40681-88-7Relevant academic research and scientific papers
Simultaneous extraction and controlled chemical functionalization of hardwood lignin for improved phenolation
Bertella, Stefania,Luterbacher, Jeremy S.
, p. 3459 - 3467 (2021)
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
Ligand-Directed Approach to Activity-Based Sensing: Developing Palladacycle Fluorescent Probes That Enable Endogenous Carbon Monoxide Detection
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.
, p. 15917 - 15930 (2020/10/02)
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.
Aerobic Photooxidative Synthesis of β-Alkoxy Monohydroperoxides Using an Organo Photoredox Catalyst Controlled by a Base
Asano, Yuya,Nagasawa, Yoshitomo,Yamaguchi, Eiji,Itoh, Akichika
, p. 409 - 412 (2018/02/21)
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.
Synthetic utility of iodic acid in the oxidation of benzylic alcohols to aromatic aldehydes and ketones
Imai, Sho,Togo, Hideo
, p. 6948 - 6954 (2016/10/13)
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.
Oxidation of alcohols to aldehydes or ketones with 1-acetoxy-1,2- benziodoxole-3(1H)-one derivatives
Iinuma, Masataka,Moriyama, Katsuhiko,Togo, Hideo
, p. 772 - 780 (2014/03/21)
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.
Oxidation of Alcohols to Aldehydes or Ketones with 1-Acetoxy-1,2-benziodoxole-3(1H)-one Derivatives
Iinuma, Masataka,Moriyama, Katsuhiko,Togo, Hideo
, p. 772 - 780 (2015/10/05)
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.
BODIPY modified silica coated magnetite nanoparticles as fluorescent hybrid material for Cu (II) detection in aqueous medium
Isaad, Jalal,El Achari, Ahmida
, p. 878 - 886 (2013/09/12)
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.
Palladium-catalyzed reductive carbonylation of aryl halides with N-formylsaccharin as a CO source
Ueda, Tsuyoshi,Konishi, Hideyuki,Manabe, Kei
supporting information, p. 8611 - 8615 (2013/09/12)
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
Dual inhibitor of MurD and MurE ligases from escherichia coli and staphylococcus aureus
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
supporting information, p. 626 - 630,5 (2020/08/31)
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.
Structure-based design of a new series of d-glutamic acid based inhibitors of bacterial UDP-N-acetylmuramoyl-l-alanine: D-glutamate ligase (MurD)
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
supporting information; experimental part, p. 4600 - 4610 (2011/09/14)
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.
