696-54-8

Usage

Uses

Used in Pesticide Industry:
4-Pyridinealdoxime is used as an intermediate for bis(hydroxyiminomethylpyridinium)butenes, which are essential reactivators of chlorpyrifos-inhibited acetylcholinesterase. This application is particularly important in the pesticide industry, as it helps counteract the negative effects of chlorpyrifos on acetylcholinesterase, an enzyme crucial for the proper functioning of the nervous system in both humans and animals.
Used in Chemical Synthesis:
4-Pyridinealdoxime is employed as an intermediate in the synthesis of various chemical compounds, including bis(hydroxyiminomethylpyridinium)butenes. Its unique structural properties and reactivity make it a valuable component in the development of new molecules with potential applications in various fields.
Used in Chromatography and NMR Characterization:
In the field of analytical chemistry, 4-Pyridinealdoxime is used for the chromatographic separation and nuclear magnetic resonance (NMR) characterization of the isomers of 1,1'-Methylenebis4-[(hydroxyimino)methyl]pyridinium dichloride. This application highlights its importance in the identification and separation of different isomers, which is crucial for understanding their properties and potential uses.

Purification Methods

Crystallise the oxime from water. [Beilstein E-isomer 21 III/IV 3533, 21/7 V 355.]

InChI:InChI=1/C6H6N2O/c9-8-5-6-1-3-7-4-2-6/h1-5,9H/b8-5-

Upstream product

• 108-89-4 picoline 
• 872-85-5 pyridine-4-carbaldehyde 
• 144605-36-7 3-pyridinecarbaldehyde 1-oxide oxime 
• 56-97-3 trimedoxime dibromide 
• 51026-61-0 oxo-[[1-[[4-(oxoazaniumylmethylidene)pyridin-1-yl]methyl]pyridine-4-ylidene]methyl]azanium dichloride 
• 7782-77-6 cis-nitrous acid 
• 54751-01-8 4-(bromomethyl)pyridine 
• 3731-53-1 4-(aminomethyl)pyridine 
• 5470-11-1 hydroxylamine hydrochloride 

Downstream Products

• 52482-30-1 1-[(6R)-2-carboxy-8-oxo-7t-((R)-2-phenyl-2-sulfo-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl]-4-(hydroxyimino-methyl)-pyridinium betaine 
• 79134-00-2 C₁₆H₂₁N₃O⁽²⁺⁾*2I^(1-) 
• 78282-65-2 1-benzyl-4-((hydroxyimino)methyl)pyridine-1-ium bromide 
• 117983-02-5 1-<(3'-butyn-1'-yloxy)methyl>-4-<(hydroxyimino)methyl>pyridinium chloride 
• 23974-15-4 N-(4-Pyridinylmethyl)acetamide 
• 62036-67-3 4-hydroxyiminomethyl-1-dodecyl pyridinium bromide 
• 872-85-5 pyridine-4-carbaldehyde 
• 100-48-1 pyridine-4-carbonitrile 
• 3731-53-1 4-(aminomethyl)pyridine 
• 2127-14-2 4-PAM 
• 57980-42-4 4-Pyridinecarbaldehyde oxime O-methyl ether 
• 1453-82-3 isonicotinamide 
• 3852-72-0 obidoxime 
• 28172-18-1 (E)-1,4-bis(4-hydroxyiminomethylpyridinium)but-2-ene dibromide 

Relevant academic research and scientific papers

Catalytic Detoxification of Organophosphorus Nerve Agents by Butyrylcholinesterase-Polymer-Oxime Bioscavengers

Organophosphorus nerve agents (OPNAs), used in chemical warfare, irreversibly inhibit essential cholinesterases (ChEs) in the cholinergic neurotransmission system. Several potent nucleophilic oximes have been approved for the treatment of acute poisoning by OPNAs, but they are rapidly cleared from blood circulation. Butyrylcholinesterase (BChE) stoichiometrically binds nerve agents, but because the molecular weight of a nerve agent is about 500-fold less than the enzyme, the bioscavenger has had limited utility. We synthesized BChE-polymer-oxime conjugates using atom transfer radical polymerization (ATRP) and azide-alkyne "click"chemistry. The activity of the BChE-polymer-oxime conjugates was dependent on the degree of oxime loading within the copolymer side chains. The covalent modification of oxime-containing copolymers prolonged the activity of BChE in the presence of the VX-and cyclosarin-fluorogenic analogues EMP-MeCyC and CMP-MeCyC, respectively. After complete inactivation by VX and cyclosarin fluorogenic analogues, the conjugates demonstrated efficient self-reactivation of up to 80% within 3-6 h. Repeated inhibition and high-level self-reactivation assays revealed that the BChE-polymer-oxime conjugates were excellent reactivators of OPNA-inhibited BChE. Recurring self-reactivation of BChE-polymer-oxime conjugates following repeated BChE inhibition by fluorogenic OPNAs (Flu-OPNAs) opens the door to developing the next generation of nerve agent "catalytic"bioscavengers.

Novel pyridinium oximes: Synthesis, molecular docking and in vitro reactivation studies

A computational approach has been attempted for the screening of 4-pyridoxinium (4P) ring based reactivators for paraoxon inhibited AChE. The oxime molecules were designed with the common 4P skeleton and varying the carbon linkers. Initially, the AChE binding capability was assessed by molecular docking with PDB:2WHP and 3ZLV, which showed important interactions with Ser298, Try124 and Trp286. These computational results were validated by an in vitro AChE binding assay, which showed binding affinities in the range of 10-90%. Finally, reactivation potency was calculated as % reactivation on paraoxon inhibited eelAChE in the concentration range of 10-5 to 10-7 M. It was observed that introduction of an aliphatic linker attached to 4-pyridoxime has a high binding affinity and hence, may act as a good reactivator as compared to the aromatic pyridoximes.

Synthesis and SAR study of simple aryl oximes and nitrofuranyl derivatives with potent activity against Mycobacterium tuberculosis

Background: Oximes and nitrofuranyl derivatives are particularly important compounds in medicinal chemistry. Thus, many researchers have been reported to possess antibacterial, antiparasitic, insecticidal and fungicidal activities. Methods: In this work, we report the synthesis and the biological activity against Mycobacterium tuberculosis H37RV of a series of fifty aryl oximes, ArCH=N-OH, I, and eight nitrofuranyl compounds, 2-nitrofuranyl-X, II. Results: Among the oximes, I: Ar = 2-OH-4-OH, 42, and I: Ar = 5-nitrofuranyl, 46, possessed the best activity at 3.74 and 32.0 μM, respectively. Also, 46, the nitrofuran compounds, II; X = MeO, 55, and II: X = NHCH2Ph, 58, (14.6 and 12.6 μM, respectively), exhibited excellent biological activities and were non-cytotoxic. Conclusion: The compound 55 showed a selectivity index of 9.85. Further antibacterial tests were performed with compound 55 which was inactive against Enterococcus faecalis, Klebisiella pneumonae, Pseudomonas aeruginosa, Staphylococcus aureus, Salmonella typhymurium and Shigel-la flexneri. This study adds important information to the rational design of new lead anti-TB drugs. Structure-activity Relationship (SAR) is reported.

Synthesis and in vitro evaluation of neutral aryloximes as reactivators of Electrophorus eel acetylcholinesterase inhibited by NEMP, a VX surrogate

Casualties caused by nerve agents, potent acetylcholinesterase inhibitors, have attracted attention from media recently. Poisoning with these chemicals may be fatal if not correctly addressed. Therefore, research on novel antidotes is clearly warranted. Pyridinium oximes are the only clinically available compounds, but poor penetration into the blood-brain barrier hampers efficient enzyme reactivation at the central nervous system. In searching for structural factors that may be explored in SAR studies, we synthesized and evaluated neutral aryloximes as reactivators for acetylcholinesterase inhibited by NEMP, a VX surrogate. Although few tested compounds reached comparable reactivation results with clinical standards, they may be considered as leads for further optimization.

Novel design of recyclable copper(II) complex supported on magnetic nanoparticles as active catalyst for Beckmann rearrangement in poly(ethylene glycol)

Copper complex-functionalized magnetic core–shell nanoparticles (Fe3O4@SiO2-Lig-Cu) were prepared and characterized using various techniques. The activity of the new catalyst was tested for the Beckmann rearrangement. The reaction conditions allow for the conversion of a wide variety of aldoximes, including aromatic and heterocyclic ones, to amides in good to excellent yields. High efficiency, mild reaction conditions, easy work-up, use of poly(ethylene glycol) as a green medium and simple purification of products are important advantages of this system. Moreover, the eco-friendly heterogeneous nanocatalyst could be easily recovered from the reaction mixture using an external magnet and reused several times.

Asymmetric Nitrone Synthesis via Ligand-Enabled Copper-Catalyzed Cope-Type Hydroamination of Cyclopropene with Oxime

We report realization of the first enantioselective Cope-type hydroamination of oximes for asymmetric nitrone synthesis. The ligand promoted asymmetric cyclopropene "hydronitronylation" process employs a Cu-based catalytic system and readily available starting materials, operates under mild conditions and displays broad scope and exceptionally high enantio- and diastereocontrol. Preliminary mechanistic studies corroborate a CuI-catalytic profile featuring an olefin metalla-retro-Cope aminocupration process as the key C-N bond forming event. This conceptually novel reactivity enables the first example of highly enantioselective catalytic nitrone formation process and will likely spur further developments that may significantly expedite chiral nitrone synthesis.

Five-membered azole heterocyclic compound and its preparation method, pharmaceutical composition and use thereof

The present invention relates to a five-membered azole heterocycle compound represented by the following general formula (I), a preparation method of the five-membered azole heterocycle compound, a drug composition of the five-membered azole heterocycle compound, and a use of the five-membered azole heterocycle compound in preparation of drugs for prevention or treatment of TGR5-mediated diseases. The formula (I) is represented by the instruction.

Copper(ii)-promoted direct conversion of methylarenes into aromatic oximes

A simple and efficient catalytic system for direct conversion of methylarenes into aromatic oximes has been developed, with Cu(OAc)2 as catalyst, NHPI (N-Hydroxyphthalimide) as additive, TBN (tert-butyl nitrite) as both the nitrogen source and the oxidant. This process proceeds under mild conditions, tolerates a wide range of substrates, affording the targeted aromatic oximes in 63-86% yields.

Copper(II)-promoted direct conversion of methylarenes into aromatic oximes

A simple and efficient catalytic system for direct conversion of methylarenes into aromatic oximes has been developed, with Cu(OAc)2 as catalyst, NHPI (N-Hydroxyphthalimide) as additive, TBN (tert-butyl nitrite) as both the nitrogen source and the oxidant. This process proceeds under mild conditions, tolerates a wide range of substrates, affording the targeted aromatic oximes in 63-86% yields.

Effective conversion of heteroaromatic ketones into primary amines via hydrogenation of intermediate ketoximes

A process to access heteroaromatic primary amines from the corresponding heteroaromatic ketones has been developed. A broad range of previously reported methods to convert ketones to primary amines was examined on heterocyclic ketones without success, including Leuckart-Wallach conditions, borane reductions, and transition-metal-catalyzed hydrogenations. Unique among the catalysts examined, Raney cobalt produced the desired primary heterocyclic amine. Raney cobalt hydrogenation of structurally varied heterocyclic ketoximes was demonstrated to form primary amines in good selectivity under mild conditions, and the products are easily isolated in high yield. Additionally, this is the first report of a systematic evaluation of the capabilities of Raney cobalt as an oxime hydrogenation catalyst.