38543-75-8

Basic information

• Product Name: 8-Hydroxy-2-methyl-5,7-dinitroquinoline
• Synonyms: 8-Hydroxy-2-methyl-5,7-dinitroquinoline;2-Methyl-5,7-dinitroquinolin-8-ol;5,7-Dinitro-2-methyl-8-quinolinol;2-methyl-5,7-dinitro-8-Quinolinol
• CAS NO: 38543-75-8
• Molecular Formula: C₁₀H₇N₃O₅
• Molecular Weight: 249
• Mol File: 38543-75-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 415.572 °C at 760 mmHg
• Flash Point: 205.131 °C
• Appearance: /
• Density: 1.605
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.731
• CAS DataBase Reference: 8-Hydroxy-2-methyl-5,7-dinitroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: 8-Hydroxy-2-methyl-5,7-dinitroquinoline(38543-75-8)
• EPA Substance Registry System: 8-Hydroxy-2-methyl-5,7-dinitroquinoline(38543-75-8)

Safety Data

• Hazardous Substances Data: 38543-75-8(Hazardous Substances Data)

Usage

General Description

8-Hydroxy-2-methyl-5,7-dinitroquinoline is a chemical compound with the molecular formula C10H8N3O4. It is a yellow-colored crystalline solid that is mainly used as a reagent in organic synthesis and as a photoluminescent material in luminescent devices. 8-Hydroxy-2-methyl-5,7-dinitroquinoline has been studied for its potential biological activities, including as an antitumor agent and as a potential inhibitor of protein kinase C. It is important to handle this compound with caution as it may pose health hazards if ingested, inhaled, or absorbed through the skin, and it may also be harmful to aquatic organisms.

InChI:InChI=1/C10H7N3O5/c1-5-2-3-6-7(12(15)16)4-8(13(17)18)10(14)9(6)11-5/h2-4,14H,1H3

Upstream product

• 826-81-3 2-methyl-8-quinolinol 

Downstream Products

• 151418-47-2 7-acetamido-2-formylquinoline-5,8-dione 

Relevant articles and documents

Cathepsin B inhibitors: Further exploration of the nitroxoline core

Human cathepsin B is a cysteine protease with many house-keeping functions, such as intracellular proteolysis within lysosomes. Its increased activity and expression have been strongly associated with many pathological processes, including cancers. We present here the design and synthesis of novel derivatives of nitroxoline as inhibitors of cathepsin B. These were prepared either by omitting the pyridine part, or by modifying positions 2, 7, and 8 of nitroxoline. All compounds were evaluated for their ability to inhibit endopeptidase and exopeptidase activities of cathepsin B. For the most promising inhibitors, the ability to reduce extracellular and intracellular collagen IV degradation was determined, followed by their evaluation in cell-based in vitro models of tumor invasion. The presented data show that we have further defined the structural requirements for cathepsin B inhibition by nitroxoline derivatives and provided additional knowledge that could lead to non-peptidic compounds with usefulness against tumor progression.

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.

QUINOLINE COMPOUNDS AS INHIBITORS OF ANGIOGENESIS, HUMAN METHIONINE AMINOPEPTIDASE, AND SIRT1, AND METHODS OF TREATING DISORDERS

Described herein are methods of inhibiting methionine aminopeptidase or SirT1, inhibiting angiogenesis, and treating disorders (or symptoms thereof) associated with methionine aminopeptidase, SirT1 and/or angiogenesis, wherein a compound of the invention