19227-13-5

Usage

Uses

Used in Pharmaceutical Industry:
4-Methylbenzamide oxime is used as a building block in drug discovery chemistry for its potential to contribute to the development of new pharmaceutical compounds.
Used in Chemical Synthesis:
4-Methylbenzamide oxime is used as a reactant in the preparation of naphthyridine-based polycyclic hetarenes from N-hydroxybenzamidines and alkynes, contributing to the synthesis of complex organic molecules.

InChI:InChI=1/C11H15NO2/c1-12-11(7-10(8-13)14-12)9-5-3-2-4-6-9/h2-6,10-11,13H,7-8H2,1H3

Upstream product

• 67-56-1 methanol 
• 104-85-8 para-methylbenzonitrile 
• 75-05-8 acetonitrile 
• 121-44-8 triethylamine 
• 41110-16-1 C₁₅H₁₄N₂O₂ 
• 68451-87-6 C₁₅H₁₃ClN₂O₂ 
• 68451-93-4 O-(p-Nitrobenzoyl)-para-tolylamidoxime 
• 125324-43-8 (3aR,9aR)-3,8-Di-p-tolyl-3a,9a-dihydro-5aH-isoxazolo[4,5-e][1,2,4]oxadiazolo[4,5-a]pyridine 
• 125338-27-4 3-p-Tolyl-5-[(E)-2-(3-p-tolyl-isoxazol-4-yl)-vinyl]-4,5-dihydro-[1,2,4]oxadiazole 
• 68451-80-9 C₁₆H₁₆N₂O₃ 
• 5470-11-1 hydroxylamine hydrochloride 
• 104-87-0 4-methyl-benzaldehyde 
• 3235-02-7 p-methylbenzaldehyde oxime 

Downstream Products

• 20069-37-8 3-(4-tolyl)-1,2,4-thiadiazole-5-(2H)-thione 
• 31827-21-1 N-ethoxycarbonyloxy-4-methyl-benzamidine 
• 110449-27-9 5-acetonyl-3-(p-tolyl)-1,2,4-oxadiazole 
• 126868-27-7 5-methyl-3-(p-tolyl)-1,2,4-oxadiazole 
• 58589-02-9 2-(3-(p-tolyl)-1,2,4-oxadiazol-5-yl)aniline 
• 91393-16-7 ethyl 3-(4-methylphenyl)-1,2,4-oxadiazole-5-carboxylate 
• 5373-86-4 3-p-tolyl-5-trichloromethyl-[1,2,4]oxadiazole 
• 31827-21-1 C₁₁H₁₄N₂O₃ 
• 77533-93-8 5,5-pentamethylene-3-p-tolyl-Δ²-1,2,4-oxadiazoline 
• 111457-47-7 6-Methyl-3-p-tolyl-4H-[1,2,4]oxadiazin-5-one 
• 111457-54-6 C₁₁H₁₃ClN₂O₂ 
• 75886-54-3 (E)-2-[(4-Methyl-benzimidoyl)-aminooxy]-but-2-enedioic acid dimethyl ester 
• 41110-16-1 O-Benzoyl-p-methyl-benzamidoxim 
• 68451-93-4 O-(p-Nitro-benzoyl)-p-methyl-benzamidoxim 

Relevant academic research and scientific papers

Synthesis and analgesic profile of novel N-containing heterocycle derivatives: Arylidene 3-phenyl-1,2,4-oxadiazole-5-carbohydrazide

This paper describes recent results of a research program aimed at the synthesis and pharmacological evaluation of new heterocyclic N-acylhydrazone (NAH) compounds, belonging to the arylidene (3-phenyl)-1,2,4-oxadiazolyl-5- carboxyhydrazide (8a-p) series.

1,2,4-Oxadiazole ring–containing pyridylpyrazole-4-carboxamides: Synthesis and evaluation as novel insecticides of the anthranilic diamide family

Herein, we describe the preparation of pyridylpyrazole-4-carboxamides containing a 1,2,4-oxadiazole ring as novel anthranilic diamide derivatives and compare their insecticidal activities to that of chlorantraniliprole, a well-established potent insectici

Discovery of 1,2,4-oxadiazole derivatives as a novel class of noncompetitive inhibitors of 3-hydroxykynurenine transaminase (HKT) from Aedes aegypti

The mosquito Aedes aegypti is the vector of arboviruses such as Zika, Chikungunya, dengue and yellow fever. These infectious diseases have a major impact on public health. The unavailability of effective vaccines or drugs to prevent or treat most of these

Boron tribromide mediated debenzylation of benzylamino and benzyloxy groups

The treatment of 2(or 4)-benzylamino substituted quinolines, 9-benzylaminoacridine, 2-benzylaminopyridine, a 4-benzyloxyquinoline, and an N-benzyloxyamidine with BBr3 yields the corresponding amino or hydroxy substituted compounds. The scope and limitations of this novel reaction are discussed.

Synthesis and Biological Screening of Novel 5-(5-Aryl-1-phenyl-1H-pyrazol-3-yl)-3-aryl-1,2,4-oxadiazole Derivatives

A new series of 5-(5-aryl-1-phenyl-1H-pyrazol-3-yl)-3-aryl-1,2,4-oxadiazole (6a-o) have been synthesized by a cyclocondensation reaction of ethyl 5-(4-chlorophenyl)-1-phenyl-1H-pyrazole-3-carboxylate (3a-c) with aryl imidoxime (5a-e). The newly synthesize

Synthesis, spectroscopic characterization and DNA/HSA binding studies of (phenyl/naphthyl)ethenyl-substituted 1,3,4-oxadiazolyl-1,2,4-oxadiazoles

Two new series of conjugated arylethenyl-1,3,4-oxadiazolyl-1,2,4-oxadiazoles were obtained and spectroscopically characterized in terms of UV-Vis absorption, fluorescence and interaction with CT-DNA and Human Serum Albumin (HSA) biomolecules. Phenyl- and 1-naphthyl-bearing examples were analysed, and the spectroscopic properties of its substitution series were compared, showing extensive conjugation in all compounds and absorption differences due to both the aryl-ethenyl subunit and substituted phenyl/phenylene at the 1,2,4-oxadiazole side. Strong binding interactions of the obtained compounds with CT-DNA and moderate HSA-association capability were observed spectroscopically, and further docking studies were performed. This journal is

Cobalt-Catalyzed, Directed Intermolecular C-H Bond Functionalization for Multiheteroatom Heterocycle Synthesis: The Case of Benzotriazine

Transition-metal-catalyzed, directed intermolecular C-H bond functionalization is synthetically useful but heavily underexplored in multiheteroatom heterocycle synthesis. Herein we report a cobalt catalytic method for the formation of a three-nitrogen-bearing benzotriazine scaffold via the coupling of arylhydrazine and oxadiazolone. This synthetic protocol features a low-cost base metal catalyst, a maximum number of heteroatoms built into a heterocycle, a distinct synthetic logic for benzotriazines, a superior step economy, and a broad substrate scope.

Design, Synthesis, and Pesticidal Activities of Pyrimidin-4-amine Derivatives Bearing a 5-(Trifluoromethyl)-1,2,4-oxadiazole Moiety

It is important to discover new pesticides with new modes of action because of the increasing evolution of pesticide resistance. In this study, a series of novel pyrimidin-4-amine derivatives containing a 5-(trifluoromethyl)-1,2,4-oxadiazole moiety were designed and synthesized. Their structures were confirmed by 1H NMR, 13C NMR, and HRMS. Bioassays indicated that the 29 compounds synthesized possessed excellent insecticidal activity against Mythimna separata, Aphis medicagini, and Tetranychus cinnabarinus and fungicidal activity against Pseudoperonospora cubensis. Among these pyrimidin-4-amine compounds, 5-chloro-N-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)-6-(1-fluoroethyl)pyrimidin-4-amine (U7) and 5-bromo-N-(2-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)benzyl)-6-(1-fluoroethyl) pyrimidin-4-amine(U8) had broad-spectrum insecticidal and fungicidal activity. The LC50 values were 3.57 ± 0.42, 4.22 ± 0.47, and 3.14 ± 0.73 mg/L for U7, U8, and flufenerim against M. separata, respectively. The EC50 values were 24.94 ± 2.13, 30.79 ± 2.21, and 3.18 ± 0.21 mg/L for U7, U8, and azoxystrobin against P. cubensis, respectively. The AChE enzymatic activity testing revealed that the enzyme activities of compounds U7, U8, and flufenerim are 0.215, 0.184, and 0.184 U/mg prot, respectively. The molecular docking results of compounds U7, U8, and flufenerim with the AChE model demonstrated the opposite docking mode between compound U7 or U8 and positive control flufenerim in the active site of AChE. The structure-activity relationships are also discussed. This work provided excellent pesticide for further optimization. Density functional theory analysis can potentially be used to design more active compounds.

Novel 1,2,4-oxadiazole derivatives as selective butyrylcholinesterase inhibitors: Design, synthesis, and biological evaluation

Alzheimer’s disease (AD) is a progressive mental disorder that brings a huge economic burden to the healthcare systems. During this illness, acetylcholine levels in the cholinergic systems gradually diminish, which results in severe memory loss and cognitive impairments. Moreover, Butyrylcholinesterase (BuChE) enzyme participates in cholinergic neurotransmission regulation by playing a prominent role in the latter phase of AD. In this study, based on donepezil, which is an effective acetylcholinesterase (AChE) inhibitor, a series of 1,2,4-oxadiazole compounds were designed, synthesized and their inhibitory activities towards AChE and BuChE enzymes were evaluated. Some structures exhibited a higher selectivity rate towards BuChE in comparison to donepezil. Notably, compound 6n with an IC50 value of 5.07 μM and an SI ratio greater than 19.72 showed the highest potency and selectivity towards BuChE enzyme. The docking result revealed that compound 6n properly fitted the active site pocket of BuChE enzyme, and formed desirable lipophilic interactions and hydrogen bonds. Moreover, according to in silico ADME studies, these compounds have proper potential for being developed as new oral anti-Alzheimer’s agents.

Design, synthesis, and biological evaluation of 1,2,4-oxadiazole-containing pyrazolo[3,4-b]pyridinones as a new series of AMPKɑ1β1γ1 activators

Adenosine monophosphate-activated protein kinase (AMPK) plays a key role in maintaining whole-body homeostasis and has been regarded as a therapeutic target for the treatment of diabetic nephropathy (DN). Herein, a series of 1,2,4-oxadiazole-containing py