950259-82-2

Upstream product

• 456-06-4 4-fluorobenzoyl hydrazide 
• 451-46-7 4-fluorobenzoic acid ethyl ester 
• 2251-76-5 2-(4-fluorophenyl)-2-oxoacetic acid 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 459-57-4 4-fluorobenzaldehyde 
• 4755-77-5 Ethyl oxalyl chloride 
• 403-43-0 4-fluorobenzoyl chloride 

Downstream Products

• 944898-08-2 C₉H₅FN₂O₃ 
• 1354791-23-3 (5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)(3-(4-(pyrrolidin-1-ylmethyl)phenoxy)azetidin-1-yl)methanone 
• 1254035-86-3 (3-(4-(2-oxa-6-azaspiro[3.3]heptan-6-ylmethyl)phenoxy)-azetidin-1-yl)(5-(4-fluorophenyl)-1,3,4-oxadiazol-2-yl)methanone 

Relevant academic research and scientific papers

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.

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.

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

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.

Design, synthesis and biological evaluation of new Axl kinase inhibitors containing 1,3,4-oxadiazole acetamide moiety as novel linker

Using the principle of bioisosteric replacement, we present a structure-based design approach to obtain new Axl kinase inhibitors with significant activity at the kinase and cellular levels. Through a stepwise structure-activity relationships exploration, a series of 6,7-disubstituted quinoline derivatives, which contain 1,3,4-oxadiazol acetamide moiety as novel Linker, were ultimately synthesized with Axl as the primary target. Most of them exhibited moderate to excellent activity, with IC50 values ranging from 0.032 to 1.54 μM against the tested cell lines. Among them, the most promising compound 47e, as an Axl kinase inhibitor (IC50 = 10 nM), shows remarkable cytotoxicity against A549, HT-29, PC-3, MCF-7, H1975 and MDA-MB-231 cell lines. More importantly, 47e also shows a significant inhibitory effect on EGFR-TKI resistant NSCLC cell lines H1975/gefitinib. Meanwhile, this study provides a novel type of linker for Axl kinase inhibitors, namely 1,3,4-oxadiazol acetamide moiety, which is out of the scope of the “5- atoms role ".

Synthesis and evaluation of 1,3,4-oxadiazole derivatives for development as broad-spectrum antibiotics

The reality and intensity of antibiotic resistance in pathogenic bacteria calls for the rapid development of new antimicrobial drugs. In bacteria, trans-translation is the primary quality control mechanism for rescuing ribosomes arrested during translation. Because trans-translation is absent in eukaryotes but necessary to avoid ribosomal stalling and therefore essential for bacterial survival, it is a promising target either for novel antibiotics or for improving the activities of the protein synthesis inhibitors already in use. Oxadiazole derivatives display strong bactericidal activity against a large number of bacteria, but their effects on trans-translation were recently questioned. In this work, a series of new 1,3,4-oxadiazole derivatives and analogs were synthesized and assessed for their efficiency as antimicrobial agents against a wide range of gram-positive and gram-negative pathogenic strains. Despite the strong antimicrobial activity observed in these molecules, it turns out that they do not target trans-translation in vivo, but they definitely act on other cellular pathways.