58960-11-5

Usage

Uses

Used in Pharmaceutical Industry:
6-Methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazine is used as a pharmaceutical intermediate for the synthesis of various drugs and active pharmaceutical ingredients. Its heterocyclic structure and functional groups can be utilized in the development of new drug candidates with potential therapeutic applications.
Used in Organic Synthesis:
6-Methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazine serves as a key building block in the synthesis of complex organic molecules. Its unique structure allows for further functionalization and modification, making it a valuable component in the preparation of various organic compounds.
Used in Material Science:
6-Methoxy-3,4-dihydro-2H-benzo[b][1,4]oxazine has potential applications in the development of new materials with specific properties. Its heterocyclic structure and functional groups can be exploited to create materials with tailored characteristics for use in various industries, such as electronics, coatings, and adhesives.

InChI:InChI=1/C9H11NO2/c1-11-7-2-3-9-8(6-7)10-4-5-12-9/h2-3,6,10H,4-5H2,1H3

Upstream product

• 5023-12-1 6-methoxy-2H-benzo[b][1,4]oxazin-3(4H)-one 
• 20734-76-3 2-amino-4-methoxyphenol 
• 106-93-4 ethylene dibromide 
• 1568-70-3 4-methoxy-2-nitrophenol 

Downstream Products

• 1202503-61-4 4-(2,4-dichlorophenyl)-6-methoxy-3,4-dihydro-2H-1,4-benzoxazine 
• 1202503-64-7 4-(2,4-dichlorophenyl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl trifluoromethanesulfonate 
• 1202503-66-9 4-(2,4-dichlorophenyl)-3,4-dihydro-2H-1,4-benzoxazin-6-ol 
• 26438-50-6 4-ethyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-ol 
• 26021-57-8 3,4-dihydro-6-hydroxy-1,4(2H)-benzoxazine 
• 1338594-89-0 3-(6-methoxy-2,3-dihydrobenzo[1,4]oxazin-4-yl)-3-methylsulfanyl-1-phenylpropenone 
• 1338594-95-8 C₁₉H₁₇NO₃ 

Relevant academic research and scientific papers

TRICYCLIC FURAN-SUBSTITUTED PIPERIDINEDIONE COMPOUND

Disclosed are a series of tricyclic furan-substituted piperidinedione compounds and an application thereof in preparing a drug for treating a disease related to CRBN protein. In particular, disclosed is a derivative compound represented by formula (I) or a pharmaceutically acceptable salt thereof.

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.

Production Method of Nitrogen-Containing Fused Ring Compounds

[Problems] The present invention provides a superior production method and a superior purification method of compounds effective for the treatment or prophylaxis of pathology showing involvement of uric acid, such as hyperuricemia, gouty tophus, acute gouty arthritis, chronic gouty arthritis, gouty kidney, urolithiasis, renal function disorder, coronary artery disease, ischemic heart disease and the like. [Means] A compound represented by the following formula [2] or a pharmaceutically acceptable salt thereof can be produced by reacting a compound represented by the following formula [3] or a salt thereof with a compound represented by the following formula [4], a salt thereof or a reactive derivative thereof. Moreover, crystallization of a compound represented by the formula [2] can be performed with industrially superior workability, and high quality crystals of a compound represented by the formula [2] can be obtained. wherein each symbol is as defined in the description.

Pharmaceutical Compositions Comprising Nitrogen-Containing Fused Ring Coumpounds

[Problems] The present invention provides pharmaceutical composition which is effective for the prophylaxis or treatment of pathology showing involvement of uric acid (hyperuricemia, gouty tophus, acute gout arthritis, chronic gout arthritis, gouty kidney, urolithiasis, renal function disorder, coronary arterial disease, ischemic heart disease and the like) and the like, and is superior in the time-course stability and dissolution property (disintegration property). [Solving Means] The pharmaceutical composition of the present invention is a pharmaceutical composition comprising a nitrogen-containing fused ring compound represented by the following formula [1] or a pharmaceutically acceptable salt thereof, and one or more pharmaceutically acceptable additives, wherein the nitrogen-containing fused ring compound or a pharmaceutically acceptable salt thereof is not in contact with a basic additive: wherein each symbol is as described in the specification.

Nitrogen-containing fused ring compounds and use thereof

A URAT1 activity inhibitor containing a nitrogen-containing fused ring compound represented by the following formula [1]: wherein each symbol is as defined in the description. The present invention is useful for the prophylaxis or treatment of pathology showing involvement of uric acid, such as hyperuricemia, gouty tophus, acute gouty arthritis, chronic gouty arthritis, gouty kidney, urolithiasis, renal function disorder, coronary artery disease, ischemic heart disease and the like.

Synthesis of substituted 4-(3-alkyl-1,2,4-oxadiazol-5-ylmethyl)-3,4-dihydro-2H-1,4-benzoxazines and 4-(1H-benzimidazol-2-ylmethyl)-3,4-dihydro-2H-1,4-benzoxazines

Substituted 2H-1,4-benzoxazines were synthesized from substituted 2-amino phenols and 1,2-dibromoethane using K2CO3 in good to excellent yields. The cyclized products were further reacted with alkyl bromides to obtain the desired N-substituted 3,4-dihydro-2H-1,4-benzoxazines.

Novel 5-HT7 receptor inverse agonists. Synthesis and molecular modeling of arylpiperazine- and 1,2,3,4-tetrahydroisoquinoline-based arylsulfonamides.

A series of arylpiperazine- and 1,2,3,4-tetrahydroisoquinoline-based arylsulfonamides was synthesized and evaluated for their interactions with the constitutively active 5-HT7 receptor. Effects on basal adenylate cyclase activity were measured using HEK-293 cells expressing the rat 5-HT7. All ligands produced a decrease of adenylate cyclase activity, indicative of their inverse agonism. Additionally, computational studies with a set of 22 inverse agonists, including these novel inverse agonists and inverse agonists known from literature, resulted in a pharmacophore model and a CoMFA model (R2 = 0.97, SE = 0.18). Docking of inverse agonists at the binding site of a model of the helical parts of the 5-HT7 receptor, based on the alpha carbon template for 7-TM GPCRs, revealed interesting molecular interactions and a possible explanation for observed structure-activity relationships.

New substituted (dihydro)benzoxazine and (dihydro)benzothiazine compounds

The invention relates to compound of formula (I): wherein: G represents an alkylene chain containing from 1 to 4 carbon atoms, A represents X represents oxygen or sulphur and R2 and R1 are as defined in the description and medicinal