51376-06-8

Usage

Uses

Used in Organic Synthesis:
5-BROMO-2,1,3-BENZOXADIAZOLE is used as a fluorescent labeling reagent for [enhancing the visibility of target molecules in biological and chemical research], allowing for the tracking and detection of specific compounds within complex systems.
Used in Pharmaceutical and Agrochemical Industries:
5-BROMO-2,1,3-BENZOXADIAZOLE is used as a building block for [the preparation of various pharmaceuticals and agrochemicals], contributing to the development of new drugs and pesticides with improved efficacy and selectivity.
Used in Optoelectronic Materials Development:
5-BROMO-2,1,3-BENZOXADIAZOLE is used as a component in the development of optoelectronic materials such as [OLEDs and organic solar cells], due to its electronic and optical properties that can enhance device performance and efficiency.
Used in Biomedical Research:
5-BROMO-2,1,3-BENZOXADIAZOLE is used as a fluorogenic probe for [the detection of proteins and nucleic acids in biological systems], facilitating the study of molecular interactions and the diagnosis of diseases at the molecular level.

InChI:InChI=1/C6H3BrN2O/c7-4-1-2-5-6(3-4)9-10-8-5/h1-3H

Upstream product

• 73686-38-1 4-bromo-[1,2]benzoquinone dioxime 
• 41153-83-7 6-bromobenzo[c][1,2,5]oxadiazole 1-oxide 
• 875-51-4 4-Bromo-2-nitroaniline 
• 36387-84-5 4-bromo-9-oxido-8-oxa-7,9-diazabicyclo[4.3.0]nona-1⁽⁹⁾,2,4,6-tetraene 
• 5228-61-5 5-bromo-2-nitroaniline 
• 847672-84-8 1-azido-4-bromo-2-nitrobenzene 
• 88-74-4 2-nitro-aniline 
• 168297-37-8 4-bromo-2-(tert-butyl-NNO-azoxy)aniline 

Downstream Products

• 54286-62-3 benzo[c][1,2,5]oxadiazole-5-carbonitrile 
• 426268-06-6 RO-458,2640 
• 54286-60-1 4,5-dicyanobenzofurazan 
• 1395071-71-2 5-(4-methoxyphenyl)benzo[c][1,2,5]oxadiazole 
• 1395071-72-3 5-(3-methoxyphenyl)-2,1,3-benzoxadiazole 
• 1395071-74-5 5-(3-cyanophenyl)-2,1,3-benzoxadiazole 
• 1170691-48-1 5-(3-aminophenyl)-2,1,3-benzoxadiazole 
• 1395071-76-7 5-(2,4-difluorophenyl)-2,1,3-benzoxadiazole 
• 1428477-26-2 1-{4-[(E)-2-(2,1,3-benzoxadiazol-5-yl)ethenyl]piperidin-1-yl}-2-[4-((1H)-tetrazol-1-yl)phenyl]ethanone 
• 1428479-63-3 1-{4-(2,1,3-benzoxadiazol-5-ylethynyl)-4-hydroxypiperidin-1-yl}-2-[4-(1H-tetrazol-1-yl)phenyl]ethanone 
• 426268-09-9 benzo[c][1,2,5]oxadiazole-5-boronic acid 
• 59660-58-1 1-(benzo[c][1,2,5]oxadiazol-5-yl)ethan-1-ol 
• 19155-88-5 benzo[c][1,2,5]oxadiazole-5-carboxylic acid 
• 36389-07-8 benzo[1,2,5]oxadiazole-5-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

COMPOSITIONS AND METHODS FOR THE TREATMENT OF CANCER

This disclosure relates to compounds, pharmaceutical compositions comprising them, and methods of using the compounds and compositions for treating diseases related to Heat Shock Transcription Factor 1 (HSF1) activity and/or function. More particularly, this disclosure relates to methods of inhibiting HSF1 activity with these compounds and pharmaceutical compositions thereof, and methods of treating diseases associated with HSF1 activity and/or function, such as cancer.

A Common, Facile and Eco-Friendly Method for the Reduction of Nitroarenes, Selective Reduction of Poly-Nitroarenes and Deoxygenation of N-Oxide Containing Heteroarenes Using Elemental Sulfur

A transition metal-free, environment-friendly and practical protocol was developed either for the reduction of nitroarenes or for the deoxygenation of N-oxide containing heteroarenes. The reaction proceeded with the use of a non-toxic and cheap feedstock as elemental sulfur in aqueous methanol under relatively mild conditions. Green chemistry credentials were widely favorable compared to traditional and industrial protocols with good E-factors and a low production of waste. The strategy allowed the efficient reduction of a large variety of substituted-nitroarenes including various o-nitroanilines as well as selective reduction of various poly-nitroarenes in excellent yields with a broad substrate scope. The protocol was successfully extended to the deoxygenation of some N-oxide containing heteroarenes, like benzofuroxans, phenazine N,N'-dioxides, pyridine N-oxides, 2H-indazole N1-oxides, quinoxaline N1,N4-dioxides and benzo[d]imidazole N1,N3-dioxides. A gram-scale example for the synthesis of luminol, in green conditions, was reported. A solid mechanism of reaction was proposed from experimental evidences.

Discovery and development of novel salicylate synthase (MbtI) furanic inhibitors as antitubercular agents

We report on the virtual screening, synthesis, and biological evaluation of new furan derivatives targeting Mycobacterium tuberculosis salicylate synthase (MbtI). A receptor-based virtual screening procedure was applied to screen the Enamine database, identifying two compounds, I and III, endowed with a good enzyme inhibitory activity. Considering the most active compound I as starting point for the development of novel MbtI inhibitors, we obtained new derivatives based on the furan scaffold. Among the SAR performed on this class, compound 1a emerged as the most potent MbtI inhibitor reported to date (Ki = 5.3 μM). Moreover, compound 1a showed a promising antimycobacterial activity (MIC99 = 156 μM), which is conceivably related to mycobactin biosynthesis inhibition.

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.

Furazan-containing bromoarenes in the Suzuki-Miyaura reaction

The palladium-catalyzed cross-coupling reactions of 3-[bromo(het)aryl] furazans and bromobenzofurazans with arylboronic acids afford target biaryls in good yields. 3-Bromo-4-phenylfurazan containing a bromine atom in the furazan ring undergoes decomposition under the reaction conditions.

1, 2 DISUBSTITUTED HETEROCYCLIC COMPOUNDS

1,2-disubstituted heterocyclic compounds which are inhibitors of phosphodiesterase 10 are described. Also described are processes, pharmaceutical compositions, pharmaceutical preparations and pharmaceutical use of the compounds in the treatment of mammals, including human(s) for central nervous system (CNS) disorders and other disorders which may affect CNS function. Among the disorders which may be treated are neurological, neurodegenerative and psychiatric disorders including, but not limited to, those associated with cognitive deficits or schizophrenic symptoms.

OXAZOLIDINONE DERIVATIVES AS ANTIMICROBIALS

The present invention relates to substituted phenyl oxazolidinones and processes for preparing thereof. This invention also relates to pharmaceutical compositions comprising compounds of the present invention. Such compounds can be useful antimicrobial ag

Large-scale Negishi coupling as applied to the synthesis of PDE472, an inhibitor of phosphodiesterase type 4D

5-[2-Methoxy-5-(4-pyridinyl)phenyl]-2,1,3-benzoxadiazole (PDE472) is a selective inhibitor of the phosphodiesterase PDE4D isoenzyme, which is a recognised drug target for the treatment of asthma. Different synthetic routes to PDE472 were investigated, and the research synthesis was optimised to prepare a phase I batch on pilot-plant scale with the focus on the elimination or minimization of inherent process risks. An important refinement of the key Negishi aryl-aryl coupling involved preforming the arylpalladium complex, which was then added to the arylzinc intermediate. Residual palladium was removed from PDE472 via crystallization of the hemi-maleate salt, which afforded drug-substance containing 2 ppm Pd.

Synthesis of 4-(8-benzo[1,2,5]oxadiazol-5-yl-[1,7]naphthyridine-6-yl)-benzoic acid: A potent and selective phosphodiesterase type 4D inhibitor

The synthesis of a 6,8-disubstituted 1,7-naphthyridine 1 and its characterization as a potent and selective phosphodiesterase type 4D inhibitor (IC50=1.5nM) are described. The compound inhibited TNFα-release from human peripheral blood mononuclear cells and was orally active in a model of adjuvant-induced arthritis in rats.

A new cyclization involving the diazonium and ortho-(tert-butyl)-NNO-azoxy groups - Synthesis of 1,2,3,4-benzotetrazine 1-oxides

The synthesis of 1,2,3,4-benzotetrazine 1-oxides (BTOs) is described. Bromo-BTOs 4b-d were prepared by the intramolecular cyclization of diazonium salts bearing an ortho-(tert-butyl)-NNO-azoxy group. BTOs bearing electron-releasing substituents were obtained by nucleophilic displacements of bromine in 4b-d. The formation of the BTO cyclic system involves the intermediate 2-(tert-butyl)-1,2,3,4-benzotetrazinium 4-oxides, which arise from an N,N-[1,21-shift of the tert-butyl group. Decomposition of BTOs involves opening of the tetrazine ring to afford ortho-azidonitroso derivatives, followed by their cyclization with the evolution of the N2 molecule to give benzofurazans. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.