4-[(7-chloroquinolin-4-yl)amino]-2-(pyrrolidin-1-ylmethyl)phenol

• ChemBase ID: 160569
• Molecular Formular: C20H20ClN3O
• Molecular Mass: 353.8453
• Monoisotopic Mass: 353.12948996
• SMILES: c1c(cc2c(c1)c(ccn2)Nc1ccc(c(c1)CN1CCCC1)O)Cl
• Canonical SMILES: Clc1ccc2c(c1)nccc2Nc1ccc(c(c1)CN1CCCC1)O
• InChI: InChI=1S/C20H20ClN3O/c21-15-3-5-17-18(7-8-22-19(17)12-15)23-16-4-6-20(25)14(11-16)13-24-9-1-2-10-24/h3-8,11-12,25H,1-2,9-10,13H2,(H,22,23)
• InChIKey: YNWCUCSDUMVJKR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-[(7-chloroquinolin-4-yl)amino]-2-(pyrrolidin-1-ylmethyl)phenol
• IUPAC Traditional name: amopyroquine hydrochloride
• Synonyms: 4-[(7-Chloro-4-quinolinyl)amino]-2-(1-pyrrolidinylmethyl)phenol; 4-[(7-Chloro-4-quinolyl)amino]-α-1-pyrrolidinyl-o-cresol; Amopyroquin; PAM-780; Propoquin; Amopyroquine

Database IDs

• CAS Number: 550-81-2
• PubChem SID: 162254704
• PubChem CID: 25194

CALCULATED PROPERTIES

• Acid pKa: 9.115237
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.02387264
• LogD (pH = 7.4): 1.9668236
• Log P: 3.46893
• Molar Refractivity: 101.3349 cm^3
• Polarizability: 40.15447 Å^3
• Polar Surface Area: 48.39 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Pale Yellow Solid
• Melting Point: 197-200°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - A634215

Antimalarial agent. The compound showed antimalarial activity similar to that of Chloroquine.

REFERENCES

• Desjardins, R., et al.: Antimicrob. Agents Chemother., 16, 710 (1979)
• McKie, J., et al.: J. Med. Chem., 41, 1367 (1979)
• Gozalbes, R., et al.: J. Pharm. Pharmacol., 52, 111 (1979)
• Marrero-Ponce, Y., et al.: Bioorg. Med. Chem., 13, 1293 (1979)