91925-82-5

Upstream product

• 99-24-1 methyl galloate 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 149-91-7 3,4,5-trihydroxybenzoic acid 

Downstream Products

• 147825-73-8 4-Benzyloxy-3-heptyloxy-5-hydroxy-benzoic acid methyl ester 
• 136805-25-9 methyl 4-(benzyloxy)-5-hydroxy-3-(tolyloxy)benzoate 
• 946424-78-8 C₃₆H₂₄N₆O₁₀Cl₂ 
• 955887-36-2 C₂₃H₃₀O₅ 
• 27065-65-2 methyl 4-benzyloxy-3,5-dimethoxybenzoate 
• 955887-38-4 C₂₅H₃₄O₅ 
• 955887-39-5 C₂₅H₃₄O₅ 
• 955887-40-8 methyl 4-(benzyloxy)-3,5-bis(hexyloxy)benzoate 
• 955887-35-1 C₂₁H₂₆O₅ 
• 1034343-20-8 C₃₀H₂₆O₁₀ 
• 1034343-25-3 methyl 4-O-benzyl-3,5-di-O-methoxymethylgallate 
• 1431081-25-2 ethyl 2,3-di-O-benzyl-4,6-O-bis(4-O-benzyl-3,5-di-O-methoxymethylgalloyl)-1-thio-β-D-glucopyranoside 
• 1431081-29-6 ethyl 2,3-di-O-benzyl-4,6-O-bis(4-O-benzylgalloyl)-1-thio-β-D-glucopyranoside 
• 1034343-24-2 4-O-benzyl-3,5-di-O-(methoxymethyl)gallic acid 

Relevant academic research and scientific papers

One-Component Multifunctional Sequence-Defined Ionizable Amphiphilic Janus Dendrimer Delivery Systems for mRNA

Efficient viral or nonviral delivery of nucleic acids is the key step of genetic nanomedicine. Both viral and synthetic vectors have been successfully employed for genetic delivery with recent examples being DNA, adenoviral, and mRNA-based Covid-19 vaccines. Viral vectors can be target specific and very efficient but can also mediate severe immune response, cell toxicity, and mutations. Four-component lipid nanoparticles (LNPs) containing ionizable lipids, phospholipids, cholesterol for mechanical properties, and PEG-conjugated lipid for stability represent the current leading nonviral vectors for mRNA. However, the segregation of the neutral ionizable lipid as droplets in the core of the LNP, the "PEG dilemma", and the stability at only very low temperatures limit their efficiency. Here, we report the development of a one-component multifunctional ionizable amphiphilic Janus dendrimer (IAJD) delivery system for mRNA that exhibits high activity at a low concentration of ionizable amines organized in a sequence-defined arrangement. Six libraries containing 54 sequence-defined IAJDs were synthesized by an accelerated modular-orthogonal methodology and coassembled with mRNA into dendrimersome nanoparticles (DNPs) by a simple injection method rather than by the complex microfluidic technology often used for LNPs. Forty four (81%) showed activity in vitro and 31 (57%) in vivo. Some, exhibiting organ specificity, are stable at 5 °C and demonstrated higher transfection efficiency than positive control experiments in vitro and in vivo. Aside from practical applications, this proof of concept will help elucidate the mechanisms of packaging and release of mRNA from DNPs as a function of ionizable amine concentration, their sequence, and constitutional isomerism of IAJDs.

Extraordinary Acceleration of Cogwheel Helical Self-Organization of Dendronized Perylene Bisimides by the Dendron Sequence Encoding Their Tertiary Structure

The cogwheel model of hierarchical self-organization provides a route to highly ordered crystalline helical columnar hexagonal arrays of perylene bisimides (PBIs) conjugated to (3,4,5)-dimethyloctyl (racemic dm8*, r) minidendrons. Cogwheel PBIs assemble with identical structural order irrespective of molecular chirality to generate helical columns jacketed with an alkyl coat with length equal to half the helical pitch, exhibiting helical deracemization in the crystal state. These assemblies were accessible only via annealing or cooling and reheating at 1 °C/min. Recently it was discovered that hybrid rr8 sequence-defined dendrons with r and linear n-octyl (8) chains enabled the formation of the cogwheel phase at 10 °C/min upon heating but not cooling. Here we report four libraries of hybrid PBIs with sequence-defined dendrons containing r and n-alkyl (CnH2n+1) chains with n = 6, 7, 9, and 10. Structural analysis of these libraries by fiber X-ray diffraction and differential scanning calorimetry reveals that the 9r9 sequence enables an extraordinary acceleration of cogwheel assembly at rates of up to 50 °C/min on heating and cooling, providing, to the best of our knowledge, the fastest crystallizing supramolecular or covalent macromolecule known. Solid-state NMR studies help to elucidate this unexpected and unprecedented extraordinary acceleration of hierarchical self-organization, which arises from a combination of crystal packing of the ideal tertiary structure and alkyl chain dynamics. This general model raises questions about the use of achiral motifs to achieve high structural order in chiral systems and the need for disorder to create order in complex biological and bioinspired synthetic systems.

Sequence-defined dendrons dictate supramolecular cogwheel assembly of dendronized perylene bisimides

A dendronized perylene bisimide (PBI) that self-organizes into hexagonal arrays of supramolecular double helices with identical single crystal-like order that disregards chirality was recently reported. A cogwheel model of selfassembly that explains this process was proposed. Accessing the highly ordered cogwheel phase required very slow heating and cooling or extended periods of annealing. Analogous PBIs with linear alkyl chains did not exhibit the cogwheel assembly. Here a library of sequence-defined dendrons containing all possible compositions of linear and racemic alkyl chains was employed to construct self-assembling PBIs. Thermal and structural analysis of their assemblies by differential scanning calorimetry (DSC) and fiber X-ray diffraction (XRD) revealed that the incorporation of n-alkyl chains accelerates the formation of the high order cogwheel phase, rendering the previously invisible phase accessible under standard heating and cooling rates. Small changes to the primary structure, as constitutional isomerism, result in significant changes to macroscopic properties such as melting of the periodic array. This study demonstrated how changes to the sequencedefined primary structure, including the relocation of methyl groups between two constitutional isomers, dictate tertiary and quaternary structure in hierarchical assemblies. This led to the discovery of a sequence that self-organizes the cogwheel assembly much faster than even the corresponding homochiral compounds and demonstrated that defined-sequence, which has long been recognized as determinant for the complex structure of biomacromolecules including proteins and nucleic acids plays the same role also in supramolecular synthetic systems.

DENDRITIC COMPOUNDS INCLUDING A CHELATING, FLUOROCHROME OR RECOGNITION AGENT, COMPOSITIONS INCLUDING SAME AND USES THEREOF

The invention relates to dendritic compounds comprising a chelating, fluorochrome or recognition agent of formula (I), to compositions comprising same, and to uses thereof, wherein in said formula (I): T, L1, D, R, L2, V and n are as defined in the description.

DENDRONIZED METALLIC OXIDE NANOPARTICLES, A PROCESS FOR PREPARING THE SAME AND THEIR USES

The present invention relates to dendronized metallic oxide nanoparticles, a process for preparing the same and their uses.

Efficient synthesis of small-sized phosphonated dendrons: Potential organic coatings of iron oxide nanoparticles

We report herein the synthesis of biocompatible small-sized phosphonated monomers and dendrons used as functional coatings of metal oxide nanoparticles, more specifically superparamagnetic iron oxides (SPIOs) for magnetic resonance imaging (MRI) and therapy through hyperthermia. The molecules were engineered to modulate their size, their hydrophilic and/or biocompatible character (poly(amido)amine versus oligoethyleneglycol), the number of anchoring phosphonate groups (monophosphonate versus phosphonic tweezers) and the number of peripheral functional groups for further grafting of dyes or specific vectors. Such a library of hydrophilic phosphonic acids opens new possibilities for the investigation of dendronized nanohybrids as theranostics.

High-yield total synthesis of (-)-strictinin through intramolecular coupling of gallates

This paper describes a total synthesis of (-)-strictinin, an ellagitannin that is 1-O-galloyl-4,6-O-(S)-hexahydroxydiphenoyl (HHDP)-β-d-glucose. In the study, total efficiency of the synthesis was improved to produce a 78% overall yield in 13 steps from d-glucose. In the synthesis, formation of the 4,6-(S)-HHDP bridge including the 11-membered bislactone ring was a key step, in which intramolecular aryl-aryl coupling was adopted. The coupling was oxidatively induced by CuCl2-n-BuNH2 with perfect control of the axial chirality, and the reaction conditions of this coupling were optimized thoroughly to achieve the quantitative formation of the bridge.

MULTIMODAL CONTRAST AND RADIOPHARMACEUTICAL AGENT FOR AN IMAGING AND A TARGETED THERAPY GUIDED BY IMAGING

The present invention relates to a multimodal contrast and radiopharmaceutical agent for an imaging and a targeted therapy guided by imaging.

Radiosynthesis of 3-(3-[18F]fluoropropoxy)-4-(benzyloxy)-N-[(1- dimethylaminocyclopentyl)methyl]-5-methoxybenzamide, a potential PET radiotracer for the glycine transporter GlyT-2

The recently described selective and potent GlyT2 antagonist, 4-benzyloxy-3, 5-dimethoxy-N-[(1-dimethylaminocyclopentyl) methyl]benzamide (IC50 = 16 nM) provided an important additional tool to further characterize GlyT2 pharmacology. In order to identify an effective PET radioligand for in vivo assessment of the GlyT-2 transporter, 3-(3-[ 18F]fluoropropoxy)-4-(benzyloxy)-N-((1-dimethylaminocyclopentyl) methyl)-5-methoxybenzamide ([18F]3), a novel analog of 4-benzyloxy-3,5-dimethoxy-N-[(1-dimethylaminocyclopentyl) methyl]benzamide was synthesized using a one-pot, two-step method. The NCA radiofluorination of 1,3-propanediol di-p-tosylate in the presence of K2CO3 and Kryptofix-222 in acetonitrile gave 81% 3-[18F]fluoropropyl tosylate, which was subsequently coupled with 4-benzyloxy-3-hydroxy-5-methoxy-N-[(1- dimethylaminocyclopentyl) methyl]-benzamide in the same reaction vessel. Solvent extraction and HPLC (Eclipse XDB-C8 column, 80/20/0.1 MeOH/H 2O/Et3N, 3.0 ml/min) gave [18F]3 in 98.5% radiochemical purity. The radiochemical yield was determined to be 14.0-16.2% at EOS, and the specific activity was 1462 ± 342 GBq/μmol. The time of synthesis and purification was 128 min. The final product was prepared as a sterile saline solution suitable for in vivo use. Copyright

Syntheses of two cytotoxic sinapyl alcohol derivatives and isolation of four new related compounds from Ligularia nelumbifolia

Phytochemical reinvestigation on Ligularia nelumbifolia afforded four novel sinapyl alcohol analogues named nelumols B-E (1-4) and three known sinapyl alcohol derivatives (5-7). Their structures were elucidated by NMR techniques. Total syntheses of cytotoxic geranyloxy sinapyl alcohol (6) and geranyloxy sinapyl aldehyde (7) were carried out via two different paths. The 4-O-benzyl-substituted analogues (20 and 27) as well as the 4-O-(2-methylbutenyl) derivatives (34 and 35) were also synthesized. The cytotoxicities of 6 and 7 were measured using A-549, HL-60, and KB cancer cell lines.