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Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
5-(3-bromophenyl)-1,3,4-oxadiazol-2-amine is used as a building block for the synthesis of various pharmaceuticals and agrochemicals. Its unique structure and properties make it a valuable component in the development of new drugs and pesticides.
Used in Materials Science:
5-(3-bromophenyl)-1,3,4-oxadiazol-2-amine has potential applications in the field of materials science, where its chemical and physical properties can be utilized to create novel materials with specific characteristics.
Used as a Fluorescent Probe in Biological Imaging:
5-(3-bromophenyl)-1,3,4-oxadiazol-2-amine can be employed as a fluorescent probe for biological imaging, allowing researchers to visualize and study biological processes and structures with enhanced precision and sensitivity.

InChI:InChI=1/C8H6BrN3O/c9-6-3-1-2-5(4-6)7-11-12-8(10)13-7/h1-4H,(H2,10,12)

Upstream product

• 3132-99-8 m-bromobenzoic aldehyde 
• 563-41-7 semicarbazide hydrochloride 
• 506-68-3 bromocyane 
• 39115-96-3 3-bromo-benzoic acid hydrazide 
• 24398-88-7 ethyl 3-bromobenzoate 
• 126651-84-1 2-(3-bromobenzoyl)hydrazinecarbothioamide 
• 1711-09-7 3-bromobenzoyl chloride 
• 38407-30-6 1-(3-bromobenzylidene)semicarbazide 

Downstream Products

• 25433-41-4 1-[5-(3-bromo-phenyl)-[1,3,4]oxadiazol-2-yl]-biguanide 
• 28054-09-3 2-(3-bromo-phenyl)-5-oxo-5H-[1,3,4]oxadiazolo[3,2-a]pyrimidine-6-carboxylic acid ethyl ester 
• 28037-27-6 {[5-(4-bromo-phenyl)-[1,3,4]oxadiazol-2-ylamino]-methylene}-malonic acid diethyl ester 
• 28004-20-8 2-(4-bromo-phenyl)-5-oxo-5H-[1,3,4]oxadiazolo[3,2-a]pyrimidine-6-carboxylic acid ethyl ester 
• 879184-33-5 N?[5?(3?bromophenyl)?1,3,4?oxadiazol?2?yl]?4?fluorobenzamide 
• 1277127-56-6 C₁₅H₉Br₂N₃O 
• 6783-25-1 1-[5-(3-bromo-phenyl)-[1,3,4]oxadiazol-2-yl]-3-phenyl-[1,3]diazetidine-2,4-dione 
• 6694-46-8 1-[5-(3-bromo-phenyl)-[1,3,4]oxadiazol-2-yl]-3-phenyl-urea 
• 28004-33-3 2-(3-bromo-phenyl)-7-methyl-[1,3,4]oxadiazolo[3,2-a]pyrimidin-5-one 

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.

Bioactive amide and α-aminophosphonate inhibitors for methicillin-resistant Staphylococcus aureus (MRSA)

Abstract: Scaffolds of 2-acylamino-1,3,4-oxadiazole have been recently developed as transglycosylase inhibitors against MRSA. In the present study, structure–activity relationships of new derivatives of 2-acylamino-1,3,4-oxadiazole were explored with focus on the substitution of the aromatic rings. The in vitro antibacterial activity of these compounds against MRSA strain was evaluated using agar disc diffusion method. These inhibitors have an amide linker between 1,3,4-oxadiazole ring and the aromatic ring B. The role of this linker on the bioactivity of the compounds was also studied. The results showed promising series of 2-α-aminophosphonate-1,3,4-oxadiazole as inhibitors for MRSA strain. Both series revealed two structural features which appear to be essential for anti-MRSA activities, the first one is the incorporation of two electron-withdrawing groups at meta- and para- positions within aromatic ring B which contributed to a higher activity against MRSA strain. The second is the new α-aminophosphonate linker serving as bio-isosteric analogue of the corresponding amide linker and giving comparable results with the amide derivatives. Graphical abstract: [Figure not available: see fulltext.].

Synthesis and amelioration of inflammatory paw edema by novel benzophenone appended oxadiazole derivatives by exhibiting cyclooxygenase-2 antagonist activity

Ten new 2(4-hydroxy-3-benzoyl) benzamide-5-phenyl-1,3,4-oxadiazole derivatives (10a–j) were synthesized by coupling 3-benzoyl-4-hydroxybenzoic acid (5) with 2-amino-5-phenyl-1,3,4-oxadiazoles (9a–j). The structures of these compounds were confirmed by IR, 1H, 13C NMR, and mass spectra, and also by elemental analyses. The anti-inflammatory activity of the compounds 10a–j were investigated by screening them against human red blood cells (HRBC) in-vitro. The results reveal that among this series, compound 10j with hydroxy substituent, particularly at the ortho position of the phenyl ring attached to the 5th carbon atom of the oxadiazole ring possess significant membrane stabilizing activity in comparison with the control. Further, in-vivo chick chorioallantoic membrane (CAM) and rat corneal anti-angiogenesis assays were performed to assess the effect of compound 10j on endothelial cell migration. This confirmed that compound 10j inhibits the proliferation of endothelial cells. Anti-inflammatory studies detected the amelioration of carrageen induced rat hind paw edema. Further in-vivo and in-silico approaches revealed the inhibition of inflammatory marker enzyme cyclooxygenase-2 (Cox-2) and myleoperoxidase (MPO). The study reports that the compound 10j effectively act against the inflammatory mediated anti-angiogenic disorders which could be translated into a new drug in future.

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

Green synthesis of 2-amino-5-substituted-1,3,4-oxadiazoles at the platinum anode in acetic acid

The electroorganic synthesis of 2-amino-5-substituted-1,3,4-oxadiazoles from the anodic oxidation of semicarbazone has been carried out at platinum anode in acetic acid under constant potential electrolysis in an undivided cell. This is an environmentally benign method in the field of synthetic organic chemistry. The products are characterized by IR, 1H and 13C NMR, and elemental analysis.