116289-25-9

Basic information

• Product Name: 4-(2-HYDROXYETHYL)AMINOQUINOLINE
• Synonyms: 4-(2-HYDROXYETHYL)AMINOQUINOLINE
• CAS NO: 116289-25-9
• Molecular Formula: C11H12N2O
• Molecular Weight: 188.23
• Mol File: 116289-25-9.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 399.289°C at 760 mmHg
• Flash Point: 195.283°C
• Appearance: /
• Density: 1.253g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.698
• CAS DataBase Reference: 4-(2-HYDROXYETHYL)AMINOQUINOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-HYDROXYETHYL)AMINOQUINOLINE(116289-25-9)
• EPA Substance Registry System: 4-(2-HYDROXYETHYL)AMINOQUINOLINE(116289-25-9)

Safety Data

• Hazardous Substances Data: 116289-25-9(Hazardous Substances Data)

Usage

Explanation

This denotes that each molecule of 4-(2-hydroxyethyl)aminoquinoline consists of 11 carbon atoms, 14 hydrogen atoms, 2 nitrogen atoms, and 1 oxygen atom.

2. Derivative Type: Aminoquinoline derivative
Explanation: This indicates that 4-(2-hydroxyethyl)aminoquinoline is a chemical compound derived from quinoline with an amino group (NH2) that is further modified by a hydroxyethyl group (–CH2CH2OH).

3. Functional Group Attachment: Hydroxyethyl group attached to the amino group
Explanation: The presence of a hydroxyethyl group attached to the amino group on the quinoline ring structure provides distinctive chemical properties, such as increased solubility in water and reactivity with other compounds.

4. Primary Use in Synthesis: Synthesis of pharmaceuticals
Explanation: 4-(2-hydroxyethyl)aminoquinoline is extensively used in the chemical synthesis of various pharmaceutical compounds, including antimalarial drugs and quinoline-based anticancer agents, highlighting its versatility and importance in medicinal chemistry.

5. Role in Antimalarial Drugs: Key component
Explanation: Its structure and reactivity make it a valuable component in the development of antimalarial drugs, contributing to the effectiveness of these medications against malaria-causing parasites.

6. Contribution to Anticancer Agents: Quinoline-based anticancer agent development
Explanation: The compound's quinoline backbone is utilized in creating novel anticancer agents, leveraging its ability to interact with cancer cells' biological pathways.

7. Potential as Antiviral Agent: Studied for viral infections treatment
Explanation: Beyond its use in synthesizing antimalarials and anticancer drugs, 4-(2-hydroxyethyl)aminoquinoline has shown potential in antiviral applications, being researched for its efficacy against various viral infections, thus expanding its scope in therapeutic uses.

This breakdown highlights the chemical complexity and multifaceted applications of 4-(2-hydroxyethyl)aminoquinoline, underscoring its significance in drug development and research in the pharmaceutical industry.

InChI:InChI=1/C11H12N2O/c14-8-7-13-11-5-6-12-10-4-2-1-3-9(10)11/h1-6,14H,7-8H2,(H,12,13)

Upstream product

• 611-36-9 quinolin-4-ol 
• 34785-11-0 4-hydroxy-3-quinoline carboxylic acid 
• 26892-90-0 ethyl 4-hydroxy-3-quinolinecarboxylate 
• 54535-22-7 diethyl (anilinomethylene)malonate 
• 62-53-3 aniline 
• 86-98-6 4,7-dichloroquinoline 
• 91066-18-1 3-(7-chloroquinolin-4-ylamino)propyl alcohol 
• 611-35-8 4-chloroquinoline 
• 141-43-5 ethanolamine 

Relevant articles and documents

Structure-function relationships in aminoquinolines: Effect of amino and chloro groups on quinoline-hematin complex formation, inhibition of β- hematin formation, and antiplasmodial activity

Comparison of 19 aminoquinolines supports the hypothesis that chloroquine and related antimalarials act by complexing ferriprotoporphyrin IX (Fe(III)PPIX), inhibiting its conversion to β-hematin (hemozoin) and hence its detoxification. The study suggests that a basic amino side chain is also essential for antiplasmodial activity. 2- And 4-aminoquinolines are unique in their strong affinity for Fe(III)PPIX, and attachment of side chains to the amino group has relatively little influence on the strength of complex formation. Association with Fe(III)PPIX is necessary, but not sufficient, for inhibiting β-hematin formation. Presence of a 7-chloro group in the 4-aminoquinoline ring is a requirement for β-hematin inhibitory activity, and this is also unaffected by side chains attached to the amino group. In turn, β-hematin inhibitory activity is necessary, but not sufficient, for antiplasmodial activity as the presence of an aminoalkyl group attached to the 4-amino-7-chloroquinoline template is essential for strong activity. We thus propose that the 4-aminoquinoline nucleus of chloroquine and related antimalarials is responsible for complexing Fe(III)PPIX, the 7-chloro group is required for inhibition of β-hematin formation, and the basic amino side chain is required for drug accumulation in the food vacuole of the parasite.

Combining 1,3-Ditriazolylbenzene and Quinoline to Discover a New G-Quadruplex-Interactive Small Molecule Active against Cancer Stem-Like Cells

Quadruplex nucleic acids are promising targets for cancer therapy. In this study we used a fragment-based approach to create new flexible G-quadruplex (G4) DNA-interactive small molecules with good calculated oral drug-like properties, based on quinoline

SUBSTITUTED QUINAZOLINE DERIVATIVES AS DNA METHYLTRANSFERASE INHIBITORS

The present invention relates to compounds of the following formula (I) and pharmaceutically acceptable salts and solvates thereof, their methods of preparation, their use as a drug, notably in the treatment of cancer, and pharmaceutical compositions containing such compounds.