5226-51-7

Usage

Uses

Used in Pharmaceutical Industry:
2,2-DIMETHYL-1,4-DIHYDRO-2H-BENZO[D][1,3]OXAZINE is used as a therapeutic agent for its antitumor properties, targeting a range of cancers due to its ability to inhibit tumor growth and progression.
Used in Research and Development:
2,2-DIMETHYL-1,4-DIHYDRO-2H-BENZO[D][1,3]OXAZINE is used as a compound in scientific research for its potential applications in drug discovery, given its diverse biological activities and the ongoing exploration of its therapeutic potential.
Used in Organic Chemistry:
2,2-DIMETHYL-1,4-DIHYDRO-2H-BENZO[D][1,3]OXAZINE is used as a valuable compound in organic chemistry for its potential to contribute to the development of new chemical entities and the advancement of chemical synthesis techniques.

InChI:InChI=1/C10H13NO/c1-10(2)11-9-6-4-3-5-8(9)7-12-10/h3-6,11H,7H2,1-2H3

Upstream product

• 5344-90-1 2-Aminobenzyl alcohol 
• 67-64-1 acetone 
• 53044-24-9 N-Phenyl-o-(hydroxymethyl)aniline 

Downstream Products

• 53165-12-1 2-<(phenylthio)methyl>aniline 
• 67-64-1 acetone 
• 91-63-4 2-methylquinoline 
• 106898-71-9 2-isopropylaminobenzyl alcohol 
• 103718-15-6 2-(isopropylamino)benzaldehyde 
• 158577-01-6 1-isopropyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 
• 174486-39-6 N-(endo-8-(3-hydroxy)propyl-8-azabicyclo[3.2.1]oct-3-yl)-1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxamide 
• 128936-15-2 2-[(2-isopropylamino)benzylthio]imidazole 
• 128936-16-3 2-[(2-isopropylamino)benzylsulfinyl]imidazole 
• 866933-46-2 Velusetrag 

Relevant academic research and scientific papers

Synthesis of (η6-arene)tricarbonylchromium derivatives of 1,4-dihydro-3,1-benzoxazines

A series of (η6-arene)tricarbonylchromium derivatives of 1,4-dihydro-3,1-benzoxazines was synthesized and characterized. The compounds were obtained by two alternative methods, namely, by the reaction of triammine(tricarbonyl)chromium with 1,4-dihydro-3,1-benzoxazines (method A) and by the condensation of (η6-2-aminobenzyl alcohol)tricarbonylchromium with various aldehydes and ketones (method B). The composition and structure of obtained compounds were established by different physicochemical methods of analysis, such as HPLC, UV, IR, 1H NMR spectroscopy, mass spectrometry, and X-ray diffraction.

Prokinetic agent for bowel preparation

The invention provides methods of bowel preparation before a diagnostic, surgical or therapeutic procedure, in particular, bowel preparation before a colonoscopy procedure, using a 5-HT4 receptor agonist as a prokinetic agent.

Quinolinone-carboxamide compounds

The invention provides novel quinolinone-carboxamide 5-HT4 receptor agonist compounds. The invention also provides pharmaceutical compositions comprising such compounds, methods of using such compounds to treat diseases associated with 5-HT4 receptor activity, and processes and intermediates useful for preparing such compounds.

Quinolinone compounds as 5-HT4 receptor agonists

The invention provides novel quinolinone-carboxamide 5-HT4 receptor agonist compounds. The invention also provides pharmaceutical compositions comprising such compounds, methods of using such compounds to treat diseases associated with 5-HT4 receptor activity, and processes and intermediates useful for preparing such compounds.

Crystalline form of a quinolinone-carboxamide compound

The invention provides a crystalline hydrochloride salt of 1-isopropyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid {(1S,3R,5R)-8-[(R)-2-hydroxy-3-(methanesulfonyl-methyl-amino)propyl]-8-azabicyclo[3.2.1]oct-3-yl}amide or a solvate thereof. The invention also provides pharmaceutical compositions comprising such crystalline salt forms, methods of using such crystalline salt forms to treat diseases associated with 5-HT4 receptor activity, and processes useful for preparing such crystalline salt forms.

Quinolinone-carboxamide compounds as 5-HT4 receptor agonists

The invention provides novel quinolinone-carboxamide 5-HT4 receptor agonist compounds. The invention also provides pharmaceutical compositions comprising such compounds, methods of using such compounds to treat diseases associated with 5-HT4 receptor activity, and processes and intermediates useful for preparing such compounds.

Synthesis and evaluation of novel 2-oxo-1,2-dihydro-3-quinolinecarboxamide derivatives as potent and selective serotonin 5-HT4 receptor agonists

A series of 8′-substituted N-(endo-8-azabicyclo[3.2.1]oct-3-yl)-1-isopropyl-2-oxo-1,2-dihydro-3-quinolin ecarboxamides were synthesized. The 5-HT4 receptor agonistic activity was evaluated using the isolated guinea pig ileum preparation. Of the compounds synthesized, N-(endo-8-(3-hydroxypropyl)-8-azabicyclo[3.2.1]oct-3-yl)-1-isopropyl-2-oxo-1, 2-dihydro-3-quinolinecarboxamide (15a, TS-951) exhibited the most potent serotonin 5-HT4 receptor agonistic activity. This compound had a high affinity for the serotonin 5-HT4 receptor although it had no affinities for other broad spectrum receptors. Furthermore, it remarkably enhanced gastrointestinal motility in conscious fed dogs without unfavorable effects that non-selective serotonin 5-HT4 receptor agonist has. TS-951 may be useful in improving gastrointestinal dysfunction.

A practical procedure for preparation of N-(endo-8-(3-hydroxy)propyl-8-azabicyclo [3.2.1]oct-3-yl)-1-isopropyl-2-oxo-1,2-dihydro-3-quinoline-carboxamide (TS-951)

Effective and convergent process for the preparation of a potent and selective 5-HT4 receptor agonist, the title compound, by reaction of 1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylic acid (6) with endo-3-amino-8-(3-hydroxypropyl)-8-azabicyclo[3.2.1]octane dihydrochloride (20) has been described. Furthermore, this process was developed to pilot plant scale. 1-Isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylic acid (6) was prepared from 2-aminobenzyl alcohol (12) in 65.6% overall yield and endo-3-amino-8-(3-hydroxypropyl)-8-azabicyclo[3.2.1]octane dihydrochloride (20) was prepared from 2,5-dimethoxyfuran (16) in 43.4% overall yield.

Synthesis and structure-activity relationships of N-substituted 2-[(2-imidazolylsulfinyl)methyl]anilines as a new class of gastric H+/K+-ATPase inhibitors

A series of N-substituted 2-[(2-imidazolylsulfinyl)methyl]anilines was synthesized and evaluated for its biological activity against H+/K+-ATPase prepared from rabbit stomach and gastric acid secretions in Heidenhain pouch dogs. Monoalkyl substituents on the nitrogen atom of the aniline moiety markedly inhibited the enzyme activity to the same degree as omeprazole, a representative H+/K+-ATPase inhibitor. Most of these compounds, administered at 3 mg/kg i.v. inhibited histamine-stimulated gastric acid secretion. The inhibitory activity of these derivatives on the enzymes at pH 6.0 was more potent than that at pH 7.4, and was distinctly correlated to stability in aqueous solution at pH 5.0.

Studies on the Benzoxazine Series. 2- Preparation and 1H and 13C NMR Structural Study of Some Substituted 1,2-Dihydro-4H-3,1-benzoxazines

In addition to the parent compounds, nine methyl-substituted 1,2-dihydro-4H-3,1-benzoxazines with and without N-methyl substitution were prepared.The chain tautomer could only be detected in the case of 1,2-dihydro-2-(p-nitrophenyl)-4H-3,1-benzoxazine in