54558-01-9

Basic information

• Product Name: 6-(3-NITROPHENYL)-3(2H)-PYRIDAZINONE
• Synonyms: 6-(3-NITROPHENYL)-3(2H)-PYRIDAZINONE;6-(3-nitrophenyl)pyridazin-3(2H)-one;3-(3-nitrophenyl)-1H-pyridazin-6-one;6-(3-Nitrophenyl)pyridazin-3-ol
• CAS NO: 54558-01-9
• Molecular Formula: C₁₀H₇N₃O₃
• Molecular Weight: 217.18
• Mol File: 54558-01-9.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• Density: 1.461 g/cm³
• CAS DataBase Reference: 6-(3-NITROPHENYL)-3(2H)-PYRIDAZINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(3-NITROPHENYL)-3(2H)-PYRIDAZINONE(54558-01-9)
• EPA Substance Registry System: 6-(3-NITROPHENYL)-3(2H)-PYRIDAZINONE(54558-01-9)

Safety Data

• Hazardous Substances Data: 54558-01-9(Hazardous Substances Data)

Upstream product

• 52239-76-6 3-(m-Nitrophenyl)-6-oxo-1,4,5,6-tetrahydropyridazine 
• 6328-00-3 4-(3-nitro-phenyl)-4-oxo-butyric acid 
• 1010448-64-2 ethyl β-(o-nitrobenzoyl)lactate 
• 298-12-4 Glyoxilic acid 
• 121-89-1 3-Nitroacetophenone 

Downstream Products

• 66548-77-4 6-(3-aminophenyl)-1,2,4-triazolo<4,3-b>pyridazine 
• 66548-76-3 3-methyl-6-[3-(amino)phenyl]-1,2,4-triazolo[4,3-b]pyridazine 
• 66548-75-2 6-(3-nitro-phenyl)-[1,2,4]triazolo[4,3-b]pyridazine 
• 66548-74-1 3-methyl-6-(3-nitrophenyl)-[1,2,4]triazolo[4,3-b]pyridazine 
• 76970-07-5 3-methyl-6-(3-acetamidophenyl)-1,2,4-triazolo<4,3-b>pyridazine 
• 108655-21-6 3-(m-Aminophenyl)pyridazine 
• 24912-36-5 6-(3-amino-phenyl)-2H-pyridazin-3-one 
• 58059-33-9 3-chloro-6-(3-nitrophenyl)pyridazine 

Relevant articles and documents

Towards discovery of novel scaffold with potent antiangiogenic activity; design, synthesis of pyridazine based compounds, impact of hinge interaction, and accessibility of their bioactive conformation on VEGFR-2 activities

Pyridazine scaffolds are considered privileged structures pertaining to its novelty, chemical stability, and synthetic feasibility. In our quest towards the development of novel scaffolds for effective vascular endothelial growth 2 (VEGFR-2) inhibition with antiangiogenic activity, four novel series of pyridazines were designed and synthesised. Five of the synthesised compounds; namely (8c, 8f, 15, 18b, and 18c) exhibited potent VEGFR-2 inhibitory potency (>80%); with IC50 values ranging from low micromolar to nanomolar range; namely compounds 8c, 8f, 15, 18c with (1.8 μM, 1.3 μM, 1.4 μM, 107 nM), respectively. Moreover, 3-[4-{(6-oxo-1,6-dihydropyridazin-3-yl)oxy}phenyl]urea derivative (18b) exhibited nanomolar potency towards VEGFR-2 (60.7 nM). In cellular assay, the above compounds showed excellent inhibition of VEGF-stimulated proliferation of human umbilical vein endothelial cells at 10 μM concentration. Finally, an extensive molecular simulation study was performed to investigate the probable interaction with VEGFR-2.

PYRIDAZINONE DERIVATIVES

Compounds of the formula (I), in which R1, R2 and R3 have the meanings indicated in Claim 1, are inhibitors of tyrosine kinases, in particular Met kinase, and can be employed, inter alia, for the treatment of tumours.

One-pot preparation of 6-substituted 3(2H)-pyridazinones from ketones

A one-pot process for the preparation of 6-phenyl-3(2H)-pyridazinone from acetophenone and glyoxylic acid has been investigated and shown to have wide utility in the preparation of 6- and 5,6-substituted 3(2H)-pyridazinones. Limitations to the process encountered with 2'-hydroxyacetophenone and with basic hetero-aromatic ketones have been overcome, and the processes described offer the rapid and efficient synthesis of many 6-substituted pyridazinones from readily available ketones.