7478-26-4

Usage

Uses

Used in Pharmaceutical Industry:
6-CHLORO-2-METHOXY-9-PHENOXYACRIDINE is used as a potential candidate for drug development due to its demonstrated biological activities. Its specific molecular structure and functional groups contribute to its potential as a new therapeutic agent for various medical conditions.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 6-CHLORO-2-METHOXY-9-PHENOXYACRIDINE is utilized for studying its anti-inflammatory and antimicrobial properties. This research can lead to the discovery of new drugs and therapeutic agents that harness these properties for treating different diseases.
Used in Agricultural Applications:
6-CHLORO-2-METHOXY-9-PHENOXYACRIDINE may also have uses in agriculture, where its chemical properties and potential reactivity could be employed for developing new products or improving existing ones, such as pesticides or herbicides.
Used in Industrial Applications:
Due to its unique chemical structure and properties, 6-CHLORO-2-METHOXY-9-PHENOXYACRIDINE could be utilized in various industrial applications, potentially contributing to the development of new materials or processes that benefit from its specific characteristics.

InChI:InChI=1/C20H14ClNO2/c1-23-15-8-10-18-17(12-15)20(24-14-5-3-2-4-6-14)16-9-7-13(21)11-19(16)22-18/h2-12H,1H3

Upstream product

• 86-38-4 6,9-dichloro-2-methoxyacridine 
• 108-95-2 phenol 

Downstream Products

• 58821-88-8 6-chloro-2-methoxy-10-methyl-10H-acridin-9-one 
• 13161-87-0 6-chloro-2-methoxyacridone 
• 101118-83-6 10-ethyl-6-chloro-2-methoxy-10H-acridin-9-one 
• 5291-50-9 6-chloro-2-methoxy-9-phenoxy-acridine-10-oxide 
• 79953-28-9 6-chloro-2-methoxy-9-(propylamino)acridine 
• 144886-27-1 (R)-2-(6-Chloro-2-methoxy-acridin-9-ylamino)-3-methyl-butan-1-ol 
• 144862-84-0 (S)-2-(6-Chloro-2-methoxy-acridin-9-ylamino)-3-phenyl-propan-1-ol 
• 144862-85-1 (R)-2-(6-Chloro-2-methoxy-acridin-9-ylamino)-3-phenyl-propan-1-ol 
• 144862-95-3 (S)-2-(6-Chloro-2-methoxy-acridin-9-ylamino)-3-phenyl-propionic acid methyl ester; hydrochloride 
• 144862-94-2 (R)-2-(6-Chloro-2-methoxy-acridin-9-ylamino)-3-phenyl-propionic acid methyl ester; hydrochloride 
• 144862-93-1 (S)-2-(6-Chloro-2-methoxy-acridin-9-ylamino)-3-(4-hydroxy-phenyl)-propionic acid methyl ester; hydrochloride 
• 103083-41-6 6-chloro-2-methoxy-9-<(5-(guan-9-yl)pentyl)amino>acridine 
• 103061-92-3 6-chloro-2-methoxy-9-<(5-(aden-9-yl)pentyl)amino>acridine 
• 84889-92-9 6-chloro-2-methoxy-9-<(5-(thym-1-yl)pentyl)amino>acridine 

Relevant academic research and scientific papers

Coupling of a competitive and an irreversible ligand generates mixed type inhibitors of Trypanosoma cruzi trypanothione reductase

9-Aminoacridines and (terpyridine)platinum(II) complexes are competitive and irreversible inhibitors, respectively, of trypanothione reductase from Trypanosoma cruzi, the causative agent of Chagas' disease. Four chimeric compounds in which 2-methoxy-6-chl

Functionalized acridin-9-yl phenylamines protected neuronal HT22 cells from glutamate-induced cell death by reducing intracellular levels of free radical species

The in vitro neuronal cell death model based on the HT22 mouse hippocampal cell model is a convenient means of identifying compounds that protect against oxidative glutamate toxicity which plays a role in the development of certain neurodegenerative diseases. Functionalized acridin-9-yl-phenylamines were found to protect HT22 cells from glutamate challenge at submicromolar concentrations. The Aryl1-NHAryl2 scaffold that is embedded in these compounds was the minimal pharmacophore for activity. Mechanistically, protection against the endogenous oxidative stress generated by glutamate did not involve up-regulation of glutathione levels but attenuation of the late stage increases in mitochondrial ROS and intracellular calcium levels. The NH residue in the pharmacophore played a crucial role in this regard as seen from the loss of neuroprotection when it was structurally modified or replaced. That the same NH was essential for radical scavenging in cell-free and cell-based systems pointed to an antioxidant basis for the neuroprotective activities of these compounds.

Synthesis of monomeric and dimeric acridine compounds as potential therapeutics in Alzheimer and prion diseases

Starting from substituted 9-chloroacridines, a series of quinacrine and spacered dimeric acridine compounds was prepared. Their ability to interrupt the protein association of prion- and Alzheimer-specific proteins and Ab peptides was explored using a fast screening system based on FACS analysis. The bis-acridines displayed a higher activity than the corresponding monomers. Among these derivatives, best results were obtained with the 2,4-dimethoxy-6-nitro compound 7h for Aβ-peptides and the 2-methoxy-6-nitro compound 7f for PrP.

Parallel synthesis of 9-aminoacridines and their evaluation against chloroquine-resistant Plasmodium falciparum

A parallel synthetic strategy to the 9-aminoacridine scaffold of the classical anti-malarial drug quinacrine (2) is presented. The method features a new route to 9-chloroacridines that utilizes triflates of salicylic acid derivatives, which are commercially available in a variety of substitution patterns. The route allows ready variation of the two diversity elements present in this class of molecules: the tricyclic aromatic heterocyclic core, and the disubstituted diamine sidechain. In this study, a library of 175 compounds was designed, although only 93 of the final products had purities acceptable for screening. Impurity was generally due to incomplete removal of 9-acridones (18), a degradation product of the 9-chloroacridine synthetic intermediates. The library was screened against two strains of Plasmodium falciparum, including a model of the drug-resistant parasite, and six novel compounds were found to have IC50 values in the low nanomolar range.

Synthesis and antiproliferative activity of some variously substituted acridine and azacridine derivatives

A group of 9-substituted acridine and azacridine derivatives (m-AMSA analogues) were synthesised following classical procedures as potential antitumour agents with inhibitory effects on DNA topoisomerase II. Some were found to have noticeable cytotoxicity against human HL-60 and HeLa cells grown in culture. Their non-covalent interactions with calf thymus DNA have been studied using fluorescence quenching. We evaluated DNA damage produced by the tested compounds by means of DNA filter elution and protein precipitation techniques. Catalytic studies carried out with purified topoisomerase confirmed these agents as antitopoisomerase inhibitors. Chemotherapy of solid-tumour-bearing mice with tested compounds allowed an aza-analogue (compound IIIb), as potent as m-AMSA but less toxic towards the host, to be recognised. (C) 2000 Editions scientifiques et medicales Elsevier SAS.

Synthesis of two acridine conjugates of the bis(phenanthroline) ligand 'Clip-Phen' and evaluation of the nuclease activity of the corresponding copper complexes

The synthesis of three novel derivatives [N-acetyl-Clip-Phen (1), Clip- Phen-hexylaminoacridine (4) and Clip-Phen-hexylchloromethoxyaminoacridine (5)] of the bis(phenanthroline) ligand 'Clip-Phen', are described. Complexation of these ligands with copper(II) afforded the 1:1 complexes as hexafluorophosphate salts. The relaxation of φX 174 DNA was used as a DNA cleavage assay, with the following results. [Cu(1)]2+ was found to show a diminished activity relative to the parent complex [Cu(Clip-Phen)]2+. However, the acridine-containing complexes [Cu(4)H]3+ and [Cu(5)H]3+ exhibited significantly enhanced cleavage efficiencies, which has been attributed to increased affinity of the complexes for DNA. UV/Vis-spectral data of the complexes in the presence of calf-thymus DNA was consistent with an intercalative mode of binding.