40728-74-3

Usage

Chemical structure

A benzoxazinone derivative with a 3,4,5-trimethoxyphenyl group attached to the phenyl ring

Pharmacological properties

Anti-inflammatory, anti-fungal, and anti-tumor activities

Potential applications

Natural herbicide, treatment of neurological disorders (inhibits acetylcholinesterase enzyme)

Industries of interest

Pharmaceutical and agricultural.

Upstream product

• 118-92-3 anthranilic acid 
• 118-41-2 Eudesmic acid 
• 91-56-5 indole-2,3-dione 
• 4521-61-3 3,4,5-Trimethoxybenzoyl chloride 
• 1431097-97-0 C₁₇H₁₆INO₅ 

Downstream Products

• 75586-78-6 methyl 2-<(3,4,5-trimethoxyphenyl)amino>benzoate 
• 83408-94-0 2-[4-Oxo-2-(3,4,5-trimethoxy-phenyl)-4H-quinazolin-3-yl]-3-phenyl-propionic acid 
• 83408-90-6 [4-Oxo-2-(3,4,5-trimethoxy-phenyl)-4H-quinazolin-3-yl]-acetic acid 
• 21878-28-4 6-chloro-2-(4-methoxyphenyl)-2,3-dihydroquinazolin-4(1H)-one 
• 83409-21-6 3-[1-Benzyl-2-oxo-2-(4-p-tolyl-piperazin-1-yl)-ethyl]-2-(3,4,5-trimethoxy-phenyl)-3H-quinazolin-4-one 
• 83409-20-5 3-[1-Benzyl-2-oxo-2-(4-phenyl-piperazin-1-yl)-ethyl]-2-(3,4,5-trimethoxy-phenyl)-3H-quinazolin-4-one 
• 83409-19-2 3-[3-Methyl-1-(4-p-tolyl-piperazine-1-carbonyl)-butyl]-2-(3,4,5-trimethoxy-phenyl)-3H-quinazolin-4-one 
• 83409-17-0 3-[2-Methyl-1-(4-p-tolyl-piperazine-1-carbonyl)-propyl]-2-(3,4,5-trimethoxy-phenyl)-3H-quinazolin-4-one 
• 83409-15-8 3-[3-Methyl-1-(4-phenyl-piperazine-1-carbonyl)-butyl]-2-(3,4,5-trimethoxy-phenyl)-3H-quinazolin-4-one 
• 83409-13-6 3-[2-Methyl-1-(4-phenyl-piperazine-1-carbonyl)-propyl]-2-(3,4,5-trimethoxy-phenyl)-3H-quinazolin-4-one 
• 83409-23-8 3-(1-Benzyl-2-morpholin-4-yl-2-oxo-ethyl)-2-(3,4,5-trimethoxy-phenyl)-3H-quinazolin-4-one 
• 83409-18-1 3-[1-Methyl-2-oxo-2-(4-p-tolyl-piperazin-1-yl)-ethyl]-2-(3,4,5-trimethoxy-phenyl)-3H-quinazolin-4-one 
• 83409-24-9 3-(1-Benzyl-2-oxo-2-piperidin-1-yl-ethyl)-2-(3,4,5-trimethoxy-phenyl)-3H-quinazolin-4-one 
• 83409-22-7 3-(1-Benzyl-2-oxo-2-pyrrolidin-1-yl-ethyl)-2-(3,4,5-trimethoxy-phenyl)-3H-quinazolin-4-one 

Relevant academic research and scientific papers

Quinazolinone-schiff's base hybrids as phosphodiesterase 4b inhibitors with dual activity against COPD and lung cancer

A series of thirty compounds of quinazolinone-Schiff's base hybrids were rationally designed, synthesized, and evaluated for their in vitro Phosphodiesterase 4B inhibition, anti-lung and anti-colon cancer activities. Compounds 9, 16, 23, 29, 30, 31, 32 an

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.

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.

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.

Copper-catalyzed C-N bond formation/rearrangement sequence: Synthesis of 4H-3,1-benzoxazin-4-ones

A facile and efficient copper-catalyzed method for the synthesis of 4H-3,1-benzoxazin-4-one derivatives has been developed. This procedure is based on a tandem intramolecular C-N coupling/rearrangement process. This method would provide a new and useful strategy for construction of N-heterocycles.

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.

2-Alkyl-2-ethanoic Acids and Their Amides as Anticonvulsant Agents

Several 2-alkyl-2-ethanoic acids (II) and their amides (IV) with diethylamine, morpholine, piperidine, pyrrolidine and piperazines have been prepared.Twenty six of them have been assayed for their anticon