486-79-3

Basic information

• Product Name: dipyrocetyl
• Synonyms: dipyrocetyl;2,3-Diacetoxybenzoic acid;2,3-diacetyloxybenzoic acid
• CAS NO: 486-79-3
• Molecular Formula: C₁₁H₁₀O₆
• Molecular Weight: 238.19
• EINECS: 207-641-7
• Mol File: 486-79-3.mol

Chemical Properties

• Melting Point: 148-150° (Rietz); mp 146-170° (Simokoriyama)
• Boiling Point: 400°Cat760mmHg
• Flash Point: 156.7°C
• Appearance: /
• Density: 1.344g/cm³
• Vapor Pressure: 4.07E-07mmHg at 25°C
• Refractive Index: 1.543
• Storage Temp.: 2-8°C
• PKA: 3.22±0.10(Predicted)
• CAS DataBase Reference: dipyrocetyl(CAS DataBase Reference)
• NIST Chemistry Reference: dipyrocetyl(486-79-3)
• EPA Substance Registry System: dipyrocetyl(486-79-3)

Safety Data

• Hazardous Substances Data: 486-79-3(Hazardous Substances Data)

Usage

Uses

Dipyrocetyl, has shown some antiinflammatory and antiarthritic activities.

InChI:InChI=1/C11H10O6/c1-6(12)16-9-5-3-4-8(11(14)15)10(9)17-7(2)13/h3-5H,1-2H3,(H,14,15)

Upstream product

• 303-38-8 2,3-Dihydroxybenzoic acid 
• 108-24-7 acetic anhydride 
• 24677-78-9 2,3-dihydroxybenzaldehyde 
• 57929-25-6 3,4-(diacetyloxy)benzoyl chloride 
• 67499-76-7 1-amino-2,3-dioxo-piperazine 

Downstream Products

• 17834-04-7 8-Hydroxywarfarin 
• 65055-19-8 2,3-bis(acetyloxy)benzoyl chloride 
• 1228969-42-3 C₆₀H₁₀₀O₉ 
• 1228969-40-1 C₂₁H₂₂O₉ 
• 1379800-25-5 C₄₇H₅₄N₄O₁₈ 
• 76218-83-2 N,N'-bis(2,3-dihydroxybenzoyl)-α,α-diaminopropane 
• 73630-99-6 N¹-{6-[(2,3-dihydroxybenzoyl)amino]hexyl}-2,3-dihydroxybenzamide 
• 71636-72-1 N¹-{2-[(2,3-dihydroxybenzoyl)amino]ethyl}-2,3-dihydroxybenzamide 

Relevant articles and documents

Antibiotic Conjugates with an Artificial MECAM-Based Siderophore Are Potent Agents against Gram-Positive and Gram-Negative Bacterial Pathogens

The development of novel drugs against Gram-negative bacteria represents an urgent medical need. To overcome their outer cell membrane, we synthesized conjugates of antibiotics and artificial siderophores based on the MECAM core, which are imported by bacterial iron uptake systems. Structures, spin states, and iron binding properties were predicted in silico using density functional theory. The capability of MECAM to function as an effective artificial siderophore in Escherichia coli was proven in microbiological growth recovery and bioanalytical assays. Following a linker optimization focused on transport efficiency, five β-lactam and one daptomycin conjugates were prepared. The most potent conjugate 27 showed growth inhibition of Gram-positive and Gram-negative multidrug-resistant pathogens at nanomolar concentrations. The uptake pathway of MECAMs was deciphered by knockout mutants and highlighted the relevance of FepA, CirA, and Fiu. Resistance against 27 was mediated by a mutation in the gene encoding ExbB, which is involved in siderophore transport.

Optimization of Artificial Siderophores as 68Ga-Complexed PET Tracers for in Vivo Imaging of Bacterial Infections

The diagnosis of bacterial infections at deep body sites benefits from noninvasive imaging of molecular probes that can be traced by positron emission tomography (PET). We specifically labeled bacteria by targeting their iron transport system with artificial siderophores. The cyclen-based probes contain different binding sites for iron and the PET nuclide gallium-68. A panel of 11 siderophores with different iron coordination numbers and geometries was synthesized in up to 8 steps, and candidates with the best siderophore potential were selected by a growth recovery assay. The probes [68Ga]7 and [68Ga]15 were found to be suitable for PET imaging based on their radiochemical yield, radiochemical purity, and complex stability in vitro and in vivo. Both showed significant uptake in mice infected with Escherichia coli and were able to discern infection from lipopolysaccharide-triggered, sterile inflammation. The study qualifies cyclen-based artificial siderophores as readily accessible scaffolds for the in vivo imaging of bacteria.

1,4,7,10-TETRAZACYCLODODECANE BASED AGENTS TO TARGET BACTERIA AND ITS USE

The present invention relates to new compounds comprising a siderophore moiety as well as a core structure able to chelate a metal ion. Optionally, the compounds may have additionally a moiety with a functional element including a marker molecule, a bioactive agent, an activity based probe suitable to monitor the aberrant expression or activity of proteins involved in the initiation and progression of bacterial infection, or a compound useful for bacterial inhibition. In a further aspect, the present invention provides a pharmaceutical composition containing said compound, for example, said pharmaceutical composition is an antibiotic. Additionally, the present invention relates to the use of said compounds in diagnostic methods, in particular, imaging methods including SPEC, PET or MRI. In an embodiment of the present invention, the compound is part of a theranostic composition having both, therapeutic as well as diagnostic activities.

Hierarchical self-assembly of metallo-dendrimers

2,3-Dihydroxybenzylic esters with Frechet-type dendritic branches as the alcohol component form, in a hierarchical self-assembly process, disk shaped dendrimers when titanium(iv) and lithium ions are added.

Studies on depigmenting activities of dihydroxyl benzamide derivatives containing adamantane moiety

Six diphenolic compounds containing adamantane moiety were synthesized and evaluated as potent inhibitors on tyrosinase activity and melanin formation in melan-a cells. The inhibitory activity of 4-adamantyl resorcinol 1 was similar to that of 4-n-butyl resorcinol in both assays. However, dihydroxyl benzamide derivatives 6a-e showed different inhibitory patterns. All derivatives significantly suppressed the cellular melanin formation without tyrosinase inhibitory activities. These behaviors indicated that the introduction of amide bond changes the binding mode of dihydroxyl groups to tyrosinase. Among derivatives, 6d (3,4-dihydroxyl compound) and 6e (2,3-dihydroxyl compound) showed stronger inhibitory activities (IC50 = 1.25 μM and 0.73 μM, respectively) as compared to 4-n-butyl resorcinol (IC50 = 21.64 μM) and hydroquinone (IC50 = 3.97 μM). This study showed that the position of dihydroxyl substituent at aromatic ring is important for the intercellular inhibition of melanin formation, and also amide linkage and adamantane moiety enhance the inhibition.

Novel quinolizidine salicylamide influenza fusion inhibitors

A novel series of quinolizidine salicylamides was synthesized as specific inhibitors of the H1 subtype of influenza A viruses. These inhibitors inhibit the pH-induced fusion process, thereby blocking viral entry into host cells. Compound 16 was the most active inhibitor in this series with an EC50 of 0.25 μg/mL in plaque reduction assay. The synthesis and the SAR of these compounds are discussed.

Synthesis and in vitro antibacterial activity of catechol-spiramycin conjugates

The first synthesis of siderophore conjugates of two macrolide antibiotics, spiramycin 1 and neospiramycin 2, which are unable to penetrate the outer membrane of Gram-negative bacteria are described. These novel conjugates were prepared by regioselective acylation of a hydroxyl function of 1 and 2 with a dihydroxybenzoic Fe(III) complexing ligand linked via a carboxyl group containing spacer to the macrolide antibiotics. The preliminary biological evaluation of these novel conjugates under standard and iron depleted conditions has shown that their antibacterial activity was comparable to that of spiramycin 1 and neospiramycin 2.

2-Amino-4-aryl thiazoles with antiasthmatic and antiinflammatory activities on the respiratory tract

2-Amino-4-aryl-thiazole derivatives have interesting pharmacological properties, particularly anthiasthmatic and antiinflammatory activities on the respiratory tract and they can be used to prepare pharmaceutical compositions useful for the treatment of bronchial hyper-reactivity.

2-oxo-1-(((substituted sulfonyl)amino)-carbonyl)azetidines

Antibacterial activity is exhibited by β-lactams having a 3-acylamino substituent and having in the 1-position an activating group of the formula STR1 wherein R is

Analogs of 3-(1-Phenyl-3-oxobutyl)-4-hydroxycoumarin (Warfarin) Prepared from Substituted Salicylic Acids

Some derivatives of salicylic acid containing substituents meta to the carboxyl group were used to prepare analogs of the anticoagulant drug warfarin, 3-(1-phenyl-3-oxobutyl)-4-hydroxycoumarin, containing substituents in either the 6- or 8-position of the coumarin ring.When the substituent was the hydroxyl group, the resulting products are previously identified metabolites of warfarin.The substituted salicylic acid is first acetylated with acetic anhydride, then either converted to the acid chloride and condensed with diethyl malonate in the presence of sodium hydroxide or converted to the mixed anhydride with formic acid and condensed with ethoxymagnesium diethyl malonate to yield, in either case, the corresponding 3-carbethoxy-4-hydroxycoumarin substituted in the 6- or 8-position of the coumarin ring.These compounds readily condense with benzalacetone to form the corresponding substituted warfarin in the presence of 5 mole percent tertiary amine catalyst.This method offers an improved route for the synthesis or 8-hydroxywarfarin.