153493-48-2

Basic information

• Product Name: 5,6-DICHLORO-[1,2,5]OXADIAZOLO[3,4-B]PYRAZINE
• Synonyms: TIMTEC-BB SBB006904;5,6-DICHLORO-[1,2,5]OXADIAZOLO[3,4-B]PYRAZINE;CBI-BB ZERO/001258
• CAS NO: 153493-48-2
• Molecular Formula: C₄Cl₂N₄O
• Molecular Weight: 190.98
• Mol File: 153493-48-2.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 240.5±50.0 °C(Predicted)
• Appearance: /
• Density: 1.851±0.06 g/cm3(Predicted)
• PKA: -8.95±0.50(Predicted)
• CAS DataBase Reference: 5,6-DICHLORO-[1,2,5]OXADIAZOLO[3,4-B]PYRAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-DICHLORO-[1,2,5]OXADIAZOLO[3,4-B]PYRAZINE(153493-48-2)
• EPA Substance Registry System: 5,6-DICHLORO-[1,2,5]OXADIAZOLO[3,4-B]PYRAZINE(153493-48-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22
• HazardClass: IRRITANT
• Hazardous Substances Data: 153493-48-2(Hazardous Substances Data)

Usage

General Description

5,6-dichloro-[1,2,5]oxadiazolo[3,4-b]pyrazine is a chemical compound with the molecular formula C4HCl2N4O. It is a heterocyclic compound that contains both nitrogen and oxygen atoms in its structure. 5,6-DICHLORO-[1,2,5]OXADIAZOLO[3,4-B]PYRAZINE has potential applications in the pharmaceutical and agricultural industries, and it may be used as a building block for the synthesis of various biologically active molecules. Additionally, it has been studied for its potential use in the development of new materials and as a component in organic electronic devices. However, this compound may also pose health and environmental hazards, and it is important to handle it with caution and in accordance with safety guidelines.

Upstream product

• 24294-89-1 [1,2,5]oxadiazolo[3,4-b]pyrazine-5,6-diol 
• 24294-89-1 Furazano[3,4-b]pyrazine-5,6(4H,7H)-dione 

Downstream Products

• 210301-72-7 5,6-diethoxyfurazano[3,4-b]pyrazine 
• 210302-26-4 N₅,N₆-bis(4-methyl-2-nitrophenyl)-[1,2,5]oxadiazolo[3,4-b]pyrazine-5,6-diamine 
• 210302-47-9 4-(6-chloro-[1,2,5]oxadiazolo[3,4-b]pyrazin-5-ylamino)-benzonitrile 
• 210302-15-1 N,N'-bis-(4-iodo-phenyl)-[1,2,5]oxadiazolo[3,4-b]pyrazine-5,6-diamine 

Relevant articles and documents

5,6-Di(2-fluoro-2,2-dinitroethoxy)furazano[3,4-: B] pyrazine: A high performance melt-cast energetic material and its polycrystalline properties

5,6-Di(2-fluoro-2,2-dinitroethoxy)furazano[3,4-b]pyrazine was synthesized in a three-step process starting from 3,4-diaminofurazan (DAF) including a significant nucleophilic substitution reaction under the catalytic effect of trisodium phosphate dodecahydrate. Characterization of this molecule indicates that it possesses a higher crystal density than that of 2,4,6-trinitrotoluene (TNT) at ambient temperature with acceptable melting-point and energetic properties approaching those of 1,3,5-trinitro-1,3,5-triazacyclohexane (RDX) but with a higher thermal stability and lower sensitivity towards impact and friction. To investigate its polycrystalline properties, differential scanning calorimetry (DSC), powder-X-ray-diffraction (PXRD) and ab initio calculation using the Viena Ab initio simulation package (VASP) were employed.

Synthesis and properties of 1,2,4-triazolo-1,2,4-triazolofurazanopyrazines

New methods for the synthesis of 1,2,4-triazolo-1,2,4-triazolofurazanopyrazines with functional substituents of various types are proposed and some properties of these compounds are studied. - Key words: 1,2,4-triazolo-1,2,4-triazolofurazanopyrazines; heterocyclization reactions; methods of synthesis.

Oxadiazolo[3,4- b]pyrazine-5,6-diamine Derivatives as Mitochondrial Uncouplers for the Potential Treatment of Nonalcoholic Steatohepatitis

Small molecule mitochondrial uncouplers are emerging as a new class of molecules for the treatment of nonalcoholic steatohepatitis. We utilized BAM15, a potent protonophore that uncouples the mitochondria without depolarizing the plasma membrane, as a lead compound for structure-activity profiling. Using oxygen consumption rate as an assay for determining uncoupling activity, changes on the 5- and 6-position of the oxadiazolopyrazine core were introduced. Our studies suggest that unsymmetrical aniline derivatives bearing electron withdrawing groups are preferred compared to the symmetrical counterparts. In addition, alkyl substituents are not tolerated, and the N-H proton of the aniline ring is responsible for the protonophore activity. In particular, compound 10b had an EC50 value of 190 nM in L6 myoblast cells. In an in vivo model of NASH, 10b decreased liver triglyceride levels and showed improvement in fibrosis, inflammation, and plasma ALT. Taken together, our studies indicate that mitochondrial uncouplers have potential for the treatment of NASH.

COMPOSITIONS AND METHODS FOR PREPARING AND USING MITOCHONDRIAL UNCOUPLERS

This disclosure provides compounds of Formula I, II, and III and pharmaceutically acceptable salts thereof for use as mitochondrial uncouplers, where the variables, e.g. R1-R9, (I) (II) (III) X1, X2, and Y1