4-Aminoquinoline

Base Information

• Chemical Name: 4-Aminoquinoline
• CAS No.: 578-68-7
• Molecular Formula: C9H8N2
• Molecular Weight: 144.176
• Hs Code.: 29334900
• European Community (EC) Number: 640-116-4
• UNII: GTE5P5L97N
• DSSTox Substance ID: DTXSID70206491
• Nikkaji Number: J1.803.795E,J79.669G
• Wikipedia: 4-Aminoquinoline
• Wikidata: Q4637104
• ChEMBL ID: CHEMBL58146
• Mol file: 578-68-7.mol

Synonyms:4-aminoquinoline

Chemical Property of 4-Aminoquinoline

Chemical Property:

• Appearance/Colour: Yellow Solid
• Vapor Pressure: 0.000147mmHg at 25°C
• Melting Point: 125 - 126oC
• Refractive Index: 1.7080 (estimate)
• Boiling Point: 332.337 °C at 760 mmHg
• PKA: 9.17(at 20℃)
• Flash Point: 181.19 °C
• PSA: 38.91000
• Density: 1.211 g/cm³
• LogP: 2.39820
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 144.068748264
• Heavy Atom Count: 11
• Complexity: 136

Purity/Quality:

99% ^*data from raw suppliers

4-Quinolinamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-36-22-41
• Safety Statements: 26-36/37/39-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CC=N2)N
• General Description: 4-Aminoquinoline derivatives, such as those incorporating 2-aminopyrimidine moieties, demonstrate potent anti-plasmodial activity against both chloroquine-sensitive and resistant strains of *Plasmodium falciparum*. These compounds exhibit dual mechanisms of action, including heme binding to inhibit β-hematin formation and interaction with AT-rich DNA, alongside potential inhibition of *Pf* DHFR, a key enzyme in parasite DNA synthesis. Structural modifications, such as spacer length and nitro group substitutions, significantly influence their efficacy, positioning them as promising candidates for novel anti-malarial therapies.

Technology Process of 4-Aminoquinoline

There total 13 articles about 4-Aminoquinoline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

→ 4-aminoquinoline (578-68-7) + 3-bromo-quinolin-4-ylamine (36825-36-2)

Guidance literature:

Reference yield:

quinoline (91-22-5) → 2-aminoquinoline (580-22-3) + 4-aminoquinoline (578-68-7)

Guidance literature:

With sodium amide; toluene; at 150 ℃;

Reference yield:

quinoline (91-22-5) + sodium amide → 2-aminoquinoline (580-22-3) + 4-aminoquinoline (578-68-7) + 2,3'-biquinoline (612-81-7)

Guidance literature:

at 80 - 150 ℃;

upstream raw materials:

quinoline

3-azidoquinoline

4-quinolyl azide

quinoline-4-carboxamide

Downstream raw materials:

4-Acetamino-chinolin

sulfanilic acid-[4]quinolylamide

Echinopsidin

1-methyl-1H-quinolin-4-one-imine; hydriodide

Refernces

2-Aminopyrimidine based 4-aminoquinoline anti-plasmodial agents. Synthesis, biological activity, structure-activity relationship and mode of action studies

10.1016/j.ejmech.2012.03.007

The study investigates the synthesis and biological evaluation of a series of 2-aminopyrimidine based 4-aminoquinoline compounds designed to combat malaria, particularly against drug-resistant strains of Plasmodium falciparum. The researchers synthesized these compounds using a protocol that involved the transformation of 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) into 2-aminopyrimidines linked to 4-aminoquinolines. The compounds were evaluated for their in vitro anti-plasmodial activity against both chloroquine-sensitive (CQS) and chloroquine-resistant (CQR) strains of P. falciparum. The study found that some of these compounds, notably 10r, exhibited potent anti-plasmodial activity, with IC50 values significantly lower than that of chloroquine (CQ), especially against the CQR strain. The structure-activity relationship (SAR) analysis revealed that the length and nature of the spacer connecting the pharmacophores, as well as the presence of substituents like nitro groups, influenced the compounds' potency. The mode of action studies indicated that these compounds bind to heme and m-oxo-heme, inhibiting the formation of b-hematin, similar to CQ. Additionally, the compounds showed binding affinity to DNA, particularly AT-rich DNA, suggesting another potential mechanism of action. Molecular docking analysis with Pf DHFR further supported the compounds' ability to interact with this enzyme, which is crucial for the parasite's DNA biosynthesis. Overall, the study highlights the potential of these hybrid compounds as new anti-malarial agents with activity against drug-resistant strains.