13161-87-0

Basic information

• Product Name: 6-chloro-2-methoxyacridin-9(10H)-one
• CAS NO: 13161-87-0
• Molecular Formula: C₁₄H₁₀ClNO₂
• Molecular Weight: 259.6877
• Mol File: 13161-87-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 439.9°C at 760 mmHg
• Flash Point: 219.8°C
• Density: 1.334g/cm³
• Vapor Pressure: 6.17E-08mmHg at 25°C
• Refractive Index: 1.625
• CAS DataBase Reference: 6-chloro-2-methoxyacridin-9(10H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-chloro-2-methoxyacridin-9(10H)-one(13161-87-0)
• EPA Substance Registry System: 6-chloro-2-methoxyacridin-9(10H)-one(13161-87-0)

Safety Data

• Hazardous Substances Data: 13161-87-0(Hazardous Substances Data)

Usage

Derivative of

Acridine

Primary Use

Medicinal chemistry and pharmaceutical research

Potential Properties

Anticancer: Exhibits potential anticancer properties
Antibacterial: Investigated for antibacterial activities
Antifungal: Investigated for antifungal activities

Contributing Groups

Chlorine Atom: Presence of a chlorine atom
Methoxy Group: Presence of a methoxy group

Therapeutic Applications

Potential use in cancer treatment and combating infectious diseases.

Upstream product

• 104-94-9 4-methoxy-aniline 
• 50-84-0 2,4 dichlorobenzoic acid 
• 69-05-6 quinacrine dihydrochloride 
• 7478-26-4 6-chloro-2-methoxy-9-phenoxyacridine 
• 80-40-0 ethyl ester of p-toluenesulfonic acid 
• 57623-77-5 2-p-anisidino-4-chloro-benzoyl chloride 
• 91-38-3 4-chloro-2-(4-methoxyphenylamino)benzoic acid 
• 86-38-4 6,9-dichloro-2-methoxyacridine 

Downstream Products

• 906434-29-5 6-Chloro-2-methoxy-9-(4-nitro-phenylsulfanyl)-acridine 
• 86-38-4 6,9-dichloro-2-methoxyacridine 

Relevant articles and documents

Reactivity of 9-aminoacridine drug quinacrine with glutathione limits its antiprion activity

Quinacrine—the drug based on 9-aminoacridine—failed in clinical trials for prion diseases, whereas it was active in in vitro studies. We hypothesize that aromatic nucleophilic substitution at C9 could be contributing factor responsible for this failure be

Discovery and Structural Optimization of Acridones as Broad-Spectrum Antimalarials

Malaria remains one of the deadliest diseases in the world today. Novel chemoprophylactic and chemotherapeutic antimalarials are needed to support the renewed eradication agenda. We have discovered a novel antimalarial acridone chemotype with dual-stage activity against both liver-stage and blood-stage malaria. Several lead compounds generated from structural optimization of a large library of novel acridones exhibit efficacy in the following systems: (1) picomolar inhibition of in vitro Plasmodium falciparum blood-stage growth against multidrug-resistant parasites; (2) curative efficacy after oral administration in an erythrocytic Plasmodium yoelii murine malaria model; (3) prevention of in vitro Plasmodium berghei sporozoite-induced development in human hepatocytes; and (4) protection of in vivo P. berghei sporozoite-induced infection in mice. This study offers the first account of liver-stage antimalarial activity in an acridone chemotype. Details of the design, chemistry, structure-activity relationships, safety, metabolic/pharmacokinetic studies, and mechanistic investigation are presented herein.

Structure-trypanodical activity relationships

A set of 9-thioalkylacridinones, has been prepared and investigated' in vitro' against T. cruzi. Structure-antiparasitic activity relationships are detailed with a view to identify the major structural parameters for the activity under consideration.