7652-29-1

Usage

Uses

Used in Pharmaceutical Industry:
6-CHLORO-2H-1,4-BENZOXAZIN-3(4H)-ONE is used as an antimicrobial and antifungal agent for its ability to combat various microorganisms and fungi, making it a promising candidate for the development of new drugs to treat infections.
Used in Agricultural Industry:
6-CHLORO-2H-1,4-BENZOXAZIN-3(4H)-ONE is used as a potential herbicide due to its ability to control the growth of unwanted plants, offering an alternative to traditional herbicides for more effective and environmentally friendly solutions.
Used in Research and Development:
6-CHLORO-2H-1,4-BENZOXAZIN-3(4H)-ONE is utilized in research and development for its potential applications in agriculture and medicine, as scientists explore its properties and effects on various organisms and diseases.

InChI:InChI=1/C8H6ClNO2/c9-5-1-2-7-6(3-5)10-8(11)4-12-7/h1-3H,4H2,(H,10,11)

Upstream product

• 21086-49-7 (4-chloro-2-nitro-phenoxy)-acetic acid 
• 13212-63-0 6-chloro-4-hydroxy-(2H)-1,4-benzoxazin-3(4H)-one 
• 1982-42-9 2,4-dichlorophenoxyacetic acid amine 
• 79-04-9 chloroacetyl chloride 
• 95-85-2 2-hydroxy-5-chloro-aniline 
• 771-26-6 4-hydroxy-2H-1,4-benzoxazin-3-one 
• 173195-16-9 2-Bromo-N-(5-chloro-2-hydroxy-phenyl)-acetamide 
• 79-07-2 Chloroacetamide 
• 56-37-1 N-benzyl-N,N,N-triethylammonium chloride 
• 105-36-2 ethyl bromoacetate 
• 71643-66-8 4-chloro-2-iodo phenol 
• 1016839-86-3 2-(4-chloro-2-nitrophenoxy)acetonitrile 
• 89-64-5 p-chloro-o-nitrophenol 
• 583-78-8 2,5-dichlorophenol 

Downstream Products

• 55894-78-5 2-benzylidene-6-chloro-4H-benzo[1,4]oxazin-3-one 
• 52042-27-0 6-chloro-4-(2,3-dihydroxy-propyl)-4H-benzo[1,4]oxazin-3-one 
• 105492-48-6 6-Chloro-4-(2-oxo-2-phenyl-ethyl)-4H-benzo[1,4]oxazin-3-one 
• 105492-49-7 6-Chloro-4-(2-oxo-2-p-tolyl-ethyl)-4H-benzo[1,4]oxazin-3-one 
• 105492-50-0 6-Chloro-4-[2-(4-chloro-phenyl)-2-oxo-ethyl]-4H-benzo[1,4]oxazin-3-one 
• 105492-51-1 6-Chloro-4-[2-(4-methoxy-phenyl)-2-oxo-ethyl]-4H-benzo[1,4]oxazin-3-one 
• 116862-22-7 6-chloro-7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one 
• 6239-11-8 [4-Chloro-2-(3-trifluoromethyl-benzoylamino)-phenoxy]-acetic acid 
• 6239-09-4 4-Chlor-2-benzamido-phenoxyessigsaeure 
• 6239-10-7 [4-Chloro-2-(4-chloro-benzoylamino)-phenoxy]-acetic acid 
• 6529-97-1 [4-Chloro-2-(4-methoxy-benzoylamino)-phenoxy]-acetic acid 
• 6239-17-4 [4-Chloro-2-(3,4-dichloro-benzoylamino)-phenoxy]-acetic acid 
• 104829-96-1 Benzoic acid N'-(6-chloro-3-oxo-2,3-dihydro-benzo[1,4]oxazine-4-carbonyl)-hydrazide 
• 104971-81-5 8-Chloro-2-phenyl-4H-5-oxa-3,9b-diaza-cyclopenta[a]naphthalene 

Relevant academic research and scientific papers

Intramolecular cyclization of N-hydroxy-2-phenoxyacetamides and 3-phenoxypropanamides

Abstract: A novel route for the preparation of 2H-1,4- benzoxazin-3(4H)one and 1,5 benzoxazepinones by intramolecular cyclization of N-hydroxy 2-phenoxyacetamide and N-hydroxy -3 phenoxypropanamide using PPA and Lewis acid has been discussed. Graphical abstract: [Figure not available: see fulltext. Caption: Preparation of 2H-1,4- benzoxazin-3(4H)one and 1,5 benzoxazepinones by electrophilic aromatic substitution from N-hydroxy 2-phenoxyacetamide and N-hydroxy -3 phenoxypropanamide and their acetyl and benzoyl derivatives using PPA and Lewis acids.]

Benzo six-membered nitrogen heterocyclic compound, preparation method and applications

The present invention provides a benzo six-membered nitrogen heterocyclic compound, a preparation method and applications, wherein the benzo six-membered nitrogen heterocyclic compound has a structurerepresented by a formula I or formula II, and can effectively inhibit the bromine domain receptor and effectively inhibit the proliferation of cancer cells. Compared with the existing reported structure types, the compound of the present invention has different binding mode, has high inhibitory activity, can be used as a drug for treating cancer, cell proliferation disorders, inflammatory diseases, autoimmune diseases, septicemia and viral infections, and has good application prospects and high application value.

Synthesis and biological evaluation of potential acetylcholinesterase inhibitors based on a benzoxazine core

With the purpose of expanding the structural variety of chemical compounds available as pharmacological tools for the treatment of Alzheimer's disease, we synthesized and evaluated a novel series of indole-benzoxazinones (Family I) and benzoxazine-arylpiperazine derivatives (Family II) for potential human acetylcholinesterase (hAChE) inhibitory properties. The most active compounds 7a and 7d demonstrated effective inhibitory profiles with Ki values of 20.3 ± 0.9 μM and 20.2 ± 0.9 μM, respectively. Kinetic inhibition assays showed non-competitive inhibition of AChE by the tested compounds. According to our docking studies, the most active compounds from both series (Families I and II) showed a binding mode similar to donepezil and interact with the same residues.

New Approach to 1,4-Benzoxazin-3-ones by Electrochemical C?H Amination

1,4-Benzoxazin-3-ones are important structural motifs in natural products and bioactive compounds. Usually, the synthesis of benzoxazinones requires transition-metal catalysts and pre-functionalized substrates such as aryl halides. However, the anodic C?H

Potential antimicrobial agents from triazole-functionalized 2H-benzo[b][1,4]oxazin-3(4H)-ones

A series of substituted triazole functionalized 2H-benzo[b][1,4]oxazin-3(4H)-ones were synthesized by employing click chemistry and further characterized based on 1H NMR, 13C NMR, IR and mass spectral studies. All the synthesized derivatives were screened for their in vitro antimicrobial activities. Further, molecular docking studies were accomplished to explore the binding interactions between 1,2,3-triazol-4-yl-2H-benzo[b][1,4]oxazin-3(4H)-one and the active site of Staphylococcus aureus (CrtM) dehydrosqualene synthase (PDB ID: 2ZCS). These docking studies revealed that the synthesized derivatives showed high binding energies and strong H-bond interactions with the dehydrosqualene synthase validating the observed antimicrobial activity data. Based on antimicrobial activity and docking studies, the compounds 9c, 9d and 9e were identified as promising antimicrobial leads.

Using gene expression database to uncover biology functions of 1,4-disubstituted 1,2,3-triazole analogues synthesized via a copper (I)-catalyzed reaction

We have synthesized bioactive 1,4-disubstituted 1,2,3-triazole analogues containing 2H-1,4-benzoxazin-3-(4H)-one derivatives via 1,3-dipolar cycloaddition in the presence of CuI. All the reactions proceeded smoothly and afforded its desired products in excellent yields. Among these analogues, 3y exhibited a better cytotoxic effect on human hepatocellular carcinoma (HCC) Hep 3B cells and displayed less cytotoxicity on normal human umbilical vein endothelial cells, compared with Sorafenib, a targeted therapy for advanced HCC. 3y also induced stronger apoptosis and autophagy. Addition of curcumin enhanced 3y-induced cytotoxicity by further induction of autophagy. Using gene expression signatures of 3y to query Connectivity Map, a glycogen synthase kinase-3 inhibitor (AR-A014418) was predicted to display similar molecular action of 3y. Experiments further demonstrate that AR-A014418 acted like 3y, and vice versa. Overall, our data suggest the chemotherapeutic potential of 3y on HCC.

Design and Synthesis of Novel Triazolyl Benzoxazine Derivatives and Evaluation of Their Antiproliferative and Antibacterial Activity

A series of novel triazolyl benzoxazine derivatives have been synthesized via Cu(I)-catalyzed ‘Click’ cycloaddition. All of the compounds were fully characterized from their spectral data, and their antiproliferative activity was evaluated against three selected human cancer cell lines: cervical cancer cells (HeLa), colorectal adenocarcinoma (HT-29), and ovarian adenocarcinoma (SKOV-3). A few representative compounds have also been evaluated for their antibacterial potential against two bacterial strains Pseudomonas aeruginosa and Bacillus subtilis.

Identification of 3-hydroxy-4[3,4-dihydro-3-oxo-2H-1,4-benzoxazin-4-yl]-2,2-dimethyldihydro-2H-benzopyran derivatives as potassium channel activators and anti-inflammatory agents

The present study described the design, synthesis and identification of 3-hydroxy-4[3,4-dihydro-3-oxo-2H-1,4-benzoxazin-4-yl]-2,2-dimethyldihydro-2H-benzopyran derivatives. Their biological activity was tested for KATP channel opener as antihypertensives, COX-1 and COX-2 activity. The results were compared with the activity of cromakalim, ibuprofen and celecoxib. The study aimed at exploring the influence of introduction of a benzoxazine substituent at position 6 of various derivatives of benzopyrans in order to improve biological activity. Several compounds were found to be equipotent or even more potent than cromakalim. Out of these nitro-substituted benzopyrans, nitro substitution at benzoxazino group possessed potent antihypertensive activity in the R/S isomers. With amino derivatives, activity remains constant when compared with standard cromakalim. Similarly, compounds 17b, 17c, 17e and 17h have exhibited around 40 % inhibition of COX-1 as compared to the inhibition of COX-2. Only two compounds 17g and 17i exhibited effective inhibition more than 50 % of COX-2 compared with the inhibition of COX-1 at a concentration of 0.3 mg/ml.

Development of small-molecule Trypanosoma brucei N-myristoyltransferase inhibitors: Discovery and optimisation of a novel binding mode

The enzyme N-myristoyltransferase (NMT) from Trypanosoma brucei has been validated both chemically and biologically as a potential drug target for human African trypanosomiasis. We previously reported the development of some very potent compounds based around a pyrazole sulfonamide series, derived from a high-throughput screen. Herein we describe work around thiazolidinone and benzomorpholine scaffolds that were also identified in the screen. An X-ray crystal structure of the thiazolidinone hit in Leishmania major NMT showed the compound bound in the previously reported active site, utilising a novel binding mode. This provides potential for further optimisation. The benzomorpholinone was also found to bind in a similar region. Using an X-ray crystallography/structure-based design approach, the benzomorpholinone series was further optimised, increasing activity against T. brucei NMT by >1000-fold. A series of trypanocidal compounds were identified with suitable in vitro DMPK properties, including CNS exposure for further development. Further work is required to increase selectivity over the human NMT isoform and activity against T. brucei. HATs off to diversity! Screening a diverse library against Trypanosoma brucei N-myristoyltransferase (NMT) identified hits based on thiazolidinone and benzomorpholine scaffolds. X-ray crystallography of these compounds bound to Leishmania major NMT revealed novel active site binding conformations. Using the structural information, the benzomorpholine scaffold was optimised to a blood-brain barrier penetrant compound with activity against TbNMT of 0.002 μm.

Microwave-assisted synthesis of benzo-[1,4]-oxazinones using MeO-PEG-OMe as solvent

Efficient one-pot microwave-assisted synthesis of various benzo-[1,4]-oxazinones via Smiles rearrangement is described. Treatment of 2-chloroacetamide, substituted 2-chlorophenols and cesium carbonate in MeO-PEG-OMe (2,000) as solvent afforded the corresp