22272-22-6

Basic information

• Product Name: 2-Chloro-3-((2-Methoxyethyl)aMino)naphthalene-1,4-dione
• Synonyms: 2-chloro-3-[(2-methoxyethyl)amino]-1,4-Naphthalenedione;2-Chloro-3-(2-methoxyethylamino);2-Chloro-3-((2-Methoxyethyl)aMino)naphthalene-1,4-dione;2-chloro-3-[(2-Methoxyethyl)aMino]-1,4-dihydronaphthalene-1,4-dione;2-Chloro-3-[(2-methoxyethyl)amino]-1,4-naphthoquinone;NSC 91098
• CAS NO: 22272-22-6
• Molecular Formula: C₁₃H₁₂ClNO₃
• Molecular Weight: 265.69228
• Mol File: 22272-22-6.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 373.4°Cat760mmHg
• Flash Point: 179.6°C
• Appearance: /
• Density: 1.33
• Vapor Pressure: 8.99E-06mmHg at 25°C
• Refractive Index: 1.59
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: 2-Chloro-3-((2-Methoxyethyl)aMino)naphthalene-1,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-3-((2-Methoxyethyl)aMino)naphthalene-1,4-dione(22272-22-6)
• EPA Substance Registry System: 2-Chloro-3-((2-Methoxyethyl)aMino)naphthalene-1,4-dione(22272-22-6)

Safety Data

• Hazardous Substances Data: 22272-22-6(Hazardous Substances Data)

Usage

Uses

2-Chloro-3-(2-methoxyethylamino)naphthalene-1,4-dione

InChI:InChI=1/C13H12ClNO3/c1-18-7-6-15-11-10(14)12(16)8-4-2-3-5-9(8)13(11)17/h2-5,15H,6-7H2,1H3

Upstream product

• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 109-85-3 2-methoxyethylamine 

Downstream Products

• 355404-34-1 N-(3-benzylamino-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-N-(2-methoxyethyl)acetamide 

Relevant articles and documents

Synthesis and biological evaluation of novel 2-arylvinyl-substituted naphtho[2,3-d]imidazolium halide derivatives as potent antitumor agents

Two series of novel 2-arylvinyl-naphtho[2,3-d]imidazol-3-ium iodide derivatives and 2-arylvinyl-naphtho[2,3-d]imidazol-3-ium bromide derivatives were designed and synthesized by the structural combination of YM155 with stilbenoids. All compounds were tested for anti-proliferative activity against PC-3, A375 and HeLa human cancer cell lines. Two of the compounds were selected for further investigation: 12b, which showed potent cytotoxicity against the three tested cell lines with IC50 values in the range of 0.06–0.21 μM, and 7l, which displayed excellent selectivity for PC-3 cells with an IC50 of only 22 nM. Western blot analysis results indicated that both 12b and 7l suppress the expression of Bcl-2 and Survivin proteins, which helps induce apoptosis. As determined by the percent of Annexin V-FITC-positive apoptotic cells, 12b was not only significantly more effective than 7l at a concentration of 100 nM in PC-3 cells but also induced apoptosis in a dose-dependent manner with more potency than 7l at a concentration of 1000 nM in A375 cells. Therefore, compound 12b was chosen for further in-depth studies investigating the mechanism of apoptosis. The results showed that it could activate caspase-3, hydrolyze PARP, and even inactivate ERK. Moreover, 12b arrested A375 cells at S phase in a time-dependent and dose-dependent manner, while having a visible effect on microtubule dynamics. In addition, (E)-2-(2-(1H-indol-3-yl)vinyl)-1-benzyl-3-(2-methoxyethyl)-4,9-dioxo-4,9-dihydro-1H-naphtho[2,3-d]imidazol-3-ium bromide (12b) exhibited significant antitumor activity when evaluated in a subcutaneous solid tumor model. Our study reveals that 2-arylvinyl-substituted naphtho[2,3-d]imidazolium scaffolding is a promising new entity for the development of multi-target anticancer drugs.

Composition for Distructing Microalgae

The present invention relates to a composition for destroying microalgae, more specifically, to a composition for destroying microalgae containing naphthoquinone compounds having a specific exchange group. The composition for destroying microalgae, according to the present invention, can prevent green tide and red tide by being processed in areas such as cultivation facilities for microalgae, areas in which the green tide or the red tide occur, or areas expected to occur the green tide or the red tide.

Antiproliferative, DNA intercalation and redox cycling activities of dioxonaphtho[2,3-d]imidazolium analogs of YM155: A structure-activity relationship study

The anticancer agent YM155 is widely investigated as a specific survivin suppressant. More recently, YM155 was found to induce DNA damage and this has raised doubts as to whether survivin is its primary target. In an effort to assess the contribution of DNA damage to the anticancer activity of YM155, several analogs were prepared and evaluated for antiproliferative activity on malignant cells, participation in DNA intercalation and free radical generation by redox cycling. The intact positively charged scaffold was found to be essential for antiproliferative activity and intercalation but was less critical for redox cycling where the minimal requirement was a pared down bicyclic quinone. Side chain requirements at the N1 and N3 positions of the scaffold were more alike for redox cycling and intercalation than antiproliferative activity, underscoring yet again, the limited structural overlaps for these activities. Furthermore, antiproliferative activities were poorly correlated to DNA intercalation and redox cycling. Potent antiproliferative activity (IC50 9-23 nM), exceeding that of YM155, was found for a minimally substituted methyl analog AB7. Like YM155 and other dioxonaphthoimidazoliums, AB7 was a modest DNA intercalator but with weak redox cycling activity. Thus, the capacity of this scaffold to inflict direct DNA damage leading to cell death may not be significant and YM155 should not be routinely classified as a DNA damaging agent.