241818-88-2

Usage

Uses

Used in Organic Chemistry and Materials Science:
2,1,3-Benzoxadiazole-5-carboxaldehyde, 5-oxime, 1-oxide is utilized as a building block for the synthesis of organic electronic materials, capitalizing on its structural attributes to enhance the performance of these materials.
Used in Fluorescent Probe Development:
It serves as a fluorescent probe for the detection of nitroreductase, a significant application in the field of biochemistry and molecular biology, where such probes are instrumental for studying enzyme activity and related biological processes.
Used in Pharmaceutical Development:
2,1,3-Benzoxadiazole-5-carboxaldehyde, 5-oxime, 1-oxide is explored for its potential antibacterial and antifungal properties, indicating its use as a precursor in the development of new pharmaceuticals targeting various infectious diseases.
Used in Agricultural Product Development:
Given its antibacterial and antifungal properties, 2,1,3-Benzoxadiazole-5-carboxaldehyde, 5-oxime, 1-oxide is also considered for use in agriculture to develop products that can protect crops from a range of pathogens, thereby enhancing crop yield and quality.

Upstream product

• 19164-42-2 5-formylbenzo[c][1,2,5]oxadiazole 1-oxide 

Downstream Products

• 36389-13-6 5-benzofuroxancarbonitrile 

Relevant academic research and scientific papers

NO donor and biological properties of different benzofuroxans

Purpose. To investigate the effect of benzofusion on NO donor properties and related biological activities of the furoxan system. The biological properties considered were the ability to increase the cytosolic levels of cGMP in C6 cells and vasodilation. Methods. NO donor properties were investigated either in the presence or the absence of cysteine by using the Griess reaction, chemiluminescence, and gas chromatography. Increase of cytosolic cGMP levels were evaluated by radioimmunoassay. Vasodilating activity was assessed on rat aorta strips precontracted with noradrenaline, in the presence and the absence of oxyhemoglobin (HbO2) and methylene blue (MB), respectively. Results. Benzofuroxan and its methyl and cyano derivatives were unable to release NO under the experimental conditions. Generally these compounds displayed feeble vasodilating properties and were able to weakly stimulate soluble guanylate cyclase (sGC). By contrast, benzodifuroxan and benzotrifuroxan were able to produce both NO. and its reduced form NO-, the nitroxyl anion. They displayed potent vasodilating properties and were able to increase cytosolic levels of cGMP in a concentration-dependent manner. Conclusions. The simple benzofuroxans considered here are devoid of the capability to release NO, they weakly stimulate sGC as well as manifest feeble vasodilating properties by a mechanism that does not involve a thiol-induced NO production. By contrast, benzodifuroxan and benzotrifuroxan behave as typical NO donor furoxans.