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Relevant academic research and scientific papers

First palladium-catalyzed denitrated coupling reaction of nitroarenes with phenols

The first palladium-catalyzed protocol for the denitrated coupling reaction of nitroarenes with phenols has been developed, achieving unsymmetrical diaryl ethers in moderate to excellent yields. The cyclopalladated ferrocenylimine (catalyst Ic) exhibited highly catalytic activity for this transformation with low catalyst loading (0.75 mol%) and short reaction time (2 h). The efficiency of this reaction was demonstrated by its compatibility with a range of groups. Moreover, the rigorous exclusion of air or moisture was not required in these transformations. Copyright

Discovery of highly potent and selective influenza virus neuraminidase inhibitors targeting 150-cavity

Encouraged by our earlier discovery of N1-selective inhibitors, the 150-cavity of influenza virus neuraminidases (NAs) could be further exploited to yield more potent oseltamivir derivatives. Herein, we report the design, synthesis and biological evaluation of a series of novel oseltamivir derivatives via the structural modifications at C5–NH2 of oseltamivir targeting 150-cavity. Among them, compound 5c bearing 4-(3-methoxybenzyloxy)benzyl group exhibited the most potent activity, which was lower or modestly improved activities than oseltamivir carboxylate (OSC) against N1 (H1N1), N1 (H5N1) and N1 (H5N1–H274Y). Specifically, there was 30-fold loss of activity against the wild-type strain H1N1. However, 5c displayed 4.85-fold more potent activity than OSC against H5N1–H274Y NA. Also, 5c demonstrated low cytotoxicity in vitro and no acute toxicity in mice. Molecular docking studies provided insights into the high potency of 5c against N1 and N1–H274Y mutant NAs. Besides, the in silico prediction of physicochemical properties and CYP enzymatic inhibitory ability of representative compounds were conducted to evaluate their drug-like properties.

Thermally stable and robust gadolinium-based metal-organic framework: Synthesis, structure and heterogeneous catalytic O-arylation reaction

Hydrothermal treatment of gadolinium nitrate and 2,6-naphthalenedicarboxylic acid (H2NDC) afforded a new metal-organic framework compound, {[Gd4(NDC)6(H2O)6]·2H2O}n(1). Compound 1 has been characterized by single-crystal X-ray crystallography, elemental analysis, FT-IR spectroscopy, therrmogravimetric analysis (TGA) and powder X-ray diffraction analysis. It is crystallized in the monoclinic system with the P21/n space group. Four crystallographically distinct Gd (III) centres are interconnected with each other through bridged carboxylato oxygen atoms and water molecules to form tetranuclear secondary building units, which are further connected through the carboxylato ligand and the network propagates along the crystallographic ac plane to form a 2D structure. Subsequent reinforcement from the remaining carboxylato oxygen atoms gives rise to a robust 3D framework structure. Thermogravimetric analysis demonstrates that compound 1 is fairly stable after dehydration under a nitrogen atmosphere. Notably, compound 1 is capable of catalyzing the O-arylation reaction efficiently between substituted phenols and bromoarene under heterogeneous conditions at 80 °C to afford unsymmetrical diarylethers.

Highly efficient heterogeneous copper-catalysed O-arylation of phenols by nitroarenes leading to diaryl ethers

The heterogeneous O-arylation of phenols by nitroarenes was achieved in DMF at 100 °C by using an MCM-41-immobilised bidentate nitrogen copper(II) complex [MCM-41-2N-Cu(OAc)2] as catalyst, yielding a variety of unsymmetrical diaryl ethers in good to excellent yields. This heterogeneous copper catalyst can be easily prepared by a simple procedure from commercially readily available and inexpensive reagents, recovered by filtration of the reaction solution and recycled at least seven times without significant loss of activity.

Heterogeneous O -arylation of nitroarenes with substituted phenols over a copper immobilized mesoporous silica catalyst

Highly porous and robust mesoporous silica, SBA-15 has been subjected to post-synthesis modification for the anchoring of copper through Schiff base moiety formation using the silicon alkoxide route. The hybrid porous material has been fully characterized by powder-XRD, electronic spectra, EPR, thermogravimetric analysis, N2 sorption measurements, and TEM and SEM/EDS studies. The efficiency of the catalyst has been assessed in the O-arylation reaction using various substituted phenols and nitroarenes in heterogeneous conditions. The catalytic coupling reaction efficiently produces unsymmetrical diaryl ethers. The impressive capability to activate substrates having electron-donating or electron-withdrawing substituents and to have a high turnover frequency in the catalytic reactions made the catalyst highly desirable.

A family of ligand and anion dependent structurally diverse Cu(II) Schiff-base complexes and their catalytic efficacy in an O-arylation reaction in ethanolic media

Two nitrato bridged dinuclear systems [Cu2(L1)2(NO3)3]NO3·H2O (1) and [Cu2(L2)2(NO3)3]NO3·MeOH (2), five monomeric complexes viz. [Cu(L3)(NO3)]NO3 (3), [Cu(L4)(NO3)]NO3 (4), [Cu(L5)(NO3)]NO3 (5), [Cu(L6)(NO3)NO3] (7), [Cu(L7)(NO3)]NO3 (8) and one hetero bi-bridged (phenoxido and water) dinuclear complex [Cu2(L2)2(H2O)2](ClO4)4·4H2O (6) have been synthesized and characterized using several physicochemical methods (L1 = 1-(N-3-methoxysalicylideneimino)-ethane-2-piperazine, L2 = 1-(N-3-ethoxysalicylideneimino)-ethane-2-piperazine, L3 = 1-(N-4′-ethoxy-α-methylasalicylideneimino)-ethane-2-piperazine, L4 = 1-(N-5′-chloro-α-methylasalicylideneimino)-ethane-2-piperazine, L5 = 1-(N-5-chlorosalicylideneimino)-ethane-2-piperazine, L6 = 1-(N-4-methoxysalicylideneimino)-ethane-2-piperazine and L7 = 1-(N-4′-methoxy-α-methylasalicylideneimino)-ethane-2-piperazine). X-ray structural analysis showed that complexes 1 and 2 are discrete dinuclear species where the pentacoordinated metal centers are bridged through a nitrate ion. In 3, 4, 5 and 8 the monomeric copper center displays a square pyramidal geometry with a weak axial Cu-O bond. In 7, the monomeric copper center shows a distorted octahedral geometry with two coordinated nitrate anions. However, in 6 the two copper centers coordinate in different manners (one is square-pyramidal and the other is distorted octahedral) and are bridged through a phenoxido group and a water molecule. All complexes efficiently catalyze the C-O coupling reaction under homogeneous conditions at 80 °C to afford unsymmetrical diaryl ethers using nitroarenes to act as an excellent electrophile. Notably, the reaction is carried out in ethanol media which facilitates the avoidance of toxic wastes. Structurally diverse copper(ii) Schiff-base complexes have rarely been used systematically in catalytic C-O coupling reactions.

Ligand-free copper-catalyzed O-arylation of nitroarenes with phenols

The first example of ligand-free copper-catalyzed O-arylation of nitroarenes with phenols was developed, achieving unsymmetrical diaryl ethers in moderate to excellent yields. This arylation proceeded smoothly without promotion of the ligands, and displayed great functional group compatibility. Thus, the method represents a new, facile, and cost-effective approach to access unsymmetrical diaryl ethers.

Discovery of CS-2100, a potent, orally active and S1P3-sparing S1P1 agonist

S1P3-sparing S1P1 agonists have attracted attention as a suppressant of autoimmunity with reduced side effects. Our synthetic efforts and extensive SAR studies led to the discovery of 10b named CS-2100 with the EC50 value of 4.0 nM for human S1P1 and over 5000-fold selectivity against S1P3. The in vivo immunosuppressive efficacy was evaluated in rats on host versus graft reaction and the ID 50 value was determined at 0.407 mg/kg. The docking studies of CS-2100 with the homology model of S1P1 and S1P3 showed that the ethyl group on the thiophene ring of CS-2100 was sterically hindered by Phe263 in S1P3, not in the case of Leu276 in S1P1. This observation gives an explanation for the excellent S1P3-sparing characteristic of CS-2100.

Efficient palladium-catalyzed coupling reactions of aryl bromides and chlorides with phenols

A convenient and general palladium-catalyzed coupling reaction of aryl bromides and chlorides with phenols was developed. Various functional groups such as nitriles, aldehydes, ketones and esters are well tolerated and the corresponding products are obtained in good to excellent yield.

Inhibitors of HCV NS5B polymerase. Part 1: Evaluation of the southern region of (2Z)-2-(benzoylamino)-3-(5-phenyl-2-furyl)acrylic acid

A novel series of nonnucleoside HCV NS5B polymerase inhibitors were prepared from (2Z)-2-(benzoylamino)-3-(5-phenyl-2-furyl)acrylic acid, a high throughput screening lead. SAR studies combined with structure based drug design focusing on the southern heterobiaryl region of the template led to the synthesis of several potent and orally bioavailable lead compounds. X-ray crystallography studies were also performed to understand the interaction of these inhibitors with HCV NS5B polymerase.