99367-44-9

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 5-(4-Methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate is used as a potential therapeutic agent for various medical applications due to its antimicrobial, anticancer, and anti-inflammatory properties. Its unique structure and biological activities make it a valuable compound for the development of new drugs and treatments.
Used in Antimicrobial Applications:
Ethyl 5-(4-Methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate is used as an antimicrobial agent to combat various bacterial and fungal infections. Its ability to inhibit the growth of pathogenic microorganisms makes it a promising candidate for the development of new antimicrobial drugs.
Used in Anticancer Applications:
Ethyl 5-(4-Methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate is used as an anticancer agent, targeting various types of cancer cells. Its potential to inhibit cancer cell growth and proliferation, as well as its ability to modulate oncological signaling pathways, make it a valuable compound for the development of novel cancer therapies.
Used in Anti-inflammatory Applications:
Ethyl 5-(4-Methoxyphenyl)-1,3,4-oxadiazole-2-carboxylate is used as an anti-inflammatory agent to alleviate inflammation and reduce the associated symptoms. Its potential to modulate inflammatory pathways and suppress the production of pro-inflammatory mediators make it a promising candidate for the development of new anti-inflammatory drugs.

Upstream product

• 3290-99-1 4-methoxybenzoic acid hydrazide 
• 4755-77-5 Ethyl oxalyl chloride 
• 7099-91-4 p-methoxybenzoylformic acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 121-98-2 methyl 4-methoxybenzoate 
• 100-07-2 4-methoxy-benzoyl chloride 
• 57844-36-7 ethyl 2-(2-(4-methoxybenzoyl)hydrazinyl)-2-oxoacetate 
• 107469-65-8 Amino-[(4-methoxy-benzoyl)-hydrazono]-acetic acid ethyl ester 

Downstream Products

• 99367-50-7 5-(4-Methoxy-phenyl)-[1,3,4]oxadiazole-2-carboxylic acid amide 
• 99367-60-9 5-(4-Methoxy-phenyl)-[1,3,4]oxadiazole-2-carboxylic acid hydrazide 
• 1254035-84-1 [5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]-[3-[4-(2-oxa-6-azaspiro[3.3]heptan-6-ylmethyl)-phenoxy]azetidin-1-yl]methanone 
• 91445-72-6 2-bromomethyl-5-(4-methoxy-phenyl)-[1,3,4]oxadiazole 
• 54014-12-9 [5-(4-methoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-methanol 
• 99367-56-3 5-(4-Methoxy-phenyl)-[1,3,4]oxadiazole-2-carboxylic acid (2-hydroxy-ethyl)-amide 
• 1354791-58-4 (3-(4-((dimethylamino)methyl)phenoxy)-azetidin-1-yl)(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)methanone 
• 1354791-47-1 (3-(4-((dimethylamino)methyl)-3-fluorophenoxy)azetidin-1-yl)(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)methanone 
• 1354791-40-4 (3-{4-[(dimethylamino)methyl]-3-methylphenoxy}azetidin-1-yl)[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]methanone 

Relevant academic research and scientific papers

Synthesis method of 1, 3, 4-oxadiazole heterocyclic compound

The invention belongs to the technical field of organic synthesis and medicines, and particularly relates to a synthesis method of a 1, 3, 4-oxadiazole heterocyclic compound. The 1, 3, 4-oxadiazole heterocyclic compound is obtained by taking a benzaldehyde derivative and a diazonium trivalent iodine reagent as raw materials, taking dichloromethane as a solvent without any catalyst under illumination and carrying out reaction at room temperature. According to the method provided by the invention, the 1, 3, 4-oxadiazole heterocyclic derivative can be obtained by a one-step method under the condition of room temperature through reaction for 10-15 hours, and the yield is 48-89%. According to the reaction, the 1, 3, 4-oxadiazole heterocyclic derivative is simply, conveniently and rapidly synthesized in one step under the illumination condition by using simple and easily available raw materials, and a simple, efficient and mild novel synthesis method is provided for synthesizing the 1, 3, 4-oxadiazole heterocyclic derivative.

N-Heterocyclic Carbene-Catalyzed Cyclization of Aldehydes with α-Diazo Iodonium Triflate: Facile Access to 2,5-Disubstituted 1,3,4-Oxadiazoles

Herein, we report a novel organocatalytic process for synthesis of complex 1,3,4-oxadiazoles from readily accessible aldehydes. By exploiting the nucleophilicity of the putative Breslow intermediate and the inherent electrophilicity of α-diazo iodonium triflate, we have found that N-heterocyclic carbene catalyst promotes efficient cyclization of various aldehydes and α-diazo iodonium triflates. The reaction proceeds under mild conditions with a wide range of functional group tolerance. The heterocyclic products can be readily further functionalized, rendering the protocol highly valuable.

Design, synthesis, and biological evaluation of phenyloxadiazole derivatives as potential antifungal agents against phytopathogenic fungi

Abstract: A novel series of picarbutrazox-inspired oxadiazole hybrids was synthesized and the derivatives’ biological activity against phytopathogenic fungi was investigated. The molecules were designed by retaining the active fragment of tetrazolyl phenyloxime ether of lead compound picarbutrazox, while introducing the potentially active oxadiazole-derived fragment. Bioassay results revealed that some of the title compounds showed potent in vivo antifungal activities to control cucumber downy mildew. Therefore, this novel oxadiazole phenyloxadiazole derivative can be used as a potential antifungal agent to control cucumber downy mildew and other phytopathogenic fungi for crop protection. Graphic abstract: [Figure not available: see fulltext.].

Design, Synthesis, and Study of the Insecticidal Activity of Novel Steroidal 1,3,4-Oxadiazoles

A series of novel steroidal derivatives with a substituted 1,3,4-oxadiazole structure was designed and synthesized, and the target compounds were evaluated for their insecticidal activity against five aphid species. Most of the tested compounds exhibited potent insecticidal activity against Eriosoma lanigerum (Hausmann), Myzus persicae, and Aphis citricola. Compounds 20g and 24g displayed the highest activity against E. lanigerum, showing LC50 values of 27.6 and 30.4 μg/mL, respectively. Ultrastructural changes in the midgut cells of E. lanigerum were detected by transmission electron microscopy, indicating that these steroidal oxazole derivatives might exert their insecticidal activity by destroying the mitochondria and nuclear membranes in insect midgut cells. Furthermore, a field trial showed that compound 20g exhibited effects similar to those of the positive controls chlorpyrifos and thiamethoxam against E. lanigerum, reaching a control rate of 89.5% at a dose of 200 μg/mL after 21 days. We also investigated the hydrolysis and metabolism of the target compounds in E. lanigerum by assaying the activities of three insecticide-detoxifying enzymes. Compound 20g at 50 μg/mL exhibited inhibitory action on carboxylesterase similar to the known inhibitor triphenyl phosphate. The above results demonstrate the potential of these steroidal oxazole derivatives to be developed as novel pesticides.

Photoredox Catalysis Enables Decarboxylative Cyclization with Hypervalent Iodine(III) Reagents: Access to 2,5-Disubstituted 1,3,4-Oxadiazoles

A novel approach to 2,5-disubstituted 1,3,4-oxadiazoles derivatives via a decarboxylative cyclization reaction by photoredox catalysis between commercially available α-oxocarboxylic acids and hypervalent iodine(III) reagent is described. This powerful transformation involves the coupling reaction between two different kinds of radical species and the formation of C-N and C-O bonds.

Synthesis method of 1, 3, 4-oxadiazole heterocyclic compound

The invention belongs to the technical field of organic synthesis and medicines, and particularly relates to a synthesis method of a 1, 3, 4-oxadiazole heterocyclic compound. The method comprises thefollowing steps: by taking a ketonic acid derivative and

Oxidation of sp3C—H bonds in N-alkylhydrazides: Access to 2,5-disubstituted 1,3,4-oxadiazole derivatives

The oxidation of sp3C[sbnd]H bonds in N-alkylhydrazides was achieved en route to the efficient synthesis of a broad series of 1,3,4-oxadiazoles. Mechanistic studies have revealed that N-acylhydrazone is a key intermediate in this catalytic transformation.

One-Pot Synthesis of Decahydropyrene via Tandem C-H Activation/Intramolecular Diels-Alder/1,3-Dipolar Cycloaddition

A novel decahydropyrene synthesis has been successfully developed involving a tandem rhodium-catalyzed C-H activation/intramolecular Diels-Alder reaction/1,3-dipolar cycloaddition cascade process by using diazole as a traceless directing group. The advantage of this one-pot strategy is a quite simple, efficient, highly stereoselective, and unique product structure.

The Development of a Manufacturing Route to an MCHr1 Antagonist

Process development work to provide an efficient manufacturing route to a MCHr1 antagonist is presented herewith. Features of this development work include a scalable manufacturing route to the useful 6-oxa-2-azaspiro[3.3]heptane building block and the use of a (soluble) alternative to sodium triacetoxyborohydride.

Development of a Large-Scale Route to an MCH1 Receptor Antagonist: Investigation of a Staudinger Ketene-Imine Cycloaddition in Batch and Flow Mode

A practical large-scale route to an MCH1 receptor antagonist is described. A Staudinger β-lactam synthesis of an imine and an in situ generated ketene was utilized as a key step for the preparation of a spiro-azetidine building block. The reaction was demonstrated in both batch and flow mode and a comparison of these techniques is described.