(S)-3-(1-aminoethyl)-6-chloroquinolin-2(1H)-one hydrochloride
[CAS# 1887009-48-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Quinoline compound
• Name: (S)-3-(1-aminoethyl)-6-chloroquinolin-2(1H)-one hydrochloride
• Synonyms: 3-[(1S)-1-aminoethyl]-6-chloro-1H-quinolin-2-one;hydrochloride
• Molecular Formula: C₁₁H₁₂Cl₂N₂O
• Molecular Weight: 259.13
• CAS Registry Number: 1887009-48-4
• SMILES: C[C@@H](C1=CC2=C(C=CC(=C2)Cl)NC1=O)N.Cl

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501

Discovory and Applicatios

(S)-3-(1-aminoethyl)-6-chloroquinolin-2(1H)-one hydrochloride is a chemical compound that has attracted attention for its potential applications in medicinal chemistry, particularly as an antimalarial agent. The substance is characterized by the presence of a quinoline ring system, which is a common structural motif found in a variety of bioactive molecules, including many antimalarial drugs. The compound also features a chloro group at the 6-position of the quinoline ring, which enhances its bioactivity, as well as an aminoethyl group at the 3-position, contributing to its pharmacological activity.

The discovery of (S)-3-(1-aminoethyl)-6-chloroquinolin-2(1H)-one hydrochloride was part of a broader effort to develop novel quinoline-based compounds with improved potency against malaria. Malaria, caused by the Plasmodium parasite, remains a significant global health issue, and there is an ongoing need for new therapeutic options, particularly in the face of rising resistance to existing drugs like chloroquine and artemisinin. Researchers have focused on optimizing quinoline derivatives for better efficacy, reduced toxicity, and the ability to overcome drug resistance.

The synthesis of (S)-3-(1-aminoethyl)-6-chloroquinolin-2(1H)-one hydrochloride typically involves several steps, including the introduction of the chloro group at the 6-position and the aminoethyl group at the 3-position of the quinoline ring. The compound is usually synthesized using conventional organic chemistry techniques, such as nucleophilic substitution and condensation reactions. The stereochemistry of the aminoethyl group is crucial for the compound’s biological activity, and synthetic strategies are designed to ensure the correct configuration.

In terms of application, (S)-3-(1-aminoethyl)-6-chloroquinolin-2(1H)-one hydrochloride has shown promise as an antimalarial agent in preclinical studies. The compound exhibits potent activity against the Plasmodium parasite, and its unique structure allows it to interact with key enzymes and pathways involved in the parasite’s survival and replication. Given the increasing issue of drug resistance, quinoline-based compounds like this one are of particular interest for their potential to provide an effective alternative to current treatments.

The compound may also have broader applications in the treatment of other parasitic diseases or in the development of other bioactive molecules. As research into its pharmacokinetics and mechanism of action continues, (S)-3-(1-aminoethyl)-6-chloroquinolin-2(1H)-one hydrochloride could play an important role in the development of new therapeutic strategies for malaria and other infectious diseases.