210302-17-3 Usage
Uses
1. Used in Pharmaceutical Industry:
N^5,N^6-bis(2-fluorophenyl)-[1,2,5]oxadiazolo[3,4-b]pyrazine-5,6-diamine is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structure and reactivity make it a valuable building block in the development of new drugs with specific therapeutic properties.
2. Used in Chemical Research:
In the field of chemical research, N^5,N^6-bis(2-fluorophenyl)-[1,2,5]oxadiazolo[3,4-b]pyrazine-5,6-diamine serves as a key compound for studying the properties and reactivity of fluorophenyl-substituted heterocycles. This can lead to a better understanding of their potential applications in various chemical processes and the development of new materials.
3. Used in Material Science:
The compound may also find applications in material science, particularly in the development of new materials with specific properties. Its unique structure and potential for further functionalization make it an interesting candidate for the design of advanced materials with tailored characteristics.
4. Used in Mitochondrial Research:
As a mitochondrial protonophore uncoupler, N^5,N^6-bis(2-fluorophenyl)-[1,2,5]oxadiazolo[3,4-b]pyrazine-5,6-diamine can be used in the study of mitochondrial function and energy metabolism. Its ability to stimulate a higher maximum rate of mitochondrial respiration without depolarizing the plasma membrane makes it a valuable tool for investigating the role of mitochondria in cellular processes and potential therapeutic targets for various diseases.
5. Used in Obesity and Metabolic Research:
N^5,N^6-bis(2-fluorophenyl)-[1,2,5]oxadiazolo[3,4-b]pyrazine-5,6-diamine has demonstrated potential in protecting against obesity and improving glycemic control in rodent models. This makes it a promising candidate for further research into the development of treatments for obesity, insulin resistance, and related metabolic disorders.
6. Used in Retinal Tissue Protection:
The compound has shown the ability to attenuate transportation-induced apoptosis in iPS-differentiated retinal tissue. This suggests that it may have potential applications in the field of ophthalmology, particularly in the development of treatments for retinal diseases and conditions associated with apoptosis.
Biochem/physiol Actions
BAM15 increases mitochondrial respiration rate and is also found to be less cytotoxic compared to other protonophore uncouplers such as carbonyl cyanide p-trifluoromethoxyphenylhydrazone. Hindered oncogenic MAPK (mitogen-activated protein kinase ) signaling leads to BAM15 induced mitochondrial apoptotic pathway activation.
Enzyme inhibitor
This novel mitochondrial uncoupler (FW = 340.29 g/mol), also named (2- fluorophenyl)-{6-[(2-fluorophenyl)amino]-(1,2,5-oxadiazolo[3,4-e]pyrazin- 5-yl)}amine, exhibits a broad effective range of H+ gradient-dissipating action without affecting plasma membrane electrophysiology. With FCCP as an equipotent positive control, BAM15 was found to be fully able to increase mitochondrial respiration in the presence of oligomycin over a broader concentration range than FCCP in both myoblasts and hepatocytes. BAM15 and FCCP had similar effects on mitochondrial depolarization in L6 myoblasts treated with concentrations of each uncoupler at 1 and 10 μM, as measured by tetramethylrhodamine (TMRM) fluorescence. Neither FCCP nor BAM15 donates electrons to the Electron Transport Chain. Although some non-protonophoric uncouplers increase proton transport into the matrix via interaction with the mitochondrial inner membrane adenine nucleotide translocase (ANT), neither BAM15 nor FCCP requires the ANT to increase mitochondrial respiration.
References
1) Kenwood et al. (2015), Structure-activity relationships of furazano[3,4-b]pyrazines as mitochondrial uncouplers; Bioorg. Med. Chem. Lett., 25 4858
2) Kenwood et al. (2013), Identification of a Novel Mitochondrial Uncoupler That Does Not Depolarize the Plasma Membrane; Mol. Metab., 3 114
3) Axelrod et al. (2020), BAM15-mediated Mitochondrial Uncoupling Protects Against Obesity and Improves Glycemic Control; EMBO Mol. Med., Jun 10; e12088
4) Alexopoulos et al. (2020), Mitochondrial Uncoupler BAM15 Reverses Diet-Induced Obesity and Insulin Resistance in Mice; Nat. Commun., 11 2397
5) Tang et al. (2019), BAM15 Attenuates Transportation-Induced Apoptosis in iPS-differentiated Retinal Tissue; Stem Cell Res. Ther., 10 64
Check Digit Verification of cas no
The CAS Registry Mumber 210302-17-3 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,1,0,3,0 and 2 respectively; the second part has 2 digits, 1 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 210302-17:
(8*2)+(7*1)+(6*0)+(5*3)+(4*0)+(3*2)+(2*1)+(1*7)=53
53 % 10 = 3
So 210302-17-3 is a valid CAS Registry Number.
210302-17-3Relevant academic research and scientific papers
Chemistry of furazano[3,4-b]pyrazines 3. Method for the synthesis of 5,6-disubstituted furazano[3,4-b]pyrazines
Starchenkov,Andrianov
, p. 1219 - 1233 (2007/10/03)
A method was developed for the synthesis of 5,6-dichlorofurazano[3,4-b]pyrazine (a compound with easily removed leaving groups). The optimum conditions for their substitution by various nucleophiles were determined. 1998 Plenum Publishing Corporation.
