45804-94-2Relevant academic research and scientific papers
Multienzymatic preparation of (-)-[3-(oxiran-2-yl)phenyl]methanol and (-)-3-(oxiran-2-yl)benzoic acid
Sello, Guido,Bernasconi, Silvana,Orsini, Fulvia,Di Gennaro, Patrizia
, p. 563 - 565 (2009)
The cascade use of enzymatic activities allows for the preparation of enantiomerically pure epoxides. In particular, using whole-cell biocatalysts we can prepare both (-)-[3-(oxiran-2-yl)phenyl]methanol and (-)-3-(oxiran-2-yl)benzoic acid in one-pot, two
Palladium-Catalyzed Selective Reduction of Carbonyl Compounds
Sarkar, Nabin,Mahato, Mamata,Nembenna, Sharanappa
, p. 2295 - 2301 (2020/05/18)
Two new examples of structurally characterized β-diketiminate analogues i.e., conjugated bis-guanidinate (CBG) supported palladium(II) complexes, [LPdX]2; [L= {(ArHN)(ArN)–C=N–C=(NAr)(NHAr)}; Ar = 2,6-Et2-C6H3], X = Cl (1), Br (2) have been reported. The synthesis of complexes 1–2 was achieved by two methods. Method A involves deprotonation of LH by nBuLi followed by the treatment of LLi (insitu formed) with PdCl2 in THF, which afforded compound 1 in good yield (75 %). In Method B, the reaction between free LH and PdX2 (X = Cl or Br) in THF allowed the formation of complexes 1 (Yield 73 %) and 2 (Yield 52 %), respectively. Moreover, these complexes were characterized thoroughly by several spectroscopic techniques (1H, 13C NMR, UV/Vis, FT-IR, and HRMS), including single-crystal X-ray structural and elemental analyses. In addition, we tested the catalytic activity of these complexes 1–2 for the hydroboration of carbonyl compounds with pinacolborane (HBpin). We observed that compound 1 exhibits superior catalytic activity when compared to 2. Compound 1 efficiently catalyzes various aldehydes and ketones under solvent-free conditions. Furthermore, both inter- and intramolecular chemoselectivity hydroboration of aldehydes over other functionalities have been established.
MODULATORS OF MAS-RELATED G-PROTEIN RECEPTOR X4 AND RELATED PRODUCTS AND METHODS
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Page/Page column 247-248, (2020/10/18)
Methods are provided for modulating MRGPR X4 generally, or for treating a MRGPR X4 dependent condition more specifically, by contacting the MRGPR X4 or administering to a subject in need thereof, respectively, an effective amount of a compound having the structure of Formula (I): (I) or a pharmaceutically acceptable isomer, racemate, hydrate, solvate, isotope, or salt thereof, wherein n, x, A, Q1, Q2, Z, R, R1, R2, R3, R4 and R5 are as defined herein. Pharmaceutical compositions containing such compounds, as well as to compounds themselves, are also provided.
Hydrosilylation of aromatic aldehydes and ketones catalyzed by mono- and tri-nuclear platinum(0) complexes
Tsuchido, Yoshitaka,Abe, Ryota,Kamono, Megumi,Tanaka, Kimiya,Tanabe, Makoto,Osakada, Kohtaro
, p. 858 - 864 (2018/05/23)
Hydrosilylation of aromatic aldehydes and acetophenone with H2SiPh2 was studied by using Pt complexes as the catalyst. Reaction of aromatic aldehydes, such as PhCHO, 4-FC6H4CHO, 4-MeC6H4CHO and 4-CF3C6H4CHO with H2SiPh2 in the presence of [Pt(PPh3)3] cata
Discovery of Potent Cyclophilin Inhibitors Based on the Structural Simplification of Sanglifehrin A
Steadman, Victoria A.,Pettit, Simon B.,Poullennec, Karine G.,Lazarides, Linos,Keats, Andrew J.,Dean, David K.,Stanway, Steven J.,Austin, Carol A.,Sanvoisin, Jonathan A.,Watt, Gregory M.,Fliri, Hans G.,Liclican, Albert C.,Jin, Debi,Wong, Melanie H.,Leavitt, Stephanie A.,Lee, Yu-Jen,Tian, Yang,Frey, Christian R.,Appleby, Todd C.,Schmitz, Uli,Jansa, Petr,Mackman, Richard L.,Schultz, Brian E.
, p. 1000 - 1017 (2017/02/19)
Cyclophilin inhibition has been a target for the treatment of hepatitis C and other diseases, but the generation of potent, drug-like molecules through chemical synthesis has been challenging. In this study, a set of macrocyclic cyclophilin inhibitors was synthesized based on the core structure of the natural product sanglifehrin A. Initial compound optimization identified the valine-m-tyrosine-piperazic acid tripeptide (Val-m-Tyr-Pip) in the sanglifehrin core, stereocenters at C14 and C15, and the hydroxyl group of the m-tyrosine (m-Tyr) residue as key contributors to compound potency. Replacing the C18-C21 diene unit of sanglifehrin with a styryl group led to potent compounds that displayed a novel binding mode in which the styrene moiety engaged in a π-stacking interaction with Arg55 of cyclophilin A (Cyp A), and the m-Tyr residue was displaced into solvent. This observation allowed further simplifications of the scaffold to generate new lead compounds in the search for orally bioavailable cyclophilin inhibitors.
Selective hydrogenation of unsaturated carbonyls by Ni-Fe-based alloy catalysts
Putro, Wahyu S.,Kojima, Takashi,Hara, Takayoshi,Ichikuni, Nobuyuki,Shimazu, Shogo
, p. 3637 - 3646 (2017/08/21)
Ni-Fe alloy catalysts prepared by a simple hydrothermal method and subsequent H2 treatment exhibited the greatest activity and selectivity for the hydrogenation of biomass-derived furfural to furfuryl alcohol among the examined second metals, such as Al, Ga, In, Co, and Ti. This work reveals that the alloying of Ni and Fe is a key factor in achieving highly selective hydrogenation of the CO moiety in unsaturated carbonyl substrates. We found that decreasing the temperature of H2 treatment (i.e. decreasing the crystallite size), e.g. Ni-Fe(2)HT-573 K (TOF = 952 h-1), increased the activity compared to that over Ni-Fe(2)HT-673 (TOF = 375 h-1) for furfural hydrogenation. This result suggests that a low-coordinated Ni-Fe alloy was imperative for the catalytic cycle. Moreover, the effect of the metal/support interface was critical; despite the high catalytic performance of Ni-Fe/TiO2, Ni-Fe/Al2O3, and Ni-Fe/CeO2, Ni-Fe supported on SiO2, taeniolite, and hydrotalcite catalysts were ineffective. Vibrational studies using FT-IR measurement confirmed that furfural was physically adsorbed on the surface of the Ni-Fe alloy catalyst via an η1(O) configuration. The synthetic scope of the Ni-Fe catalytic system was very broad; various types of unsaturated carbonyls, such as unsaturated aromatics, unconjugated aliphatics, and a large substituent, were selectively converted into the corresponding unsaturated alcohols.
Green, Multi-Gram One-Step Synthesis of Core–Shell Nanocomposites in Water and Their Catalytic Application to Chemoselective Hydrogenations
Urayama, Teppei,Mitsudome, Takato,Maeno, Zen,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi
supporting information, p. 17962 - 17966 (2016/12/16)
We devise a new and green route for the multi-gram synthesis of core–shell nanoparticles (NPs) in one step under organic-free and pH-neutral conditions. Simply mixing core and shell metal precursors in the presence of solid metal oxides in water allowed for the facile fabrication of small CeO2-covered Au and Ag nanoparticles dispersed on metal oxides in one step. The CeO2-covered Au nanoparticles acted as a highly efficient and reusable catalyst for a series of chemoselective hydrogenations, while retaining C=C bonds in diverse substrates. Consequently, higher environmental compatibility and more efficient energy savings were achieved across the entire process, including catalyst preparation, reaction, separation, and reuse.
Fast and selective iron-catalyzed transfer hydrogenations of aldehydes
Wienh?fer, Gerrit,Westerhaus, Felix A.,Junge, Kathrin,Beller, Matthias
, p. 156 - 159 (2013/10/01)
An efficient iron-based catalyst system consisting of Fe(BF)4$6H2O and P(CH2CH2PPh2)3 [tetraphos, (PP3)] is presented for the highly selective transfer hydrogenation of aromatic, aliphatic, and a,b-unsaturated aldehydes. A wide range of substrates including aldehydes with other reducible functional groups gave the corresponding alcohols in good yields. Formic acid is applied as a cheap, environmentally benign and easy to handle hydrogen source. Notable features of the presented methodology are the fast reactions under mild conditions. Advantageously compared to most transfer hydrogenations, no stoichiometric amounts of base additives are required.
Remarkable effect of bases on core-shell AgNP@CeO2 nanocomposite-catalyzed highly chemoselective reduction of unsaturated aldehydes
Mitsudome, Takato,Matoba, Motoshi,Yamamoto, Masaaki,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi
, p. 660 - 662 (2013/07/05)
A highly dispersed coreshell silver nanoparticleceria nanocomposite catalyst (AgNP@CeO2-D) was prepared. The addition of bases was found to enhance the catalytic efficiency of AgNP@CeO2-D significantly in the chemoselective reduction of diverse unsaturated aldehydes to the corresponding unsaturated alcohols.
Core-shell AgNP@CeO2 nanocomposite catalyst for highly chemoselective reductions of unsaturated aldehydes
Mitsudome, Takato,Matoba, Motoshi,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi
supporting information, p. 5255 - 5258 (2013/05/22)
Selective silver: A core-shell AgNP-CeO2 nanocomposite (AgNP@CeO2) acted as an effective catalyst for the chemoselective reductions of unsaturated aldehydes to unsaturated alcohols with H2 (see figure). Maximizing the AgNP-CeO2 interaction successfully induced the heterolytic cleavage of H2, resulting in highly chemoselective reductions. Furthermore, a highly dispersed AgNP@CeO2 system was also developed that exhibited a higher activity than the original AgNP@CeO2. Copyright
