5023-12-1

Basic information

• Product Name: 6-METHOXY-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE
• Synonyms: 6-METHOXY-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE;6-Methoxy-4H-benzo[1,4]oxazin-3-one;6-(Methyloxy)-2H-1,4-benzoxazin-3(4H)-one;6-Methoxy-2H-1,4-benzoxazin-3(4H)-one;6-methoxy-4H-1,4-benzoxazin-3-one
• CAS NO: 5023-12-1
• Molecular Formula: C₉H₉NO₃
• Molecular Weight: 179.17
• Product Categories: pharmacetical
• Mol File: 5023-12-1.mol
• Article Data: 21

Chemical Properties

• Melting Point: 162-164℃
• Boiling Point: 355.5 °C at 760 mmHg
• Flash Point: 168.8 °C
• Appearance: /
• Density: 1.245
• Vapor Pressure: 3.12E-05mmHg at 25°C
• Refractive Index: 1.546
• CAS DataBase Reference: 6-METHOXY-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-METHOXY-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE(5023-12-1)
• EPA Substance Registry System: 6-METHOXY-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE(5023-12-1)

Safety Data

• RIDADR: UN 3077 9 / PGIII
• Hazardous Substances Data: 5023-12-1(Hazardous Substances Data)

Usage

Description

6-METHOXY-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE is a heterocyclic organic compound with the molecular formula C9H7NO3, belonging to the oxazine family. It features a benzene ring fused to an oxazine ring, with a methoxy group attached to the benzene ring. This unique molecular structure endows it with potential pharmaceutical and biological applications, making it a promising candidate for the development of new drugs and medications.

Uses

Used in Pharmaceutical Industry:
6-METHOXY-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE is used as a pharmaceutical compound for its potential role in the development of new drugs and medications. Its unique molecular structure and properties make it an intriguing target for further research and potential applications in various therapeutic areas.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 6-METHOXY-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE serves as a valuable research tool for understanding its biological activities and exploring its potential as a lead compound in drug discovery. Its heterocyclic nature and specific functional groups may offer insights into novel mechanisms of action and therapeutic targets.
Used in Drug Design and Optimization:
6-METHOXY-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE is utilized in drug design and optimization processes to create structurally related analogs with improved pharmacological properties. By modifying its molecular structure, researchers can optimize its potency, selectivity, and pharmacokinetic profile, leading to the development of more effective and safer drugs.
Used in Biological Assays and Screening:
In biological assays and high-throughput screening, 6-METHOXY-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE is employed as a test compound to evaluate its interactions with various biological targets, such as enzymes, receptors, and ion channels. This information is crucial for understanding its mechanism of action and potential therapeutic applications.
Used in Chemical Synthesis:
6-METHOXY-2H-BENZO[B][1,4]OXAZIN-3(4H)-ONE is also used as a starting material or intermediate in the synthesis of other related compounds with potential applications in various industries, including pharmaceuticals, agrochemicals, and materials science. Its unique structure and reactivity make it a valuable building block for the development of novel molecules with diverse properties and functions.

InChI:InChI=1/C9H9NO3/c1-12-6-2-3-8-7(4-6)10-9(11)5-13-8/h2-4H,5H2,1H3,(H,10,11)

Upstream product

• 598-42-5 glycolamide 
• 36404-30-5 3,4-dichloroanisole 
• 67-56-1 methanol 
• 1002464-45-0 2-(4-methoxy-2-nitrophenoxy)acetonitrile 
• 20734-76-3 2-amino-4-methoxyphenol 
• 771-26-6 4-hydroxy-2H-1,4-benzoxazin-3-one 
• 109364-95-6 ethyl 2-[4-methoxy-2-nitrophenoxy]acetate 
• 37682-31-8 ethyl o-nitrophenoxyacetate 
• 89441-85-0 6-acetoxy-2H-1,4-benzoxazin-3(4H)-one 
• 33252-96-9 4-acetoxy-(2H)-1,4-benzoxazin-3(4H)-one 
• 1568-70-3 4-methoxy-2-nitrophenol 
• 79-04-9 chloroacetyl chloride 
• 69884-06-6 4-hydroxy-6-methoxy-(2H)-1,4-benzoxazin-3(4H)-one 
• 53412-38-7 6-hydroxy-3,4-dihydro-2H-1,4-benzoxazin-3-one 

Downstream Products

• 26438-50-6 4-ethyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-ol 
• 53412-38-7 6-hydroxy-3,4-dihydro-2H-1,4-benzoxazin-3-one 
• 26021-57-8 3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine 
• 62490-86-2 2-benzylidene-4-(3-dimethylamino-propyl)-6-methoxy-4H-benzo[1,4]oxazin-3-one 
• 58960-11-5 6-methoxy-3,4-dihydro-2H-benzo[1,4]oxazine 
• 6239-12-9 [2-(3,4-Dichloro-benzoylamino)-4-methoxy-phenoxy]-acetic acid 
• 62490-80-6 2-benzylidene-6-methoxy-4H-benzo[1,4]oxazin-3-one 

Relevant articles and documents

OXAZINE-BASED FLUOROPHORE COMPOUNDS FOR NERVE-SPECIFIC IMAGING

This invention concerns novel oxazine-based fluorophore compounds useful in invivo nerve imaging, as well as compositions comprising them and methods for their use.

Synthesis, docking, 3-D-qsar, and biological assays of novel indole derivatives targeting serotonin transporter, dopamine D2 receptor, and mao-a enzyme: In the pursuit for potential multitarget directed ligands

A series of 27 compounds of general structure 2,3-dihydro-benzo[1,4]oxazin-4-yl)-2-{4-[3-(1H-3indolyl)-propyl]-1-piperazinyl}-ethanamides, Series I: 7(a-o) and (2-{4-[3-(1H-3-indolyl) -propyl]-1-piperazinyl}-acetylamine)-N-(2-morfolin-4-yl-ethyl)-fluorinated benzamides Series II: 13(a-l) were synthesized and evaluated as novel multitarget ligands towards dopamine D2 receptor, serotonin transporter (SERT), and monoamine oxidase-A (MAO-A) directed to the management of major depressive disorder (MDD). All the assayed compounds showed affinity for SERT in the nanomolar range, with five of them displaying Ki values from 5 to 10 nM. Compounds 7k, Ki = 5.63 ± 0.82 nM, and 13c, Ki = 6.85 ± 0.19 nM, showed the highest potencies. The affinities for D2 ranged from micro to nanomolar, while MAO-A inhibition was more discrete. Nevertheless, compounds 7m and 7n showed affinities for the D2 receptor in the nanomolar range (7n: Ki = 307 ± 6 nM and 7m: Ki = 593 ± 62 nM). Compound 7n was the only derivative displaying comparable affinities for SERT and D2 receptor (D2/SERT ratio = 3.6) and could be considered as a multitarget lead for further optimization. In addition, docking studies aimed to rationalize the molecular interactions and binding modes of the designed compounds in the most relevant protein targets were carried out. Furthermore, in order to obtain information on the structure-activity relationship of the synthesized series, a 3-D-QSAR CoMFA and CoMSIA study was conducted and validated internally and externally (q2 = 0.625, 0.523 for CoMFA and CoMSIA and r2ncv = 0.967, 0.959 for CoMFA and CoMSIA, respectively).

Design, synthesis and characterization of potent microtubule inhibitors with dual anti-proliferative and anti-angiogenic activities

Microtubule has been an important target for anticancer drug development. Here we report the discovery and characterization of a series of fused 4-aryl-4H-chromene-based derivatives as highly potent microtubule inhibitors. Among a total of 37 derivatives synthesized, 23 exhibited strong in vitro anti-proliferative activities against A375 human melanoma cells. The relationship between the biological activities of these microtubule inhibitors and their chemical structure variations was analyzed. Studies of compounds 27a, 19a and 9a in parallel with colchicine as the positive control compound in a panel of biological assays revealed that these compounds blocked cell cycle progression, increased apoptosis, and inhibited HUVEC capillary tube formation at low nanomolar concentrations. The most potent compound 27a was also tested in eight additional cancer cell lines besides A375 cells and two non-cancer cells and showed potent and selective activity on these cancer cells. To understand the molecular and structure mechanism of action of these compounds, tubulin polymerization and molecular docking studies were carried out for 27a as the representative. The results were consistent with the mechanism by which 27a interacts with the colchicine binding site on tubulin and disrupts tubulin polymerization. With potent dual actions of microtubule destabilization and vascular disruption described above, this small molecule can serve as a valuable research probe of the function and role of microtubules in human diseases and promising lead for developing new therapeutic agents.