2138-98-9

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-5-(2-chlorophenyl)-1,3,4-oxadiazole is used as a reactant in the synthesis of various quinazolinone derivatives, which have been studied for their antimicrobial activity against a range of bacteria and fungi. This application is significant in the development of new drugs to combat antibiotic-resistant infections.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2-Amino-5-(2-chlorophenyl)-1,3,4-oxadiazole serves as a key intermediate for the production of various compounds with potential applications in different industries, such as pharmaceuticals, agrochemicals, and materials science. Its unique structure allows for further functionalization and modification to create new molecules with desired properties.

InChI:InChI=1/C9H7ClN2O/c1-6-11-12-9(13-6)7-4-2-3-5-8(7)10/h2-5H,1H3

Upstream product

• 5315-85-5 2-[(2-chlorophenyl)methylene]hydrazinecarboxamide 
• 830-86-4 4-(o-chloro)benzoylthiosemicarbazide 
• 89-98-5 2-chloro-benzaldehyde 
• 4426-72-6 hydrazine carboxamide 
• 118-91-2 ortho-chlorobenzoic acid 
• 5315-85-5 C₈H₈ClN₃O 
• 5814-05-1 2-chlorobenzoylhydrazide 
• 563-41-7 semicarbazide hydrochloride 

Downstream Products

• 14768-88-8 N-[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-acetamide 
• 6694-43-5 1-[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-3-phenyl-urea 
• 14632-11-2 N-[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-propionamide 
• 59940-08-8 2-chloro-N-[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-acetamide 
• 89757-61-9 3-Chloro-N-[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-propionamide 
• 90147-10-7 4-Chloro-N-[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-butyramide 
• 59940-12-4 N,N-diethyl-glycine 5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-ylamide 
• 59940-22-6 N-[5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-2-piperidin-1-yl-acetamide 
• 59940-17-9 N,N-diphenyl-glycine 5-(2-chloro-phenyl)-[1,3,4]oxadiazol-2-ylamide 
• 34257-08-4 2-(2-chloro-phenyl)-6,7-dihydro-[1,3,4]oxadiazolo[3,2-a]pyrimidin-5-one 
• 1335198-42-9 7-(4-(5-(2-chlorophenyl)-1,3,4-oxadiazol-2-yl)piperazin-1-yl)-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 1335198-49-6 C₂₅H₂₁ClFN₅O₄ 
• 90736-27-9 2-Chloro-5-(2-chloro-phenyl)-[1,3,4]oxadiazole 

Relevant academic research and scientific papers

Synthesis, antibacterial activities and molecular docking study of thiouracil derivatives containing oxadiazole moiety

A series of novel thiouracil derivatives 9 containing an oxadiazole moiety have been synthesized by structural modification of a lead SecA inhibitor, 2. These compounds have been evaluated for their antibacterial activities against Bacillus amyloliquefaciens, Staphylococcus aureus and Bacillus subtilis. Among them, compounds 9g and 9n exhibited promising antibacterial activities against the tested strains. Compound 9g was also tested for its inhibitory activities against SecA ATPase, and the IC50 value of compound 9g was 19.9 μg/mL, lower than that of compound 2 (20.8 μg/mL). Molecular docking work indicates that compound 9g likely occupies the pocket formed by SecA IRA2 and NBD domain.

Synthesis, telomerase inhibitory and anticancer activity of new 2-phenyl-4H-chromone derivatives containing 1,3,4-oxadiazole moiety

Based on previous studies, 66 2-phenyl-4H-chromone derivatives containing amide and 1,3,4-oxadiazole moieties were prepared as potential telomerase inhibitors. The results showed most of the title compounds exhibited significantly inhibitory activity on telomerase. Among them, some compounds demonstrated the most potent telomerase inhibitory activity (IC50 50 = 6.41 μM). In addition, clear structure–activity relationships were summarised, indicating that the substitution of the methoxy group and the position, type and number of the substituents on the phenyl ring had significant effects on telomerase activity. Among them, compound A33 showed considerable inhibition against telomerase. Flow cytometric analysis showed that compound A33 could arrest MGC-803 cell cycle at G2/M phase and induce apoptosis in a concentration-dependent way. Meanwhile, Western blotting revealed that this compound could reduce the expression of dyskerin, which is a fragment of telomerase.

Ultrapotent Inhibitor of Clostridioides difficile Growth, Which Suppresses Recurrence in Vivo

Clostridioides difficile is the leading cause of healthcare-associated infection in the U.S. and considered an urgent threat by the Centers for Disease Control and Prevention (CDC). Only two antibiotics, vancomycin and fidaxomicin, are FDA-approved for the treatment of C. difficile infection (CDI), but these therapies still suffer from high treatment failure and recurrence. Therefore, new chemical entities to treat CDI are needed. Trifluoromethylthio-containing N-(1,3,4-oxadiazol-2-yl)benzamides displayed very potent activities [sub-μg/mL minimum inhibitory concentration (MIC) values] against Gram-positive bacteria. Here, we report remarkable antibacterial activity enhancement via halogen substitutions, which afforded new anti-C. difficile agents with ultrapotent activities [MICs as low as 0.003 μg/mL (0.007 μM)] that surpassed the activity of vancomycin against C. difficile clinical isolates. The most promising compound in the series, HSGN-218, is nontoxic to mammalian colon cells and is gut-restrictive. In addition, HSGN-218 protected mice from CDI recurrence. Not only does this work provide a potential clinical lead for the development of C. difficile therapeutics but also highlights dramatic drug potency enhancement via halogen substitution.

Synthesis of indole-tethered [1,3,4]thiadiazolo and [1,3,4]oxadiazolo[3,2-a]pyrimidin-5-one hybrids as anti-pancreatic cancer agents

New indole-tethered [1,3,4]thiadiazolo[3,2-a]pyrimidin-5-one (8a-j) and [1,3,4]oxadiazolo[3,2-a]pyrimidin-5-one hybrids (9a-e) were synthesized using [4+2] cycloaddition reactions of functionalized 1,3-diazabuta-1,3-dienes with indole-ketenes. All molecul

Ultrasound-assisted synthesis of 2-amino-1,3,4-oxadiazoles through NBS-mediated oxidative cyclization of semicarbazones

A ultrasound-assisted oxidative cyclization of semicarbazones using N-bromosuccinimide in the presence of sodium acetate was established providing efficient and rapid access to a variety of 2-amino-1,3,4-oxadiazoles. Moreover, the new synthetic protocol provides a simple procedure utilizing a safer oxidizing system that affords the target products in high regioselectivity, satisfactory yields, and elevated purities.

A 2-amino-5-substituted -1, 3, 4-oxadiazoles and its preparation method and application

The invention relates to 2-amido-5-substituted-1,3,4-oxadiazole as well as a preparation method and application thereof. The preparation method comprises the following steps: adding semicarbazone, manganese dioxide and pyridine into a reaction vessel, rea

Photocatalytic oxidative heterocyclization of semicarbazones: An efficient approach for the synthesis of 1,3,4-oxadiazoles

Abstract A highly efficient eosin Y catalyzed oxidative heterocyclization of semicarbazones was established under visible-light photoredox catalysis using CBr4 as a bromine source. The protocol renders a rapid, mild, and efficient access to val

A convenient synthesis of 5-substituted 2-amino-1,3,4-oxadiazoles from corresponding acylthiosemicarbazides using iodine and Oxone

A convenient methodology has been developed for the synthesis of substituted 2-amino-1,3,4-oxadiazoles from corresponding acylthiosemicarbazides using catalytic amount of iodine/KI in the presence of Oxone as a bulk oxidant. This offers the adv

Mild and convenient one-pot synthesis of 2-amino-1,3,4-oxadiazoles promoted by trimethylsilyl isothiocyanate (TMSNCS)

A mild, convenient, and efficient one-pot synthesis of amino-1,3,4- oxadiazoles is described. In situ preparation of various thiosemicarbazides by the reaction of different carboxylic acid hydrazides with trimethylsilyl isothiocyanate (TMSNCS), followed by cyclodesulfurization of thiosemicarbazides under basic conditions in the presence of I2/KI resulted in 2-amino-1,3,4-oxadiazoles in high yields (79-94%).

Electrochemical synthesis of 2-amino-5-substituted-1,3,4-oxadiazole derivatives and evaluation of antibacterial activity

Some new 2-amino-5-substituted-1,3,4-oxadiazoles have been synthesized at platinum electrode through the electrochemical oxidation of semicarbazone at room temperature and studied for their antibacterial activity. This is an environmentally benign method in the field of electroorganic synthesis under controlled potential electrolysis in an undivided cell. The electrolysis have been carried out in the acetonitrile solvent and lithium perchlorate is used as a supporting electrolyte. Two platinum plates are used as working as well as counter electrode and saturated calomel electrode as the reference electrode. These compounds have been characterized by microanalyses, IR, Mass, 1H NMR and 13C NMR spectral data. All the compounds have been evaluated for their antibacterial activity against Klebsilla penumoniae, Escherichia coli, Streptococcus aureus and Shigella dysenteriea at 25 and 50 ppm concentrations.