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1916-59-2

1916-59-2 | 2-Amino-3H-phenoxazin-3-one

CAS No: 1916-59-2 Catalog No: AG00387C MDL No:

Product Description

Catalog Number:
AG00387C
Chemical Name:
2-Amino-3H-phenoxazin-3-one
CAS Number:
1916-59-2
Molecular Formula:
C12H8N2O2
Molecular Weight:
212.2041
IUPAC Name:
2-aminophenoxazin-3-one
InChI:
InChI=1S/C12H8N2O2/c13-7-5-9-12(6-10(7)15)16-11-4-2-1-3-8(11)14-9/h1-6H,13H2
InChI Key:
RDJXPXHQENRCNG-UHFFFAOYSA-N
SMILES:
O=c1cc2oc3ccccc3nc2cc1N
NSC Number:
94945

Properties

Complexity:
434  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
212.059g/mol
Formal Charge:
0
Heavy Atom Count:
16  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
212.208g/mol
Monoisotopic Mass:
212.059g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
64.7A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1  

Literature

Title Journal
Enhancement of cytotoxic and pro-apoptotic effects of 2-aminophenoxazine-3-one on the rat hepatocellular carcinoma cell line dRLh-84, the human hepatocellular carcinoma cell line HepG2, and the rat normal hepatocellular cell line RLN-10 in combination with 2-deoxy-D-glucose. Oncology reports 20120201
Involvement of endoplasmic reticulum stress-mediated CHOP (GADD153) induction in the cytotoxicity of 2-aminophenoxazine-3-one in cancer cells. International journal of oncology 20111001
2-Aminophenoxazine-3-one and 2-amino-4,4α-dihydro-4α,7-dimethyl-3H-phenoxazine-3-one cause cellular apoptosis by reducing higher intracellular pH in cancer cells. Proceedings of the Japan Academy. Series B, Physical and biological sciences 20110511
Rapid decrease of intracellular pH associated with inhibition of Na+/H+ exchanger precedes apoptotic events in the MNK45 and MNK74 gastric cancer cell lines treated with 2-aminophenoxazine-3-one. Oncology reports 20110201
Selectively induced apoptosis in human neutrophils in the presence of oxidative phenoxazines, 2-amino-4,4α-dihydryo-4α-7H-phenoxazine-3-one and 2-aminophenoxazine-3-one, preceded by decrease of intracellular pH, depolarization of the mitochondria, and inhibition of superoxide generation. Journal of pharmacological sciences 20110101
Structure-activity relationship of benzoxazinones and related compounds with respect to the growth inhibition and alpha-amylase activity in cress seedlings. Journal of plant physiology 20101015
A copper-containing oxidase catalyzes C-nitrosation in nitrosobenzamide biosynthesis. Nature chemical biology 20100901
Structure and antibacterial activity of the silver(I) complex of 2-aminophenoxazine-3-one. Metallomics : integrated biometal science 20100801
Anticancer activity of phenoxazines produced by bovine erythrocytes on colon cancer cells. Oncology reports 20100601
2-Aminophenoxazine-3-one induces cellular apoptosis by causing rapid intracellular acidification and generating reactive oxygen species in human lung adenocarcinoma cells. International journal of oncology 20100301
In vitro antibacterial activity of Phx-3 against Helicobacter pylori. Biological & pharmaceutical bulletin 20100101
Inhibitory effects of 2-amino-3H-phenoxazin-3-one on the melanogenesis of murine B16 melanoma cell line. Bioscience, biotechnology, and biochemistry 20100101
2-aminophenoxazine-3-one prevents pulmonary metastasis of mouse B16 melanoma cells in mice. Journal of pharmacological sciences 20100101
Phenoxazine derivatives suppress the infections caused by herpes simplex virus type-1 and herpes simplex virus type-2 intravaginally inoculated into mice. Journal of pharmacological sciences 20100101
Anticancer effects of phenoxazine derivatives revealed by inhibition of cell growth and viability, disregulation of cell cycle, and apoptosis induction in HTLV-1-positive leukemia cells. Journal of pharmacological sciences 20090501
Mitochondrial depolarization and apoptosis associated with sustained activation of c-jun-N-terminal kinasein the human multiple myeloma cell line U266 induced by 2-aminophenoxazine-3-one. Molecular medicine reports 20090101
Anti-inflammatory and immunomodulatory properties of 2-amino-3H-phenoxazin-3-one. Biological & pharmaceutical bulletin 20081001
Suppression of the proliferation of cancer cell lines, KB-3-1 and K562 cells preceded by a decrease in intracellular pH caused by phenoxazine derivatives. Oncology reports 20080501
Phenoxazine derivatives inactivate human cytomegalovirus, herpes simplex virus-1, and herpes simplex virus-2 in vitro. Journal of pharmacological sciences 20080301
Synthesis and testing of chromogenic phenoxazinone substrates for beta-alanyl aminopeptidase. Organic & biomolecular chemistry 20080221
Capillary electrophoresis enzyme immunoassay for alpha-fetoprotein and thyroxine in human serum with electrochemical detection. Journal of separation science 20080201
Apoptosis induction preceded by mitochondrial depolarization in multiple myeloma cell line U266 by 2-aminophenoxazine-3-one. Biological & pharmaceutical bulletin 20080101
Investigation of the interaction between ssDNA and 2-aminophenoxazine-3-one and development of an electrochemical DNA biosensor. Oligonucleotides 20080101
CE-based simultaneous liquid-phase noncompetitive enzyme immunoassay for three tumor markers in human serum using electrochemical detection. Electrophoresis 20071201
A tetracopper(II)-tetraradical cuboidal core and its reactivity as a functional model of phenoxazinone synthase. Inorganic chemistry 20071112
Silica-immobilized enzymes for multi-step synthesis in microfluidic devices. Biotechnology and bioengineering 20071015
Interactions of Bacillus mojavensis and Fusarium verticillioides with a benzoxazolinone (BOA) and its transformation product, APO. Journal of chemical ecology 20071001
Caspase-independent cell death revealed in human gastric cancer cell lines, MKN45 and KATO III treated with phenoxazine derivatives. Oncology reports 20070201
Phenoxazine derivatives 2-amino-4,4alpha-dihydro-4alpha-phenoxazine-3-one and 2-aminophenoxazine-3-one-induced apoptosis through a caspase-independent mechanism in human neuroblastoma cell line NB-1 cells. Biological & pharmaceutical bulletin 20070201
Phenoxazine derivatives induce caspase-independent cell death in human glioblastoma cell lines, A-172 and U-251 MG. Oncology reports 20070101
2-aminophenoxazine-3-one suppresses the growth of mouse malignant melanoma B16 cells transplanted into C57BL/6Cr Slc mice. Biological & pharmaceutical bulletin 20061101
Actinomycins with altered threonine units in the beta-peptidolactone. Journal of natural products 20060801
Microsphere-based protease assays and screening application for lethal factor and factor Xa. Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501
Anticancer effects of phenoxazine derivatives combined with tumor necrosis factor-related apoptosis-inducing ligand on pancreatic cancer cell lines, KLM-1 and MIA-PaCa-2. Oncology reports 20060401
Effects of some benzoxazinoids on in vitro growth of Cephalosporium gramineum and other fungi pathogenic to cereals and on Cephalosporium stripe of winter wheat. Journal of agricultural and food chemistry 20060222
Structure-activity relationship (SAR) studies of benzoxazinones, their degradation products, and analogues. Phytotoxicity on problematic weeds Avena fatua L. and Lolium rigidum Gaud. Journal of agricultural and food chemistry 20060222
Fate of benzoxazinone allelochemicals in soil after incorporation of wheat and rye sprouts. Journal of agricultural and food chemistry 20060222
Transformation of benzoxazinones and derivatives and microbial activity in the test environment of soil ecotoxicological tests on Poecilus cupreus and Folsomia candida. Journal of agricultural and food chemistry 20060222
QSAR models for Daphnia magna toxicity prediction of benzoxazinone allelochemicals and their transformation products. Journal of agricultural and food chemistry 20060222
New aminophenoxazinones from a marine Halomonas sp.: fermentation, structure elucidation, and biological activity. The Journal of antibiotics 20060201
Chlamydia pneumoniae growth inhibition in human monocytic THP-1 cells and human epithelial HEp-2 cells by a novel phenoxazine derivative. Journal of medical microbiology 20051201
Transformation products of 2-benzoxazolinone (BOA) in soil. Chemosphere 20050901
Differentiation and apoptosis in human malignant melanoma G-361 cells induced by 2-aminophenoxazine-3-one. Oncology reports 20050701
2-amino-phenoxazine-3-one attenuates glucose-induced augmentation of embryonic form of myosin heavy chain, endothelin-1 and plasminogen activator inhibitor-1 in human umbilical vein endothelial cells. Biological & pharmaceutical bulletin 20050501
Biotransformation of 2-benzoxazolinone to 2-amino-(3H)-phenoxazin-3-one and 2-acetylamino-(3H)-phenoxazin-3-one in soil. Journal of chemical ecology 20050501
Structure-Activity Relationships (SAR) studies of benzoxazinones, their degradation products and analogues. phytotoxicity on standard target species (STS). Journal of agricultural and food chemistry 20050209
Degradation studies on benzoxazinoids. Soil degradation dynamics of (2R)-2-O-beta-D-glucopyranosyl-4-hydroxy-(2H)- 1,4-benzoxazin-3(4H)-one (DIBOA-Glc) and its degradation products, phytotoxic allelochemicals from Gramineae. Journal of agricultural and food chemistry 20050209
Phenoxazine compounds produced by the reactions with bovine hemoglobin show antimicrobial activity against non-tuberculosis mycobacteria. The Tohoku journal of experimental medicine 20040501
Kinetics and mechanism of the ferroxime(II)-catalysed biomimetic oxidation of 2-aminophenol by dioxygen. A functional phenoxazinone synthase model. Dalton transactions (Cambridge, England : 2003) 20040407
Antitumor agents. 1. Synthesis, biological evaluation, and molecular modeling of 5H-pyrido[3,2-a]phenoxazin-5-one, a compound with potent antiproliferative activity. Journal of medicinal chemistry 20021121
Hydroxylated 2-amino-3H-phenoxazin-3-one derivatives as products of 2-hydroxy-1,4-benzoxazin-3-one (HBOA) biotransformation by Chaetosphaeria sp., an endophytic fungus from Aphelandra tetragona. Zeitschrift fur Naturforschung. C, Journal of biosciences 20020101

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