4502-10-7

Usage

Preparation

Also obtained by bioconversion of nitro precursor using recombinant Escherichia coli strains.

InChI:InChI=1/C8H9NO2/c1-5(10)6-3-2-4-7(11)8(6)9/h2-4,11H,9H2,1H3

Upstream product

• 33852-43-6 1-(3-methoxy-2-nitrophenyl)ethanone 
• 53967-72-9 1-(5-hydroxy-6-nitrophenyl)ethanone 
• 484-78-6 3-hydroxykynurenine 
• 16714-26-4 1-(2-azido-phenyl)-ethanone 
• 577-59-3 2-acetylnitrobenzene 
• 1181825-29-5 3-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole 
• 83-34-1 3-Methylindole 
• 15865-57-3 2-nitro-3-methoxybenzoyl chloride 
• 121-71-1 3-Hydroxyacetophenone 
• 4127-53-1 3-methylbenzo[c]isoxazole 

Downstream Products

• 34277-05-9 1,9-diacetyl-2-amino-3H-phenoxazin-3-one 
• 106595-00-0 9-acetyl-2-hydroxy-phenoxazin-3-one 
• 107922-48-5 (5-acetyl-2-oxo-2H-benzo[1,4]oxazin-3-yl)-acetic acid ethyl ester 
• 37469-58-2 1,8,13-triacetyltriphenodioxazine 
• 109369-42-8 11-acetyl-4H-pyrido[3,2-a]phenoxazine-1,5-dione 
• 37469-59-3 1,1',1''-benzo[5,6][1,4]oxazino[2,3-b]phenoxazine-1,6,10-triyl-tris-ethanone 
• 37469-56-0 1,1'-benzo[5,6][1,4]oxazino[2,3-b]phenoxazine-1,6-diyl-bis-ethanone 
• 37469-61-7 1-acetyl-benzo[5,6][1,4]oxazino[2,3-b]phenoxazine-6-carboxylic acid methyl ester 
• 37469-69-5 1-acetyl-9-methyl-benzo[5,6][1,4]oxazino[2,3-b]phenoxazine-6-carboxylic acid methyl ester 
• 86712-32-5 1,8,13-triacetyl-7,14-dihydrotriphenodioxazine 
• 86712-35-8 1,13-dicarbomethoxy-8-acetyl-7,14-dihydrotriphenodioxazine 
• 70735-79-4 4-acetylbenzoxazdin-2(3H)-one 
• 1038743-82-6 C₁₃H₁₅NO₂ 
• 1333389-48-2 5-ethyl-1,4,5,13-tetrahydro-5,8-dihydroxy-12-methyl-3H,15H-oxepino[3',4':6,7]indolizino[1,2-b]quinoline-3,15-dione 

Relevant academic research and scientific papers

Synthesis of 4-acetylbenzoxazolin-2(3H)-one reported from Zea mays

A three-step alternative synthesis of 4-acetylbenzoxazolin-2(3H)-one (4) is reported. Starting from inexpensive 3-hydroxyacetophenone (1) 3-hydroxy- 2-nitroacetophenone (2) is prepared by nitration followed by catalytic hydrogenation to yield 2-amino-3-hydroxyacetophenone (3) in which a C=O unit is inserted by means of bis(trichloromethyl)carbonate (triphosgene) in the presence of triethylamine to afford 4 in 35% overall yield.

One-pot oxidative hydrolysis-oxidative cleavage of 7-borylindoles enables access to: O -amidophenols and 4-acylbenzoxazoles

7-Borylindoles undergo a one-pot oxidative-hydrolysis of the arylboronate and oxidative cleavage of the indole C2-C3 double bond to afford o-amidophenol derivatives. Subsequent cyclisation delivers benzoxazoles bearing an acyl group at C4, a substitution pattern common to fungal-derived benzoxazole alkaloids. Using 7-borylindoles as substrates to access functionalised o-amidophenols circumvents the difficult preparation of these compounds from arenes, streamlining access to substituted 4-acylbenzoxazoles in the process.

Topoisomerase I-mediated antiproliferative activity of 10-substituted and 12-substituted homocamptothecins

Homocamptothecin (hCPT) is an E-ring modified camptothecin (CPT) analogue, which showed pronounced inhibitory activity of topoisomerase I. In search of novel hCPT-type anticancer agents, two series of hCPT derivatives were synthesized and evaluated in vitro against three human tumor cell lines. The results indicated that the 10-substituted hCPT derivatives had a considerably higher cytotoxic activity than the 12-substituted ones. Among the 10-substituted compounds, 8a, 8b, 9b, and 9i showed an equivalent or even more potent activity than the positive control drug topotecan against the lung cancer cell line A-549. Moreover, the hCPT analogues 8a and 8b exhibited a higher topoisomerase I inhibitory activity than CPT at a concentration of 100 μM. Copyright

Biomimetic Synthesis of 4-Acetylbenzoxazolin-2(3H)-one Isolated from Zea mays

4-Acctylbenzoxazolin-2(3H)-one has been prepared biomimetically during attempts to synthesize the hemiacetalic hydroxamic acid 5-acetyl-2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one by the immediate degradation of this unstable compound generated as an intermediate. Thus, 4-acetylbenzoxazolin-2(3H)one recently isolated from Zea mays kernels, and similar to other benzoxazolin-2(3H)-ones known from plant sources, is assumed to have originated from the degradation of natural 5-acetyl-2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one which in turn could have been enzymatically released by a β-glucosidase from the corresponding 2-β-D-glucoside.