2169-27-9

Upstream product

• 2411-83-8 methyl-2,3-dihydroxybenzoate 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 303-38-8 2,3-Dihydroxybenzoic acid 

Downstream Products

• 936254-46-5 1,8-bis-(2,3-dibenzyloxybenzoyloxy)octane 
• 1300025-12-0 tert-butyl-3-(4-((4-(2,3-bis(benzyloxy)benzamido)butyl)(3-(2-,3-bis(benzyloxy)benzamido)propyl)amino)-4-oxobutanamido)propylcarbamate 
• 1300025-13-1 C₃₃H₄₁N₅O₁₁ 
• 23806-63-5 3-(benzyloxy)-2-hydroxybenzoic acid 
• 16053-97-7 2,3-dihydroxybenzohydroxamic acid 
• 20734-66-1 1,2-dihydroxy-3-aminobenzene 
• 1334660-40-0 ethyl 2,3-bis(benzyloxy)phenylcarbamate 

Relevant academic research and scientific papers

Catechol-Based Ligands as Potential Metal Chelators Inhibiting Redox Activity in Alzheimer's Disease

The loss of homeostasis of redox metal ions, namely, copper and iron, has been considered to be an important contributing factor in neuronal death observed in the brain of patients affected by Alzheimer's disease (AD). Specific ligands able to regulate the homeostasis of copper and, to a lesser extent, iron ions in the brain have therefore been considered to be potential drugs for the treatment of AD. Herein, the synthesis and metal coordination properties of a series of ligands based on a bis(2,3-dihydroxyalkylbenzamide) scaffold, which are potentially able to regulate the homeostasis of redox metal ions, are reported. These catechol-based ligands exhibit high specific affinities for CuII and FeIII, and a lower affinity for ZnII, which indicates that they may interact with redox metal ions without disturbing the structural and dynamic role of zinc chelation in many proteins. These ligands inhibit the reduction of dioxygen induced by CuII–Aβ1–16, and this suggests that they may be able to efficiently reduce the oxidative stress induced by metal-loaded amyloids in the AD brain.

DOUBLE-HEADED PROTEASE INHIBITOR

The present invention provides a compound that is highly safe and useful in the prevention, alleviation, and/or treatment of various diseases involving enteropeptidase inhibition and/or trypsin inhibition, a pharmaceutical composition containing the compo

CONDENSED HETEROCYCLIC COMPOUND

The present invention relates to a condensed heterocyclic compound that has an enteropeptidase inhibitory effect and is useful in the treatment or prevention of obesity, diabetes mellitus, or the like, and a medicament containing the same. Specifically, t

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.

Synthesis and antibacterial activity of catecholate-ciprofloxacin conjugates

The development of an efficient route to obtain artificial siderophore-antibiotic conjugates active against Gram-negative bacteria is crucial. Herein, a practical access to triscatecholate enterobactin analogues linked to the ciprofloxacin along with their antibacterial evaluation are described. Two series of conjugates were obtained with and without a piperazine linker which is known to improve the pharmacokinetics profile of a drug. A monocatecholate-ciprofloxacin conjugate was also synthesized and evaluated. The antibacterial activities against Pseudomonas aeruginosa for some conjugates are related to the iron concentration in the culture medium and seem to depend on the bacterial iron uptake systems.

Identification of novel matrix metalloproteinase inhibitors by screening of phenol fragments library

In the last 20 years, a great variety of synthetic, low molecular weight MMP inhibitors (MMPIs) have been synthesized and tested, although none has reached clinical utility. Exploration of novel ZBGs and development of non-hydroxamate MMPI has become a focus in current research. It's well-known that polyphenols can produce beneficial effects on human health by their antioxidant properties as well as they have the ability to block gelatinase activity. In this work we tested a series of selected phenols as MMP inhibitors. The most interesting hit (B6) shows sub-micromolar activity against MMP-2 (IC50 0.59 ± 0.05 μM, LE = 1.07) and a fairly good selectivity spectrum. A screening of selected phenols against four matrix metalloproteinases is reported. Eight phenols showed a very interesting activity and selective profile. The most interesting hit (B6) presents a sub-micromolar activity against MMP-2 (IC50 0.59±0.05μM). Copyright

Chemical synthesis and biological evaluation of gallidermin-siderophore conjugates

The lantibiotic gallidermin was modified at lysine residues by regioselective attachment of derivatives of pyochelin, agrobactin and desferrioxamine B with the objective of having siderophore receptors of Gram-negative bacteria transport the antibiotic-iron chelator conjugate through the outer membrane. All of the conjugates retained activity against the Gram-positive indicator strain, Lactococcus lactis subsp. cremoris HP. However, testing of the conjugates against several Gram-negative strains yielded unexpected results. Bacteria treated with 100 μM of the conjugates complexed with Fe3+ grew better than bacteria grown in iron-free media but worse than bacteria grown in the same media supplemented with 10 μM FeCl 3. Although these findings indicate that the conjugates are unable to inhibit the growth of Gram-negative bacteria, they indicate penetration of the outer membrane and provide structure-activity information for design of other lantibiotic conjugates. The synthetic strategy is applicable for linking biomarkers or fluorescence probes to gallidermin for studies on its localization and mode of action. As there are many lantibiotics that operate with unknown mechanisms of action, this chemical approach provides a means to modify such peptides with biomarkers for biological investigations.

Synthesis and biological activity of analogues of vanchrobactin, a siderophore from Vibrio anguillarum serotype O2

Several analogues of vanchrobactin, a catechol siderophore isolated from the bacterial fish pathogen Vibrio anguillarum serotype O2 strain RV22, have been synthesized. The biological evaluation of these novel compounds showed that most of them are active as siderophores, as determined by growth promotion assays using the producer strain, as well as V. anguillarum serotype O1, Salmonella enterica, and Erwinia chrysanthemi. These compounds also gave a positive chrome azurol-S (CAS) test. On the basis of these results, we were able to deduce some structure-activity relationships. Furthermore, we found an analogue with siderophore activity that has appropriate functionality (an amino group) for use as an antibiotic vector to be employed in a "Trojan horse strategy". This journal is The Royal Society of Chemistry.

Synthesis and investigation of a chiral enterobactin analogue based on a macrocyclic peptide scaffold

A chiral C3-symmetric enterobactin analogue (1) has been synthesized by attachment of three 2,3-dihydroxybenzoyl units to a chiral oxazole-containing macrocyclic peptide scaffold. Complex formation kinetics and stoichiometry with various metal ions were investigated by spectrophotometric methods. In the cases of AlIII, InIII and FeIII complexes, UV absorption and CD kinetics showed nonlinearity, which results from slow conformational changes of the octahedral complexes. Virtual binding constants were determined from UV absorption data and showed selective binding of GaIII in preference to FeIII, by two orders of magnitude. CD spectroscopy revealed highly diastereoselective binding of Al III, GaIII, InIII, FeIII and Ge IV ions at room temperature, corresponding to the helical chirality opposite to that of the analogous enterobactin complexes. Ab initio calculations confirmed the energetic stabilization of the A isomers relative to the A isomers.

Vanchrobactin: absolute configuration and total synthesis

The stereochemistry of vanchrobactin, a siderophore produced by the bacterial fish pathogenVibrio anguillarum serotype O2, was elucidated by chiral capillary electrophoresis analysis and total synthesis as N-[N′-(2,3-dihydroxybenzoyl)-d-arginyl]-l-serine.