Phenazine-1-carboxamide

Base Information

• Chemical Name: Phenazine-1-carboxamide
• CAS No.: 550-89-0
• Molecular Formula: C13H9N3O
• Molecular Weight: 223.234
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID10203545
• Nikkaji Number: J11.574F
• Wikidata: Q27131710
• Metabolomics Workbench ID: 62083
• ChEMBL ID: CHEMBL463748
• Mol file: 550-89-0.mol

Synonyms:PA-1-CA cpd;phenazine-1-carboxamide

Chemical Property of Phenazine-1-carboxamide

Chemical Property:

• Appearance/Colour: green-yellow solid
• Vapor Pressure: 3.68E-11mmHg at 25°C
• Melting Point: 242oC
• Boiling Point: 526.1°C at 760 mmHg
• PKA: 14.33±0.30(Predicted)
• Flash Point: 272°C
• PSA: 68.87000
• Density: 1.371g/cm³
• LogP: 2.58220
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 223.074561919
• Heavy Atom Count: 17
• Complexity: 307

Purity/Quality:

97% ^*data from raw suppliers

Oxychloroaphine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)N=C3C=CC=C(C3=N2)C(=O)N
• General Description: Phenazine-1-carboxamide and its derivatives, particularly those with electron-withdrawing substituents such as methoxy groups, exhibit significant antitumor activity, with the 9-methoxy derivative showing notable efficacy against Lewis lung carcinoma. These compounds function as potential DNA-intercalating agents, and their cytotoxicity is influenced by the electronic properties of the substituents, making them promising candidates for further development as antitumor drugs.

Technology Process of Phenazine-1-carboxamide

There total 10 articles about Phenazine-1-carboxamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

tubermycin B (2538-68-3,102646-59-3) → phenazine-1-carboxamide (550-89-0)

Guidance literature:

With thionyl chloride; und anschliessend Behandeln mit konz.wss.NH₃;

Reference yield:

phenazine-1-carboxylic acid chloride → phenazine-1-carboxamide (550-89-0)

Guidance literature:

With ammonia; In dichloromethane; water; at 20 ℃; Inert atmosphere;

DOI:10.1039/c3ob42416b

Reference yield:

phenazine-1-carboxylic acid methyl ester (3225-19-2) → phenazine-1-carboxamide (550-89-0)

Guidance literature:

With ammonium hydroxide;

upstream raw materials:

tubermycin B

phenazine-1-carboxylic acid methyl ester

5,10-dihydro-phenazine-1-carboxylic acid amide

anthranilic acid

Downstream raw materials:

phenazin-1-ylamine

tubermycin B

Refernces

Potential antitumor agents. 51. Synthesis and antitumor activity of substituted phenazine-1-carboxamides

10.1021/jm00388a017

The research investigates the synthesis and antitumor activity of substituted phenazine-1-carboxamides as potential antitumor agents. The study aims to explore the structure-activity relationships (SAR) of these compounds and identify derivatives with enhanced antitumor properties. The researchers synthesized a series of N-[2-(dimethylamino)ethyl]phenazine-1-carboxamides with various substituents (such as methyl, methoxy, and chloro groups) at different positions on the phenazine ring. Key chemicals used in the synthesis include phenazine-1-carboxylic acids, N-[2-(dimethylamino)ethyl]amine, and coupling agents like 1,1'-carbonyldiimidazole or thionyl chloride. The study found that the cytotoxicity of the phenazine-1-carboxamides correlates positively with the electron-withdrawing power of the substituent groups, with 9-substituted compounds showing the most activity. The most active compound identified was the 9-methoxy derivative, which demonstrated significant antitumor activity against Lewis lung carcinoma in mice, comparable to the best DNA-intercalating agents described to date. The research concludes that the phenazine-1-carboxamide series holds promise for further development as antitumor drugs, with clear guidelines provided for future work based on the observed SAR.

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