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General Description

2-(4-Chlorophenyl)-5-phenyl-1,3,4-oxadiazole is a chemical compound with the molecular formula C14H8ClN3O. It belongs to the oxadiazole class of compounds, which are known for their diverse biological activities and potential applications in pharmaceuticals and agrochemicals. This particular compound has been studied for its potential as an anti-cancer agent, and has shown promising results in inhibiting the growth of tumor cells. It also exhibits fluorescent properties, making it useful for applications in the field of materials science. Additionally, it has been investigated for its potential as an anti-microbial and anti-inflammatory agent. The compound's unique structure and potential biological activities make it a subject of ongoing research in the field of medicinal chemistry and drug discovery.

Upstream product

• 31061-79-7 benzoic acid (4-chlorobenzylidene)hydrazide 
• 104-88-1 4-chlorobenzaldehyde 
• 613-94-5 benzoic acid hydrazide 
• 100-52-7 benzaldehyde 
• 536-40-3 4-chlorobenzoic acid hydrazide 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 65-85-0 benzoic acid 
• 93-58-3 benzoic acid methyl ester 
• 122-01-0 4-chloro-benzoyl chloride 
• 100-47-0 benzonitrile 
• 873-76-7 para-Chlorobenzyl alcohol 
• 611-74-5 N,N-dimethylbenzamide 
• 7099-88-9 4-chlorophenylglyoxylic acid 
• 611-73-4 Benzoylformic acid 

Relevant academic research and scientific papers

Neuroprotective evaluation of novel substituted 1,3,4-oxadiazole and aroylhydrazone derivatives

The paper reports on the facile and convenient synthesis of a series of novel 2,5-substituted 1,3,4-oxadiazoles 3a-f and that of aroylhydrazone-based molecular hybrids 5a-g from readily available starting materials. The structure of the compounds was confirmed by IR, 1H NMR, 13C NMR and HRESI-MS spectral data. The toxicological potential of the compounds was evaluated by monitoring the synaptosomal viability and the levels of reduced glutathione in rat brain synaptosomes, isolated by Percoll gradient. The neuroprotective effects were assessed in vitro in a model of 6-hydroxydopamine-induced neurotoxicity. Administered alone, at a concentration of 40 μM, most of the 1,3,4-oxadiazole derivatives and all of the hydrazone derivatives exhibited weak statistically significant neurotoxic effects, compared to the control. Two of the compounds from the novel oxadiazoles 3a and 3d did not have any toxicity. In a model of 6-OHDA-induced oxidative stress, again 3a and 3d and all aroylhydrazone derivatives 5a-g revealed statistically significant neuroprotective effect by preserving the synaptosomal viability and the level of reduced glutathione, against the toxic agent. Some of the compounds may have neuroprotective effects due to possible stabilization of the synaptosomal membrane and/or because of the preserved reduced glutathione. Additionally, all the compounds display a good predicted ADME profile.

Design, synthesis, modelling studies and biological evaluation of 1,3,4-oxadiazole derivatives as potent anticancer agents targeting thymidine phosphorylase enzyme

A series of novel 1,3,4-oxadiazole derivatives with substituted phenyl ring were designed and synthesized with an objective of discovering newer anti-cancer agents targeting thymidine phosphorylase enzyme (TP). The 1,3,4-oxadiazole derivatives were synthesized by simple and convenient methods in the lab. Chemical structure of the all the synthesized compounds were characterized by IR, 1H NMR and mass spectral methods and evaluated for cytotoxicity by MTT method against two breast cancer cell lines (MCF-7 and MDA-MB-231). Further, results of TP assay identified that 1,3,4-oxadiazole molecules displayed anti-cancer activity partially by inhibition of phosphorylation of thymidine. The TP assay identified SB8 and SB9 as potential inhibitors with anti-cancer activity against both the cell lines. The molecular docking studies recognized the orientation and binding interaction of molecule at the active site amino acid residues of TP (PDB: 1UOU). Acute toxicity studies of compound SB8 at the dose of 5000 mg/kg has identified no signs of clinical toxicity was observed. The SARs study of synthesized derivatives revealed that the substitution of phenyl ring with electron withdrawing group at ortho position showed significant TP inhibitory activity compared to para substitution. The experimental data suggests that 1,3,4-oxadiazole with substituted phenyl can be taken as a lead for the design of efficient TP inhibitors and active compounds which can be taken up for further studies.

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.

COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME

The present specification provides a compound represented by chemical formula 1 and an organic light emitting device including the same. The compound may improve lifespan characteristics of the organic light emitting device.

Electrochemical Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles from α-Keto Acids and Acylhydrazines Under Mild Conditions

1,3,4-Oxadiazoles are a kind of useful heterocycles which can be frequently found in materials and bioactive molecules. In this study, intermolecular electrochemical cyclization between α-keto acids and acylhydrazines has been developed for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles with the yield up to 91 %. This transformation can be run under mild reaction conditions in the absence of external oxidant, base and transition metal catalyst. Both symmetrical and unsymmetrical 2,5-disubstituted 1,3,4-oxadiazoles could be prepared according to the careful choice of the substrate combination. Gram scale synthesis also illustrates the potential application of this protocol in large preparation.

Harnessing Autoxidation of Aldehydes: In Situ Iodoarene Catalyzed Synthesis of Substituted 1,3,4-Oxadiazole, in the Presence of Molecular Oxygen

Isobutyraldehyde underwent auto-oxidation in the presence of molecular oxygen to generate an acyloxy radical under a "metal-free" environment. They were subsequently exploited in situ to afford hypervalent iodines with p-anisolyl iodide which generated substituted 1,3,4-oxadiazoles in moderate to excellent yields from N′-arylidene acetohydrazides. The reaction strategy tolerated diverse substitution on the hydrazide substrates. Control experiments and literature precedence supported the formation of an in situ iodosylarene complex that facilitates the formation of products.

Microwave-mediated Green synthesis of oxadiazole derivatives against inflammatory disease

A rapid and efficient microwave-mediated Green synthesis of oxadiazole derivatives (2a-e) is described based on reaction between benzohydrazide and various substituted benzoic acids. The use of microwave irradiation to carry out chemical reactions provide

Photocatalyzed facile synthesis of 2,5-diaryl 1,3,4-oxadiazoles with polyaniline-?g-C3N4-TiO2 composite under visible light

PANI (polyaniline)-g-C3N4-TiO2 composite was prepared and found to be efficient for the synthesis of 2,5-diaryl 1,3,4-oxadiazoles under visible light. This reaction involved decarboxylation and cyclization from α-keto acids with acylhydrazines, and a broad scope of substrates were tolerated to provide the desired products in moderate to good yields. Control experiments indicated that a radical pathway was involved in the present photocatalytic reaction and a synergistic effect may exist in the ternary composite. Moreover, this semiconductor photocatalyst could be readily recovered and showed good reusability with only slight decrease in the catalytic activity after six consecutive runs.

Synthesis of 2,5-disubstituted 1,3,4-oxadiazoles by visible-light-mediated decarboxylation–cyclization of hydrazides and diketones

A visible-light-induced synthesis of 2,5-disubstituted 1,3,4-oxadiazoles from simple diketones and hydrazides with the assistant of the photocatalyst eosin Y catalyzed decarboxylation and cyclization under mild conditions has been discovered. The reaction tolerates a wide range of functional groups and gives a variety of valuable 1,3,4-oxadiazoles in moderate to good yields. Finally, a plausible reaction mechanism was proposed.

Three-component synthesis method of oxadiazole compound

The invention relates to a synthesis method of an oxadiazole compound shown in formula (III). The method comprises steps as follows: a compound shown in formula (1), a compound shown in formula (II) and an amine source compound react at 80-100 DEG C for 6-10 h in the presence of an organic solvent, a catalyst, base and an additive, after-treatment is performed after the reaction ends, and the compound shown in formula (III) is obtained, wherein R1 is C1-C6 alkyl groups, phenyl groups or phenyl groups substituted with substitute groups, substitute groups are C1-C6 alkyl groups, C1-C6 alkoxy groups or halogen, and R2 is H, C1-C6 alkyl groups, C1-C6 alkoxy groups or halogen. A specific three-component reaction system is adopted in the method, comprehensive synergism of a specific catalytic system is combined, so that a target product can be obtained at the high yield, and the method has good application prospect and value.