39132-77-9

Usage

Uses

Used in Pharmaceutical Industry:
2,1,3-Benzoxadiazole, 5,6-dimethyl-, 1-oxide is used as a building block for the synthesis of new pharmaceuticals. Its unique structure and properties contribute to the development of innovative drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, 2,1,3-Benzoxadiazole, 5,6-dimethyl-, 1-oxide serves as a key component in the synthesis of various agrochemicals. Its incorporation into these compounds can enhance their effectiveness in agricultural applications.
Used in Materials Science:
2,1,3-Benzoxadiazole, 5,6-dimethyl-, 1-oxide is utilized in the development of new materials with specific properties. Its unique structure allows for the creation of materials with tailored characteristics for various applications.
Used in Fluorescence Microscopy and Imaging:
Due to its fluorescent properties, 2,1,3-Benzoxadiazole, 5,6-dimethyl-, 1-oxide is employed in the field of fluorescence microscopy and imaging. It can be used as a fluorescent marker or probe to visualize and study biological processes and structures at the molecular level.

InChI:InChI=1/C8H8N2O2/c1-5-3-7-8(4-6(5)2)10(11)12-9-7/h3-4H,1-2H3

Upstream product

• 1027598-42-0 1-Azido-4,5-dimethyl-2-nitro-benzene 
• 6970-77-0 N-(4,5-dimethyl-2-nitrophenyl)acetamide 
• 6972-71-0 4,5-dimethyl-2-nitrobenzenamine 
• 95-64-7 4-amino-o-xylene 
• 2198-54-1 N-(3,4-dimethylphenyl)acetamide 

Downstream Products

• 27017-88-5 (6,7-dimethyl-1,4-dioxy-3-phenyl-quinoxalin-2-yl)-phenyl-methanone 
• 1189641-33-5 C₂₃H₂₄N₂O₆ 
• 1334542-00-5 3-(2-aminophenyl)-6,7-dimethylquinoxalin-2-amine 
• 1334541-77-3 6,7-dimethyl-3-(5-methyl-2-nitrophenyl)quinoxalin-2-amine 
• 1334541-69-3 6,7-dimethyl-3-(2-nitrophenyl)quinoxalin-2-amine 
• 1323954-31-9 3-(2-acetoxybenzamido)-2-cyano-6,7-dimethylquinoxaline 1,4-dioxide 

Relevant academic research and scientific papers

Cu-Catalyzed π-Core Evolution of Benzoxadiazoles with Diaryliodonium Salts for Regioselective Synthesis of Phenazine Scaffolds

The Cu-catalyzed regioselective synthesis of phenazine N-oxides was realized from benzoxadiazoles and diaryliodonium salts. The process was initiated by the electrophilic arylation of benzoxadiazoles with diaryliodonium salts and followed by benzocyclization reactions. The further reduction of N-oxides in situ to phenazine scaffolds and deviation to organic fluorescent materials were readily accomplished.

Radical Chemistry and Cytotoxicity of Bioreductive 3-Substituted Quinoxaline Di-N-Oxides

The radical chemistry and cytotoxicity of a series of quinoxaline di-N-oxide (QDO) compounds has been investigated to explore the mechanism of action of this class of bioreductive drugs. A series of water-soluble 3-trifluoromethyl (4-10), 3-phenyl (11-19)

Synthesis, biological evaluation and structure-activity relationships of new quinoxaline derivatives as anti-Plasmodium falciparum agents

We report the synthesis and antimalarial activities of eighteen quinoxaline and quinoxaline 1,4-di-N-oxide derivatives, eight of which are completely novel. Compounds 1a and 2a were the most active against Plasmodium falciparum strains. Structure-activity

Hypoxia-Selective Agents Derived from Quinoxaline 1,4-Di-N-oxides

Hypoxic cells, which are a common feature of solid tumors, but not normal tissues, are resistant to both anticancer drugs and radiation therapy.Thus the identification of drugs with selective toxicity toward hypoxic cells is an important objective in anticancer chemotherapy.The benzotriazine di-N-oxide (SR 4233, Tirapazamine) has been shown to be an efficient and selective cytotoxin for hypoxic cells.Since the bioreductive activation of Tirapazamine is thought to be due to the presence of the 1,4-di-N-oxide moiety, a series of 3-aminoquinoxaline-2-carbonitrile 1,4-di-N-oxides with a range of electron-donating and -withdrawing substituents in the 6- and /or 7- positions has been synthesized and evaluated for toxicity to hypoxic cells.Electrochemical studies of the quinoxaline di-N-oxides and Tirapazamine showed that as the electron-withdrawing nature of the 6(7)-substituent increases, the reduction potential becomes more positive and the compound is more readily reduced.Apart from the unsubstituted 6a and the 6,7-dimethyl derivative 6c, the quinoxaline di-N-oxide have reduction potentials significantly more positive than Tirapazamine (Epc -0.90 V).The most potent cytotoxins to cells in culture were the 6,7-dichloro and 6,7-difluoro derivatives 6i and 6l, which were 30-fold more potent than Tirapazamine.The 6(7)-fluoro and 6(7)-chloro compounds, 6e and 6h, showed the greatest hypoxia selectivity.Four of the compounds, 6e, 6f, 6h and 6i, killed the inner cells of multicellular tumor spheroids in vitro.In vivo Balb/c mice tolerated a dose of these four compounds twice the size of that of Tirapazamine.This study demonstrates that quinoxaline 1,4-di-N-oxides could provide useful hypoxia-selective therapeutic agents.

Formation and Rearrangement of Adducts from Benzyne and Substituted 2,1,3-Benzoselenadiazoles

A series of 5-(1,2-benzoselenazol-3-yl)pentadienonitrile derivatives (2) has been prepared by addition of benzyne to substituted 2,1,3-benzoselenadiazoles.Some of these adducts rearrange either thermally or photochemically to give 2-(2-pyridyl)phenyl selenocyanates (7), which are reduced to 2-phenylpyridine derivatives (6) or hydrolysed to give ultimately, diselenides (9).The crystal structure of one benzyne adduct (2b) is reported and the mechanism of its rearrangement discussed.