26215-14-5

Basic information

• Product Name: 7-AMINO-2H-1,4-BENZOXAZIN-3(4H)-ONE
• Synonyms: TIMTEC-BB SBB010445;7-AMINO-2H-1,4-BENZOXAZIN-3(4H)-ONE;7-AMINO-4H-BENZO[1,4]OXAZIN-3-ONE;7-amino-2H-benzo[b][1,4]oxazin-3(4H)-one;7-amino-2H-1,4-benzoxazin-3(4H)-one(SALTDATA: FREE);7-Amino-3,4-dihydro-3-oxo-2H-1,4-benzoxazine;7-aMino-3,4-dihydro-2H-1,4-benzoxazin-3-one
• CAS NO: 26215-14-5
• Molecular Formula: C₈H₈N₂O₂
• Molecular Weight: 164.16
• Mol File: 26215-14-5.mol

Chemical Properties

• Melting Point: 215-218°C
• Boiling Point: 434.8 °C at 760 mmHg
• Flash Point: 216.7 °C
• Appearance: /
• Density: 1.344 g/cm³
• Vapor Pressure: 9.23E-08mmHg at 25°C
• Refractive Index: 1.624
• Storage Temp.: 2-8°C(protect from light)
• PKA: 12.43±0.20(Predicted)
• CAS DataBase Reference: 7-AMINO-2H-1,4-BENZOXAZIN-3(4H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 7-AMINO-2H-1,4-BENZOXAZIN-3(4H)-ONE(26215-14-5)
• EPA Substance Registry System: 7-AMINO-2H-1,4-BENZOXAZIN-3(4H)-ONE(26215-14-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 22-52
• HazardClass: IRRITANT
• Hazardous Substances Data: 26215-14-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H8N2O2/c9-5-1-2-6-7(3-5)12-4-8(11)10-6/h1-3H,4,9H2,(H,10,11)

Upstream product

• 5466-88-6 3,4-dihydro-3-oxo-2H-1,4-benzoxazine 
• 95-55-6 2-amino-phenol 
• 121-88-0 5-Nitro-2-aminophenol 
• 81721-86-0 7-nitro-4H-benzo[1,4]oxazin-3-one 

Downstream Products

• 575474-01-0 3,4-dihydro-2H-1,4-benzoxazin-7-amine 
• 130137-52-9 1-phenyl-3-(3-oxo-2H-1,4-benzoxazin-7-yl)-2,3-dihydro-2-thioxo-4,6(1H,5H)-pyrimidinedione 
• 130137-53-0 1-(4-Chloro-phenyl)-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-7-yl)-2-thioxo-dihydro-pyrimidine-4,6-dione 
• 130137-54-1 1-(4-Bromo-phenyl)-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-7-yl)-2-thioxo-dihydro-pyrimidine-4,6-dione 

Relevant articles and documents

Anticonvulsant and toxicity evaluation of newer 4H-benzo[1,4]oxazin-3-ones: The effect of two hydrogen bonding domains

A series of (Z)-2-(substituted aryl)-N-(3-oxo-4-(substituted carbamothioyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl) hydrazine carboxamides (6a-r) was synthesized using 2-amino-5-nitrophenol as a starting material. All the synthesized compounds possessed two hydrogen-bonding domains and their effect on the activity was studied thereof. The anticonvulsant activity was assessed by the maximal electroshock test (MES), subcutaneous pentylenetetrazole test (scPTZ) and intraperitoneal thiosemicarbazide test (ipTSC). Compounds (6b, 6h, 6i, and 6p) were found to be the most potent of the series as they showed 83-100% protection in the MES test. They also displayed considerable activity in the chemically induced seizure tests. Most of the tested compounds were devoid of the neurotoxic and hepatotoxic effects. A series of (Z)-2-(substituted aryl)-N-(3-oxo-4-(substituted carbamothioyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin- 7-yl) hydrazine carboxamides (6a-r) was synthesized. Four compounds were found to be very promising as far as efficacy and safety is concerned. They may act as lead molecules for future investigations. Copyright

PHARMACOPHORES, COMPOUNDS AND METHODS HAVING APPLICATION IN THE TREATMENT OF CANCER THROUGH INHIBITION OF CYP17A1 AND CYP19A1

The invention provides pharmacophores for use in the design, screening and identification of inhibitors of CYP17A1 and CYP19A1 enzymes. A preferred pharmacophore has a spatial arrangement of atoms as shown in the accompanying Figure 1, wherein: ? A represents hydrogen bond acceptors; ? D represents hydrogen bond donors; and ? R represents aromatic rings. Compounds conforming to the preferred pharmacophore are provided for use as medicaments in the treatment of cancer, especially prostate cancer and breast cancer. By way of example, these compounds include N-(4-ethylphenyl)-5-(2-hydroxy-5-methoxybenzoyl)-2-imino-2H-pyran-3-carboxamide and 2-(4-sulfamoylphenoxy) ethyl 2-amino-3-methylbenzoate. Also provided are methods for the treatment of prostate cancer and breast cancer using the compounds of the invention as well as their salts, solvates, hydrates, primary metabolites and prodrugs. Methods of inhibiting CYP17A1 and CYP19A1, and hence of inhibiting androgen activity in a subject, are disclosed. The invention also provides processes for designing, screening and identifying compounds which can inhibit CYP17A1 and CYP19A1.

ALKYL-SUBSTITUTED 3' COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY

The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): wherein R1, R2, Ar, m and n are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.

CONDENSED HETEROCYCLIC COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY

The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I) wherein R1, A, B, D, E, G, Q, Ar, n, m, and p are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.

ACYCLIC COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY

The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): wherein R1, R2, R5, Q, G, Ar, m, and n are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.

4'-AMINO CYCLIC COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY

The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): formula (I) wherein Cy is selected from formula (Il) and wherein R1, R2, R3, Q, G, Ar, m, n and p are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.

PYRROLIDINE-SUBSTITUTED AZAINDOLE COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY

The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): wherein R1, R2, A, B, D, E, G, Ar, and n are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.

Synthesis of 2-(4-substituted benzyl-1,4-diazepan-1-yl)-N-(3,4-dihydro-3- oxo-2H-benzo[b][1,4]oxazin-7-yl)acetamides and their positive inotropic evaluation

Herein we describe the discovery of compound 3g, a potent positive inotropic agent compared with the standard drug, milrinone. Compound 3g was developed from a series of 2-(4-substitutedbenzyl-1,4-diazepan-1-yl)-N-(3,4- dihydro-3-oxo-2H-benzo[b][1,4]oxazin-7-yl) acetamides found in an evaluation of inotropic activity by measuring left atrium stroke volume on isolated rabbit heart preparations. Several compounds showed favorable activities, but 3g was the most potent, with 7.68 ± 0.14% increased stroke volume (milrinone 2.38 ± 0.05%) at 1 × 10-5 M in our in vitro study. The chronotropic effects of compounds having significant inotropic effects were also evaluated.

3' SUBSTITUTED COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY

The present disclosure provides compounds having affinity for the 5-HT6 receptor which are of the formula (I): wherein Q, R1, R4, m and Ar are as defined herein. The disclosure also relates to methods of preparing such compounds, compositions containing such compounds, and methods of use thereof.

Synthesis of 2-(4-substitutedmethylpiperazin-1-yl)-N-(3,4-dihydro-3-oxo-2H-benzo[b][1,4]oxazin-7-yl)acetamides and their positive inotropic evaluation

In an attempt to search for more potent positive inotropic agents, a series of 2-(4-substitutedmethylpiperazin-1-yl)-N-(3,4-dihydro-3-oxo-2H-benzo[b][1,4]oxazin-7-yl)acetamides were synthesized and their positive inotropic activities were evaluated by measuring left atrium stroke volume on isolated rabbit heart preparations. Several compounds showed favorable activities compared with the standard drug, milrinone, among which 2-(4-(4-methylbenzyl)piperazin-1-yl)-N-(3,4-dihydro-3-oxo-2H-benzo[b][1,4]oxazin-7-yl)acetamide 4e showed the most potent activity with the 5.09 ± 0.00% increased stroke volume (milrinone 1.67 ± 0.64%) at a concentration of 1 × 10-5 M in our in vitro study. The chronotropic effects of those compounds having significant inotropic effects were also evaluated in this work.