2-Amino-3H-phenoxazin-3-one

Base Information

• Chemical Name: 2-Amino-3H-phenoxazin-3-one
• CAS No.: 1916-59-2
• Molecular Formula: C12H8 N2 O2
• Molecular Weight: 212.208
• Hs Code.: 2934999090
• European Community (EC) Number: 690-502-1
• NSC Number: 94945
• UNII: J4CM69VF7H
• DSSTox Substance ID: DTXSID60172691
• Nikkaji Number: J50.194H
• Wikipedia: Questiomycin_A
• Wikidata: Q15424786
• Metabolomics Workbench ID: 44427
• ChEMBL ID: CHEMBL146710
• Mol file: 1916-59-2.mol

Synonyms:2-acetylamino-(3H)-phenoxazin-3-one;2-aminophenoxazine-3-one;3-aminophenoxazone;Phx-3 cpd;questinomycine A;questiomycin A

Chemical Property of 2-Amino-3H-phenoxazin-3-one

Chemical Property:

• Vapor Pressure: 1.99E-05mmHg at 25°C
• Melting Point: 249-250 °C
• Refractive Index: 1.6000 (estimate)
• Boiling Point: 362°Cat760mmHg
• PKA: 2.73±0.20(Predicted)
• Flash Point: 172.7°C
• PSA: 69.12000
• Density: 1.45g/cm³
• LogP: 2.45620
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 212.058577502
• Heavy Atom Count: 16
• Complexity: 434

Purity/Quality:

99% ^*data from raw suppliers

QuestiomycinA ^*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=C(C(=O)C=C3O2)N
• Description: Questiomycin A is a phenoxazine and a chromophore that has been found in Streptomyces and has antibacterial and anticancer activities. It is active against M. scrofulaceum, M. marinum, and M. intracellulare (MICs = 2.8, 11.3, and 5.6 μg/ml, respectively) but not M. tuberculosis, M. smegmatis, M. kansasii, or M. fortuitum (MICs = >45 μg/ml). It is also inactive against E. coli, P. aeruginosa, S. tymphimurium, S. aureus, or L. monocytogenes. It is cytotoxic to a variety of cancer cells, including MCF-7, A549, MIA PaCa-2, and LoVo-1 cells (IC50s = 1.67, 5.48, 7.16, and 20.03 μM, respectively) as well as human umbilical vein endothelial cells (HUVECs) but not human embryonic lung fibroblast cells (HELs; IC50s = 16.06 and >50 μM, respectively). Questiomycin A reduces the increased intracellular pH in a variety of cancer cell lines, as well as in HUVECs and HELs. It prevents lung metastasis in a B16 mouse melanoma model of metastasis when administered at a dose of 0.5 mg/kg simultaneously with B16 cells or every three days. It is also a chromophore product of the reducing agent 2-aminophenol oxidation (as 2-amino-phenoxazine-3-one) and has been used as a readout in the study of catalytic oxidation of 2-aminophenol by various metal-containing complexes. It has an absorbance of 435 nm in methanol.
• Uses: Questiomycin A is a phenoxazine produced by several Streptomyces species and some fungi and bacteria. Questiomycin A is weakly active against bacteria, fungi, plants and tumour cell lines, and inhibits aromatase and sulfatases. Questiomycin, like other phenoxazines, stimulates cell growth and turnover in vitro, an activity possibly related to their ability to form stable free radicals. More recently, questiomycin A has been shown to inhibit pulmonary metastasis caused by mouse melanoma cells. Questiomycin A and related phenoxazines are important dereplication standards in discovery research to eliminate leads due to high amounts of weakly potent actives. Questiomycin A is a natural antimicrobial agent produced by agriculturally important species such as maize, rye, and wheat.

Technology Process of 2-Amino-3H-phenoxazin-3-one

There total 38 articles about 2-Amino-3H-phenoxazin-3-one 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: 80.0%

2-azidophenol (24541-44-4) → 2-aminophenoxazin-3-one (1916-59-2)

Guidance literature:

With cobalt(II) 5,10,15,20-tetraphenylporphyrin; In chlorobenzene; at 50 ℃; for 18h; Mechanism; Schlenk technique; Inert atmosphere;

DOI:10.3390/molecules21020242

Reference yield: 80.0%

2-amino-phenol (95-55-6) + 4a-hydroperoxy-N5-ethyl-N3-methyllumiflavin (59587-26-7) → 2-aminophenoxazin-3-one (1916-59-2)

Guidance literature:

With potassium tert-butylate; In tert-butyl alcohol; at 30 ℃; Product distribution; Rate constant; Mechanism; var. aminophenols and aminonaphthols;

DOI:10.1021/ja00163a037

Reference yield: 51.0%

4-(phenylimino)cyclohexa-2,5-dienone (2406-04-4) + 2-amino-phenol (95-55-6) → 2-aminophenoxazin-3-one (1916-59-2)

Guidance literature:

In ethanol; for 0.416667h;

DOI:10.1007/BF00515634

upstream raw materials:

2-amino-phenol

benzofurazan oxide

3H-Phenoxazin-3-on

2-acetylamino-3H-phenoxazin-3-one

Downstream raw materials:

2-(4-nitro-benzylidenamino)-phenoxazin-3-one

2-acetylamino-3H-phenoxazin-3-one

4-(5H-oxazolo[4,5-b]phenoxazin-2-yl)-aniline

2-p-tolyl-5H-oxazolo[4,5-b]phenoxazine