24912-35-4

Basic information

• Product Name: 6-[4-Aminophenyl]pyridazin-3(2H)-one
• Synonyms: 6-[4-Aminophenyl]pyridazin-3(2H)-one
• CAS NO: 24912-35-4
• Molecular Formula: C₁₀H₉N₃O
• Molecular Weight: 187.2
• Mol File: 24912-35-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 292-299 °C(Solv: water (7732-18-5))
• Appearance: /
• Density: 1.33 g/cm³
• PKA: 11.29±0.40(Predicted)
• CAS DataBase Reference: 6-[4-Aminophenyl]pyridazin-3(2H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-[4-Aminophenyl]pyridazin-3(2H)-one(24912-35-4)
• EPA Substance Registry System: 6-[4-Aminophenyl]pyridazin-3(2H)-one(24912-35-4)

Safety Data

• Hazardous Substances Data: 24912-35-4(Hazardous Substances Data)

Usage

General Description

6-[4-Aminophenyl]pyridazin-3(2H)-one, also known as 4-Aminoantipyrine, is a chemical compound with the molecular formula C11H10N4O. It is a pyridazinone derivative that is commonly used as an intermediate in the synthesis of pharmaceutical and agrochemical products. 4-Aminoantipyrine has a wide range of applications, including as a reagent in the determination of glucose and peroxidase, as well as in the synthesis of dyes. It is also used as a biomarker for monitoring oxidative damage and is being investigated for its potential anti-inflammatory and antioxidant properties. The compound has attracted interest in the scientific and medical communities due to its diverse applications and potential therapeutic benefits.

Upstream product

• 105537-49-3 3-(p-Nitrophenyl)-6-oxo-1,6-dihydropyridazine 
• 100-19-6 (4-nitrophenyl)ethanone 
• 19064-67-6 6-chloro-2H-pyridazin-3-one 
• 214360-73-3 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline 

Downstream Products

• 86798-72-3 4,5-dihydro-6-<4-(4H-1,2,4-triazol-4-yl)phenyl>-3(2H)pyridazinone 
• 109890-19-9 N-<<<4-(1,4,5,6-tetrahydro-6-oxo-3-pyridazinyl)phenyl>amino>thiooxomethyl>benzamide 
• 109890-23-5 N-(2-chloroethyl)-N'-<4-(1,4,5,6-tetrahydro-6-oxo-3-pyridazinyl)phenyl>urea 
• 131741-04-3 (4-(6-oxo-1,6-dihydropyridazin-3-yl)phenyl)carbohydrazonoyl dicyanide 
• 98326-38-6 6-[4-(4'-pyridyl)aminophenyl]-3(2H)-pyridazinone 

Relevant articles and documents

NOVEL HYDRAZONE DERIVATIVE WITH ARYL OR HETEROARYL GROUP SUBSTITUTED AT TERMINAL AMINE GROUP THEREOF AND USE THEREOF

The present invention relates to novel hydrazone derivatives in which a terminal amine group is substituted with an aryl group or a heteroaryl group, and uses thereof.

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.