3565-26-2

Basic information

• Product Name: 5-NITROSO-8-HYDROXYQUINOLINE
• Synonyms: NSC 3852;5-Nitroso-8-cinnolinol;5-nitroso-8-quinolino;8-Quinolinol, 5-nitroso-;Hydron III;hydroniii;RMH-79;8-HYDROXY-5-NITROSOQUINOLINE
• CAS NO: 3565-26-2
• Molecular Formula: C₉H₆N₂O₂
• Molecular Weight: 174.16
• EINECS: 222-650-6
• Mol File: 3565-26-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 245 °C
• Boiling Point: 305.12°C (rough estimate)
• Flash Point: 197.7°C
• Appearance: /
• Density: 1.40
• Vapor Pressure: 4.4E-07mmHg at 25°C
• Refractive Index: 1.5651 (estimate)
• Storage Temp.: Store at RT
• Solubility: insoluble in EtOH; insoluble in H2O; ≥7.35 mg/mL in DMSO
• CAS DataBase Reference: 5-NITROSO-8-HYDROXYQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-NITROSO-8-HYDROXYQUINOLINE(3565-26-2)
• EPA Substance Registry System: 5-NITROSO-8-HYDROXYQUINOLINE(3565-26-2)

Safety Data

• Hazard Codes: Xn
• Statements: 5-40-20/21/22
• Safety Statements: 36/37
• Hazardous Substances Data: 3565-26-2(Hazardous Substances Data)

Usage

Chemical Properties

slightly yellow to yellow-green powder

Biological Activity

Histone deacetylase inhibitor. Causes cell differentiation and antiproliferative activity in MCF-7 human breast cancer cells in vitro and displays antitumor activity in vivo .

Safety Profile

Poison by intravenous and intraperitoneal routes. Many nitroso compounds are carcinogens. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

references

[1]. martirosyan a, leonard s, shi x, et al. actions of a histone deacetylase inhibitor nsc3852 (5-nitroso-8-quinolinol) link reactive oxygen species to cell differentiation and apoptosis in mcf-7 human mammary tumor cells. j pharmacol exp ther, 2006, 317(2): 546-552. [2]. strobl js, seibert cw, li y, et al. inhibition of toxoplasma gondii and plasmodium falciparum infections in vitro by nsc3852, a redox active antiproliferative and tumor cell differentiation agent. j parasitol, 2009, 95(1): 215-223.

InChI:InChI=1/C9H6N2O2/c12-8-4-3-7(11-13)6-2-1-5-10-9(6)8/h1-5,12H

Upstream product

• 148-24-3 8-quinolinol 

Downstream Products

• 13207-66-4 5-amino-8-hydroxyquinoline 
• 4008-48-4 nitroxoline 
• 74440-55-4 5-nitro-7-(pyrrolidin-1-ylmethyl)quinolin-8-ol 
• 1417737-63-3 7-((benzylamino)methyl)-5-nitroquinolin-8-ol 
• 74440-54-3 5-nitro-7-(piperidin-1-ylmethyl)quinolin-8-ol 
• 1378240-55-1 7-((4-(4-fluorophenyl)piperazin-1-yl)methyl)-5-nitroquinolin-8-ol 
• 312536-49-5 7-((4-(2-methoxyphenyl)piperazin-1-yl)methyl)-5-nitroquinolin-8-ol 
• 76289-27-5 5-nitro-7-((4-phenylpiperazin-1-yl)methyl)quinolin-8-ol 
• 74440-59-8 7-((4-methylpiperazin-1-yl)methyl)-5-nitroquinolin-8-ol 
• 74440-53-2 7-(morpholinomethyl)-5-nitroquinolin-8-ol 

Relevant articles and documents

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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.

Substituted oxines inhibit endothelial cell proliferation and angiogenesis

Two substituted oxines, nitroxoline (5) and 5-chloroquinolin-8-yl phenylcarbamate (22), were identified as hits in a high-throughput screen aimed at finding new anti-angiogenic agents. In a previous study, we have elucidated the molecular mechanism of antiproliferative activity of nitroxoline in endothelial cells, which comprises of a dual inhibition of type 2 human methionine aminopeptidase (MetAP2) and sirtuin 1 (SIRT1). Structure-activity relationship study (SAR) of nitroxoline offered many surprises where minor modifications yielded oxine derivatives with increased potency against human umbilical vein endothelial cells (HUVEC), but with entirely different as yet unknown mechanisms. For example, 5-nitrosoquinolin-8-ol (33) inhibited HUVEC growth with sub-micromolar IC50, but did not affect MetAP2 or MetAP1, and it only showed weak inhibition against SIRT1. Other sub-micromolar inhibitors were derivatives of 5-aminoquinolin-8-ol (34) and 8-sulfonamidoquinoline (32). A sulfamate derivative of nitroxoline (48) was found to be more potent than nitroxoline with the retention of activities against MetAP2 and SIRT1. The bioactivity of the second hit, micromolar HUVEC and MetAP2 inhibitor carbamate 22 was improved further with an SAR study culminating in carbamate 24 which is a nanomolar inhibitor of HUVEC and MetAP2. The Royal Society of Chemistry 2012.