1874-41-5

Usage

Uses

Used in Organic Synthesis and Medicinal Chemistry:
2-(3-Methoxyphenyl)-5-phenyl-1,3,4-oxadiazole is used as a building block in organic synthesis and medicinal chemistry for the synthesis of various biologically active compounds. Its unique structure allows for the creation of diverse molecules with potential therapeutic applications.
Used in Anti-Inflammatory and Antibacterial Applications:
In the pharmaceutical industry, 2-(3-Methoxyphenyl)-5-phenyl-1,3,4-oxadiazole is used as an anti-inflammatory and antibacterial agent. Its potential pharmacological properties make it a promising candidate for the development of new drugs to treat inflammation and bacterial infections.
Used as a Fluorescent Marker in Research:
2-(3-Methoxyphenyl)-5-phenyl-1,3,4-oxadiazole is used as a fluorescent marker in biological and chemical research. Its fluorescent properties allow researchers to track and visualize various biological processes and chemical reactions, contributing to a better understanding of these phenomena.

InChI:InChI=1/C15H12N2O2/c1-18-13-9-5-8-12(10-13)15-17-16-14(19-15)11-6-3-2-4-7-11/h2-10H,1H3

Upstream product

• 7154-74-7 N'-benzoyl-3-methoxybenzohydrazide 
• 73096-36-3 5-(3-methoxyphenyl)-1H-tetrazole 
• 98-88-4 benzoyl chloride 
• 5785-06-8 3-methoxybenzoic hydrazide 
• 93-97-0 benzoic acid anhydride 
• 119072-55-8 tert-butylisonitrile 
• 766-85-8 3-methoxy-1-iodobenzene 
• 613-94-5 benzoic acid hydrazide 
• 65-85-0 benzoic acid 
• 26767-10-2 2-(3-methoxyphenyl)glyoxylic acid 
• 591-50-4 iodobenzene 

Relevant academic research and scientific papers

The preparation, characterization and catalytic activity of Ni NPs supported on porous alginate-g-poly(p-styrene sulfonamide-co-acrylamide)

Herein, we report the synthesis of nickel nanoparticles under mild conditions using porous alginate-g-poly(p-styrene sulfonamide-co-acrylamide) as a protecting/stabilizing agent and sodium borohydride as a reducing agent. The porous cross-linked polymeric support was preparedviacombining the use of sol-gel, nanocasting, and crosslinking techniques, in which thep-styrene sulfonamide monomer (PSSA) andN,N′-methylene-bis (acrylamide) (MBA) cross-linker underwent copolymerization on the surface of sodium alginate in the presence of a SiO2nanoparticle (NP) template (Alg-PSSA-co-ACA). The prepared catalyst (Alg-PSSA-co-ACA@Ni) showed high catalytic activity for the one-step synthesis of 1,3,4-oxadiazoles from the reaction of hydrazides and aryl iodides through isocyanide insertion/cyclization.

One-pot cyclization/decarboxylation of α-keto acids and acylhydrazines for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles under transition-metal-free conditions

A one-pot KI/TBHP-mediated oxidative cyclization of α-keto acids with acylhydrazines was developed. A series of functional 2,5-disubstituted 1,3,4-oxadiazoles were synthesized through a tandem keto amine condensation followed by oxidative cyclization and decarboxylation reactions. This procedure was achieved under transition-metal-free conditions and showed advantages including readily available materials, mild reaction conditions and good group tolerance.

2,5-Diaryloxadiazoles and their precursors as novel inhibitors of cathepsins B, H and L

High levels of cathepsins indicated in various pathological conditions like arthritis, cancer progressions, and atherosclerosis explains the need to explore potential inhibitors of these proteases which can be of great therapeutic significance. We, in the present work, report the synthesis of some 2,5-diaryloxadiazoles from N-subsitutedbenzylidenebenzohydrazides. The synthesized compounds were screened for their inhibitory potential on cathepsins B, H and L. Structure Activity Relationship studies show that 2,5-diaryloxadiazoles were less inhibitory than their precursors. 1i and 2k have been found to be most inhibitory to cathepsins B and L. Their Ki values have been calculated as 11.38 × 10-8 M and 66.4 × 10-8 M for cathepsin B and 4.2 × 10-9 M and 47.31 × 10-9 M for cathepsin L, respectively. However, cathepsin H activity was maximally inhibited by compounds, 1e and 2c with Ki values of 4.4 × 10-7 M and 5.6 × 10-7 M, respectively. Enzyme kinetic studies suggest that these compounds are competitive inhibitors to the enzymes. The results have been compared with docking results obtained using iGemDock.

Palladium-catalyzed one-pot synthesis of diazoles via tert-butyl isocyanide insertion

An efficient one-pot palladium-catalyzed reaction for the synthesis of diazoles from readily available hydrazides and aryl halide via isocyanide insertion/cyclization sequence has been developed. This methodology efficiently constructs diazoles in good to excellent yields with the advantages of wide functional group tolerance and operational simplicity.

2,4,6-Tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine as a new recyclable hypervalent iodine(III) reagent for chlorination and oxidation reactions

The synthesis of 2,4,6-tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine, as a new recyclable nonpolymeric analogue of (dichloroiodo)benzene, is achieved in two steps using 2,4,6-trichloro-1,3,5-triazine and 4-iodophenol. The application of 2,4,6-tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine for the chlorination reaction of various activated arenes, olefin, and 1,3-diketone is demonstrated. The reagent 2,4,6-tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine can be applied also for the oxidative synthesis of 1,3,4-oxadiazoles and 1,2,4-thiadiazoles under mild conditions in excellent yields. The recyclability of the 2,4,6-tris[(4-dichloroiodo)phenoxy)]-1,3,5-triazine was possible owing to the facile recovery and reuse of the coproduced 2,4,6-tris(4-iodophenoxy)-1,3,5- triazine from the reaction mixture due to its practical insolubility in methanol. Georg Thieme Verlag Stuttgart, New York.

1,3,4-Oxadiazole formation as traceless release in solid phase organic synthesis

Oxadiazoles were generated upon a dehydrative cyclization reaction with 2-acyl hydrazides bound to the polymeric support via one of their N atoms using TFAA as a dehydration agent.

The Hydroxy Derivatives of 2,5-Diphenyl-1,3,4-oxadiazole

An unambiguous synthesis for each of the monohydroxy derivatives of 2,5-diphenyl-1,3,4-oxadiazole is reported.