58605-10-0

Usage

Chemical Properties

white powder or granules

InChI:InChI=1/C22H20O4/c1-24-22(23)19-12-20(25-15-17-8-4-2-5-9-17)14-21(13-19)26-16-18-10-6-3-7-11-18/h2-14H,15-16H2,1H3

Upstream product

• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 99-10-5 3,5-Dihydroxybenzoic acid 

Downstream Products

• 28917-43-3 3,5-dibenzyloxybenzoic acid 
• 24131-31-5 3,5-dibenzyloxybenzyl alcohol 
• 934243-80-8 2-iodo-3,5-bis(phenylmethoxy)benzenemethanol 
• 934243-67-1 2-iodo-3,5-bis(phenylmethoxy)-(2',2'-dimethylpropanoyloxymethyl)benzene 
• 883196-48-3 3-{3,5-bis[3-(3,4-bis(dodecyl-1-oxy)phenyl)propyl-1-oxy]phenyl}propan-1-ol 
• 883196-50-7 3-{3,5-bis[3-(3,4-bis(dodecyl-1-oxy)phenyl)propyl-1-oxy]phenyl}propyl bromide 
• 883196-47-2 methyl 3-{3,5-bis[3-(3,4-bis(dodecyl-1-oxy)phenyl)propyl-1-oxy]phenyl}propionate 
• 14615-72-6 3,5-dibenzyloxybenzaldehyde 
• 64794-00-9 methyl 3-(3'.5'-dihydroxyphenyl)propanoate 
• 64793-97-1 3,5-bis(benzyloxy)cinnamic acid 
• 64793-98-2 methyl 3-(3'.5'-dibenzyloxyphenyl)prop-2E-enoate 
• 811416-88-3 N-(3,5-dibenzyloxybenzyl)-N-methylamine 
• 71186-11-3 methyl 5-(3',5'-dihydroxyphenyl)-pentenoate 
• 77523-20-7 methyl 5-(3',5'-dihydroxyphenyl)-2(R,S)-methylpentenoate 

Relevant academic research and scientific papers

Synthesis and comparative structure-activity study of carbohydrate-based phenolic compounds as α-glucosidase inhibitors and antioxidants

Twenty-one natural and unnatural phenolic compounds containing a carbohydrate moiety were synthesized and their structure-activity relationship (SAR) was evaluated for α-glucosidase inhibition and antioxidative activity. Varying the position of the galloyl unit on the 1,5-anhydro -D-glucitol (1,5-AG) core resulted in changes in the α-glucosidase inhibitory activity and notably, particularly strong activity was demonstrated when the galloyl unit was present at the C-2 position. Furthermore, increasing the number of the galloyl units significantly affected the α-glucosidase inhibition, and 2,3,4,6-tetra-galloyl-1,5-AG (54) and 2,3,4,6-tetra-galloyl-d-glucopyranose (61) exhibited excellent activities, which were more than 13-fold higher than the α-glucosidase inhibitory activity of acertannin (37). Moreover, a comparative structure-activity study suggested that a hemiacetal hydroxyl functionality in the carbohydrate core and a biaryl bond of the 4,6-O-hexahydroxydiphenoyl (HHDP) group, which are components of ellagitannins including tellimagrandin I, are not necessary for the α-glucosidase inhibitory activity. Lastly, the antioxidant activity increased proportionally with the number of galloyl units.

Synthesis, structure activity relationship and in vitro anti-influenza virus activity of novel polyphenol-pentacyclic triterpene conjugates

It is urgently necessary to develop more effective anti-influenza agents due to the continuous emergence of drug-resistant strains of influenza virus. Our earlier studies have identified that certain pentacyclic triterpene derivatives are effective inhibitors of influenza virus infection. In the present study, a series of C-28 modified pentacyclic triterpene derivatives via conjugation with a series of polyphenols were synthesized, and their antiviral activities against influenza A/WSN/33 (H1N1) virus in MDCK (Madin-Darby canine kidney) cells were evaluated. Four compounds 23m, 23o, 23q and 23s displayed robust anti-influenza potency with averaged IC50 values at the low-micromole level, surpassing the potency of oseltamivir. In addition, the in vitro cytotoxic activity of the four conjugates against MDCK cells showed no toxicity at 100 μM. Further mechanism studies of compound 23s, one of the best representative conjugates with IC50 value of 5.80 μM and a selective index (SI) value of over 17.2, by hemagglutination inhibition (HI), surface plasmon resonance and molecular modeling indicated that this conjugate bound tightly to the viral envelope hemagglutinin (KD = 15.6 μM), thus blocking the invasion of influenza viruses into host cells.

Dendritic architectures by orthogonal thiol-maleimide "click" and furan-maleimide dynamic covalent chemistries

A set of dendrons and dendrimers is synthesized divergently using an orthogonal combination of kinetically-driven thiol-maleimide "click" chemistry and thermodynamically reversible furan-maleimide cycloaddition/retrocycloaddition reactions. Growth is controlled by taking advantage of the selective thiol-ene addition of thiols to the electron withdrawn alkene of maleimide in the presence of electron rich alkene of oxanorbornene. Subsequent activation of growing dendrons/dendrimers requires only heat to induce the dynamic covalent liberation of peripheral furan protecting groups. The methodology introduced provides a new route to multifunctional dendrimers that could, in principle, be synthesized by introducing different branched monomers at any stage of dendrimer growth, allowing dendrimer architectures and properties to be better tailored to their intended applications.

Benzoic hydroxamate-based iron complexes as model compounds for humic substances: Synthesis, characterization and algal growth experiments

A series of monomeric and dimeric FeIII complexes bearing benzoic hydroxamates as O,O-chelates has been prepared and characterized by elemental analysis, IR spectroscopy, UV-Vis spectroscopy, electrospray ionization mass spectrometry (ESI-MS), cyclic voltammetry, EPR spectroscopy and for some examples by X-ray diffraction analysis. The stability of the synthesized complexes in pure water and seawater was monitored over 24 h by means of UV-Vis spectrometry. The ability to release iron from the synthesized model complexes has been investigated with algae growth experiments.

Visual detection of fluoride ions

Dendrimer-hydrazides are coupled to polycyclic aromatic hydrocarbons for use in the visual detection of the presence of low levels of fluoride in a sample. The dendrimers can have a phenyl core, a first generation of aralkyl ethers, and an optional second generation of aralkyl ethers. The compounds form gels with solvents. In the presence of fluoride ion, the gels undergo color changes and/or gel to liquid phase change.

Synthesis of Curvulone B Using the 2-Chlorobenzyl Protecting Group

A total synthesis of curvulone B has been completed using a Friedel-Crafts reaction and a highly cis-selective intramolecular oxa-Michael addition. The 2-chlorobenzyl protecting group was employed and found to have much greater Lewis acid stability compared to the simple benzyl group.

Effect of the bulkiness of the end functional amide groups on the optical, gelation, and morphological properties of oligo(p-phenylenevinylene) π-gelators

Herein, we describe the role of end functional groups in the self-assembly of amide-functionalized oligo(p-phenylenevinylene) (OPV) gelators with different end-groups. The interplay between hydrogen-bonding and π-stacking interactions was controlled by the bulkiness of the end functional groups, thereby resulting in aggregates of different types, which led to the gelation of a wide range of solvents. The variable-temperature UV/Vis absorption and fluorescence spectroscopic features of gelators with small end-groups revealed the formation of 1D H-type aggregates in CHCl3. However, under fast cooling in toluene, 1D H-type aggregates were formed, whereas slow cooling resulted in 2D H-type aggregates. OPV amide with bulky dendritic end-group formed hydrogen-bonded random aggregates in toluene and a morphology transition from vesicles into fibrous aggregates was observed in THF. Interestingly, the presence of bulky end-group enhanced fluorescence in the xerogel state and aggregation in polar solvents. The difference between the aggregation properties of OPV amides with small and bulky end-groups allowed the preparation of self-assembled structures with distinct morphological and optical features. Buying in bulk: OPV amides with small end-groups self-assemble into 2D/1D aggregates in toluene and 1D aggregates in CHCl3. Bulky end-groups impede fluorescence quenching in the self-assembled state by blocking π-stacking and facilitate morphological transition in THF.

A detailed investigation of light-harvesting efficiency of blue color emitting divergent iridium dendrimers with peripheral phenylcarbazole units

The increase in phosphorescence efficiency was estimated by the energy transfer mechanism for divergent iridium dendrimers with peripheral phenylcarbazole units. A series of Ir-core/phenylcarbazole-end dendrons of the type, Ir(dfppy)2(pic-Czsu

Biomimetic synthesis of active isorhapontigenin dimers

Synthetic isorhapontigenin was treated with several kinds of inorganic reagents and peroxidase so as to prepare active stilbene dimers. Among them, silver acetate in methanol gave two new isorhapontigenin dimers 4 and 5, together with four known natural stilbene dimers 2, 3, 6, and 7. Their structures and relative configurations were determined on the basis of spectral analysis, and their possible formation mechanisms were discussed, respectively. Compounds 2, 6, and 7 were artificially synthesized for the first time. All the products were evaluated for anti-inflammatory activities.

Structure-activity relationships for vitamin D3-based aromatic a-ring analogues as hedgehog pathway inhibitors

A structure-activity relationship study for a series of vitamin D3-based (VD3) analogues that incorporate aromatic A-ring mimics with varying functionality has provided key insight into scaffold features that result in potent, selective Hedgehog (Hh) pathway inhibition. Three analogue subclasses containing (1) a single substitution at the ortho or para position of the aromatic A-ring, (2) a heteroaryl or biaryl moiety, or (3) multiple substituents on the aromatic A-ring were prepared and evaluated. Aromatic A-ring mimics incorporating either single or multiple hydrophilic moieties on a six-membered ring inhibited the Hh pathway in both Hh-dependent mouse embryonic fibroblasts and cultured cancer cells (IC50 values 0.74-10 μM). Preliminary studies were conducted to probe the cellular mechanisms through which VD3 and 5, the most active analogue, inhibit Hh signaling. These studies suggested that the anti-Hh activity of VD3 is primarily attributed to the vitamin D receptor, whereas 5 affects Hh inhibition through a separate mechanism.