885-70-1

Basic information

• Product Name: 5H-BENZO[E]PYRIDO[3,2-B][1,4]DIAZEPIN-6(11H)-ONE
• Synonyms: 5,6-Dihydro-6-oxo-11H-pyrido[2,3-b][1,4]benzodiazepine;5H-BENZO[E]PYRIDO[3,2-B][1,4]DIAZEPIN-6(11H)-ONE;5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one;LS 75;11H-Pyrido[2,3-b][1,4]benzodiazepine-6(5H)-one;5,11-dihydropyrido[2,3-b][1,4]benzodiazepin-6-one;5,11-Dihydropyrido[2,3-b][1,4]benzodiazepin-6-one AK-36728;6H-Pyrido[2,3-b][1,4]benzodiazepin-6-one, 1,5-dihydro-
• CAS NO: 885-70-1
• Molecular Formula: C₁₂H₉N₃O
• Molecular Weight: 211.22
• EINECS: 212-944-2
• Mol File: 885-70-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: 292-293℃
• Boiling Point: 336℃
• Flash Point: 157℃
• Appearance: /
• Density: 1.275
• Vapor Pressure: 0.000119mmHg at 25°C
• Refractive Index: 1.627
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: 11.58±0.20(Predicted)
• CAS DataBase Reference: 5H-BENZO[E]PYRIDO[3,2-B][1,4]DIAZEPIN-6(11H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5H-BENZO[E]PYRIDO[3,2-B][1,4]DIAZEPIN-6(11H)-ONE(885-70-1)
• EPA Substance Registry System: 5H-BENZO[E]PYRIDO[3,2-B][1,4]DIAZEPIN-6(11H)-ONE(885-70-1)

Safety Data

• Hazardous Substances Data: 885-70-1(Hazardous Substances Data)

Usage

Uses

5,11-Dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one, can be used in the synthesis of fluorescent pirenzepine derivatives, used as potential bitopic ligands of the Human M1 Muscarinic receptor.

Synthesis

In a 1000 ml reaction flask,Add 600 ml of butanol,100 g of 2-amino-N- (2-chloropyridyl-3-yl) benzamide,2 ml of concentrated sulfuric acid,The reaction was refluxed for 3 hours at a reaction temperature of 80 ° C,Cooled to room temperature,filter,Washed with acetone,50-60 ° C in vacuo to give 98 g of a pale yellow solid product,Yield 98percent, purity 99percent.

InChI:InChI=1/C12H9N3O/c16-12-8-4-1-2-5-9(8)14-11-10(15-12)6-3-7-13-11/h1-7H,(H,13,14)(H,15,16)

Upstream product

• 6298-19-7 2-chloro-3-aminopyridine 
• 87-25-2 2-ethoxycarbonylaniline 
• 62-53-3 aniline 
• 84772-30-5 3-(2'-aminobenzoyl)aminopiperidin-2-one 
• 118-48-9 isatoic anhydride 
• 1892-22-4 3-aminopiperidin-2-one 
• 84446-21-9 3-(2'-chlorobenzoyl)amino-2-chloropyridine 
• 610-14-0 2-nitrobenzyl chloride 
• 552-16-9 ortho-nitrobenzoic acid 
• 1028-86-0 N-(2-chloro-pyridin-3-yl)-2-nitro-benzamide 
• 39620-04-7 2-amino-3-chloropyridine 
• 134-20-3 2-carbomethoxyaniline 
• 956-30-9 2-amino-N-(2-chloropyridin-3-yl)benzamide 
• 84772-31-6 2,3,4,4a,5,11-hexahydro-6H-pyrido<2,3-b><1,4>benzodiazepin-6-one 

Downstream Products

• 126856-99-3 6-(2-(4-methyl-1-piperazinyl)acetamido)-11H-pyrido<2,1-b>quinazolin-11-one 
• 28797-61-7 pirenzepine 
• 88369-39-5 5,11-dihydro-11-benzyl-6H-pyrido<2,3-b><1,4>benzodiazepin-6-one 
• 88369-40-8 5,11-Dibenzyl-5,11-dihydro-benzo[e]pyrido[3,2-b][1,4]diazepin-6-one 
• 28797-48-0 11-(chloroacetyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one 
• 87571-97-9 5,11-dihydro-11-phenyloxycarbonyl-6H-pyrido[2,3-b][1,4]-benzodiazepin-6-one 
• 1338243-36-9 tert-butyl (1-(4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)benzyl)piperidin-4-yl)carbamate 
• 1338243-49-4 tert-butyl 4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)phenethylcarbamate 
• 1338241-82-9 4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)benzyl methanesulfonate 
• 1338241-41-0 (4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)phenyl)methanol 
• 1338242-45-7 3-(4-(chloromethyl)phenyl)-9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepine 
• 1338243-47-2 tert-butyl (1-(4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)benzoyl)piperidin-4-yl)carbamate 
• 1338243-70-1 4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)benzoic acid 
• 1338241-43-2 methyl 4-(9H-benzo[f]pyrido[2,3-b][1,2,4]triazolo[4,3-d][1,4]diazepin-3-yl)benzoate 

Relevant articles and documents

AZABICYCLO AND DIAZEPINE DERIVATIVES FOR TREATING OCULAR DISORDERS

The present invention provides in one aspect azabicycio and diazepine derivatives useful as modulators of muscarinic receptors. In another aspect, the present invention provides pharmaceutical compositions for treating ocular diseases, the compositions comprising at least one muscarinic receptor modulator. Formulae (I) & (II):

Pirenzepine hydrochloride key intermediate preparation method

The present invention discloses a pirenzepine hydrochloride key intermediate preparation method, wherein (2-halo-3-pyridyl) carbamic acid and aniline are adopted as starting raw materials, aniline is adopted as a reaction solvent, and under the effect of an alkali and cuprous iodide, a one-step reaction is performed to obtain 5,11-dihydro-6H-pyrido[2,3-B][1,4]benzodiazepine-6-ketone. According to the present invention, the novel 5,11-dihydro-6H-pyrido[2,3-B][1,4]benzodiazepine-6-ketone synthesis method is provided, the step of the method is simple, and the yield is up to more than 99%; the aniline is the reaction solvent, and is further the raw material, such that the raw material (2-halo-3-pyridyl) carbamic acid can completely react, the reaction yield is increased, the cost increase and the environmental pollution due to the use of other solvents are avoided, and the excess aniline can be continuously used after the treatment distillation so as to substantially save the cost and protect the environment; and the synthesis method has good industrial prospects.

Fluorescent pirenzepine derivatives as potential bitopic ligands of the human M1 muscarinic receptor

Following a recent description of fluorescence resonance energy transfer between enhanced green fluorescent protein (EGFP)-fused human muscarinic M1 receptors and Bodipy-labeled pirenzepine, we synthesized seven fluorescent derivatives of this antagonist in order to further characterize ligand-receptor interactions. These compounds carry Bodipy [558/568], Rhodamine Red-X [560/580], or Fluorolink Cy3 [550/570] fluorophores connected to pirenzepine through various linkers. All molecules reversibly bind with high affinity to M1 receptors (radioligand and energy transfer binding experiments) provided that the linker contains more than six atoms. The energy transfer efficiency exhibits modest variations among ligands, indicating that the distance separating EGFP from the fluorophores remains almost constant. This also supports the notion that the fluorophores may bind to the receptor protein. Kinetic analyses reveal that the dissociation of two Bodipy derivatives (10 or 12 atom long linkers) is sensitive to the presence of the allosteric modulator brucine, while that of all other molecules (15-24 atom long linkers) is not. The data favor the idea that these analogues might interact with both the acetylcholine and the brucine binding domains.