1744-91-8

Usage

Uses

Used in Organic Semiconductor Materials:
9-chloro-3-nitroacridine is used as a building block for the development of organic semiconductor materials, leveraging its unique structure and properties to enhance the performance of these materials in electronic devices.
Used in Organic Light-Emitting Diodes (OLEDs):
In the field of OLEDs, 9-chloro-3-nitroacridine is utilized as a component to improve the efficiency and stability of light-emitting devices, contributing to advancements in display and lighting technologies.
Used in Solar Cells:
9-chloro-3-nitroacridine is employed in the fabrication of solar cells, where its properties can potentially increase the efficiency of energy conversion and contribute to the development of more sustainable energy solutions.
Used in Synthesis of Heterocyclic Compounds:
As a valuable intermediate, 9-chloro-3-nitroacridine is used in the synthesis of various heterocyclic compounds, which are essential in pharmaceutical, chemical, and material science applications.
Used in Pharmaceutical Agents:
9-chloro-3-nitroacridine is utilized in the development of pharmaceutical agents, where its unique chemical structure can be harnessed to create new drugs with potential therapeutic benefits.

InChI:InChI=1/C13H7ClN2O2/c14-13-9-3-1-2-4-11(9)15-12-7-8(16(17)18)5-6-10(12)13/h1-7H

Upstream product

• 49551-01-1 2-anilino-4-nitrobenzoic acid 
• 10025-87-3 trichlorophosphate 
• 27693-70-5 N-(3-nitrophenyl)anthranilic acid 
• 56739-54-9 N-(3-nitrophenyl)anthranilic acid methyl ester 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 88-67-5 2-Iodobenzoic acid 
• 100959-22-6 methyl 2-bromo-4-nitrobenzoate 
• 32082-98-7 methyl 4-nitro-2-(phenylamino)benzoate 
• 62-53-3 aniline 
• 99-60-5 2-chloro-4-nitrobenzoic acid 

Downstream Products

• 32841-11-5 6-Nitro-9-phenoxyacridin 
• 14251-96-8 3-Nitro-acridin 
• 1744-92-9 3-nitro-9,10-dihydroacridin-9-one 
• 14252-03-0 3-nitro-9-aminoacridine 
• 64894-92-4 4-(3-nitroacridin-9-ylamino)benzoic acid 
• 6237-24-7 N,N-dimethyl-N'-(3-nitro-9-acridinyl)-1,3-propanediamine 

Relevant academic research and scientific papers

3-Nitroacridine derivatives arrest cell cycle at G0/G1 phase and induce apoptosis in human breast cancer cells may act as DNA-target anticancer agents

DNA is considered to be one of the most promising targets for anticancer agents. Acridine analogues have anticancer activity based on DNA binding and topoisomerases inhibition. However, due to the side effects, resistance and low bioavailability, a few have entered into clinical usage and the mechanisms of action are not fully understood. Novel acridine derivatives are needed for effective cancer therapy. A series of novel 3-nitroacridine-based derivatives were synthesized, their DNA binding and anticancer activities were evaluated. The chemical modifications at position 9 of the 3-nitroacridine were crucial for DNA affinity, thus optimizing anticancer activity. UV–Vis and circular dichroism (CD) spectroscopy indicated interaction of compounds with DNA, and the binding modes were intercalation and groove binding. MTT assay and clonogenic assay showed that compounds 1, 2 and 3 had obvious cell growth inhibition effect. They induced cell apoptosis in human breast cancer cells in a dose-dependent manner, and exhibited anticancer effect via DNA damage as well as cell cycle arrest at G0/G1 phage. Using confocal fluorescent microscope, the apoptotic features were observed. The results suggested that compounds 1–3 with high DNA binding affinity and good inhibitory effect of cancer cell proliferation can be developed as prime candidates for further chemical optimization.

NOVEL NUCLEIC ACID MODIFIERS

The present inventions generally relate to site-specific delivery of nucleic acid modifiers and includes novel DNA-binding proteins and effectors that can be rapidly programmed to make site-specific DNA modifications. The present inventions also provide a synthetic all-in-one genome editor (SAGE) systems comprising designer DNA sequence readers and a set of small molecules that induce double-strand breaks, enhance cellular permeability, inhibit NHEJ and activate HDR, as well as methods of using and delivering such systems.

Identification of novel 3-nitroacridines as autophagy inducers in gastric cancer cells

Dysregulated autophagy is involved in various human disorders including cancer. An autophagy-associated cell death pathway can be seen as a back-up cell death mechanism in cancer cells that are deficient in the apoptosis pathway. Therefore, many attempts have been made to induce autophagy for anticancer therapy. Anti-apoptotic Bcl-2 family proteins Bcl-2 and Bcl-xL can inhibit autophagy via binding to the BH3-only protein Beclin 1, an essential autophagy stimulator. In a previous study, we discovered several small molecule Beclin 1 mimetics as autophagy inducers through high-throughput screening and structural optimization, in which 3-nitroacridine warrants further exploration. Here, a series of novel 3-nitroacridine derivatives were designed, synthesized, and their pharmaceutical activities and mechanism of action were investigated against gastric cancer cell lines. As a result, compounds 3, 4, and 9 displayed potent cytotoxicity and induced autophagy in MGC-803 and SGC-7901 gastric cancer cells. Besides, compounds 3 and 9 also inhibited the migration of SGC-7901 cells. The development of 3-nitroacridine analogues as autophagy inducers is not only likely to be a potential strategy for cancer therapy, but it will also facilitate a better understanding of the complicated roles of autophagy in normal physiology and pathophysiology.

Design, synthesis and evaluation of acridine derivatives as multi-target Src and MEK kinase inhibitors for anti-tumor treatment

Clinical studies have shown enhanced anticancer effects of combined inhibition of Src and MEK kinases. Development of multi-target drugs against Src and MEK is of potential therapeutic advantage against cancers. As a follow-up of our previous studies, and by using molecular docking method, we designed and synthesized a new series of 9-anilinoacridines containing phenyl-urea moieties as potential novel dual Src and MEK inhibitors. The anti-proliferative assays against K562 and HepG-2 tumor cells showed that most of the derivatives displayed good cytotoxicity in vitro. In particular, kinase inhibition assays showed that compound 8m inhibited Src (59.67%) and MEK (43.23%) at 10 μM, and displayed moderate inhibitory activity against ERK and AKT, the downstream effectors of both Src and MEK. Moreover, compound 8m was found to induce K562 cells apoptosis. Structure-activity relationships of these derivatives were analyzed. Our study suggested that acridine scaffold, particularly compound 8m, is of potential interest for developing novel multi-target Src and MEK kinase inhibitors.

NOVEL FLUORESCENT DYES AND USES THEREOF

The present invention relates to fluorescent dyes based on acridine derivatives and use of such dyes, for example, in biochemical and/or cell based assays. A preferred feature of some of the dyes described is their long fluorescence lifetimes and their us