3213-99-8

Usage

Chemical family

Oxadiazole family

Physical state

White to off-white solid

Solubility

Insoluble in water

Common use

Building block in the synthesis of pharmaceutical and agrochemical products

Biological activities

a. Antifungal
b. Antituberculosis
c. Anticonvulsant

Potential applications

Medicinal chemistry and drug development

Diverse properties

Contributes to its use in various fields and applications

Upstream product

• 107465-71-4 N-phenylacetyl-benzimidic acid ethyl ester 
• 2566-22-5 DL-N-benzoylphenylalanine 
• 140-29-4 phenylacetonitrile 
• 19227-11-3 N'-hydroxy-2-phenylethanimidamide 
• 98-88-4 benzoyl chloride 
• 100-52-7 benzaldehyde 
• 65-85-0 benzoic acid 
• 201230-82-2 carbon monoxide 
• 19227-11-3 (Z)-N'-hydroxy-2-phenylacetimidamide 
• 70541-10-5 N-benzoyl-N-nitroso-DL-phenylalanine 
• 98283-97-7 N-benzoyloxy-2-phenyl-acetamidine 

Downstream Products

• 80823-83-2 N-(4-Ethyl-phenyl)-N'-[1-phenyl-1-(5-phenyl-[1,2,4]oxadiazol-3-yl)-meth-(Z)-ylidene]-hydrazine 
• 4765-56-4 glycosminine 
• 116751-89-4 1-Benzoyl-3-benzyl-2-methyl-isourea 
• 116751-87-2 N-{1-[(Z)-Methoxyimino]-2-phenyl-ethyl}-benzamide 

Relevant academic research and scientific papers

Beyond direct Nrf2 activation; reinvestigating 1,2,4-oxadiazole scaffold as a master key unlocking the antioxidant cellular machinery for cancer therapy

Harnessing the antioxidant cellular machinery has sparked considerable interest as an efficient anticancer strategy. Activating Nrf2, the master switch of the cellular redox system, suppresses ROS, alleviates oxidative stress, and halts cancer progression

An Efficient Synthesis of Functionalized 2 H -1,3,5-Oxadiazines via Metal-Carbenoid-Induced 1,2,4-Oxadiazole Ring Cleavage

A high-yielding method for the synthesis of 2 H -1,3,5-oxadiazines by rhodium(II)- or copper(II)-catalyzed reaction of 1,2,4-oxadiazoles with α-diazo esters has been developed. The reaction proceeds via attack of the metallocarbenoid on the oxadiazole N2 atom followed by ring opening/1,6-electrocyclization and enables the introduction of alkyl, aryl, oxy, and amino substituents into the 6-position and electron-withdrawing groups into the 2-position of 1,3,5-oxadiazine. The N2-attack and the N4-attack of the carbenoid cause different oxadiazole ring openings, which are controlled by the substitution at C5. The presence of a substituent at this position is a prerequisite for the N2-attack to occur, leading to the formation of 1,3,5-oxadiazines.

Synthesis of 3,5-Disubstituted 1,2,4-Oxadiazoles from Amidoximes and Aldehydes in the Superbasic System NaOH/DMSO

Abstract: A new procedure has been proposed for the synthesis of 3,5-disubstituted 1,2,4-oxadiazoles by reaction of amidoximes with aldehydes in the superbasic system NaOH/DMSO at room temperature. The scope of the proposed procedure has been demonstrated by 15 syntheses from various amidoximes and aromatic aldehydes with 27–76% yields. The procedure is inapplicable to aliphatic aldehydes.

Synthesis and evaluation of 1,2,4-oxadiazole derivatives as potential anti-inflammatory agents by inhibiting NF-κB signaling pathway in LPS-stimulated RAW 264.7 cells

In this study, a series of compounds with 1,2,4-oxadiazole core was designed and synthesized for the optimization of JC01, an anti-inflammatory hit identified from our in-house compound library using NF-κB pathway luciferase assay and NO production assay.

One-pot synthesis of 1,2,4-oxadiazoles from carboxylic acids using 4-(dimethylamino)pyridinium acetate as efficient, regenerable, and green catalyst with ionic liquid character

A recyclable bifunctional acid-base organocatalyst with ionic liquid character has been prepared and its catalytic activity for the preparation of oxadiazoles has been investigated.

Hypervalent iodine in synthesis. 75. A convenient synthesis of oxadiazoles by palladium-catalyzed carbonylation and cyclization of diaryliodonium salts and amidoximes

3,5-Disubstituted-1,2,4-oxadiazoles were prepared in one-pot procedure in moderate yields via the palladium-catalyzed carbonylation of diaryliodonium salts with amidoximes under one atmosphere of carbon monoxide followed by intramolecular dehydrative cycl

Phosphonic acid derivatives as inhibitors of protein tyrosine phosphatase 1B (PTP-1B)

The invention encompasses the novel class of compounds represented by formula I, which are inhibitors of the PTP-1B enzyme. The invention also encompasses pharmaceutical compositions and methods of treating or preventing PTP-1B mediated diseases, including diabetes, obesity, and conditions related to diabetes.

THE PHOTOELIMINATION OF N-NITROSO-N-ACETYL-α-AMINO-ACIDS; A NEW SYNTHESIS OF 1,2,4-OXADIAZOLES

The excitation of N-nitroso-N-acetyl-α-aminoacids, nitrosopeptide model compounds, under neutral and weakly basic conditions, caused the homolysis of the N-N bond followed by decarboxylation to give hyponitrous acid (HNO) and N-acetylimines which were susceptible to nucleophilic addition.While weak bases caused the carboxylate group to assist intramolecular rearrangement to a small extent, they functioned primarily to provide nucleophilic NO-, which initiated nucleophilic attack leading to the C-nitroso derivatives.These C-nitroso derivatives spontaneously cyclized to 1,2,4-oxadiazoles much more rapidly than tautomerism to the corresponding oximes; the latter oximes failed to cyclize under the basic conditions.