861146-12-5

Basic information

• Product Name: Ethyl 3-(4-bromophenyl)-1,2,4-oxadiazole-5-carboxylate
• Synonyms: Ethyl 3-(4-bromophenyl)-1,2,4-oxadiazole-5-carboxylate;XDJVQNUMZNYBSC-UHFFFAOYSA-N
• CAS NO: 861146-12-5
• Molecular Formula: C₁₀H₇BrN₂O₃
• Molecular Weight: 297.1
• Mol File: 861146-12-5.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Ethyl 3-(4-bromophenyl)-1,2,4-oxadiazole-5-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 3-(4-bromophenyl)-1,2,4-oxadiazole-5-carboxylate(861146-12-5)
• EPA Substance Registry System: Ethyl 3-(4-bromophenyl)-1,2,4-oxadiazole-5-carboxylate(861146-12-5)

Safety Data

• Hazardous Substances Data: 861146-12-5(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Ethyl 3-(4-bromophenyl)-1,2,4-oxadiazole-5-carboxylate is used as a building block in organic synthesis for the preparation of other biologically active molecules. Its unique structure, including the bromine atom and the oxadiazole ring, allows for the creation of diverse chemical entities with potential applications in various fields.
Used in Medicinal Chemistry:
In the pharmaceutical industry, Ethyl 3-(4-bromophenyl)-1,2,4-oxadiazole-5-carboxylate is used as a starting material for the development of new drugs. Its structural features may contribute to interesting pharmacological properties, making it a valuable candidate for research and development in drug discovery.
Used in Material Science:
Ethyl 3-(4-bromophenyl)-1,2,4-oxadiazole-5-carboxylate may also find applications in material science due to the potential of oxadiazole-based compounds to exhibit specific properties, such as thermal stability and chemical resistance, which can be utilized in the development of advanced materials for various applications.

Upstream product

• 5781-53-3 monomethyl oxalyl chloride 
• 19227-14-6 (Z)-4-bromo-N′-hydroxybenzimidamide 
• 623-00-7 4-bromobenzenecarbonitrile 

Downstream Products

• 861146-15-8 3-(4-bromo-phenyl)-[1,2,4]oxadiazole-5-carboxylic acid hydrazide 

Relevant articles and documents

Development of 1,2,4-Oxadiazoles as Potent and Selective Inhibitors of the Human Deacetylase Sirtuin 2: Structure–Activity Relationship, X-ray Crystal Structure, and Anticancer Activity

Sirt2 is a target for the treatment of neurological, metabolic, and age-related diseases including cancer. Here we report a series of Sirt2 inhibitors based on the 1,2,4-oxadiazole scaffold. These compounds are potent Sirt2 inhibitors active at single-digit μM level by using the Sirt2 substrate a-tubulin-acetylLys40 peptide and inactive up to 100 μM against Sirt1, -3, and -5 (deacetylase and desuccinylase activities). Their mechanism of inhibition is uncompetitive toward both the peptide substrate and NAD+, and the crystal structure of a 1,2,4-oxadiazole analog in complex with Sirt2 and ADP-ribose reveals its orientation in a still unexplored subcavity useful for further inhibitor development. Tested in leukemia cell lines, 35 and 39 induced apoptosis and/or showed anti proliferative effects at 10 or 25 μM after 48 h. Western blot analyses confirmed the involvement of Sirt2 inhibition for their effects in NB4 and in U937 cells. Our results provide novel Sirt2 inhibitors with a compact scaffold and structural insights for further inhibitor improvement.

Conjugation of N-acylhydrazone and 1,2,4-oxadiazole leads to the identification of active antimalarial agents

Malaria, caused by several Plasmodium species, is the major life-threatening parasitic infection worldwide. Due to the parasite resistance to quinoline based drugs, the search for antimalarial agents is necessary. Here, we report the structural design, sy

Optimization of anti-Trypanosoma cruzi oxadiazoles leads to identification of compounds with efficacy in infected mice

We recently showed that oxadiazoles have anti-Trypanosoma cruzi activity at micromolar concentrations. These compounds are easy to synthesize and show a number of clear and interpretable structure-activity relationships (SAR), features that make them attr