3598-22-9

Upstream product

• 67-56-1 methanol 
• 1078-61-1 dihydrocaffeic acid 
• 71038-25-0 methyl (E)-3-(3,4-bis(benzyloxy)phenyl)acrylate 
• 331-39-5 caffeic acid 
• 121-33-5 vanillin 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 3843-74-1 methyl 3,4-dihydroxycinnamate 
• 1782-52-1 4-(2-methoxycarbonylethyl)-(1,2)-benzoquinone 
• 5597-50-2 3-(4-hydroxyphenyl)propionic acid methyl ester 
• 501-97-3 4-hydroxyphenylpropionic acid 
• 100976-84-9 ethyl 3,4-diacetoxycinnamate 
• 74257-25-3 ethyl caffeate 
• 54429-62-8 (E)-3-(3,4-bis(benzyloxy)phenyl)acrylic acid 
• 1699-58-7 3,4-bis(benzyloxy)benzyl alcohol 

Downstream Products

• 1782-52-1 4-(2-methoxycarbonylethyl)-(1,2)-benzoquinone 
• 263277-21-0 3-(3'-hydroxy-4'-benzyloxyphenyl)propionic acid 
• 568584-16-7 3-(3,4-bis-benzyloxy-phenyl)-propionic acid methyl ester 
• 27798-73-8 methyl 3-(3,4-dimethoxyphenyl)propionate 
• 63212-99-7 (4E,6E)-1-(3,4-dihydroxyphenyl)-7-phenylhepta-4,6-dien-3-one 
• 1220910-99-5 C₁₆H₁₅BO₄ 
• 1239597-88-6 methyl 3-[3,4-bis-{(4'-(dodecyloxy)-biphenyl-4-yl)-methoxy}phenyl]propanoate 
• 1239597-71-7 bethyl 3-[3,4-bis{4-(dodecyloxy)benzyloxy}phenyl]propanoate 
• 46118-02-9 3-(3',4'-dihydroxyphenyl)-1-propanol 

Relevant academic research and scientific papers

Comparative study of the antioxidant activities of some lipase-catalyzed alkyl dihydrocaffeates synthesized in ionic liquid

The solubility limitations of phenolic acids in many lipidic environments are now greatly improved by their enzymatic esterification in ionic liquids (ILs). Herein, four different ILs were tested for the esterification of dihydrocaffeic acid with hexanol

Cell imaging of dopamine receptor using agonist labeling iridium(III) complex

Dopamine receptor expression is correlated with certain types of cancers, including lung, breast and colon cancers. In this study, we report luminescent iridium(iii) complexes (11-14) as intracellular dopamine receptor (D1R/D2R) cell imaging agents. Compl

An integrated nanoplatform for theranostics via multifunctional core-shell ferrite nanocubes

Magnetic core-shell ferrite nanocubes (MNCs) were prepared by a two-step pyrolysis. The MNCs not only exhibit an excellent magnetothermal effect, but also can be used as T2 magnetic resonance (MR) imaging agents. To obtain their good biocompati

1-Methyl-1,4-cyclohexadiene as a Traceless Reducing Agent for the Synthesis of Catechols and Hydroquinones

Pro-aromatic and volatile 1-methyl-1,4-cyclohexadiene (MeCHD) was used for the first time as a valid H-atom source in an innovative method to reduce ortho or para quinones to obtain the corresponding catechols and hydroquinones in good to excellent yields. Notably, the excess of MeCHD and the toluene formed as the oxidation product can be easily removed by evaporation. In some cases, trifluoroacetic acid as a catalyst was added to obtain the desired products. The reaction proceeds in air and under mild conditions, without metal catalysts and sulfur derivatives, resulting in an excellent and competitive method to reduce quinones. The mechanism is attributed to a radical reaction triggered by a hydrogen atom transfer from MeCHD to quinones, or, in the presence of trifluoroacetic acid, to a hydride transfer process.

COMPOSITION AND METHODS FOR TETHERING BIOACTIVE PEPTIDES TO METAL OXIDE SURFACES

In various aspects, embodiments of the present invention are directed to a series of multivalent dendrons containing a bioactive peptide domain and surface-binding catechol domains. In some embodiments, these multivalent dendrons were obtained through sol

(-)-Tarchonanthuslactone: Design of New Analogues, Evaluation of their Antiproliferative Activity on Cancer Cell Lines, and Preliminary Mechanistic Studies

Natural products containing the α,β-unsaturated δ-lactone skeleton have been shown to possess a variety of biological activities. The natural product (-)-tarchonanthuslactone (1) possessing this privileged scaffold is a popular synthetic target, but its biological activity remains underexplored. Herein, the total syntheses of dihydropyran-2-ones modeled on the structure of 1 were undertaken. These compounds were obtained in overall yields of 17-21 % based on the Keck asymmetric allylation reaction and were evaluated in vitro against eight different cultured human tumor cell lines. We further conducted initial investigation into the mechanism of action of selected analogues. Dihydropyran-2-one 8 [(S,E)-(6-oxo-3,6-dihydro-2H-pyran-2-yl)methyl 3-(3,4-dihydroxyphenyl)acrylate], a simplified analogue of (-)-tarchonanthuslactone (1) bearing an additional electrophilic site and a catechol system, was the most cytotoxic and selective compound against six of the eight cancer cell lines analyzed, including the pancreatic cancer cell line. Preliminary studies on the mechanism of action of compound 8 on pancreatic cancer demonstrated that apoptotic cell death takes place mediated by an increase in the level of reactive oxygen species. It appears as though compound 8, possessing two Michael acceptors and a catechol system, may be a promising scaffold for the selective killing of cancer cells, and thus, it deserves further investigation to determine its potential for cancer therapy. Fighting the big C: We describe the synthesis of a new family of analogues based on the scaffold of the natural product (-)-tarchonanthuslactone; these compounds were evaluated in vitro against tumor cell lines. We further conducted an initial investigation into the mechanism of action, including the inhibition of phosphatases and glutathione-S-transferase and the production of reactive oxygen species.

Catechol-based substrates of chalcone synthase as a scaffold for novel inhibitors of PqsD

A new strategy for treating Pseudomonas aeruginosa infections could be disrupting the Pseudomonas Quinolone Signal (PQS) quorum sensing (QS) system. The goal is to impair communication among the cells and, hence, reduce the expression of virulence factors and the formation of biofilms. PqsD is an essential enzyme for the synthesis of PQS and shares some features with chalcone synthase (CHS2), an enzyme expressed in Medicago sativa. Both proteins are quite similar concerning the size of the active site, the catalytic residues and the electrostatic surface potential at the entrance of the substrate tunnel. Hence, we evaluated selected substrates of the vegetable enzyme as potential inhibitors of the bacterial protein. This similarity-guided approach led to the identification of a new class of PqsD inhibitors having a catechol structure as an essential feature for activity, a saturated linker with two or more carbons and an ester moiety bearing bulky substituents. The developed compounds showed PqsD inhibition with IC50 values in the single-digit micromolar range. The binding mode of these compounds was investigated by Surface Plasmon Resonance (SPR) experiments revealing that their interaction with the protein is not influenced by the presence of the anthranilic acid bound to active site cysteine. Importantly, some compounds reduced the signal molecule production in cellulo.

Carbon nanotubes supported tyrosinase in the synthesis of lipophilic hydroxytyrosol and dihydrocaffeoyl catechols with antiviral activity against DNA and RNA viruses

Hydroxytyrosol and dihydrocaffeoyl catechols with lipophilic properties have been synthesized in high yield using tyrosinase immobilized on multi-walled carbon nanotubes by the Layer-by-Layer technique. All synthesized catechols were evaluated against a large panel of DNA and RNA viruses, including Poliovirus type 1, Echovirus type 9, Herpes simplex virus type 1 (HSV-1), Herpes simplex virus type 2 (HSV-2), Coxsackievirus type B3 (Cox B3), Adenovirus type 2 and type 5 and Cytomegalovirus (CMV). A significant antiviral activity was observed in the inhibition of HSV-1, HSV-2, Cox B3 and CMV. The mechanism of action of the most active dihydrocaffeoyl derivative was investigated against a model of HSV-1 infection.

Design, synthesis and biological evaluation of small molecular polyphenols as entry inhibitors against H5N1

To find novel compounds against H5N1, three series of known or novel small molecular polyphenols were synthesized and tested in vitro for anti-H5N1 activity. In addition, the preliminary structure-antiviral activity relationships were elaborated. The results showed that some small molecular polyphenols had better anti-H5N1 activity, and could serve as novel virus entry inhibitors against H 5N1, likely targeting to HA2 protein. Noticeably, compound 4a showed the strongest activity against H5N1 among these compounds, and the molecular modeling analysis also suggested that this compound might target to HA2 protein. Therefore, compound 4a is well qualified to serve as a lead compound or scaffold for the further development of H 5N1 entry inhibitor.

Tyrosinase and Layer-by-Layer supported tyrosinases in the synthesis of lipophilic catechols with antiinfluenza activity

Catechol derivatives with lipophilic properties have been selectively synthesized by tyrosinase in high yield avoiding long and tedious protection/deprotection steps usually required in traditional procedures. The synthesis was effective also with immobilized tyrosinase able to perform for more runs. The novel catechols were evaluated against influenza A virus, that continue to represent a severe threat worldwide. A significant antiviral activity was observed in derivatives characterized by antioxidant activity and long carbon alkyl side-chains, suggesting the possibility of a new inhibition mechanism based on both redox and lipophilic properties.