16063-03-9

Basic information

• Product Name: 2-(3-nitrophenyl)-4H-3,1-benzoxazin-4-one
• Synonyms: 2-(3-nitrophenyl)-4H-3,1-benzoxazin-4-one;2-(3-NITROPHENYL)-3,1-BENZOXAZIN-4(4H)-ONE
• CAS NO: 16063-03-9
• Molecular Formula: C₁₄H₈N₂O₄
• Molecular Weight: 268.2243
• Mol File: 16063-03-9.mol

Chemical Properties

• Boiling Point: 421.7 °C at 760 mmHg
• Flash Point: 208.8 °C
• Appearance: /
• Density: 1.43 g/cm³
• Vapor Pressure: 2.55E-07mmHg at 25°C
• Refractive Index: 1.679
• CAS DataBase Reference: 2-(3-nitrophenyl)-4H-3,1-benzoxazin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-nitrophenyl)-4H-3,1-benzoxazin-4-one(16063-03-9)
• EPA Substance Registry System: 2-(3-nitrophenyl)-4H-3,1-benzoxazin-4-one(16063-03-9)

Safety Data

• Hazardous Substances Data: 16063-03-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Applications:
2-(3-nitrophenyl)-4H-3,1-benzoxazin-4-one is used as a pharmaceutical agent for its potential anti-inflammatory and antioxidant effects. Its unique chemical structure allows it to modulate various biological pathways, offering potential therapeutic benefits in treating inflammation and oxidative stress-related conditions.
Used in Biomedical Research:
In the Biomedical Research Industry, 2-(3-nitrophenyl)-4H-3,1-benzoxazin-4-one is used as a fluorescent probe for biological imaging applications. Its fluorescent properties enable researchers to visualize cellular and molecular processes, contributing to a better understanding of biological mechanisms and the development of new diagnostic and therapeutic strategies.
Used in Chemical Research:
2-(3-nitrophenyl)-4H-3,1-benzoxazin-4-one is utilized as a chemical compound in the Chemical Research Industry for further exploration of its properties and potential applications. Its unique structure and pharmacological potential make it an interesting subject for the development of new chemical entities and materials with various uses.

InChI:InChI=1/C14H8N2O4/c17-14-11-6-1-2-7-12(11)15-13(20-14)9-4-3-5-10(8-9)16(18)19/h1-8H

Upstream product

• 60498-41-1 2-(3-nitrobenzamido)benzoic acid 
• 118-92-3 anthranilic acid 
• 121-90-4 m-nitrobenzoic acid chloride 
• 121-92-6 3-nitrobenzoic acid 
• 551-93-9 2-aminoacetophenone 
• 91-56-5 indole-2,3-dione 
• 1221897-77-3 1-(3-nitrobenzoyl)-1H-indole-2,3-dione 
• 82525-37-9 methyl 2-(3-nitrobenzoylamino)benzoate 
• 2159-38-8 2-(3'-nitrobenzoyl)benzoic acid 

Downstream Products

• 60498-41-1 2-(3-nitrobenzamido)benzoic acid 
• 1001060-35-0 N-[2-(3H-imidazo[4,5-b]pyridin-2-yl)phenyl]-3-nitrobenzamide 
• 1001060-36-1 N-[2-(6-bromo-3H-imidazo[4,5-b]pyridin-2-yl)phenyl]-3-nitrobenzamide 
• 93256-31-6 4-chloro-2-(3-nitrophenyl)quinazoline 
• 34637-85-9 2-(3-nitrophenyl)-(3H)-4-quinazolinone 

Relevant articles and documents

Silver-Mediated Synthesis of 4H-Benzoxazin-4-ones by Intramolecular Decarboxylative O-Acylation Reactions with α-Oxocarboxylic Acid

The first example of an intramolecular decarboxylative acylation reaction for the synthesis of 4H-benzoxazin-4-one derivatives has been described. The silver-mediated reaction has a broad substrate scope and provides a mild and rapid approach to the corre

Design, Synthesis, and Pharmacological Characterization of N-(4-(2 (6,7-Dimethoxy-3,4-dihydroisoquinolin-2(1H)yl)ethyl)phenyl)quinazolin-4-amine Derivatives: Novel Inhibitors Reversing P-Glycoprotein-Mediated Multidrug Resistance

P-glycoprotein (P-gp)-mediated multidrug resistance (MDR) is a principal obstacle for successful cancer chemotherapy. A novel P-gp inhibitor with a quinazoline scaffold, 12k, was considered to be the most promising for in-depth study. 12k possessed high potency (EC50 = 57.9 ± 3.5 nM), low cytotoxicity, and long duration of activity in reversing doxorubicin (DOX) resistance in K562/A02 cells. 12k also boosted the potency of other MDR-related cytotoxic agents with different structures, increased accumulation of DOX, blocked P-gp-mediated Rh123 efflux, and suppressed P-gp ATPase activity in K562/A02 MDR cells. However, 12k did not have any effects on CYP3A4 activity or P-gp expression. In particular, 12k had a good half-life and oral bioavailability and displayed no influence on DOX metabolism to obviate the side effects closely related to increased plasma concentrations of cytotoxic agents in vivo.

Mechanochemical Synthesis of Substituted 4H-3,1-Benzoxazin-4-ones, 2-Aminobenzoxazin-4-ones, and 2-Amino-4H-3,1-benzothiazin-4-ones Mediated by 2,4,6-Trichloro-1,3,5-triazine and Triphenylphosphine

A mild and convenient approach for the synthesis of 2-substituted 4H-3,1-benzoxazin-4-ones, 2-aminobenzoxazin-4-ones, and 2-amino-4H-3,1-benzothiazin-4-ones under solvent-assisted grinding is reported. In the presence of 2,4,6-trichloro-1,3,5-triazine and

BCL-3 INHIBITORS

The present application relates to compounds of any one of Formulae I, Ia, Ib, Ic, Id, Ie, and If. Compounds of Formula (I) have the structure, wherein A, B, Y, Z, R2, R4, R5, R6, Rq and q are as defined herein. The compounds can be used as inhibitors of Bcl-3 and can be used for the treatment of cancer, particularly metastatic cancer.

Selective Oxidative Decarbonylative Cleavage of Unstrained C(sp3)-C(sp2) Bond: Synthesis of Substituted Benzoxazinones

A transition metal (TM)-free practical synthesis of biologically relevant benzoxazinones has been established via a selective oxidative decarbonylative cleavage of an unstrained C(sp3)-C(sp2) bond employing iodine, sodium bicarbonate, and tbutyl hydroperoxide in DMSO at 95 °C. Control experiments and Density Functional Theory (DFT) calculations suggest that the reaction involves a [1,5]H shift and extrusion of CO gas as the key steps. The extrusion of CO has also been established using PMA-PdCl2.

2-BENZOYLAMINOBENZAMIDE DERIVATIVES AS BCL-3 INHIBITORS

The invention relates to a compound of general formula (I): wherein R1, R2, R3, R4, Q, m and n are as defined herein. The compounds are inhibitors of Bcl3 and are useful for the treatment of cancer, particularly

Synthesis of 2-Aryl-4H-3,1-Benzoxazin-4-ones: A Class of α-Chymotrypsin Inhibitors

Twenty one derivatives of 2-aryl-4H-3,1-benzoxazin-4-one were synthesized and their potential therapeutically significance and structureactivity relationship were tested against α-chymotrypsin. Majority of synthesized compounds showed significant in vitro α-chymotrypsin inhibitory properties having IC50values in the range of 5.42 ± 1.66 - 41.27 ± 1.33 μM, whereas standard inhibitor chymostatin have IC50 value 7.13 ± 1.06 μM. In the present series compounds 2-(2-fluorophenyl)-4H-3,1-benzoxazin-4-one (3h), 2-(2-bromophenyl)-4H-3,1- benzoxazin-4-one (3n) and 2-(1-naphthyl)-4H-3, 1-benzoxazin-4-one (3t) with IC50values 7.22 ± 0.75, 6.99 ± 0.29 and 5.42 ± 1.66 μM, respectively were found to be most active members of series, even better than standard inhibitor a-chymostatin.

Synthesis and antimicrobial activity of 2-Aryl-4H-3,1-benzoxazin-4-ones

Twenty derivatives of 2-aryl-4H-3,1-benzoxazin-4-one synthesized and their potential therapeutically significance tested against two strains of Gram positive bacteria (Staphylococcus aureus and Bacillus subtilis) and four strains of Gram negative bacteria (Shigella flexnari, Escherichia coli, Salmonella typhi and Pseudomonas aeruginsoa) by agar well diffusion method. The 2-(3-nitrophenyl)-4H-3,1-benzoxazin-4-one (3f) recorded significant antibacterial activity against Bacillus subtilis whereas 2-(4-bromophenyl)-4H-3, 1-benzoxazin-one (3o) exhibited weak antibacterial activity against Staphylococcus aureus. Further 2-(2-methylphenyl)-4H-3,1-benzoxazin-4-one (3b) showed significant activity against Shigella Flexnari, Escherichia coli, Pseudomonas aeruginsoa and Salmonella typhi. The antibacterial activity of synthesized derivatives of 2-aryl-4H-3,1-benzoxazin-4-one was compared to reference standard antibiotics amoxycillin, streptomycin, kanamycin and ciprofloxacin. The present study revealed that 2-aryl-4H-3,1-benzoxazin-4-ones possess good bactericidal activity against a panel of bacteria causing common bacterial diseases and therefore opens the possibility of finding latest clinically useful antibacterial compounds. The synthesized compounds were characterized by 1H NMR, EI, FT-IR and elemental analysis.

Facile synthesis and herbicidal evaluation of 2-Aryl-4H-3, 1-benzoxazin-4-ones

The present work deals with the synthesis of 4H-3,1-benzoxazin-4-ones carrying an aryl functional group at position-2. Synthesized compounds tested for herbicidal activity at three different doses (500 μg/mL, 50 μg/mL and 5μg/mL). Most of the compounds exhibited significant herbicidal activity against Lemna aequinocitalis welv. at higher dose (500 μg/mL). Among the tested compounds 2-phenyl-4H-3,1-benzoxazin-4-one (3a) and 2-(3-chlorophenyl)- 4H-3,1-benzoxazin-4- one (3l) completely inhibited the plant growth at 500 and 50 μg/mL concentrations. All the synthetic compounds were characterized by FT-IR, 1H NMR, EI-MS and elemental analysis.

A new synthesis of 2-substituted 4H-3,1-benzoxazin-4-ones by cyanuric chloride cyclodehydration of N-benzoyl- and N-acylanthranilic acids

A new and a convenient method for the synthesis of aryl- and alkyl-2-substituted 4H-3,1-benzoxazin-4-ones by cyclodehydration of N-benzoyl- and N-acylanthranilic acid by cyanuric chloride is described.