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59-49-4 | 2-Benzoxazolinone
CAS No: 59-49-4 Catalog No: AG003GKT MDL No:MFCD00005716
Product Description
Catalog Number:
AG003GKT
Chemical Name:
2-Benzoxazolinone
CAS Number:
59-49-4
Molecular Formula:
C7H5NO2
Molecular Weight:
135.1201
MDL Number:
MFCD00005716
IUPAC Name:
3H-1,3-benzoxazol-2-one
InChI:
InChI=1S/C7H5NO2/c9-7-8-5-3-1-2-4-6(5)10-7/h1-4H,(H,8,9)
InChI Key:
ASSKVPFEZFQQNQ-UHFFFAOYSA-N
SMILES:
Oc1nc2c(o1)cccc2
EC Number:
200-430-0
UNII:
3X996Q809V
NSC Number:
3812
Properties
Complexity:
158
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
135.032g/mol
Formal Charge:
0
Heavy Atom Count:
10
Hydrogen Bond Acceptor Count:
2
Hydrogen Bond Donor Count:
1
Isotope Atom Count:
0
Molecular Weight:
135.122g/mol
Monoisotopic Mass:
135.032g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
38.3A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
1.2
Literature
| Title | Journal |
|---|---|
| Identification of novel 2-benzoxazolinone derivatives with specific inhibitory activity against the HIV-1 nucleocapsid protein. | European journal of medicinal chemistry 20180210 |
| Design, synthesis and structure-activity relationships of novel benzoxazolone derivatives as 18 kDa translocator protein (TSPO) ligands. | Bioorganic & medicinal chemistry 20120915 |
| Synthesis and biological activities of some 1,3-benzoxazol-2(3H)-one derivatives as anti-quorum sensing agents. | Arzneimittel-Forschung 20120701 |
| BOA detoxification of four summer weeds during germination and seedling growth. | Journal of chemical ecology 20120701 |
| Synthesis and structure-activity relationship of aminopyridines with substituted benzoxazoles as c-Met kinase inhibitors. | Bioorganic & medicinal chemistry letters 20120615 |
| Concentrations and allelopathic effects of benzoxazinoid compounds in soil treated with rye (Secale cereale) cover crop. | Journal of agricultural and food chemistry 20120509 |
| Xenobiotic- and jasmonic acid-inducible signal transduction pathways have become interdependent at the Arabidopsis CYP81D11 promoter. | Plant physiology 20120501 |
| 3-Anilinomethyl-5-chloro-1,3--benzoxazol-2(3H)-one. | Acta crystallographica. Section E, Structure reports online 20120501 |
| A neutral diphosphate mimic crosslinks the active site of human O-GlcNAc transferase. | Nature chemical biology 20120101 |
| Phytotoxic effect of 2-benzoxazolinone (BOA) against some vegetable crops. | Journal of environmental biology 20120101 |
| Cyanamide mode of action during inhibition of onion (Allium cepa L.) root growth involves disturbances in cell division and cytoskeleton formation. | Planta 20110901 |
| Allelochemical stress inhibits growth, leaf water relations, PSII photochemistry, non-photochemical fluorescence quenching, and heat energy dissipation in three C3 perennial species. | Journal of experimental botany 20110801 |
| Benzoxazolin-2(3H)-one (BOA) induced changes in leaf water relations, photosynthesis and carbon isotope discrimination in Lactuca sativa. | Plant physiology and biochemistry : PPB 20110801 |
| Early senescence induced by 2-3H-benzoxazolinone (BOA) in Arabidopsis thaliana. | Journal of plant physiology 20110615 |
| Design, synthesis and biological evaluation of new 2-benzoxazolinone derivatives as potential cholinesterase inhibitors for therapy of alzheimer's disease. | Die Pharmazie 20110601 |
| Mining a cathepsin inhibitor library for new antiparasitic drug leads. | PLoS neglected tropical diseases 20110501 |
| Determination of brain cytochrome P450 2E1 activity in rat with the probe of chlorzoxazone by liquid chromatography-mass spectrometry. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20110201 |
| The use of endophytes to obtain bioactive compounds and their application in biotransformation process. | Biotechnology research international 20110101 |
| Synthesis, Antiinflammatory and Antimicrobial Activity of Some New 1-(3-Phenyl-3,4-Dihydro-2H-1,3-Benzoxazin-6-yl)-Ethanone Derivatives. | Indian journal of pharmaceutical sciences 20110101 |
| Development, evaluation and application of 3D QSAR Pharmacophore model in the discovery of potential human renin inhibitors. | BMC bioinformatics 20110101 |
| 3-Benzyl-6-(2-chloro-benzo-yl)-1,3-benzoxazol-2(3H)-one. | Acta crystallographica. Section E, Structure reports online 20101201 |
| Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. | Bioorganic & medicinal chemistry letters 20101101 |
| 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 |
| Optimization of N-benzyl-benzoxazol-2-ones as receptor antagonists of macrophage migration inhibitory factor (MIF). | Bioorganic & medicinal chemistry letters 20101001 |
| The discovery of a series of N-substituted 3-(4-piperidinyl)-1,3-benzoxazolinones and oxindoles as highly brain penetrant, selective muscarinic M1 agonists. | Bioorganic & medicinal chemistry letters 20100915 |
| A 3D-pharmacophore model for sigma2 receptors based on a series of substituted benzo[d]oxazol-2(3H)-one derivatives. | Bioorganic & medicinal chemistry letters 20100501 |
| Synthesis of benzoxazolones from nitroarenes or aryl halides. | Organic letters 20100219 |
| Reduced photosynthetic activity is directly correlated with 2-(3H)-benzoxazolinone accumulation in lettuce leaves. | Journal of chemical ecology 20100201 |
| Comparative transcriptional profiling-based identification of raphanusanin-inducible genes. | BMC plant biology 20100101 |
| Antioxidant activity of benzoxazolinonic and benzothiazolinonic derivatives in the LDL oxidation model. | Bioorganic & medicinal chemistry 20091115 |
| Phytochemical screening and polyphenolic antioxidant activity of aqueous crude leaf extract of Helichrysum pedunculatum. | International journal of molecular sciences 20091101 |
| Synthesis, biological evaluation, and three-dimensional in silico pharmacophore model for sigma(1) receptor ligands based on a series of substituted benzo[d]oxazol-2(3H)-one derivatives. | Journal of medicinal chemistry 20090910 |
| Enantioseparation of benzoxazolinone aminoalcohols and their aminoketone precursors, potential adrenergic ligands, by analytical and preparative liquid chromatography on amylose chiral stationary phases and characterization of the enantiomers. | Chirality 20090801 |
| FDB2 encodes a member of the arylamine N-acetyltransferase family and is necessary for biotransformation of benzoxazolinones by Fusarium verticillioides. | Journal of applied microbiology 20090801 |
| 2-3H-Benzoxazolinone (BOA) induces loss of salt tolerance in salt-adapted plants. | Plant biology (Stuttgart, Germany) 20090701 |
| Synthesis and characterization of some new 2(3H)-benzoxazolones with analgesic and antiinflammatory activities. | Journal of enzyme inhibition and medicinal chemistry 20090201 |
| Substituted benzo[d]oxazol-2(3H)-one derivatives with preference for the sigma1 binding site. | European journal of medicinal chemistry 20090101 |
| Evidence for alteration of fungal endophyte community assembly by host defense compounds. | The New phytologist 20090101 |
| Differential patterns of reactive oxygen species and antioxidative mechanisms during atrazine injury and sucrose-induced tolerance in Arabidopsis thaliana plantlets. | BMC plant biology 20090101 |
| Effects of four benzoxazinoids on gibberellin-induced alpha-amylase activity in barley seeds. | Journal of plant physiology 20081201 |
| The natural compound benzoxazolin-2(3H)-one selectively retards cell cycle in lettuce root meristems. | Phytochemistry 20080801 |
| Microarray expression profiling of Arabidopsis thaliana L. in response to allelochemicals identified in buckwheat. | Journal of experimental botany 20080801 |
| Development of a pressurized liquid extraction-solid-phase extraction followed by liquid chromatography-electrospray ionization tandem mass spectrometry method for the quantitative determination of benzoxazolinones and their degradation products in agricultural soil. | Journal of chromatography. A 20080201 |
| cis-Jasmone induces accumulation of defence compounds in wheat, Triticum aestivum. | Phytochemistry 20080101 |
| Synthesis and anticonvulsant activity of 5-chloro-2(3H)-benzoxazolinone-3-acetyl-2-(o/p-substituted benzal) hydrazone derivatives. | Arzneimittel-Forschung 20080101 |
| Antimicrobial Activity of Acanthus ilicifolius (L.). | Indian journal of pharmaceutical sciences 20080101 |
| Synthesis of 7-azabicyclo[2.2.1]heptane and 2-oxa-4-azabicyclo[3.3.1]non-3-ene derivatives by base-promoted heterocyclization of alkyl N-(cis(trans)-3,trans(cis)-4-dibromocyclohex-1-yl)carbamates and N-(cis(trans)-3,trans(cis)-4-dibromocyclohex-1-yl)-2,2,2-trifluoroacetamides. | The Journal of organic chemistry 20071109 |
| Interactions of Bacillus mojavensis and Fusarium verticillioides with a benzoxazolinone (BOA) and its transformation product, APO. | Journal of chemical ecology 20071001 |
| 1-Acylthiosemicarbazides, 1,2,4-triazole-5(4H)-thiones, 1,3,4-thiadiazoles and hydrazones containing 5-methyl-2-benzoxazolinones: synthesis, analgesic-anti-inflammatory and antimicrobial activities. | Bioorganic & medicinal chemistry 20070901 |
| Phytotoxic effects of 21 plant secondary metabolites on Arabidopsis thaliana germination and root growth. | Journal of chemical ecology 20070701 |
| O-linked N-acetylglucosaminyltransferase inhibition prevents G2/M transition in Xenopus laevis oocytes. | The Journal of biological chemistry 20070427 |
| Analgesic and antiinflammatory activities of some new Mannich bases of 5-nitro-2-benzoxazolinones. | Archives of pharmacal research 20070401 |
| Rational design, synthesis, and structure-activity relationship of benzoxazolones: new potent mglu5 receptor antagonists based on the fenobam structure. | Bioorganic & medicinal chemistry letters 20070301 |
| Zea mays: benzoxazolinone detoxification under sulfur deficiency conditions--a complex allelopathic alliance including endophytic Fusarium verticillioides. | Journal of chemical ecology 20070201 |
| Cytotoxic Mannich bases of 6-(3-aryl-2-propenoyl)-2(3H)-benzoxazolones. | European journal of medicinal chemistry 20070101 |
| Plants used traditionally to treat malaria in Brazil: the archives of Flora Medicinal. | Journal of ethnobiology and ethnomedicine 20070101 |
| In vitro characterization of SLV308 (7-[4-methyl-1-piperazinyl]-2(3H)-benzoxazolone, monohydrochloride): a novel partial dopamine D2 and D3 receptor agonist and serotonin 5-HT1A receptor agonist. | Synapse (New York, N.Y.) 20061215 |
| 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 |
| Synthesis and anti-HIV activity of new alkenyldiarylmethane (ADAM) non-nucleoside reverse transcriptase inhibitors (NNRTIs) incorporating benzoxazolone and benzisoxazole rings. | Bioorganic & medicinal chemistry 20060401 |
| Determination of benzoxazinone derivatives in plants by combining pressurized liquid extraction-solid-phase extraction followed by liquid chromatography-electrospray mass spectrometry. | Journal of agricultural and food chemistry 20060222 |
| Concentration of benzoxazinoids in roots of field-grown wheat (Triticum aestivum L.) varieties. | Journal of agricultural and food chemistry 20060222 |
| Quantification of benzoxazinone derivatives in wheat (Triticum aestivum) varieties grown under contrasting conditions in Denmark. | Journal of agricultural and food chemistry 20060222 |
| 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 |
| Joint action of benzoxazinone derivatives and phenolic acids. | Journal of agricultural and food chemistry 20060222 |
| Herbicidal effects of soil-incorporated wheat. | 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 |
| Elucidating the transformation pattern of the cereal allelochemical 6-methoxy-2-benzoxazolinone (MBOA) and the trideuteriomethoxy analogue [D3]-MBOA in soil. | 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 |
| Influence of the soil composition on the effects of benzoxazinoid allelochemicals on two soil nontarget organisms. | Journal of agricultural and food chemistry 20060222 |
| Ecotoxicological effects of benzoxazinone allelochemicals and their metabolites on aquatic nontarget organisms. | 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 |
| Effects of the benzoxazolinone BOA, selected degradation products and structure related pesticides on soil organisms. | Ecotoxicology (London, England) 20060201 |
| Glucosides from MBOA and BOA detoxification by Zea mays and Portulaca oleracea. | Journal of natural products 20060101 |
| 2-Benzoxazolinone (BOA) induced oxidative stress, lipid peroxidation and changes in some antioxidant enzyme activities in mung bean (Phaseolus aureus). | Plant physiology and biochemistry : PPB 20060101 |
| Relationship between grain yield, osmotic adjustment and benzoxazinone content in Triticum aestivum L. cultivars. | Zeitschrift fur Naturforschung. C, Journal of biosciences 20060101 |
| Effect of 2-benzoxazolinone (BOA) on seedling growth and associated biochemical changes in mung bean (Phaseolus aureus). | Zeitschrift fur Naturforschung. C, Journal of biosciences 20060101 |
| Whole plant response of lettuce after root exposure to BOA (2(3H)-benzoxazolinone). | Journal of chemical ecology 20051101 |
| Enantioseparation of chiral N-imidazole derivatives by electrokinetic chromatography using highly sulfated cyclodextrins: mechanism of enantioselective recognition. | Electrophoresis 20051001 |
| Activity of Hydroxamic Acids from Secale cereale Against the Plant-Parasitic Nematodes Meloidogyne incognita and Xiphinema americanum. | Phytopathology 20051001 |
| Transformation products of 2-benzoxazolinone (BOA) in soil. | Chemosphere 20050901 |
| Synthesis of some 2(3H)-benzoxazolone derivatives and their in-vitro effects on human leukocyte myeloperoxidase activity. | Archiv der Pharmazie 20050901 |
| Hydroxamic acid content and toxicity of rye at selected growth stages. | Journal of chemical ecology 20050801 |
| Dissecting defense-related and developmental transcriptional responses of maize during Ustilago maydis infection and subsequent tumor formation. | Plant physiology 20050701 |
| Detoxification and transcriptome response in Arabidopsis seedlings exposed to the allelochemical benzoxazolin-2(3H)-one. | The Journal of biological chemistry 20050610 |
| Predictive three-dimensional quantitative structure-activity relationship of cytochrome P450 1A2 inhibitors. | Journal of medicinal chemistry 20050602 |
| 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 |
| Dose-response-a challenge for allelopathy? | Nonlinearity in biology, toxicology, medicine 20050401 |
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| Enantiomeric resolution of new aromatase inhibitors by liquid chromatography on cellulose chiral stationary phases. | Journal of separation science 20050301 |
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| 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 |
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| Synthesis and biological evaluation with plant cells of new fosmidomycin analogues containing a benzoxazolone or oxazolopyridinone ring. | Journal of enzyme inhibition and medicinal chemistry 20041201 |
| Chiral separation of N-imidazole derivatives, aromatase inhibitors, by cyclodextrin-capillary zone electrophoresis. Mechanism of enantioselective recognition. | Electrophoresis 20040801 |
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| 3-[4-(4-fluorophenyl)piperazin-1-ylmethyl]-5-methyl-1,3-benzoxazol-2(3H)-one and 3-[4-(2-fluorophenyl)piperazin-1-ylmethyl]-5-methyl-1,3-benzoxazol-2(3H)-one. | Acta crystallographica. Section C, Crystal structure communications 20040401 |
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