74440-59-8

Basic information

• Product Name: 7-[(4-methylpiperazin-1-yl)methyl]-5-nitroquinolin-8-ol
• Synonyms: 7-((4-Methyl-1-piperazinyl)methyl)-5-nitro-8-quinolinol; 8-Quinolinol, 7-((4-methyl-1-piperazinyl)methyl)-5-nitro-
• CAS NO: 74440-59-8
• Molecular Formula: C₁₅H₁₈N₄O₃
• Molecular Weight: 302.3284
• Mol File: 74440-59-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 506.1°C at 760 mmHg
• Flash Point: 259.9°C
• Density: 1.346g/cm³
• Vapor Pressure: 7.26E-11mmHg at 25°C
• Refractive Index: 1.669
• CAS DataBase Reference: 7-[(4-methylpiperazin-1-yl)methyl]-5-nitroquinolin-8-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 7-[(4-methylpiperazin-1-yl)methyl]-5-nitroquinolin-8-ol(74440-59-8)
• EPA Substance Registry System: 7-[(4-methylpiperazin-1-yl)methyl]-5-nitroquinolin-8-ol(74440-59-8)

Safety Data

• Hazardous Substances Data: 74440-59-8(Hazardous Substances Data)

Upstream product

• 109-01-3 1-methyl-piperazine 
• 50-00-0 formaldehyd 
• 4008-48-4 nitroxoline 
• 148-24-3 8-quinolinol 
• 3565-26-2 5-nitroso-8-hydroxyquinoline 

Relevant articles and documents

Synthesis and anti-phytopathogenic activity of 8-hydroxyquinoline derivatives

Phytopathogenic fungi have become a serious threat to the quality of agricultural products, food security and human health globally, necessitating the need to discover new antifungal agents with de novo chemical scaffolds and high efficiency. A series of 8-hydroxyquinoline derivatives were designed and synthesized, and their antifungal activity was evaluated against five phytopathogenic fungi. In vitro assays revealed that most of the tested compounds remarkably impacted the five target fungi and their inhibitory activities were better than that of the positive control azoxystrobin. Compound 2, in particular, exhibited the highest potency among all the tested compounds, with an EC50 of 0.0021, 0.0016, 0.0124, 0.0059 and 0.0120 mM respectively against B. cinerea, S. sclerotiorum, F. graminearum, F. oxysporum and M. oryzae, followed by compound 5c. The morphological observations of optical microscopy and scanning electron microscopy revealed that compounds 2 and 5c caused mycelial abnormalities of S. sclerotiorum. Futhermore, the results of in vivo antifungal activity of compounds 2 and 5c against S. sclerotiorum showed that 5c possessed stronger protective and curative activity than that of 2, and the curative effects of 5c at 40 and 80 μg mL-1 (84.18% and 95.44%) were better than those of azoxystrobin (77.32% and 83.59%). Therefore, compounds 2 and 5c are expected to be novel lead structures for the development of new fungicides.

Discovery of inhibitors of Burkholderia pseudomallei methionine aminopeptidase with antibacterial activity

Evaluation of a series of MetAP inhibitors in an in vitro enzyme activity assay led to the first identification of potent molecules that show significant growth inhibition against Burkholderia pseudomallei. Nitroxoline analogues show excellent inhibition potency in the BpMetAP1 enzyme activity assay with the lowest IC50 of 30 nM and inhibit the growth of B. pseudomallei and B. thailandensis at concentrations ≥31 μM.

Biologically active Mannich bases derived from nitroxoline.

A series of compounds with various basic side chains were derived from 5-nitro-8-hydroxyquinoline (nitroxoline). Aminomethylation of nitroxoline led exclusively to the formation of o-substituted phenolic Mannich bases. Depending on the kind of the primary