74272-78-9

Upstream product

• 2169-27-9 Methyl 2,3-bis(benzyloxy)benzoate 
• 303-38-8 2,3-Dihydroxybenzoic acid 
• 100-39-0 benzyl bromide 
• 2411-83-8 methyl-2,3-dihydroxybenzoate 
• 24677-78-9 2,3-dihydroxybenzaldehyde 
• 100-44-7 benzyl chloride 
• 95922-26-2 benzyl 2,3-bis(benzyloxy)benzoate 
• 5779-91-9 2,3-bis(benzyloxy)benzaldehyde 

Downstream Products

• 141210-61-9 N¹,N⁸-bis(2,3-dibenzyloxybenzoyl)-N⁴-(4-nitrobenzyloxycarbonyl)-spermidine 
• 69146-58-3 2,3-bis(benzyloxy)benzoyl chloride 
• 74272-81-4 2,3-bis(benzyloxy)-N-(3-(4-(2,3-bis(benzyloxy)benzamido)butylamino)propyl)benzamide 
• 159434-45-4 C₇₅H₇₅N₃O₉ 
• 159434-41-0 2,3-Bis-benzyloxy-N-(1-pent-4-enyl-hex-5-enyl)-benzamide 
• 159434-46-5 C₇₂H₇₁N₃O₉ 
• 167275-82-3 (3R,4S)-4-Benzyloxycarbonylamino-8-(2,3-bis-benzyloxy-benzoylamino)-3-hydroxy-octanoic acid ethyl ester 
• 171667-83-7 C₇₁H₆₈N₄O₁₀ 
• 205598-62-5 (S)-2-(2,3-Bis-benzyloxy-benzoylamino)-succinamide 
• 205598-65-8 (-)-(2S)-1,2,4-tris[(2,3-dibenzyloxybenzoyl)amino]butane 
• 201535-47-9 1,2,7-tris-[(2,3-dibenzyloxybenzoyl)amino]heptane 

Relevant academic research and scientific papers

Nanomechanics of Anion-πInteraction in Aqueous Solution

Noncovalent interactions play a constitutive role in numerous biological processes, including biomolecular adhesion, recognition, and transport. Unlike π-πand cation-πinteractions, anion-πinteraction was only recently and computationally recognized to par

CONJUGATES AND CONJUGATES FOR USE IN PREVENTING OR TREATING OF BRAIN DAMAGE AND NEURODEGENERATIVE DISEASES

The present invention relates to conjugates comprising one or more compounds selected from of (i) an anti-inflammatory compound, and/or (ii) an antioxidant compound, and/or (iii) and antibiotic compound and/or, (iv) a metal chelating compound and at least

Synthetic Mimics of Native Siderophores Disrupt Iron Trafficking in Acinetobacter baumannii

Many pathogenic bacteria biosynthesize and excrete small molecule metallophores, known as siderophores, that are used to extract ferric iron from host sources to satisfy nutritional need. Native siderophores are often structurally complex multidentate chelators that selectively form high-affinity octahedral ferric iron complexes with defined chirality recognizable by cognate protein receptors displayed on the bacterial cell surface. Simplified achiral analogues can serve as synthetically tractable siderophore mimics with potential utility as chemical probes and therapeutic agents to better understand and treat bacterial infections, respectively. Here, we demonstrate that synthetic spermidine-derived mixed ligand bis-catecholate monohydroxamate siderophores (compounds 1-3) are versatile structural and biomimetic analogues of two native siderophores, acinetobactin and fimsbactin, produced by Acinetobacter baumannii, a multidrug-resistant Gram-negative human pathogen. The metal-free and ferric iron complexes of the synthetic siderophores are growth-promoting agents of A. baumannii, while the Ga(III)-complexes are potent growth inhibitors of A. baumannii with MIC values 1 μM. The synthetic siderophores compete with native siderophores for uptake in A. baumannii and maintain comparable apparent binding affinities for ferric iron (KFe) and the siderophore-binding protein BauB (Kd). Our findings provide new insight to guide the structural fine-tuning of these compounds as siderophore-based therapeutics targeting pathogenic strains of A. baumannii.

PEPTOID-BASED CHELATING LIGANDS FOR SELECTIVE METAL CHELATION

The present disclosure provides peptoid-based chelating ligands, corresponding cyclic peptoids, and methods of making thereof. Functional groups may be tailored for high metal binding affinity and selectivity. The side chains of a cyclic peptoid according to the present disclosure may be selected based on, for example, high affinity for actinide or other metal ions, selectivity for actinide or other metal ions, the ability to recover a metal once it is bound to the peptoid, and whether the overall peptoid should be hydrophobic or hydrophilic. Unlike siderophores, peptoid-based chelating ligands of the present disclosure are not readily hydrolyzed under physiological conditions. Therefore, peptoid-based chelating ligands may be, for example, used to treat actinide (e.g., iron and lead) poisoning in vivo. Moreover, peptoid-based chelating ligands of the present disclosure may be used for medical imaging, chelation therapy, drug delivery, and separation technologies, for example.

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

Hexadentate β-Dicarbonyl(bis-catecholamine) Ligands for Efficient Uranyl Cation Decorporation: Thermodynamic and Antioxidant Activity Studies

The special linear dioxo cation structure of the uranyl cation, which relegates ligand coordination to an equatorial plane perpendicular to the O=U=O vector, poses an unusual challenge for the rational design of efficient chelating agents. Therefore, the

Impact of Molecular Architecture and Adsorption Density on Adhesion of Mussel-Inspired Surface Primers with Catechol-Cation Synergy

Marine mussels secrete proteins rich in residues containing catechols and cationic amines that displace hydration layers and adhere to charged surfaces under water via a cooperative binding effect known as catechol-cation synergy. Mussel-inspired adhesives containing paired catechol and cationic functionalities are a promising class of materials for biomedical applications, but few studies address the molecular adhesion mechanism(s) of these materials. To determine whether intramolecular adjacency of these functionalities is necessary for robust adhesion, a suite of siderophore analog surface primers was synthesized with systematic variations in intramolecular spacing between catechol and cationic functionalities. Adhesion measurements conducted with a surface forces apparatus (SFA) allow adhesive failure to be distinguished from cohesive failure and show that the failure mode depends critically on the siderophore analog adsorption density. The adhesion of these molecules to muscovite mica in an aqueous electrolyte solution demonstrates that direct intramolecular adjacency of catechol and cationic functionalities is not necessary for synergistic binding. However, we show that increasing the catechol-cation spacing by incorporating nonbinding domains results in decreased adhesion, which we attribute to a decrease in the density of catechol functionalities. A mechanism for catechol-cation synergy is proposed based on electrostatically driven adsorption and subsequent binding of catechol functionalities. This work should guide the design of new adhesives for binding to charged surfaces in saline environments.

Mimicking salmochelin S1 and the interactions of its Fe(III) complex with periplasmic iron siderophore binding proteins CeuE and VctP

A mimic of the tetradentate stealth siderophore salmochelin S1, was synthesised, characterised and shown to form Fe(III) complexes with ligand-to-metal ratios of 1:1 and 3:2. Circular dichroism spectroscopy confirmed that the periplasmic binding proteins

Identification of the Ferric-Acinetobactin Outer Membrane Receptor in Aeromonas salmonicida subsp. salmonicida and Structure-Activity Relationships of Synthetic Acinetobactin Analogues

Aeromonas salmonicida subsp. salmonicida, the causative agent of furunculosis in several fish species, produces acinetobactin and amonabactin as siderophores. In a previous study, we chemically characterized these siderophores and proposed a biosynthetic

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.