16492-13-0

Usage

Uses

Used in Dye and Pigment Production:
9-Chloro-2-methoxyacridine is used as a dye and pigment in various industries, such as textiles and plastics, due to its vibrant yellow color and fluorescent properties.
Used in Biochemistry:
As a fluorescent stain, 9-chloro-2-methoxyacridine is employed in biochemistry for staining and visualizing specific biological structures, such as proteins and nucleic acids, under ultraviolet light.
Used as a pH Indicator:
9-Chloro-2-methoxyacridine is utilized as a pH indicator in various applications, including environmental monitoring and chemical analysis, to detect changes in pH levels.

InChI:InChI=1/C14H10ClNO/c1-17-9-6-7-13-11(8-9)14(15)10-4-2-3-5-12(10)16-13/h2-8H,1H3

Upstream product

• 13501-67-2 N-(p-methoxyphenyl)anthranilic acid 
• 65-85-0 benzoic acid 
• 104-94-9 4-methoxy-aniline 
• 118-91-2 ortho-chlorobenzoic acid 
• 89224-95-3 5-methoxy-2-(phenylamino)benzoic acid 
• 118-92-3 anthranilic acid 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 88-65-3 2-bromobenzoic-acid 
• 90-04-0 2-methoxy-phenylamine 

Downstream Products

• 90171-91-8 [4-(2-Methoxy-acridin-9-ylamino)-phenyl]-phosphoramidic acid dimethyl ester; hydrochloride 
• 3295-60-1 2-methoxyacridine 
• 102941-08-2 N-[4-(2-Methoxy-acridin-9-ylamino)-3-methylamino-phenyl]-methanesulfonamide; hydrochloride 
• 1352304-42-7 2-methoxy-9-(2-aminoanilino)acridine hydrochloride 
• 1610849-83-6 2-methoxy-9-(2-amino-4,5-dimethylanilino)acridine hydrochloride 
• 1563126-83-9 1-(2-methoxy-4-(2-methoxyacridin-9-ylamino) phenylamino)-3-morpholinopropan-2-ol hydrochloride 
• 1563535-78-3 1-(2-methoxy-4-(2-methoxyacridin-9-ylamino) phenylamino)-3-morpholinopropan-2-ol 
• 1404206-12-7 1-(diethylamino)-3-(2-methoxy-4-(2-methoxyacridin-9-ylamino)phenylamino)propan-2-ol 
• 1563535-81-8 1-(2-(dimethylamino)ethylamino)-3-(2-methoxy-4-(2-methoxyacridin-9-ylamino)phenyl-amino)propan-2-ol 
• 1563126-84-0 1-(2-methoxy-4-(2-methoxyacridin-9-ylamino) phenylamino)-3-(piperazin-1-yl)propan-2-ol hydrochloride 
• 1563535-79-4 1-(2-methoxy-4-(2-methoxyacridin-9-ylamino) phenylamino)-3-(piperazin-1-yl)propan-2-ol 
• 1563127-03-6 1-(2-methoxy-4-(2-methoxyacridin-9-ylamino) phenylamino)-3-(piperidin-1-yl)propan-2-ol hydrochloride 
• 1404206-16-1 1-(2-methoxy-4-(2-methoxyacridin-9-ylamino) phenylamino)-3-(piperidin-1-yl)propan-2-ol 
• 38915-78-5 2-[2-(2-methoxy-acridin-9-ylamino)-ethylamino]-ethanol; dihydrochloride 

Relevant academic research and scientific papers

N-o-substituted phenyl benzamide-4-methylamino acridine compound as well as preparation method and application thereof

The invention discloses an N-o-substituted phenyl benzamide-4-methylamino acridine compound as well as a preparation method and application thereof. The compound is characterized in that the compoundis a compound with a structural formula shown as a formula I or pharmaceutically acceptable salt, ester or solvate thereof, wherein R1 is H, OCH3, OCH2CH3, F, Cl, Br, CF3, NO2 or straight-chain alkylwith a carbon atom number of 1-5; R2 is H, OCH3, OCH2CH3, F, Cl, Br, CF3, NO2 or straight-chain alkyl with a carbon atom number of 1 to 5; R3 is NH2, NHCH3, NHCH2CH3, OH, COOH, and SH, and R4 is H, OCH3 or linear alkyl with 1-5 carbon atoms and the like. The compound has the advantages that the compound can effectively inhibit DNA topoisomerase I, and proliferation of I-type HDAC and/or eukaryotictumor cells, and prevents and/or treats tumors.

Synthesis and Antibacterial Activity of New N9-Substituted Acridine-9-amines

A method for the synthesis of N9-substituted acridine-9-amines by reacting 9-chloroacridines with 2-(2-methyl-5- nitro-1H-imidazol-1-yl)ethanamine was developed. The synthesized compounds showed high antibacterial ability against B. subtilis bacteria compared with rivanol and metronidazole.

Design, synthesis and biological research of novel N-phenylbenzamide-4-methylamine acridine derivatives as potential topoisomerase I/II and apoptosis-inducing agents

A series of novel N-phenylbenzamide-4-methylamine acridine derivatives were designed and synthesized based initially on the structure of amsacrine (m-AMSA). Molecular docking suggested that the representative compound 9a had affinity for binding DNA topoisomerase (Topo) II, which was comparable with that of m-AMSA, and furthermore that 9a could have preferential interactions with Topo I. After synthesis of 9a and analogues 9b-9f, these were all tested in vitro and the synthesized compounds displayed potent antiproliferative activity against three different cancer cell lines (K562, CCRF-CEM and U937). Among them, compounds 9b, 9c and 9d exhibiting the highest activity with IC50 value ranging from 0.82 to 0.91 μM against CCRF-CEM cells. In addition, 9b and 9d also showed high antiproliferative activity against U937 cells, with IC50 values of 0.33 and 0.23 μM, respectively. The pharmacological mechanistic studies of these compounds were evaluated by Topo I/II inhibition, western blot assay and cell apoptosis detection. In summary, 9b effectively inhibited the activity of Topo I/II and induced DNA damage in CCRF-CEM cells and, moreover, significantly induced cell apoptosis in a concentration-dependent manner. These observations provide new information and guidance for the structural optimization of more novel acridine derivatives.

4-methylaminoacridine-N-phenylbenzamide compound and preparation method and application thereof

The invention discloses a 4-aminomethylacridine-N-phenylbenzamide compound and a preparation method and application thereof. The compound is characterized in that the compound is a compound with a structural formula shown in the formula I or a pharmaceutically acceptable salt, ester or solvate of the compound with the structural formula shown in the formula I, wherein R1 is H, OCH3, OCH2CH3, Cl, Br, CF3, NO2 or a linear alkyl group with 1 to 5 carbon atoms, R2 is H, OCH3, OCH2CH3, Cl, Br, CF3, NO2 or a linear alkyl group with 1 to 5 carbon atoms, R3 is H, OCH3, OCH2CH3, Cl, Br, CF3, NO2 or a linear alkyl group with 1 to 5 carbon atoms, and n = 1, 2, 3 or 4, the advantages are that the compound can effectively inhibit the activity of DNA topoisomerases, inhibits the proliferation of eukaryotic tumor cells, and prevents and / or treats tumors.

Synthesis and biological study of acridine-based imidazolium salts

A new series of acridine based imidazolium salts was synthesized and evaluated for in vitro cytotoxicity against human cancer cell lines by an MTT assay. The synthesis applied a coupling of imidazoles with 9-chloroacridines, which originated from an Ullmann condensation of a 2-chloro-benzoic acid with an aniline. The target compounds were obtained in high yields. The DPPH assay indicated considerable antioxidant activity for target compounds with simple and short alkyl chains on the imidazole, while increasing chain length and the introduction of an additional π-electron system in most cases reduced the activity. All compounds exhibited low biotoxicity against non-cancerous cell lines, whereas a few compounds showed promising anticancer activity. Unlike for the reference drugs Tamoxifen and Paclitaxel, the anticancer activity of acridine imidazolium ions is specific for only selected cancer types. Reasonable fluorescent behaviour of the products provide potential for visualization of the distribution of active drugs in tissue.

With anti-tumor activity of the acridine - 1, 3, 4 - oxdiazole compound and its preparation and use

The present invention discloses an acridine-1,3,4-oxadiazole compound having anti-tumor activity, a preparation method and uses thereof, wherein the structural formula is as the follow. According to the present invention, the acridine-1,3,4-oxadiazole com

Design, synthesis and biological evaluation of 4-amidobenzimidazole acridine derivatives as dual PARP and Topo inhibitors for cancer therapy

PARP-1 could repair the DNA damages induced by Topo inhibitors, therefore inhibiting Topo and PARP-1 simultaneously might be able to overcome resistance and improve outcomes. In this study a series of 4-amidobenzimidazole acridines were designed and synthesized as dual Topo and PARP-1 inhibitors. Compound 11l displayed good inhibitory activities against Topo and PARP-1, as well as significantly inhibited cancer cells proliferation. Further mechanistic evaluations indicated that 11l treatment in MCF-7 cells induced accumulated DNA double-strand breaks, prompted remarkable apoptosis, and caused prominent G0/G1 cell cycle arrest. Moreover, 11l greatly suppressed tumor growth in mice, and displayed favorable metabolic properties in liver microsomes. Our study suggested that single agents inhibiting Topo and PARP concurrently might be an alternative for cancer therapy and 11l represented a potential lead compound for development of antitumor agents.

Application of 2-methoxy-9-acridine benzamido thiourea in preparation of acetylcholinesterase inhibitor

The invention discloses an application of 2-methoxy-9-acridine benzamido thiourea in preparation of an acetylcholinesterase inhibitor. The constitutional formula (I) of 2-methoxy-9-acridine benzamido thiourea is as shown in the specification. The 2-methox

Application of 2-methoxy-9-acridine(4-methoxybenzamido) thiourea to preparing of acetylcholin esterase inhibitor

The invention discloses an application of 2-methoxy-9-acridine(4-methoxybenzamido) thiourea to preparing of an acetylcholin esterase inhibitor. The structural formula of the 2-methoxy-9-acridine(4-methoxybenzamido)thiourea is shown as the formula (I). The

Acridine -1, 2, 4-triazole-5-thione compounds and its preparation method and application

The invention discloses an acridine-1,2,4-triazole-5-thioketone compound and a preparation method and applications of the acridine-1,2,4-triazole-5-thioketone compound. The preparation method of the compound comprises the following steps: 1) by taking an