22814-13-7

Basic information

• Product Name: 2,3-dihydro-4H-pyridazino[4,5-b]indol-4-one
• Synonyms: 9H-2,3,9-Triaza-fluoren-1-ol;5H-Pyridazino[4,5-b]indol-4-ol;3H,4H,5H-Pyridazino[4,5-b]indol-4-one;4H-Pyridazino[4,5-b]indol-4-one, 3,5-dihydro-
• CAS NO: 22814-13-7
• Molecular Formula: C₁₀H₇N₃O
• Molecular Weight: 185.1821
• Mol File: 22814-13-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 326-328 °C(Solv: 1,4-dioxane (123-91-1))
• Density: 1.55g/cm³
• Refractive Index: 1.798
• PKA: 13.24±0.20(Predicted)
• CAS DataBase Reference: 2,3-dihydro-4H-pyridazino[4,5-b]indol-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-dihydro-4H-pyridazino[4,5-b]indol-4-one(22814-13-7)
• EPA Substance Registry System: 2,3-dihydro-4H-pyridazino[4,5-b]indol-4-one(22814-13-7)

Safety Data

• Hazardous Substances Data: 22814-13-7(Hazardous Substances Data)

Usage

General Description

2,3-dihydro-4H-pyridazino[4,5-b]indol-4-one, also known as CI-163, is a chemical compound with the molecular formula C11H10N2O. It is a bicyclic heterocyclic compound containing a pyridazine ring fused with an indole ring. 2,3-dihydro-4H-pyridazino[4,5-b]indol-4-one has been studied for its potential pharmacological properties, including its activity as a central nervous system depressant and its potential use in the treatment of anxiety and stress-related disorders. It has also shown potential as an anti-inflammatory agent and has been investigated for its potential in the treatment of asthma. 2,3-dihydro-4H-pyridazino[4,5-b]indol-4-one may have various other potential applications in medicinal chemistry and pharmaceutical research.

Upstream product

• 5055-39-0 indole-2-carbohydrazide 
• 3770-50-1 2-carbethoxyindole 
• 64932-49-6 1H-indole-2-carboxylic acid N²-formyl-hydrazide 
• 18450-27-6 ethyl 3-formyl-1H-indole-2-carboxylate 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 85076-68-2 4-chloro-5H-pyridazino[4,5-b]indole 

Relevant articles and documents

Discovery of hydrazide-based pyridazino[4,5-b]indole scaffold as a new phosphoinositide 3-kinase (PI3K) inhibitor for breast cancer therapy

Herein, the mono and dialkylation of pyridazino[4,5-b]indole were achieved with a set of alkylating agents, including amyl bromide, allyl bromide, benzyl bromide and ethyl chloroacetate in the presence of K2CO3/acetone or KOH/DMSO. The hydrazinolysis of mono and di-esters10and11gave the target hydrazides12and13, which displayed promising, potent, and significant cytotoxic activity against the MCF-7 cell line with IC50values of 4.25 and 5.35 μm compared to that of the standard drug 5-FU (IC506.98 μm), respectively. RT-PCR analysis of the most active compound12was performed to determine its mode of action through the up-regulation of pro-apoptotic genes and inhibition of anti-apoptotic and PI3K/AKT/mTOR genes. The findings were consistent with the proposed mechanism illustrated in thein silicostudy. Further, thein vivoanalysis exhibited its potent anti-cancer activity through the prolongation of survival parameters, and inhibition of ascetic fluid parameters in EAC-bearing mice.

Potentially Tautomeric 1,2-Dihydro-1-oxo-5H-pyridazinoindole and 3,4-Dihydro-4-oxo-5H-pyridazinoindole

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4-Hydrazino-5H-pyridazino (4,5-b) indole, a new antihypertensive agent

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