- A simple and effective method for chemoselective esterification of phenolic acids
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A new method for efficient and chemoselective esterification of phenolic acids in KHCO3/alkyl halide/DMF reaction system is described, by which a series of phenoic acid esters were obtained in excellent yields.
- Guo, Wei,Li, Junfei,Fan, Ningjuan,Wu, Weiwei,Zhou, Peiwen,Xia, Chizhong
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- Effect of natural and synthetic benzyl benzoates on calmodulin
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The present investigation describes the effect of the spasmolytic benzylbenzoates 1-9 from Brickellia veronicifolia on CaM using a functional in vitro enzymatic assay. Bovine brain PDE1 was used as a monitoring enzyme. The most active natural inhibitors of the system CaM-PDE1 were benzyl benzoates 3-5, which inhibited the activity of PDE1 in a concentration-dependent manner. In addition, three series of analogs of compound 4, compounds 10a-32a, were prepared and assayed. The benzyl benzoates from the first series, namely 10a-24a, possess no substituents on ring B but different number and position of hydroxyl or methoxy groups in ring A. The second group (25-32a), on the other hand, possesses an A ring identical to that on compound 4, but different substituents in Ring B. The most active compounds were 14a, 15a and 30a. These compounds were two to six times more potent than chlorpromazine, a well known CaM inhibitor. Benzyl benzoates 14a and 15a have methoxyl groups at C-2/C-4 and C-3/C-4 in ring A, respectively; while 30a, in addition to the methoxyl groups at C-2/C-6 of ring A, hold a benzoyloxy moiety at C-3′ of ring B. Kinetic studies revealed that compounds 3, 4, 14a, 15a and 30a behave as competitive CaM antagonists.
- Rivero-Cruz, Blanca,Rivero-Cruz, Isabel,Rodriguez-Sotres, Rogelio,Mata, Rachel
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- Chemoselective esterification of phenolic acids in the presence of sodium bicarbonate in ionic liquids
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Chemoselective esterification of phenolic acids with dialkyl sulphates or alkyl halides in the presence of sodium bicarbonate in 1,3-dialkylimidazolium ionic liquids is reported in excellent yields and less reaction time as compared to organic solvents. Copyright Taylor & Francis Group, LLC.
- Ambika,Singh, Pradeep Pratap,Chauhan
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- Targeted Delivery of mRNA with One-Component Ionizable Amphiphilic Janus Dendrimers
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Targeted and efficient delivery of nucleic acids with viral and synthetic vectors is the key step of genetic nanomedicine. The four-component lipid nanoparticle synthetic delivery systems consisting of ionizable lipids, phospholipids, cholesterol, and a PEG-conjugated lipid, assembled by microfluidic or T-tube technology, have been extraordinarily successful for delivery of mRNA to provide Covid-19 vaccines. Recently, we reported a one-component multifunctional sequence-defined ionizable amphiphilic Janus dendrimer (IAJD) synthetic delivery system for mRNA relying on amphiphilic Janus dendrimers and glycodendrimers developed in our laboratory. Amphiphilic Janus dendrimers consist of functional hydrophilic dendrons conjugated to hydrophobic dendrons. Co-assembly of IAJDs with mRNA into dendrimersome nanoparticles (DNPs) occurs by simple injection in acetate buffer, rather than by microfluidic devices, and provides a very efficient system for delivery of mRNA to lung. Here we report the replacement of most of the hydrophilic fragment of the dendron from IAJDs, maintaining only its ionizable amine, while changing its interconnecting group to the hydrophobic dendron from amide to ester. The resulting IAJDs demonstrated that protonated ionizable amines play dual roles of hydrophilic fragment and binding ligand for mRNA, changing delivery from lung to spleen and/or liver. Replacing the interconnecting ester with the amide switched the delivery back to lung. Delivery predominantly to liver is favored by pairs of odd and even alkyl groups in the hydrophobic dendron. This simple structural change transformed the targeted delivery of mRNA mediated with IAJDs, from lung to liver and spleen, and expands the utility of DNPs from therapeutics to vaccines.
- Zhang, Dapeng,Atochina-Vasserman, Elena N.,Maurya, Devendra S.,Liu, Matthew,Xiao, Qi,Lu, Juncheng,Lauri, George,Ona, Nathan,Reagan, Erin K.,Ni, Houping,Weissman, Drew,Percec, Virgil
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supporting information
p. 17975 - 17982
(2021/11/10)
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- MONOMER, POLYMER, COMPENSATION FILM, OPTICAL FILM, AND DISPLAY DEVICE
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A monomer is represented by Chemical Formula 1: wherein, in Chemical Formula 1, R1, R2, o, p, L1, A1, Ra, m, and n are the same as defined in the detailed description.
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Paragraph 0330-0333; 0405-0409
(2019/02/13)
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- NUCLEIC ACID CONJUGATE
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The present invention provides a nucleic acid conjugate in which a sugar chain ligand is bonded to an oligonucleotide via a linker, the sugar chain ligand having O-bonded mannose at its non-reducing end.
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Paragraph 0593-0596
(2019/07/10)
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- PROTEIN AGGREGATION INHIBITOR AND PROTEIN AGGREGATION INHIBITING METHOD
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PROBLEM TO BE SOLVED: To provide a protein aggregation inhibitor capable of inhibiting protein aggregation and preparing a protein solution with a low viscosity. SOLUTION: The protein aggregation inhibitor contains a compound represented by the general formula (1) in the figure. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
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Paragraph 0252; 00253; 0257
(2018/02/27)
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- Amphiphilic α-helix mimetics based on a benzoylurea scaffold
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The design and synthesis of amphiphilic benzoylurea α-helix mimetics is described. These conformationally constrained molecules allow for the correct angular and spatial projection of hydrophobic and hydrophilic groups and thus the reproduction of side-chains on both faces of an α-helix.
- Thompson, Sam,Hamilton, Andrew D.
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supporting information; experimental part
p. 5780 - 5782
(2012/08/28)
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- Synthesis and phase behavior of branched esters derived from cyclohexylbenzoic acid
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A branched aldehyde on the basis of cyclohexylbenzoates and 3,5-dihydroxybenzoates was synthesized. For the characteristic of intermediates and the target substance TLC, elemental analysis, IR, NMR spectroscopy, and differential scanning calorimetry were
- Chervonova,Gruzdev,Kolker
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experimental part
p. 2288 - 2293
(2012/03/12)
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- Synthesis and structure of upper-rim 1,3-alternate tetraoxacalix[2]arene[2] triazine azacrowns and change of cavity in response to fluoride anion
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(Chemical Equation Presented) The upper-rim 1,3-alternate tetraoxacalix[2]arene[2]triazine azacrowns were constructed effectively by macrocyclic condensation reaction of diamines with dichlorinated tetraoxacalix[2]arene[2]triazine intermediates that were
- Hou, Bao-Yong,Wang, De-Xian,Yang, Hai-Bo,Zheng, Qi-Yu,Wang, Mei-Xiang
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p. 5218 - 5226
(2008/02/09)
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- Propeller-like hydrogen-bonded banana-melamine complexes inducing helical supramolecular organizations
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The results of the study presented here show a new example of the use of liquid crystals and the interactions involved in the mesomorphic state to build up complex molecular organizations. We have pursued a design strategy in which hydrogen bonding allows
- Barbera, Joaquin,Puig, Laura,Romero, Pilar,Serrano, Jose Luis,Sierra, Teresa
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p. 4487 - 4492
(2007/10/03)
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- Synthesis, self-assembly, and characterization of supramolecular polymers from electroactive dendron rodcoil molecules
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We report here the synthesis and self-assembly of a series of three molecules with dendron rodcoil architecture that contain conjugated segments of oligo(thiophene), oligo(phenylene-vinylene), and oligo(phenylene). Despite their structural differences, all three molecules yield similar self-assembled structures. Electron and atomic force microscopy reveals the self-assembly of the molecules into high aspect ratio ribbon-like nanostructures which at low concentrations induce gelation in nonpolar solvent. Self-assembly results in a blue-shifted absorption spectrum and a red-shifted, quenched fluorescence spectrum, indicating aggregation of the conjugated segments within the ribbon-like structures. The assembly of these molecules into one-dimensional nanostructures is a route to π-π stacked supramolecular polymers for organic electronic functions. In the oligo(thiophene) derivative, self-assembly leads to a 3 orders of magnitude increase in the conductivity of iodine-doped films due to self-assembly. We also found that electric field alignment of these supramolecular assemblies can be used to create arrays of self-assembled nanowires on a device substrate.
- Messmore, Benjamin W.,Hulvat, James F.,Sone, Eli D.,Stupp, Samuel I.
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p. 14452 - 14458
(2007/10/03)
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- Supramolecular helical stacking of metallomesogens derived from enantiopure and racemic polycatenar oxazolines
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The present report undertakes a challenge of general interest in supramolecular chemistry: the achievement of helical organizations with controlled structure. To achieve this target we considered the possibility of inducing supramolecular chirality using molecules that were designed to organize into columnar mesophases. The use of oxazoline-derived ligands and metal coordination served as tools to prepare molecules with a phasmidic-like structure, which show columnar organization in the liquid crystalline state. To ensure the formation of chiral mesophases, these complexes bear stereogenic centers in the rigid coordination environment of the metal. X-ray and circular dichroism experiments have revealed that chirality transfer does indeed take place from the chiral molecule to the columnar liquid crystal organization. This chiral columnar organization appears as a helix consisting of stacks of molecules that rotate with respect to one another along the column while maintaining their mean planes parallel to each other. In fact, it has been concluded that packing of these polycatenar molecules must be more efficient upon rotation of a molecule with respect to the adjacent one along the column. Furthermore, the same type of helical supraorganization has been found to be present in the mesophase of the racemic mixture and the mixture of diastereomers prepared from the racemic ligand. In this case, segregation of the optical isomers is proposed to occur to give rise to both types of helix (right-handed and left-handed).
- Barbera, Joaquin,Cavero, Emma,Lehmann, Matthias,Serrano, Jose-Luis,Sierra, Teresa,Vazquez, Jesus T.
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p. 4527 - 4533
(2007/10/03)
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- Synthesis of the benzophenone fragment of balanol via an intramolecular cyclization event
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Studies are reported on the use of either a 7-exo radical cyclization or an intramolecular Heck reaction as the key step for the construction of the benzophenone fragment of the PKC inhibitor, balanol. Whereas, the former approach was unsuccessful, the Heck reaction proved to be viable for the coupling of two fully functionalized aryl subunits affording regioselectively a biaryl seven-membered lactone with an exocyclic alkene as the major component, in contrast to the competing eight-membered ring lactone. Hydrolysis of the lactone followed by oxidative cleavage of the alkene with ruthenium tetraoxide completed this short synthesis of the benzophenone unit.
- Denieul, Marie-Pierre,Laursen, Bolette,Hazell, Rita,Skrydstrup, Troels
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p. 6052 - 6060
(2007/10/03)
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- Synthesis, Metal-binding Properties and Polypeptide Solubilization of 'Crowned' Arborols
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The first dendritic crown ether polymers ('crowned' arborols: G1, G2 and G3) have been synthesized and characterized.The convergent synthetic method was found to be more convenient than the divergent synthetic metod.The building block in the branch was pr
- Nagasaki, Takeshi,Kimura, Onari,Ukon, Masakatsu,Arimori, Susumu,Hamashi, Itaru,Shinkai, Seiji
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