2876-17-7

Basic information

• Product Name: 1-METHOXYPHENAZINE
• Synonyms: 1-METHOXYPHENAZINE
• CAS NO: 2876-17-7
• Molecular Formula: C₁₃H₁₀N₂O
• Molecular Weight: 210.23
• Mol File: 2876-17-7.mol
• Article Data: 13

Chemical Properties

• Melting Point: 171 °C
• Boiling Point: 393.8°Cat760mmHg
• Flash Point: 131.8°C
• Appearance: /
• Density: 1.25g/cm³
• Vapor Pressure: 4.71E-06mmHg at 25°C
• Refractive Index: 1.697
• CAS DataBase Reference: 1-METHOXYPHENAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHOXYPHENAZINE(2876-17-7)
• EPA Substance Registry System: 1-METHOXYPHENAZINE(2876-17-7)

Safety Data

• Hazardous Substances Data: 2876-17-7(Hazardous Substances Data)

Usage

General Description

1-Methoxyphenazine is a chemical compound that belongs to the phenazine class of compounds. It is a tricyclic antipsychotic drug that acts as a dopamine antagonist. 1-Methoxyphenazine is primarily used for the treatment of schizophrenia and other psychotic disorders. Its mechanism of action involves blocking the receptors in the brain that respond to dopamine, thereby reducing the symptoms of psychosis. The compound is also known to have sedative and antiemetic effects, making it a versatile drug for managing a range of symptoms associated with psychiatric disorders. However, it is important to note that 1-Methoxyphenazine may also have potential side effects, including drowsiness, dizziness, dry mouth, and blurred vision, and should be used under the supervision of a healthcare professional.

InChI:InChI=1/C13H10N2O/c1-16-12-8-4-7-11-13(12)15-10-6-3-2-5-9(10)14-11/h2-8H,1H3

Upstream product

• 74-88-4 methyl iodide 
• 7664-93-9 sulfuric acid 
• 60855-15-4 3-methoxy-[1,2]benzoquinone 
• 95-54-5 1,2-diamino-benzene 
• 1427288-36-5 2-(3-methoxyphenyl)-1,3-dihydro-1H-benzo[d]1,3,2-diazaborole 
• 4103-29-1 1-(2 bromophenyl)-2-phenyldiazene 
• 1227476-15-4 Azobenzene 
• 615-36-1 2-bromoaniline 
• 17128-10-8 4-[(2-bromophenyl)diazenyl]-N,N-dimethylaniline 
• 67853-37-6 2-bromo-1-methoxy-3-nitrobenzene 
• 106-40-1 4-bromo-aniline 
• 62-53-3 aniline 
• 2538-68-3 tubermycin B 
• 528-71-2 phenazin-1-ol 

Downstream Products

• 3225-16-9 1-phenylphenazine 
• 39022-48-5 N-phenylphenazin-1-amine 
• 2881-89-2 1-Amino-4-methoxy-phenazin 
• 528-71-2 phenazin-1-ol 
• 65162-13-2 1-methoxy-5-methylphenazinium methyl sulfate 

Relevant articles and documents

An Efficient Buchwald-Hartwig/Reductive Cyclization for the Scaffold Diversification of Halogenated Phenazines: Potent Antibacterial Targeting, Biofilm Eradication, and Prodrug Exploration

Bacterial biofilms are surface-attached communities comprised of nonreplicating persister cells housed within a protective extracellular matrix. Biofilms display tolerance toward conventional antibiotics, occur in ～80% of infections, and lead to >500000 deaths annually. We recently identified halogenated phenazine (HP) analogues which demonstrate biofilm-eradicating activities against priority pathogens; however, the synthesis of phenazines presents limitations. Herein, we report a refined HP synthesis which expedited the identification of improved biofilm-eradicating agents. 1-Methoxyphenazine scaffolds were generated through a Buchwald-Hartwig cross-coupling (70% average yield) and subsequent reductive cyclization (68% average yield), expediting the discovery of potent biofilm-eradicating HPs (e.g., 61: MRSA BAA-1707 MBEC = 4.69 μM). We also developed bacterial-selective prodrugs (reductively activated quinone-alkyloxycarbonyloxymethyl moiety) to afford HP 87, which demonstrated excellent antibacterial and biofilm eradication activities against MRSA BAA-1707 (MIC = 0.15 μM, MBEC = 12.5 μM). Furthermore, active HPs herein exhibit negligible cytotoxic or hemolytic effects, highlighting their potential to target biofilms.

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An umpolung strategy for rapid access to thermally activated delayed fluorescence (TADF) materials based on phenazine

Herein, Ag(I)-promoted regioselective intramolecular radical nucleophilic addition/rearrangement of 2-aryl diazaboroles has been accomplished for the first time to construct phenazine structures. This protocol is an umpolung strategy based on the classical electrophilic mechanism, and therefore, a reversed regioselectivity was observed, which provides an opportunity to prepare sterically hindered phenazines. The resulting thermally activated delayed fluorescence (TADF) materials based on phenazine exhibit emission bands from green to red with high quantum yields and moderate fluorescence lifetimes as solid films.

Design, synthesis and biological evaluations of diverse Michael acceptor-based phenazine hybrid molecules as TrxR1 inhibitors

A series of novel phenazine derivatives (1~27) containing the Michael acceptor scaffolds were designed and synthesized in this study. Some compounds exhibited selective cytotoxicity against Bel-7402 cancer cell line in vitro, in which compound 26 were found to have the best antiproliferative activity. Meanwhile, compound 26 showed no obvious cell toxicity against human normal liver epithelial L02 cells, which means this compound possessed a better safety potential. In the following research, compound 26 was verified to inhibit TrxR1 enzyme activity, ultimately resulting in cellular molecular mechanism events of apoptosis including growth of intracellular ROS level, depletion of reduced Trx1, liberation of ASK1 and up-regulation of p38, respectively. Together, all these evidences implicated that compound 26 acted as the TrxR1 inhibitor against Bel-7402 cells, and could activate apoptosis through the ROS-Trx-ASK1-p38 pathway.