1673-45-6

Usage

Uses

Used in Pharmaceutical Industry:
5-(3-CHLOROPHENYL)-1,3,4-OXADIAZOL-2-AMINE is used as a potential pharmaceutical agent for its possible biological activity. 5-(3-CHLOROPHENYL)-1,3,4-OXADIAZOL-2-AMINE's unique structure allows it to be a candidate for the development of new drugs, particularly in the areas of medicinal chemistry where its properties can be harnessed to target specific biological pathways or receptors.
Used in Agricultural Industry:
In the agricultural sector, 5-(3-CHLOROPHENYL)-1,3,4-OXADIAZOL-2-AMINE is used as a potential active ingredient in agrochemicals. Its chemical properties may offer pesticidal or herbicidal activity, contributing to the development of more effective and targeted crop protection products.
Used in Academic Research:
5-(3-CHLOROPHENYL)-1,3,4-OXADIAZOL-2-AMINE is utilized as a subject of study in academic research for its structural and chemical properties. Researchers in the field of chemistry and related disciplines may explore its reactivity, synthesis pathways, and potential applications in material science, providing insights into new areas of chemical compound development.
Used as a Building Block in Synthesis:
5-(3-CHLOROPHENYL)-1,3,4-OXADIAZOL-2-AMINE serves as a valuable building block in the synthesis of various compounds across different industries. Its unique structure can be modified or combined with other chemical entities to create new molecules with specific properties, broadening its utility in drug discovery, material development, and other chemical applications.

InChI:InChI=1/C8H6ClN3O/c9-6-3-1-2-5(4-6)7-11-12-8(10)13-7/h1-4H,(H2,10,12)

Upstream product

• 2905-65-9 methyl 3-chlorobenzoate 
• 563-41-7 semicarbazide hydrochloride 
• 587-04-2 m-Chlorobenzaldehyde 
• 1673-47-8 3-chlorobenzhydrazide 
• 618-46-2 m-Chlorobenzoyl chloride 
• 881-74-3 2-(3-chlorobenzoyl)hydrazinecarbothioamide 

Downstream Products

• 72481-49-3 [5-(3-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-phosphorimidic acid trichloride 
• 72481-54-0 [5-(3-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-phosphoramidic acid dichloride 
• 1338084-21-1 C₁₈H₁₇ClN₆O₄ 
• 1338083-66-1 C₁₃H₉ClN₆O₃ 
• 1338084-45-9 C₁₃H₈ClN₅O₃ 
• 1338083-88-7 C₁₅H₁₂ClN₅O₃ 
• 1277127-58-8 C₁₅H₉Cl₂N₃O 
• 72481-64-2 N-[5-(3-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-N',N''-di-p-tolyl-phosphamide 
• 72481-59-5 N-[5-(3-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-N',N''-diphenyl-phosphamide 
• 6694-44-6 1-[5-(3-chloro-phenyl)-[1,3,4]oxadiazol-2-yl]-3-phenyl-urea 

Relevant academic research and scientific papers

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.

Efficient synthesis of novel conjugated 1,3,4-oxadiazole-peptides

We were interested in the design and synthesis of novel bioisosteric analogues of leuprolide acetate containing the oxadiazole moiety at the C- or N-terminal of the peptide. An efficient approach for the synthesis of 2-amino-1,3,4-oxadiazoles through the reaction of hydrazide with ammonium thiocyanate and desulfurization reaction of the thiosemicarbazides using different coupling reagents was employed. These compounds are bioisosteres of the amide bond. Furthermore, the coupling of 2-amino-1,3,4-oxadiazoles at the C-terminal of leuprolide analogues was carried out, using a coupling reagent in the solution phase. On the other hand, the addition of a 2-amino-1,3,4-oxadiazole to the N-terminal of the peptide sequence was carried out through the reaction of the 2-amino-1,3,4-oxadiazole with succinic anhydride that led to the formation of a carboxylic acid moiety. Addition of the synthesized oxadiazole containing carboxylic acid to the peptide sequence was performed using a coupling reagent and on the surface of the resin. The synthesized peptides containing the oxadiazole moiety at the C- or N-terminal of the peptide sequence are peptidomimetics of leuprolide acetate. All of the synthesized peptides were purified using preparative HPLC and their structures were confirmed using HR-MS (ESI).

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

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

Discovery and biophysical characterization of 2-amino-oxadiazoles as novel antagonists of PqsR, an important regulator of Pseudomonas aeruginosa virulence

The human pathogen Pseudomonas aeruginosa employs alkyl quinolones for cell-to-cell communication. The Pseudomonas quinolone signal (PQS) regulates various virulence factors via interaction with the transcriptional regulator PqsR. Therefore, we consider t

A Facile microwave assisted synthesis and spectral analysis of 2-amino-5-substituted phenyl-1,3,4-oxadiazoles

An efficient synthesis for the preparation of some 2-amino-5-substituted phenyl-1,3,4-oxadiazoles by using both conventional and microwave method have been devised. The obtained results revealed that, microwave assisted technique is efficient, eco-friendl

Microwave assisted synthesis and spectral analysis of schiff bases derived from 2-amino-5-aryl-1,3,4-oxadiazoles

Microwave assisted synthesis of new Schiff bases derived from 2-amino-5-substituted aryl-1,3,4-oxadiazoles with substituted aromatic aldehyde have been carried out. The chemical structures of the prepared Schiff bases have been investigated by analytical

2,5-Disubstituted-1,3,4-oxadiazoles/thiadiazole as surface recognition moiety: Design and synthesis of novel hydroxamic acid based histone deacetylase inhibitors

The enzymatic inhibition of histone deacetylase activity has come out as a novel and effectual means for the treatment of cancer. Two novel series of 2-[5-(4-substitutedphenyl)-[1,3,4]-oxadiazol/thiadiazol-2-ylamino] -pyrimidine-5-carboxylic acid (tetrahydro-pyran-2-yloxy)-amides were designed and synthesized as novel hydroxamic acid based histone deacetylase inhibitors. The antiproliferative activities of the compounds were investigated in vitro using histone deacetylase inhibitory assay and MTT assay. The synthesized compounds were also tested for antitumor activity against Ehrlich ascites carcinoma cells in Swiss albino mice. The efforts were also made to establish structure-activity relationships among synthesized compounds. The results of the present studying indicates 2,5-disubstituted 1,3,4-oxadiazole/thiadiazole as promising surface recognition moiety for development of newer hydroxamic acid based histone deacetylase inhibitor.