- Simultaneous extraction and controlled chemical functionalization of hardwood lignin for improved phenolation
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Lignin is a promising candidate for the replacement of fossil-based materials, due to its natural abundance and aromatic structure. This same structure poses major challenges to lignin's exploitation for material development. The harsh conditions generall
- Bertella, Stefania,Luterbacher, Jeremy S.
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Read Online
- Ligand-Directed Approach to Activity-Based Sensing: Developing Palladacycle Fluorescent Probes That Enable Endogenous Carbon Monoxide Detection
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Carbon monoxide (CO) is an emerging gasotransmitter and reactive carbon species with broad anti-inflammatory, cytoprotective, and neurotransmitter functions along with therapeutic potential for the treatment of cardiovascular diseases. The study of CO chemistry in biology and medicine relative to other prominent gasotransmitters such as NO and H2S remains challenging, in large part due to limitations in available tools for the direct visualization of this transient and freely diffusing small molecule in complex living systems. Here we report a ligand-directed activity-based sensing (ABS) approach to CO detection through palladium-mediated carbonylation chemistry. Specifically, the design and synthesis of a series of ABS probes with systematic alterations in the palladium-ligand environment (e.g., sp3-S, sp3-N, sp2-N) establish structure-activity relationships for palladacycles to confer selective reactivity with CO under physiological conditions. These fundamental studies led to the development of an optimized probe, termed Carbon Monoxide Probe-3 Ester Pyridine (COP-3E-Py), which enables imaging of CO release in live cell and brain settings, including monitoring of endogenous CO production that triggers presynaptic dopamine release in fly brains. This work provides a unique tool for studying CO in living systems and establishes the utility of a synthetic methods approach to activity-based sensing using principles of organometallic chemistry.
- Brewer, Thomas F.,Bruemmer, Kevin J.,Chang, Christopher J.,H?fler, Denis,Jurss, Jonah W.,Michel, Brian W.,Morstein, Johannes,Rezgui, Samir P.,Saitoe, Minoru,Ueno, Kohei,Walvoord, Ryan R.
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p. 15917 - 15930
(2020/10/02)
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- Aerobic Photooxidative Synthesis of β-Alkoxy Monohydroperoxides Using an Organo Photoredox Catalyst Controlled by a Base
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Transition-metal-free synthesis of β-alkoxy monohydroperoxides via aerobic photooxidation using an acridinium photocatalyst was developed. This method enables the synthesis of some novel hydroperoxides. The peroxide source is molecular oxygen, which is cost-effective and atomically efficient. Magnesium oxide plays an important role as a base in the catalytic system.
- Asano, Yuya,Nagasawa, Yoshitomo,Yamaguchi, Eiji,Itoh, Akichika
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p. 409 - 412
(2018/02/21)
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- Synthetic utility of iodic acid in the oxidation of benzylic alcohols to aromatic aldehydes and ketones
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Various primary and secondary benzylic alcohols were efficiently oxidized to aromatic aldehydes and aromatic ketones with iodic acid in DMF at 60?°C for 2?h and with iodic acid in the presence of TEMPO (5?mol?%) in DMF at room temperature, respectively. The former method was effective for the oxidation of sterically hindered alcohols at 60?°C and the latter method was effective for the oxidation of less sterically hindered alcohols at room temperature.
- Imai, Sho,Togo, Hideo
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p. 6948 - 6954
(2016/10/13)
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- Oxidation of alcohols to aldehydes or ketones with 1-acetoxy-1,2- benziodoxole-3(1H)-one derivatives
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Various benzylic and aliphatic alcohols were smoothly oxidized to the corresponding aromatic aldehydes and ketones as well as aliphatic ketones by treatment with 1-acetoxy-5-nitro-1,2-benziodoxole-3(1H)-one (ANBX), 1-acetoxy-5-bromo-1,2-benziodoxole-3(1H)-one (ABBX), 1-acetoxy-5-chloro-1,2- benziodoxole-3(1H)-one (ACBX), and 1-acetoxy-5-fluoro-1,2-benziodoxole-3(1H)-one (AFBX). These new tri-valent iodine compounds were prepared from 5-substituted 2-iodobenzoic acids and meta-chloroperoxybenzoic acid (m-CPBA). ANBX and ABBX were the most effective reagents for this oxidation of alcohols, and this present reaction is very attractive because of the ease of product isolation and the reusability of the reagents.
- Iinuma, Masataka,Moriyama, Katsuhiko,Togo, Hideo
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p. 772 - 780
(2014/03/21)
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- Oxidation of Alcohols to Aldehydes or Ketones with 1-Acetoxy-1,2-benziodoxole-3(1H)-one Derivatives
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Various benzylic and aliphatic alcohols were smoothly oxidized to the corresponding aromatic aldehydes and ketones as well as aliphatic ketones by treatment with 1-acetoxy-5-nitro-1,2-benziodoxole-3(1H)-one (ANBX), 1-acetoxy-5-bromo-1,2-benziodoxole-3(1H)-one (ABBX), 1-acetoxy-5-chloro-1,2-benziodoxole-3(1H)-one (ACBX), and 1-acetoxy-5-fluoro-1,2-benziodoxole-3(1H)-one (AFBX). These new trivalent iodine compounds were prepared from 5-substituted 2-iodobenzoic acids and meta-chloroperoxybenzoic acid (m-CPBA). ANBX and ABBX were the most effective reagents for this oxidation of alcohols, and this present reaction is very attractive because of the ease of product isolation and the reusability of the reagents.
- Iinuma, Masataka,Moriyama, Katsuhiko,Togo, Hideo
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p. 772 - 780
(2015/10/05)
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- BODIPY modified silica coated magnetite nanoparticles as fluorescent hybrid material for Cu (II) detection in aqueous medium
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A novel ratiometric fluorescent sensor for copper II based on silica coated magnetite hybrid fluorescent material functionalized with boron-dipyrromethene containing a di (2-picolyl) amine was prepared and characterized. The binding abilities of the functionalized silica coated magnetite nanoparticles towards different metal ions have been examined by fluorescence spectroscopy, and displays high selectivity and sensitivity for Copper II among the all tested metals in Ethanol/water: 8:2.
- Isaad, Jalal,El Achari, Ahmida
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p. 878 - 886
(2013/09/12)
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- Palladium-catalyzed reductive carbonylation of aryl halides with N-formylsaccharin as a CO source
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Easy peasy: The title reaction employs N-formylsaccharin, which is an easily accessible crystalline compound, as an effective CO source. The reactions proceed with a small excess of the CO source at moderate temperatures and were successfully applied to a wide range of aryl bromides. DMF=N,N- dimethylformamide, dppb=1,4-bis-(diphenylphosphino)butane. Copyright
- Ueda, Tsuyoshi,Konishi, Hideyuki,Manabe, Kei
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supporting information
p. 8611 - 8615
(2013/09/12)
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- Dual inhibitor of MurD and MurE ligases from escherichia coli and staphylococcus aureus
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MurD and MurE ligases, consecutive enzymes participating in the intracellular steps of bacterial peptidoglycan biosynthesis, are important targets for antibacterial drug discovery. We have designed, synthesized, and evaluated the first d-glutamic acid-containing dual inhibitor of MurD and MurE ligases from Escherichia coli and Staphylococcus aureus (IC50 values between 6.4 and 180 μM) possessing antibacterial activity against Gram-positive S. aureus and its methicillin-resistant strain (MRSA) with minimal inhibitory concentration (MIC) values of 8 μg/mL. The inhibitor was also found to be noncytotoxic for human HepG2 cells at concentrations below 200 μM.
- Tomasic, Tihomir,Sink, Roman,Zidar, Nace,Fic, Anja,Gobec, Stanislav,Zega, Anamarija,Kikelj, Danijel,Masic, Lucija Peterlin,Contreras-Martel, Carlos,Dessen, Andrea,Patin, Delphine,Blanot, Didier,Mueller-Premru, Manica
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supporting information
p. 626 - 630,5
(2020/08/31)
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- Structure-based design of a new series of d-glutamic acid based inhibitors of bacterial UDP-N-acetylmuramoyl-l-alanine: D-glutamate ligase (MurD)
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MurD ligase is one of the key enzymes participating in the intracellular steps of peptidoglycan biosynthesis and constitutes a viable target in the search for novel antibacterial drugs to combat bacterial drug-resistance. We have designed, synthesized, and evaluated a new series of d-glutamic acid-based Escherichia coli MurD inhibitors incorporating the 5-benzylidenethiazolidin-4- one scaffold. The crystal structure of 16 in the MurD active site has provided a good starting point for the design of structurally optimized inhibitors 73-75 endowed with improved MurD inhibitory potency (IC50 between 3 and 7 μM). Inhibitors 74 and 75 showed weak activity against Gram-positive Staphylococcus aureus and Enterococcus faecalis. Compounds 73-75, with IC 50 values in the low micromolar range, represent the most potent d-Glu-based MurD inhibitors reported to date.
- Toma?i?, Tihomir,Zidar, Nace,?ink, Roman,Kova?, Andreja,Blanot, Didier,Contreras-Martel, Carlos,Dessen, Andréa,Müller-Premru, Manica,Zega, Anamarija,Gobec, Stanislav,Kikelj, Danijel,Peterlin Ma?i?, Lucija
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supporting information; experimental part
p. 4600 - 4610
(2011/09/14)
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- PYRIDINE DERIVATIVES SUBSTITUTED BY HETEROCYCLIC RING AND PHOSPHONOAMINO GROUP, AND ANTI-FUNGAL AGENT CONTAINING SAME
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Anti-fungal agent having excellent anti-fungal action physicochemical properties including safety and water solubility. Compound represented by formula (I), or salt thereof: wherein R1 represents hydrogen, halogen, amino, R11-NH- wherein R11 represents C1-6 alkyl, hydroxy C1-6 alkyl, C1-6 alkoxy C1-6 alkyl, or C1-6alkoxycarbonyl C1-6 alkyl, R12-(CO)-NH- wherein R12 represents C1-6 alkyl group or C1-6 alkoxy C1-6 alkyl, C1-6 alkyl, hydroxy C1-6 alkyl, cyano C1-6 alkyl, C1-6 alkoxy, or C1-6 alkoxy C1-6 alkyl or a phosphonoamino group; R2 represents hydrogen, C1-6 alkyl, amino, or a di C1-6 alkylamino group or a phosphonoamino group; one of X and Y is nitrogen while the other is nitrogen or oxygen; ring A represents a 5- or 6-member heteroaryl ring or a benzene ring which may have a halogen atom or 1 or 2 C1-6 alkyl groups; Z represents a single bond, a methylene group, an ethylene group, oxygen, sulfur, -CH2O-, -OCH2-, -NH-, -CH2NH-, -NHCH2-, -CH2S-, or -SCH2-; R3 represents hydrogen or halogen or C1-6 alkyl, C3-8 cycloalkyl, C6-10 aryl, a 5- or 6-member heteroaryl group or a 5- or 6-member nonaromatic heterocyclic group which may have 1 or 2 substituents; and R4 represents hydrogen or halogen; provided that either R1 or R2 represents a phosphonoamino group.
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Page/Page column 127
(2009/04/24)
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- Unimolecular binary half-adders with orthogonal chemical inputs
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Unimolecular half-adders based upon an arylvinyl-bipyridyl fluorophore platform were demonstrated where all the chemical input combinations were fully processed by half-adder molecules to generate the arithmetic results of the entire truth table. The Roya
- Zhang, Lu,Whitfield, Wesley A.,Zhu, Lei
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p. 1880 - 1882
(2008/12/22)
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- Unmodified nano-powder magnetite catalyzes a four-component aza-Sakurai reaction
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A new catalyst for an old material: magnetite is an excellent Lewis acid catalyst for the four-component aza-Sakurai reaction. The process could be repeated up to 15-times without losing effectiveness, with the catalyst recycling being as easy as the use of a simple magnet. The catalyst is selective and could discriminate between aldehyde and ketone functionalities, catalyzing first the reaction with the higher electrophilic aldehyde.
- Martinez, Ricardo,Ramon, Diego J.,Yus, Miguel
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supporting information; experimental part
p. 1235 - 1240
(2009/05/30)
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- Heterocycles substituted pyridine derivatives and antifungal agent containing thereof
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An object of the present invention is to provide an antifungal agent which has excellent antifungal effects and is superior in terms of its physical properties, safety and metabolic stability. According to the present invention, there is disclosed a compound represented by the following formula (I), or a salt thereof: wherein R1 represents a hydrogen atom, a halogen atom, an amino group, a C1-6 alkyl group, a C1-6 alkoxy group or a C1-6 alkoxy C1-6 alkyl group; R2 represents a hydrogen atom, a C1-6 alkyl group, an amino group or a di C1-6 alkylamino group; one of X and Y is a nitrogen atom while the other is a nitrogen atom or an oxygen atom; ring A represents a 5- or 6-member heteroaryl ring or a benzene ring which may have a halogen atom, or 1 or 2 C1-6 alkyl groups; Z represents a single bond, a methylene group, an ethylene group, an oxygen atom, a sulfur atom, —CH2O—, —OCH2—, —NH—, —CH2NH—, —NHCH2—, —CH2S—, or —SCH2—; R3 represents a hydrogen atom, a halogen atom, a C1-6 alkyl group, a C3-8 cycloalkyl group, a C6-10 aryl group, a 5- or 6-member heteroaryl group, or 5- or 6-member non-aromatic heterocyclic group which may have 1 or 2 substituents; and R4 represents a hydrogen atom or a halogen atom.
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Page/Page column 128
(2010/11/27)
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- DENDRON AND DENDRIMER, METHOD OF PRODUCING THE SAME, AND METHOD OF PRODUCING A THIOACETAL COMPOUND
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A dendron or dendrimer, which has, as a recurring unit of each branch, a structure of formula (I): Wherein TC designates a linkage to a former generation in the direction to a focal point of the dendron or a core of the dendrimer; TT designates a linkage to a next generation in the direction to a terminal; X is a divalent group comprised of at least one heteroatom; L?1#191 and L?2#191 each are a divalent linking group; R is a hydrogen atom or a substituent; and a method of producing a dendron or a dendrimer; and a method of producing a thioacetal compound.
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Page/Page column 32
(2008/06/13)
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- Synthesis of dendrimers with terminal formyl groups
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A method for preparation of dendrons and dendrimers with formyl groups at the terminal aromatic rings, ether bonds in the branching blocks, and ester bonds in the core of the macromolecules is proposed. A way for the selective synthesis of p-hydroxymethylbenzaldehyde is described.
- Loim,Kelbyscheva
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p. 2080 - 2085
(2007/10/03)
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- Photochemistry of 1-Alkoxy- and 1-(Benzyloxy)-9,10-anthraquinones in Methanol: A Facile Process for the Preparation of Aldehydes and Ketones
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The facile production of acid sensitive aldehydes and ketones via photochemical intramolecular δ-hydrogen atom transfer in 1-alkoxy- and 1-(benzyloxy)-9,10-anthraquinones (1) was investigated.Irradiation of 1 in argon purged methanol generates the primary photoproducts, 1-(RCH(OMe)O)- and 1-(ArCH(OMe)O)-9,10-anthrahydroquinones (2), respectively.Upon exposure to air, the intermediate anthrahydroquinone is rapidly converted to the corresponding aldehyde and 1-hydroxy-9,10-anthraquinone (3), which can be recycled.Aldehydes containing an acetal or ketal were prepared in high yields using this photoprocess.Apparent rate constants for the photodemethylation of 1-methoxy-2-X-9,10-anthraquinones (X = H, Me, Et, Pr, i-Bu, and benzyl) were measured and found to vary by a factor of 10 separating the slowest anthraquinone (X = H) and the fastest (X = benzyl), indicating a strong dependency upon the size of the substituent at the 2-position.These rate constants are ascribed to equilibrium populations of conformers in the geometry required for the reaction in the n,?* triplet state.
- Blankespoor, Ronald L.,Smart, Robert P.,Batts, Eric D.,Kiste, Alan A.,Lew, Rebecca E.,Vliet, Marc E. Vander
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p. 6852 - 6859
(2007/10/03)
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- SYNTHESIS OF THE O-METHYLOXIMES AND NITRONES OF A SERIES OF 4-BENZALDEHYDES AND THEIR BIOLOGICAL ACTIVITY
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The O-methyloximes and nitrones of a series of 4-benzaldehydes were synthesized, and their fungicidal activity was determined.It was established that all the synthesized compounds exhibit low activity during in vitro experiments and high activity during in vivo experiments, and the O-methyloximes are more active than the corresponding nitrones.
- Krimer, M.Z.,Styngach, E.P.,Rekhter, M.A.,Grushetskaya, G.N.,Uzhavka, Z.N.,et al.
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p. 1545 - 1550
(2007/10/02)
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- Synthesis of O-methyloximes and nitrones of a series of substituted 4-benzaldehydes and their fungicidal activity
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O-Methyloximes and nitrones of a series of substituted 4-(2-hydroxy-2-(1H-1,2,4-triazol-1-ylmethyl)cyclohexylidenemethyl>benzaldehydes have been synthesized, and their fungicidal activity has been assayed.All of them exhibit low fungicidal activity in the
- Krimer, M. Z.,Makaev, F. Z.,Kal'yan, Yu. B.,Tashchi, V. P.,Putsykin, Yu. G.
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p. 1995 - 2000
(2007/10/02)
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