rodolfo,Méndez, Francisco,Martínez, Roberto,Ni?o-Moreno, Perla Del Carmen,Ojeda-Fuentes, Luis Enrique,Richaud, Arlette,Zerme?o-Macías, María de los ángeles
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- Microwave-assisted synthesis and luminescent activity of imidazo[1,2-a]pyridine derivatives
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In this work, a series of phenacyl bromide derivatives was synthesized and employed as key intermediate for the synthesis of substituted imidazo[1,2-a]pyridines. First, phenacyl bromide molecules were obtained from the bromination reaction of acetophenones assisted by microwave irradiation, obtaining the products 4a-v in a 15 minutes reaction with yields in the range of 50% to 99%. Subsequently, the conjugation of these molecules with 2-aminopyridine conduced to the production of imidazo[1,2-a]pyridine derivatives (7a-v) in a 60-second reaction with yields of 24% to 99%. Improved yields were determined with respect to those obtained with more tedious methodologies like thermally and mechanically assisted routes. Intense luminescence emissions in the purple and blue regions of the electromagnetic spectra were observed under UV excitation according to the nature of the substituents. This environmentally friendly methodology is expected to constitute an important class of organic compounds for the development of biomarkers, photochemical sensors, and medicinal applications.
- Rodríguez, Juan C.,Maldonado, Rony A.,Ramírez-García, Gonzalo,Díaz Cervantes, Erik,de la Cruz, Fabiola N.
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p. 2279 - 2287
(2020/03/16)
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- Synthesis and preliminary photopolymerization evaluation of novel photoinitiators containing phototrigger to overcome oxygen inhibition in the UV- curing system
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In this work, two types of novel photoinitiaors containing phototrigger were prepared to overcome oxygen inhibition in the UV- curing system in the absence of hydrogen donor. The structures of prepared novel photoinitiators were determined by nuclear magnetic resonance (NMR) and high resolution MS (HR[sbnd]MS) spectra data. The photo chemical behavior and photo-reactivity were also evaluated by ultraviolet-visible (UV–vis) spectroscopy and real-time Fourier transform infrared spectroscopy (RT-FTIR), respectively. The results show the prepared photoinitiators exhibit remarkable redshift compared to the commercial BP (benzophenone) and Irgacure 907 (2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one), fast photolysis by C[sbnd]S bond, good photo initiation and significant overcoming oxygen inhibition for some compounds, which can be used as one-component photoinitiator candidates.
- Chen, Wenbin,Wang, Lei,Liu, Xinyue,Chen, Bo,Zhao, Guofeng
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- In(OTf)3-catalyzed intramolecular hydroarylation of α-phenylallyl β-ketosulfones - synthesis of sulfonyl 1-benzosuberones and 1-tetralones
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In(OTf)3-catalyzed intramolecular hydroarylation of α-phenylallyl β-ketosulfones provides sulfonyl 1-benzosuberones and 1-tetralones in moderate to good yields in refluxing (CH2Cl)2under open-vessel and easy-operation reaction conditions. A plausible mechanism is proposed and discussed. This highly regioselective protocol provides an atom-economic ring-closure route.
- Chang, Meng-Yang,Chang, Yu-Lun,Lai, Kai-Xiang
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p. 18231 - 18244
(2020/06/08)
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- Microwave-Assisted multicomponent synthesis of benzo[f]pyrrolo[1,2-a]quinoline derivatives
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We present an efficient one-pot, three component microwave-assisted synthesis of benzo[f]pyrrolo[1,2-a]quinoline derivatives starting from benzo[f]quinoline, 2-bromo-acetophenones or 2-chloro-(N-phenyl)acetamides and electron-deficient alkynes. This synthetic strategy provides a direct and easy access to a range of novel benzo[f]pyrrolo[1,2-a]quinoline derivatives. The method has the advantages of considerable shorter reaction time, reduced solvent consumption, operational simplicity and minimal impact on the environment. Nine new benzo[f]pyrrolo[1,2-a]quinoline derivatives have been synthesized with the new method and they are fully characterized.
- Deleanu, Calin,Draghici, Constantin,Dumitrascu, Florea,Georgescu, Emilian,Georgescu, Florentina,Marinescu, Daniela,Nicolescu, Alina
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- Functionality study of chalcone-hydroxypyridinone hybrids as tyrosinase inhibitors and influence on anti-tyrosinase activity
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In an attempt to synthesise new tyrosinase inhibitors, we designed and synthesised a series of chalcone-hydroxypyridinone hybrids as potential tyrosinase inhibitors adopting strategic modifications of kojic acid. All the newly synthesised compounds were characterised by NMR and mass spectrometry. Initial screening of the target compounds demonstrated that compounds 1a, 1d, and 1n had relatively strong inhibitory activities against tyrosinase monophenolase, with IC50 values of 3.07 ± 0.85, 2.25 ± 0.8 and 2.75 ± 1.19 μM, respectively. The inhibitory activity against monophenolase was 6- to 8-fold higher than that of kojic acid. Compounds 1a, 1d, and 1n also showed inhibition of diphenolase, with IC50 values of 17.05 ± 0.07, 11.70 ± 0.03 and 19.3 ± 0.28 μM, respectively. The inhibition kinetics of diphenolase indicates that compounds 1a and 1d induce reversible inhibition on tyrosinase. Finally, we found that copper coordination should be one of the important inhibitory mechanism of these compounds in tyrosinase.
- Singh, L. Ravithej,Chen, Yu-Lin,Xie, Yuan-Yuan,Xia, Wei,Gong, Xing-Wen,Hider, Robert C.,Zhou, Tao
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p. 1562 - 1567
(2020/08/07)
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- Highly Selective Oxidation and Depolymerization of α,γ-Diol-Protected Lignin
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Lignin oxidation offers a potential sustainable pathway to oxygenated aromatic molecules. However, current methods that use real lignin tend to have low selectivity and a yield that is limited by lignin degradation during its extraction. We developed stoichiometric and catalytic oxidation methods using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as oxidant/catalyst to selectively deprotect the acetal and oxidize the α-OH into a ketone. The oxidized lignin was then depolymerized using a formic acid/sodium formate system to produce aromatic monomers with a 36 mol % (in the case of stoichiometric oxidation) and 31 mol % (in the case of catalytic oxidation) yield (based on the original Klason lignin). The selectivity to a single product reached 80 % (syringyl propane dione, and 10–13 % to guaiacyl propane dione). These high yields of monomers and unprecedented selectivity are attributed to the preservation of the lignin structure by the acetal.
- Lan, Wu,de Bueren, Jean Behaghel,Luterbacher, Jeremy S.
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p. 2649 - 2654
(2019/02/01)
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- ANTIBACTERIAL COMPOUNDS
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The present invention relates to compounds of general formula (II),to compositions comprising these compounds and to methods of treating Enterobacteriaceae bacterial diseases and infections using the compounds. The compounds find application in the treatment of infection with, and diseases caused by, Enterobacteriaceae.
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Page/Page column 79-80
(2019/05/22)
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- Identification and characterization of benzo[d]oxazol-2(3H)-one derivatives as the first potent and selective small-molecule inhibitors of chromodomain protein CDYL
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Chemical probes of epigenetic ‘readers’ of histone post-translational modifications (PTMs) have become powerful tools for mechanistic and functional studies of their target proteins in physiology and pathology. However, only limited ‘reader’ probes have been developed, which restricted our understanding towards these macromolecules and their roles in cells or animals. Here, we reported a structure-guided approach to develop and characterize benzo [d]oxazol-2(3H)-one analogs as the first potent and selective small-molecule inhibitors of chromodomain Y-like (CDYL), a histone methyllysine reader protein. The binding conformation between the chromodomain of CDYL and the modified peptidomimetics was studied via molecular docking and dynamic simulations, facilitating subsequent virtual screening of tens of hits from Specs chemical library validated by SPR technique (KD values: from 271.1 μM to 5.4 μM). Further design and synthesis of 43 compounds helped to interpret the structure-activity relationship (SAR) that lead to the discovery of novel small-molecule inhibitors of CDYL. Compound D03 (KD: 0.5 μM) was discovered and showed excellent selectivity among other chromodomain proteins, including CDYL2 (>140 folds), CDY1 (no observed binding) and CBX7 (>32 folds). Moreover, we demonstrated that D03 engaged with endogenous CDYL in a dose-dependent manner, and perturbed the recruitment of CDYL onto chromatin, resulting in transcriptional derepression of its target genes. Finally, the results showed that D03 promoted the development and branching of neurodendrites by inhibiting CDYL in hippocampal and cortical cultured neurons. This study not only discovers the first selective small-molecule inhibitors of CDYL, but provids a new chemical tool to intervene the dynamic nature of bio-macromolecules involved in epigenetic mechanism.
- Yang, Lixin,Liu, Yongqing,Fan, Minghua,Zhu, Guiwang,Jin, Hongwei,Liang, Jing,Liu, Zhenming,Huang, Zhuo,Zhang, Liangren
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- Design, synthesis and biological evaluation of flexible and rigid analogs of 4H-1,2,4-triazoles bearing 3,4,5-trimethoxyphenyl moiety as new antiproliferative agents
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Several flexible and rigid analogs of 4H-1,2,4-triazoles (compounds 8a-g and 9a-g) bearing trimethoxyphenyl pharmacophoric unit, were designed and synthesized as potential anticancer agents. The in vitro cytotoxic assay indicated that both flexible and rigid analogs (8 and 9, respectively) can potentially inhibit the growth of cancerous cells (A549, MCF7, and SKOV3), with IC50 values less than 5.0 μM. Furthermore, compounds 10a-l as regional isomers of compounds 9 exhibited remarkable cytotoxic activity with IC50 values ranging from 0.30 to 5.0 μM. The rigid analogs 9a, 10h and 10k were significantly more potent than etoposide against MCF7, SKOV3 and A549 cells, respectively. These compounds showed high selectivity towards cancer cells over normal cells, as they had no significant cytotoxicity against L929 cells. In addition, the representative compounds 9a and 10h could inhibit the tubulin polymerization at micro-molar levels. By determining changes in the colchicine-tubulin fluorescence, it was suggested that compound 10h could bind to the tubulin at the colchicine pocket. The molecular docking study further confirmed the inhibitory activity of promising compounds 9a, 10h and 10k on tubulin polymerization through binding to the colchicine-binding site.
- Ansari, Mahsa,Shokrzadeh, Mohammad,Karima, Saeed,Rajaei, Shima,Hashemi, Seyedeh Mahdieh,Mirzaei, Hassan,Fallah, Marjan,Emami, Saeed
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- Formal Synthesis of Indolizidine and Quinolizidine Alkaloids from Vinyl Cyclic Carbonates
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Cyclic carbonates have long been considered relatively inert molecules acting as protecting groups in complex multistep synthetic routes. This study shows that a concise, yet modular synthesis of indolizidine and quinolizidine alkaloids can be developed from vinyl-substituted cyclic carbonate (VCC) intermediates. Through a highly stereoselective palladium-catalyzed allylic alkylation reaction, these alkaloid motifs can be assembled in four synthetic and only two column purification steps. The combined results help to further advance functionalized cyclic carbonates as useful and reactive intermediates in natural product synthesis.
- Cristòfol, àlex,B?hmer, Christian,Kleij, Arjan W.
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supporting information
p. 15055 - 15058
(2019/11/16)
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- COMPOUNDS AND USES THEREOF
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The present invention features compounds useful in the treatment of neurological disorders. The compounds of the invention, alone or in combination with other pharmaceutically active agents, can be used for treating or preventing neurological disorders.
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Page/Page column 132; 133
(2018/05/17)
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- Iridium-catalysed primary alcohol oxidation and hydrogen shuttling for the depolymerisation of lignin
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Lignin is a potentially abundant renewable resource for the production of aromatic chemicals, however its selective depolymerisation is challenging. Here, we report a new catalytic system for the depolymerisation of lignin to novel, non-phenolic monoaromatic products based on the selective β-O-4 primary alcohol dehydrogenation with a Cp?Ir-bipyridonate catalyst complex under basic conditions. We show that this system is capable of promoting the depolymerisation of model compounds and isolated lignins via a sequence of selective primary alcohol dehydrogenation, retro-aldol (Cα-Cβ) bond cleavage and in situ stabilisation of the aldehyde products by transfer (de)hydrogenation to alcohols and carboxylic acids. This method was found to give good to excellent yields of cleavage products with both etherified and free-phenolic lignin model compounds and could be applied to real lignin to generate a range of novel non-phenolic monomers including diols and di-acids. We additionally show, by using the same catalyst in a convergent, one-pot procedure, that these products can be selectively channelled towards a single di-acid product, giving much simpler product mixtures as a result.
- Lancefield, Christopher S.,Teunissen, Lucas W.,Weckhuysen, Bert M.,Bruijnincx, Pieter C. A.
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supporting information
p. 3214 - 3221
(2018/07/31)
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- Phosphodiesterase 4 inhibitor morusin M derivative and uses thereof
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The present invention relates to a phosphodiesterase 4 inhibitor morusin M derivative and a preparation method thereof, wherein specifically the morusin M has a structure represented by a formula (I) or a pharmaceutically acceptable salt thereof, and can be used as a PDE4 inhibitor in the treatment so as to be prepared into a suitable pharmaceutical dosage form for the treatment of inflammatory diseases. The formula (I) is defined in the specification.
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- Design, synthesis and in vitro cytotoxicity studies of novel β-carbolinium bromides
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A series of novel β-carbolinium bromides has been synthesized from easily accessible β-carbolines and 1-aryl-2-bromoethanones. The newly synthesized compounds were evaluated for their in vitro anticancer activity. Among the synthesized derivatives, compounds 16l, 16o and 16s exhibited potent anticancer activity with IC50values of 50= 3.16–7.93 μM). In order to test the mechanism of cell death, we exposed castration resistant prostate cancer cell line (C4-2) to compounds 16l and 16s, which resulted in increased levels of cleaved PARP1 and AO/EB staining, indicating that β-carbolinium salts induce apoptosis in these cells. Additionally, the most potent β-carbolines 16l and 16s were found to inhibit tubulin polymerization.
- Venkataramana Reddy,Mishra, Shriprada,Tantak, Mukund P.,Nikhil, Kumar,Sadana, Rachna,Shah, Kavita,Kumar, Dalip
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supporting information
p. 1379 - 1384
(2017/03/08)
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- Synthesis and bioevaluation of N,4-diaryl-1,3-thiazole-2-amines as tubulin inhibitors with potent antiproliferative activity
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A series of N,4-diaryl-1,3-thiazole-2-amines containing three aromatic rings with an amino linker were designed and synthesized as tubulin inhibitors and evaluated for their antiproliferative activity in three human cancer cell lines. Most of the target compounds displayed moderate antiproliferative activity, and N-(2,4-dimethoxyphenyl)-4-(4-methoxyphenyl)-1,3-thiazol-2-amine (10s) was determined to be the most potent compound. Tubulin polymerization and immunostaining experiments revealed that 10s potently inhibited tubulin polymerization and disrupted tubulin microtubule dynamics in a manner similar to CA-4. Moreover, 10s effectively induced SGC-7901 cell cycle arrest at the G2/M phase in both concentrationand time-dependent manners. The molecular docking results revealed that 10s could bind to the colchicine binding site of tubulin.
- Sun, Maolin,Xu, Qile,Xu, Jingwen,Wu, Yue,Wang, Yueting,Zuo, Daiying,Guan, Qi,Bao, Kai,Wang, Jian,Wu, Yingliang,Zhang, Weige
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- Discovery of novel 2-(3-phenylpiperazin-1-yl)-pyrimidin-4-ones as glycogen synthase kinase-3β inhibitors
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We herein describe the results of further evolution of glycogen synthase kinase (GSK)-3β inhibitors from our promising compounds containing a 2-phenylmorpholine moiety. Transformation of the morpholine moiety into a piperazine moiety resulted in potent GSK-3β inhibitors. SAR studies focused on the phenyl moiety revealed that a 4-fluoro-2-methoxy group afforded potent inhibitory activity toward GSK-3β. Based on docking studies, new hydrogen bonding between the nitrogen atom of the piperazine moiety and the oxygen atom of the main chain of Gln185 has been indicated, which may contribute to increased activity compared with that of the corresponding phenylmorpholine analogues. Effect of the stereochemistry of the phenylpiperazine moiety is also discussed.
- Usui, Yoshihiro,Uehara, Fumiaki,Hiki, Shinsuke,Watanabe, Kazutoshi,Tanaka, Hiroshi,Shouda, Aya,Yokoshima, Satoshi,Aritomo, Keiichi,Adachi, Takashi,Fukunaga, Kenji,Sunada, Shinji,Nabeno, Mika,Saito, Ken-Ichi,Eguchi, Jun-ichi,Yamagami, Keiji,Asano, Shouichi,Tanaka, Shinji,Yuki, Satoshi,Yoshii, Narihiko,Fujimura, Masatake,Horikawa, Takashi
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p. 3726 - 3732
(2017/07/27)
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- Green synthesis of novel quinoxaline sulfonamides with antibacterial activity
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A facile and efficient method was investigated for the synthesis of different quinoxalines by the reaction of o-phenylene diamine and 2-bromoacetophenones. This procedure was carried out in ethanol under catalyst-free conditions. Several sulfonamides were synthesized from 2-(4-methoxyphenyl)-quinoxaline in two steps. At first chlorosulfonation of 2-(4-methoxyphenyl) quinoxaline was done using chlorosulfonic acid and led to 2-methoxy-5-quinoxalin-2-yl-benzenesulfonyl chloride. Then quinoxaline sulfonamides were synthesized by the reaction of quinoxaline sulfonyl chloride with different aromatic amines under solvent-free conditions. All the products were obtained in excellent yields after an easy work-up and were evaluated for antibacterial activities against Staphylococcus spp. and Escherichiacoli bacteria.
- Alavi, Sima,Mosslemin, Mohammad Hossein,Mohebat, Razieh,Massah, Ahmad Reza
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p. 4549 - 4559
(2017/07/22)
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- Citric Acid-catalyzed Synthesis of 2,4-Disubstituted Thiazoles from Ketones via C–Br, C–S, and C–N Bond Formations in One Pot: A Green Approach
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An improved and greener protocol has been developed for the synthesis of 2,4-disubstituted thiazoles via C–Br, C–S, and, C–N bond formations in a single step from readily available ketones, N-bromosuccinimide (NBS), and thiourea catalyzed by citric acid in a mixture of ethanol and water (3:1) under reflux conditions. This method has the advantages of freedom from the isolation of lachrymatory α-bromoketones, ease of carrying out, cleaner reaction profile, broad substrate scope, freedom from chromatographic purification, and suitability for large-scale synthesis.
- Gundala, Trivikram Reddy,Godugu, Kumar,Nallagondu, Chinna Gangi Reddy
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p. 1408 - 1416
(2017/10/23)
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- Photocatalytic Oxidation of Lignin Model Systems by Merging Visible-Light Photoredox and Palladium Catalysis
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Lignin valorization has long been recognized as a sustainable solution for the renewable production of aromatic compounds. Two-step oxidation/reduction strategies, whereby the first oxidation step is required to "activate" lignin systems for controlled fragmentation reactions, have recently emerged as viable routes toward this goal. Herein we describe a catalytic protocol for oxidation of lignin model systems by combining photoredox and Pd catalysis. The developed dual catalytic protocol allowed the efficient oxidation of lignin model substrates at room temperature to afford the oxidized products in good to excellent yields.
- K?rk?s, Markus D.,Bosque, Irene,Matsuura, Bryan S.,Stephenson, Corey R. J.
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supporting information
p. 5166 - 5169
(2016/10/14)
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- Dehydrozingerone Inspired Styryl Hydrazine Thiazole Hybrids as Promising Class of Antimycobacterial Agents
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Series of styryl hydrazine thiazole hybrids inspired from dehydrozingerone (DZG) scaffold were designed and synthesized by molecular hybridization approach. In vitro antimycobacterial activity of synthesized compounds was evaluated against Mycobacterium tuberculosis H37Rv strain. Among the series, compound 6o exhibited significant activity (MIC = 1.5 μM; IC50 = 0.48 μM) along with bactericidal (MBC = 12 μM) and intracellular antimycobacterial activities (IC50 = 0.098 μM). Furthermore, 6o displayed prominent antimycobacterial activity under hypoxic (MIC = 46 μM) and normal oxygen (MIC = 0.28 μM) conditions along with antimycobacterial efficiency against isoniazid (MIC = 3.2 μM for INH-R1; 1.5 μM for INH-R2) and rifampicin (MIC = 2.2 μM for RIF-R1; 6.3 μM for RIF-R2) resistant strains of Mtb. Presence of electron donating groups on the phenyl ring of thiazole moiety had positive correlation for biological activity, suggesting the importance of molecular hybridization approach for the development of newer DZG clubbed hydrazine thiazole hybrids as potential antimycobacterial agents.
- Hampannavar, Girish A.,Karpoormath, Rajshekhar,Palkar, Mahesh B.,Shaikh, Mahamadhanif S.,Chandrasekaran, Balakumar
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supporting information
p. 686 - 691
(2016/07/26)
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- Total synthesis of protosappanin A and its derivatives via palladium catalyzed ortho C-H activation/C-C cyclization under microwave irradiation
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A total synthesis method for protosappanin A, which is a complex natural product with many biological activities, was developed with 6 linear steps. Dibenzo[b,d]oxepinones as the key intermediates of the synthetic route were prepared by a palladium-catalyzed ortho C-H activation/C-C cyclization under microwave irradiation. 25 derivatives of protosappanin A were obtained.
- Liu, Jiaqi,Zhou, Xuan,Wang, Chenglong,Fu, Wanyong,Chu, Wenyi,Sun, Zhizhong
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supporting information
p. 5152 - 5155
(2016/05/02)
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- Synthesis and antimicrobial activity evaluation of new dithiocarbamate derivatives bearing thiazole/benzothiazole rings
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The synthesis of 2-(substituted phenyl)-2-oxoethyl 4-(pyrimidin-2-yl)piperazin-1-carbodithiodate (A1-A24) derivatives and 2-(4-substituted thiazol-2-ylamino)-2-oxoethyl 4-(pyrimidin-2-yl)piperazin-1-carbodithiodate (B1-B14) derivatives was undertaken starting from the potassium salt of 4-(2-pyrimidinyl)piperazine dithiocarbamate. The structures of the obtained compounds were elucidated by1H NMR,13C NMR, MS spectral data, and elemental analysis. The antimicrobial activity of the thirty eight newly synthesized compounds were tested against 12 microorganism strains using the microdilution technique. Compounds 2-(4-ethoxycarbonylthiazol-2-ylamino)-2-oxoethyl 4-(pyrimidin-2-yl)piperazin-1-carbodithiodate (B12), 2-(3-fluorophenyl)-2-oxoethyl 4-(pyrimidin-2-yl)piperazin-1-carbodithiodate (A18) and 2-(3,4-difluorophenyl)-2-oxoethyl 4-(pyrimidin-2-yl)piperazin-1-carbodithiodate (A21) were determined to possess high antimicrobial activity.
- Yurtta?, Leyla,?zkay, Yusuf,Duran, Murat,Turan-Zitouni, Gülhan,?zdemir, Ahmet,Cantürk, Zerrin,Kü?üko?lu, Kaan,Kaplanc?kl?, Zafer As?m
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p. 1166 - 1173
(2016/07/27)
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- Palladium-Catalyzed Chemo- and Enantioselective C?O Bond Cleavage of α-Acyloxy Ketones by Hydrogenolysis
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A chemoselective C?O bond cleavage of the ester alkyl side-chain of α-acyloxy ketones was realized for the first time by a highly efficient palladium-catalyzed hydrogenolysis (S/C=6000, the highest catalytic efficiency by far). Furthermore, a kinetic resolution of α-acyloxy ketones was first developed by enantioselective hydrogenolysis with good yields and up to 99 % ee.
- Chen, Jianzhong,Zhang, Zhenfeng,Liu, Delong,Zhang, Wanbin
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supporting information
p. 8444 - 8447
(2016/07/19)
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- Stereoselective synthesis of cis-2,6-disubstituted morpholines and 1,4-oxathianes by intramolecular reductive etherification of 1,5-diketones
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A simple and efficient, Lewis acid catalysed reductive etherification strategy for the stereoselective synthesis of cis-2,6- disubstituted morpholines and 1,4-oxathianes starting from readily available 1,5-diketones has been developed. The strategy is used in the total synthesis of morpholine-based natural products (±)-chelonin A and formal total synthesis of (±)-chelonin C.
- Gharpure, Santosh J.,Anuradha, Dandela,Prasad, Jonnalagadda V. K.,Rao, Pidugu Srinivasa
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- Hydrogenolysis of a γ-Acetylated Lignin Model Compound with a Ruthenium-Xantphos Catalyst
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Catalytic hydrogenolysis of a γ-acetylated dimer lignin model compound is effected using a Ru-xantphos catalyst. Mechanistic investigations show mono-aryl degradation products are generated from the β-O-4 substrate as well as a terminal alkene ketone dimer (bis-aryl) that further dimerizes to a tetra-aryl product. Preliminary results using an acetylated kraft lignin as a substrate are also discussed. Graphical Abstract: [Figure not available: see fulltext.]
- Wu, Adam,Lauzon, Jean Michel,James, Brian R.
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p. 511 - 518
(2015/08/04)
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- Synthesis and in-vitro evaluation of 2-amino-4-arylthiazole as inhibitor of 3D polymerase against foot-and-mouth disease (FMD)
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Foot-and-mouth disease (FMD) is a highly contagious vesicular disease of livestock caused by a highly variable RNA virus, foot-and-mouth disease virus (FMDV). One of the targets to suppress expansion of and to control FMD is 3D polymerase (FMDV 3Dpol). In this study, 2-amino-4-arylthiazole derivatives were synthesized and evaluated for their inhibitory activity against FMDV 3Dpol. Among them, compound 20i exhibited the most potent functional inhibition (IC50 = 0.39μM) of FMDV 3D polymerase and compound 24a (EC50=13.09 μM) showed more potent antiviral activity than ribavirin (EC50=1367 μM) and T1105 (EC50=347 μM) with IBRS-2 cells infected by the FMDV O/SKR/2010 strain.
- Jeong, Kwi-Wan,Lee, Jung-Hun,Park, Sun-Mi,Choi, Joo-Hyung,Jeong, Dae-Youn,Choi, Dong-Hwa,Nam, Yeonju,Park, Jong-Hyeon,Lee, Kwang-Nyeong,Kim, Su-Mi,Ku, Jin-Mo
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p. 387 - 397
(2015/09/01)
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- SELECTIVE C-O BOND CLEAVAGE OF OXIDIZED LIGNIN AND LIGNIN-TYPE MATERIALS INTO SIMPLE AROMATIC COMPOUNDS
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A method to cleave C-C and C-0 bonds in β-Ο-4 linkages in lignin or lignin sub-units is described. The method includes oxidizing at least a portion of secondary benzylic alcohol groups in β-Ο-4 linkages in the lignin or lignin sub-unit to corresponding ketones and then leaving C-0 or C-C bonds in the oxidized lignin or lignin sub-unit by reacting it with an organic carboxylic acid, a salt of an organic carboxylic acids, and/or an ester of an organic carboxylic acids. The method may utilize a metal or metal-containing reagent or proceed without the metal or metal-containing reagent.
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Page/Page column 22
(2015/10/05)
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- 2-((Benzimidazol-2-yl)thio)-1-arylethan-1-ones: Synthesis, crystal study and cancer stem cells CD133 targeting potential
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In order to develop a potent anti-tumor agent that can target both cancer stem cells and the bulk of tumor cells, a series of 2-((benzimidazol-2-yl)thio)-1-arylethan-1-ones 5a-o was synthesized. All compounds were evaluated for their anti-proliferative activity towards colon HT-29 cancer cell line. In addition, their inhibitory effect against cell surface expression of CD133, a potent cancer stem cells (CSCs) marker, in the same cells was evaluated by flow cytometry at 10 μM. Compound 5l emerged as the most active anti-proliferative analog against HT-29 (IC50 Combining double low line 18.83 ± 1.37 μM), that almost equipotent as 5-fluorouracil (IC50 Combining double low line 15.83 ± 1.63 μM) with 50.11 ± 4.05% inhibition effect on CD133 expression, suggested dual targeted effect. Also, compounds 5h, 5j, 5k and 5m-o inhibited the expression of CD133 with more than 50%. The SAR study pointed out the significance of substitution of the pendent phenyl group with lipophilic electron-donating groups or replacing it by 2-thienyl or 2-furyl groups.
- Abdel-Aziz, Hatem A.,Ghabbour, Hazem A.,Eldehna, Wagdy M.,Al-Rashood, Sara T.A.,Al-Rashood, Khalid A.,Fun, Hoong-Kun,Al-Tahhan, Mays,Al-Dhfyan, Abdullah
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- Iron-catalysed oxidative cleavage of lignin and β-O-4 lignin model compounds with peroxides in DMSO
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Simple FeCl3-derived iron catalysts are used for the cleavage of β-O-4 linkages in lignin and lignin model compounds. The degradation of the β-O-4 linkages and the resinol structures in both organosolv and kraft lignin was proven by 2D-NMR (HSQC) experiments, and the oxidative depolymerisation of these lignin sources was confirmed by GPC. Key reactive species facilitating this cleavage are methyl radicals generated from H2O2 and DMSO.
- Mottweiler, Jakob,Rinesch, Torsten,Besson, Claire,Buendia, Julien,Bolm, Carsten
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supporting information
p. 5001 - 5008
(2015/11/16)
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- Base-catalysed cleavage of lignin β-O-4 model compounds in dimethyl carbonate
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A base-catalysed transformation and cleavage of lignin β-O-4 model compounds in dimethyl carbonate is reported. The reaction system consists of readily available bases and inexpensive dimethyl carbonate as a solvent and reagent, affording methoxy benzene or 2-aryloxyvinyl benzene derivatives in good to very good yields. The applicability of the system for the bond cleavage in an organosolv lignin sample was demonstrated.
- Dabral, Saumya,Mottweiler, Jakob,Rinesch, Torsten,Bolm, CarstenU
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supporting information
p. 4908 - 4912
(2015/11/11)
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- New synthesis of (±)-cherylline and mono- and dimethyl ethers
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The synthesis of 4-aryl-1,2,3,4-tetrahydroisoquinolines is achieved via the ether rearrangement methodology. Subsequent reactions yielded cherylline and ether derivatives of amaryllidaceac alkaloids. Copyright
- Pailla, Uma Reddy,Arava, Veera Reddy,Ravindhranath
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p. 2232 - 2238
(2014/07/07)
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- Fe(TAML)Li/(diacetoxyiodo)benzene-mediated oxidation of alcohols: Evidence for mild and selective C-O and C-C oxidative cleavage in lignin model transformations
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A novel combination of Fe(TAML)Li and (diacetoxyiodo)- benzene for the oxidation of primary and secondary alcohols at 25 °C in acetone is reported. In view of the interesting ability of this system to selectively cleave specific types of C-C bonds of elaborated alcohols, the application of this novel combination to the oxidative cleavage of lignin model molecules was investigated. Considering the numerous supported versions of the oxidant as well as the mild conditions employed, the developed methodology appears to be a promising lignin depolymerization strategy.
- Napoly, Francois,Jean-Gerard, Ludivine,Goux-Henry, Catherine,Draye, Micheline,Andrioletti, Bruno
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p. 781 - 787
(2014/03/21)
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- Facile methods for the synthesis of 5-aryl and 5-iodo pyrrolo[2,3-d] pyrimidines
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An efficient and environmentally benign one-pot method has been developed for the synthesis of 4-amino-5-arylpyrrolo[2,3-d]pyrimidines. Phthalimido acetophenones were reacted with cyanoacetamide to give 2-amino-4-phenyl-1H- pyrrole-3-carboxamides, which were further converted to 5-aryl-3H-pyrrolo[2,3-d] pyrimidin-4-ones. A novel method is also developed for the synthesis of 4-amino-5-iodopyrrolo[2,3-d]pyrimidines.
- Venkata Rao,Raghu Prasad,Raghuram Rao
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p. E380-E383
(2014/11/07)
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- Design and synthesis of novel carbazolo-thiazoles as potential anti-mycobacterial agents using a molecular hybridization approach
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Various substituted carbazolo-thiazoles (compounds 6a-6o) were synthesized in good yields using a molecular hybridization approach. The synthesized compounds were evaluated for their in vitro anti-tubercular activity against Mycobacterium tuberculosis H37Rv strain at the National Institute of Allergy and Infectious Diseases (Bethesda, MD, USA). Among the tested series, compound 6c (minimum inhibitory concentration 21 μM) showed the most promising anti-mycobacterial activity. Brief structure-activity relationship studies showed that the electron-donating groups (OCH3 and OH), particularly on the phenyl ring of the thiazole motif, had a positive correlation with the anti-mycobacterial activity. In addition, they displayed low cytotoxicity against a mammalian Vero cell line using the MTT assay, thereby having a high therapeutic index. This study shows the importance of molecular hybridization and the scope for the development of carbazole-thiazole compounds as potential anti-mycobacterial agents.
- Shaikh, Mahamadhanif S.,Palkar, Mahesh B.,Patel, Harun M.,Rane, Rajesh A.,Alwan, Wesam S.,Shaikh, Mahidansha M.,Shaikh, Iqbal M.,Hampannavar, Girish A.,Karpoormath, Rajshekhar
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p. 62308 - 62320
(2015/02/19)
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- SELECTIVE AEROBIC ALCOHOL OXIDATION METHOD FOR CONVERSION OF LIGNIN INTO SIMPLE AROMATIC COMPOUNDS
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Described is a method to oxidize lignin or lignin sub-units. The method includes oxidation of secondary benzylic alcohol in the lignin or lignin sub-unit to a corresponding ketone in the presence of unprotected primarily aliphatic alcohol in the lignin or lignin sub-unit. The optimal catalyst system consists of HNO3 in combination with another Br?nsted acid, in the absence of a metal-containing catalyst, thereby yielding a selectively oxidized lignin or lignin sub-unit. The method may be carried out in the presence or absence of additional reagents including TEMPO and TEMPO derivatives.
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Paragraph 0059
(2014/09/03)
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- 2- and 3-substituted imidazo[1,2-a]pyrazines as inhibitors of bacterial type IV secretion
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A novel series of 8-amino imidazo[1,2-a]pyrazine derivatives has been developed as inhibitors of the VirB11 ATPase HP0525, a key component of the bacterial type IV secretion system. A flexible synthetic route to both 2- and 3-aryl substituted regioisomers has been developed. The resulting series of imidazo[1,2-a]pyrazines has been used to probe the structure-activity relationships of these inhibitors, which show potential as antibacterial agents.
- Sayer, James R.,Walldn, Karin,Pesnot, Thomas,Campbell, Frederick,Gane, Paul J.,Simone, Michela,Koss, Hans,Buelens, Floris,Boyle, Timothy P.,Selwood, David L.,Waksman, Gabriel,Tabor, Alethea B.
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p. 6459 - 6470
(2015/01/09)
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- Bronsted acidic ionic liquid accelerated halogenation of organic compounds with N-halosuccinimides (NXS)
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The Bronsted-Acidic ionic liquid 1-methyl-3-(4-sulfobutyl) imidazolium triflate [BMIM(SO3H)][OTf] was demonstrated to act efficiently as solvent and catalyst for the halogenation of activated organic compounds with N-halosuccinimides (NXS) under mild conditions with short reaction times. Methyl aryl ketones were converted into a-halo and a,a-dihaloketones, depending on the quantity of NXS used. Ketones with activated aromatic rings were selectively halogenated, however in some cases mixtures of a-halogenated ketone and ring-halogenated ketones were obtained. Activated aromatics were regioselectively ring halogenated to give mono- and dihalo-substituted products. The [BMIM(SO3H)][OTf] ionic liquid (IL-A) was successfully reused eight times in a representative monohalogenation reaction with no noticeable decrease in efficiency. An effective halogenation scale-up in this IL is also presented. The reactivity trend and the observed chemo- and regioselectiivities point to an ET process in these IL-promoted halofunctionalization reactions.
- Vrazic, Dejan,Jereb, Marjan,Laali, Kenneth K.,Stavber, Stojan
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- Chemoselective metal-free aerobic alcohol oxidation in lignin
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An efficient organocatalytic method for chemoselective aerobic oxidation of secondary benzylic alcohols within lignin model compounds has been identified. Extension to selective oxidation in natural lignins has also been demonstrated. The optimal catalyst system consists of 4-acetamido-TEMPO (5 mol %; TEMPO = 2,2,6,6-tetramethylpiperidine-N-oxyl) in combination with HNO3 and HCl (10 mol % each). Preliminary studies highlight the prospect of combining this method with a subsequent oxidation step to achieve C-C bond cleavage.
- Rahimi, Alireza,Azarpira, Ali,Kim, Hoon,Ralph, John,Stahl, Shannon S.
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supporting information
p. 6415 - 6418
(2013/06/05)
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- Synthesis of (+)-septicine using intramolecular McMurry coupling: A Chiron approach
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Total synthesis of secophenanthroindolizidine alkaloid (+)-septicine 1 was accomplished using the McMurry coupling for the construction of indolizidine ring, using L-glutamicacid as chiral source. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
- Reddy, K. Umamaheshwar,Reddy, A. Panasa
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supporting information
p. 2678 - 2684
(2013/07/26)
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- Palladium-catalyzed asymmetric hydrogenation of α-acyloxy-1- arylethanones
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First hand: The first example of a palladium-catalyzed asymmetric hydrogenation of α-acyloxy ketones (1) was accomplished to give the hydrogenated products 2 with by far the highest catalytic efficiency in up to quantitative conversions and excellent enantioselectivities. The hydrogenated products could serve as important intermediates for the preparation of many drug candidates. TFE=2,2,2-trifluoroethanol. Copyright
- Chen, Jianzhong,Liu, Delong,Butt, Nicholas,Li, Chao,Fan, Dongyang,Liu, Yangang,Zhang, Wanbin
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supporting information
p. 11632 - 11636
(2013/11/06)
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- Synthesis and initial biological evaluation of substituted 1-phenylamino-2-thio-4,5-dimethyl-1H-imidazole derivatives
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In this work, some new 2-[(4,5-dimethyl-1-(arylamino)-1H-imidazol-2-yl) thio]-1-(aryl)ethanone derivatives were synthesized and investigated for their antibacterial, antifungal and anticancer activities. Toxicity of the most effective compounds was established by performing Brine-Shrimp lethality assay. Antifungal activity of the compounds was found to be higher than antibacterial and anticancer activities of the compounds.
- Yurttas, Leyla,Duran, Murat,Demirayak, Seref,Gencer, Huelya Karaca,Tunali, Yagmur
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supporting information
p. 6764 - 6768
(2014/01/06)
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