13129-58-3

Usage

Uses

Used in Pharmaceutical and Biomedical Applications:
6-Methoxyphenazin-1-ol is used as an active pharmaceutical ingredient for its antibacterial and antitumor properties. Its unique structure allows it to target and inhibit the growth of various bacteria and tumor cells, making it a promising candidate for the development of new drugs to combat antibiotic-resistant infections and cancer.
Used in Organic Electronics:
6-Methoxyphenazin-1-ol is utilized as a component in organic electronic devices due to its electronic properties. Its ability to modulate electronic behavior makes it suitable for applications such as organic light-emitting diodes (OLEDs), organic solar cells, and organic field-effect transistors (OFETs), contributing to the advancement of flexible and eco-friendly electronic technologies.
Used as a Colorimetric Sensor:
In the field of analytical chemistry, 6-Methoxyphenazin-1-ol serves as a colorimetric sensor for detecting various analytes. Its structural features enable it to undergo color changes upon interaction with specific substances, providing a visual and potentially quantitative assessment of analyte concentrations. This makes it useful for environmental monitoring, medical diagnostics, and other sensing applications where a simple and direct readout is desired.
Overall, 6-Methoxyphenazin-1-ol's diverse applications across different industries highlight its versatility and potential for further research and development.

Upstream product

• 91-23-6 2-Nitroanisole 
• 13398-79-3 1,6-dimethoxyphenazine 
• 90-04-0 2-methoxy-phenylamine 
• 69-48-7 phenazine-1,6-diol 
• 485-80-3 S-adenosyl-L-methionine 
• 23462-25-1 phenazine-1,6-dicarboxylic acid 
• 112970-44-2 2-bromo-3-methoxyaniline 
• 74-88-4 methyl iodide 

Downstream Products

• 13129-57-2 1-hydroxy-6-methoxyphenazine N₁₀-oxide 
• 13925-12-7 1-hydroxy-6-methoxy-phenazine-N₅,N₁₀-dioxide 
• 1350729-67-7 1-(t-butyldiphenylsilyloxy)-6-methoxyphenazine 

Relevant academic research and scientific papers

Functional and Structural Analysis of Phenazine O -Methyltransferase LaPhzM from Lysobacter antibioticus OH13 and One-Pot Enzymatic Synthesis of the Antibiotic Myxin

Myxin is a well-known antibiotic that had been used for decades. It belongs to the phenazine natural products that exhibit various biological activities, which are often dictated by the decorating groups on the heteroaromatic three-ring system. The three rings of myxin carry a number of decorations, including an unusual aromatic N5,N10-dioxide. We previously showed that phenazine 1,6-dicarboxylic acid (PDC) is the direct precursor of myxin, and two redox enzymes (LaPhzS and LaPhzNO1) catalyze the decarboxylative hydroxylation and aromatic N-oxidations of PDC to produce iodinin (1.6-dihydroxy-N5,N10-dioxide phenazine). In this work, we identified the LaPhzM gene from Lysobacter antibioticus OH13 and demonstrated that LaPhzM encodes a SAM-dependent O-methyltransferase converting iodinin to myxin. The results further showed that LaPhzM is responsible for both monomethoxy and dimethoxy formation in all phenazine compounds isolated from strain OH13. LaPhzM exhibits relaxed substrate selectivity, catalyzing O-methylation of phenazines with non-, mono-, or di-N-oxide. In addition, we demonstrated a one-pot biosynthesis of myxin by in vitro reconstitution of the three phenazine-ring decorating enzymes. Finally, we determined the X-ray crystal structure of LaPhzM with a bound cofactor at 1.4 ? resolution. The structure provided molecular insights into the activity and selectivity of the first characterized phenazine O-methyltransferase. These results will facilitate future exploitation of the thousands of phenazines as new antibiotics through metabolic engineering and chemoenzymatic syntheses.

Total synthesis and antileukemic evaluations of the phenazine 5,10-dioxide natural products iodinin, myxin and their derivatives

A new efficient total synthesis of the phenazine 5,10-dioxide natural products iodinin and myxin and new compounds derived from them was achieved in few steps, a key-step being 1,6-dihydroxyphenazine di-N-oxidation. Analogues prepared from iodinin, including myxin and 2-ethoxy-2-oxoethoxy derivatives, had fully retained cytotoxic effect against human cancer cells (MOLM-13 leukemia) at atmospheric and low oxygen level. Moreover, iodinin was for the first time shown to be hypoxia selective. The structure-activity relationship for leukemia cell death induction revealed that the level of N-oxide functionality was essential for cytotoxicity. It also revealed that only one of the two phenolic functions is required for activity, allowing the other one to be modified without loss of potency.

DNA strand cleavage by the phenazine di- N -oxide natural product myxin under both aerobic and anaerobic conditions

Heterocyclic N-oxides are an interesting class of antitumor agents that selectively kill the hypoxic cells found in solid tumors. The hypoxia-selective activity of the lead compound in this class, tirapazamine, stems from its ability to undergo intracellu