66266-36-2

Usage

InChI:InChI=1/C12H6N2O4/c15-11-8-3-1-2-6-4-7(14(17)18)5-9(10(6)8)12(16)13-11/h1-5H,(H,13,15,16)

Upstream product

• 81-83-4 1,8-Naphthalimide 
• 81-84-5 1,8-Naphthalic anhydride 
• 3027-38-1 3-nitro-1,8-naphthalic anhydride 

Downstream Products

• 26491-50-9 5-nitro-2-phenyl-1H-benzo[de]isoquinoline-1,3(2H)-dione 

Relevant academic research and scientific papers

Novel chiral naphthalimide-cycloalkanediamine conjugates: Design, synthesis and antitumor activity

A novel series of enantiopure naphthalimide-cycloalkanediamine conjugates were designed, synthetized and evaluated for in vitro cytotoxicity against human colon adenocarcinoma (LoVo), human lung adenocarcinoma (A549), human cervical carcinoma (Hela) and human promyelocytic leukemia cell lines (HL-60). The cytotoxicity of the compounds was highly dependent on size and relative stereochemistry of the cycloalkyl ring as well as length of the spacer. By contrast, any kind of enantioselection was observed for each pair of enantiomers. Flow cytometric analysis indicated that compounds 22 and 23 could effectively induce G2/M arrest in the four previous cell lines despite a mild apoptotic effect.

Cleaner production of disperse florescent dyes in supercritical CO2 and their applications in dyeing polyester fabric

Supercritical carbon dioxide (scCO2) is commonly used as an excellent solvent in chemical reactions and dyeing fields because of its advantages. In this work, three coumarin and 1,8-naphthalimide fluorescent dyes (DAMC, NP-NH, and NP-dimethyl) were successfully constructed on the basis of the Au/titanium dioxide (Au/TiO2) catalytic reduction of nitro in scCO2 instead of SnCl2/hydrochloric acid solution, and their structures were confirmed correctly by mass spectrometry (MS) and nuclear magnetic resonance (NMR). The cleaner synthesis and dyeing polyester fabrics of coumarin derivative (DAMC) in the presence or absence of N-methyl-pyrrolidone (NMP) were first studied by employing stepwise and synchronous methods. All results for DAMC indicated that the synchronous synthesis and dyeing method is more beneficial. Here, the synchronous synthesis and dyeing polyester fabrics of 1,8-naphthalimide derivatives (NP–NH and NP-dimethyl) in scCO2 were also investigated. Through the comprehensive analysis of color strength (K/S) value and fixation rate, the optimal temperatures and pressures of synthesis and dyeing for NP-NH and NP-dimethyl were obtained in the absence or presence of NMP. The dyed fabrics with NP-NH and NP-dimethyl exhibited yellow or yellowish-brown in daylight and bright fluorescent yellowish-green in ultraviolet light. All results showed that the clean production of fluorescent dyes (DAMC, NP-NH, and NP-dimethyl) can be realized by the hydrogenation of nitro with efficient Au/TiO2 catalyst in scCO2, meanwhile, the synchronous synthesis and dyeing method was proposed for the synthesized dyes. The realization of synchronous synthesis and dyeing fabrics for fluorescent dyes in scCO2 is an effective way to prevent environment pollution brought by the processes of synthesis and dyeing. Thus, the constructing and dyeing strategy of fluorescent dyes will be beneficial to the sustainable development of environment.

Amino-containing naphthalimide dye in supercritical CO2 Method for synthesizing and dyeing

The invention discloses an amino-containing naphthalimide dye in supercritical CO2 Synthesis and dyeing methods in supercritical carbon dioxide (CO)2 The nitro-substituted naphthalimide compound is a dye precursor and Au / TiO as a s

Preparation method of 1,8-disubstituted naphthalene series polycyclic aromatic hydrocarbon mononitration derivative

The invention provides a preparation method of 1,8-disubstituted naphthalene series polycyclic aromatic hydrocarbon mononitration derivative. The preparation method is characterized by comprising thefollowing steps: S1, dissolving 1,8-disubstituted naphthalene series polycyclic aromatic hydrocarbon and subgroup metal nitrate in an organic solvent, performing a nitration reaction under 10-60 DEG Cfor 4-10 h, and then monitoring by TLC (Thin layer chromatography) till a raw material point disappears to finish the reaction; S2, cooling a product obtained in S1 to room temperature, performing suction filtration, washing filter cake with 5-10 mL of H2O and anhydrous C2H5OH separately, and performing vacuum drying to obtain the 1,8-disubstituted naphthalene series polycyclic aromatic hydrocarbon mononitration derivative. According to the preparation method of the 1,8-disubstituted naphthalene series polycyclic aromatic hydrocarbon mononitration derivative, the product yield is 93%-96%; theproduct purity is 98%-99.5%; compared with the prior art, the preparation method has the characteristics of high product yield, high purity, low cost and simple process, and is easy to industrialize.

Preparation method of 1,8-disubstituted naphthalene mononitration derivative

The invention provides a preparation method of 1,8-disubstituted naphthalene mononitration derivative. The preparation method is characterized by comprising the following steps: S1, taking 1,8-disubstituted naphthalene as a raw material, taking main group metal nitrate as a nitration reagent, dissolving the 1,8-disubstituted naphthalene and the main group metal nitrate in an organic solvent, performing a nitration reaction under 10-60 DEG C for 4-10 h, and then monitoring by TLC (Thin layer chromatography) till a raw material point disappears to finish the reaction; S2, cooling a product obtained in step S1 to room temperature, performing suction filtration, washing filter cake with 5-10 mL of H2O and anhydrous C2H5OH separately, and performing vacuum drying to obtain the 1,8-disubstitutednaphthalene mononitration derivative. According to the preparation method of the 1,8-disubstituted naphthalene mononitration derivative, the product yield can reach 90%-95%; the product purity reaches 98.5%-99.6%; compared with the prior art, the preparation method has the characteristics of high product yield, high purity, low cost and simple process, and is easy to industrialize.

Identification of benzo[cd]indol-2(1H)-ones as novel Atg4B inhibitors via a structure-based virtual screening and a novel AlphaScreen assay

Targeting autophagy is a promising therapeutic strategy for cancer treatment. As a result, the identification of novel autophagy inhibitors is an emerging field of research. Herein, we report the development of a novel AlphaScreen HTS assay that combined

Small Molecule Microarray Based Discovery of PARP14 Inhibitors

Poly(ADP-ribose) polymerases (PARPs) are key enzymes in a variety of cellular processes. Most small-molecule PARP inhibitors developed to date have been against PARP1, and suffer from poor selectivity. PARP14 has recently emerged as a potential therapeutic target, but its inhibitor development has trailed behind. Herein, we describe a small molecule microarray-based strategy for high-throughput synthesis, screening of >1000 potential bidentate inhibitors of PARPs, and the successful discovery of a potent PARP14 inhibitor H10 with >20-fold selectivity over PARP1. Co-crystallization of the PARP14/H10 complex indicated H10 bound to both the nicotinamide and the adenine subsites. Further structure–activity relationship studies identified important binding elements in the adenine subsite. In tumor cells, H10 was able to chemically knockdown endogenous PARP14 activities.

Copper-catalyzed direct N-arylation of naphthalimides using diaryliodonium Salts

An effective copper-catalyzed N-arylation of naphthal-imides with diaryliodonium salts in toluene at 100 °C has been developed. This cross-coupling reaction gives the desired N-arylated 1,8-naphthalimides in moderate to good yields. The synthetic potentia

3-Nitro-naphthalimide and nitrogen mustard conjugate NNM-25 induces hepatocellular carcinoma apoptosis via PARP-1/p53 pathway

Hepatocellular carcinoma (HCC) is one of the main causes of death in cancer. Some naphthalimide derivatives exert high anti-proliferative effects on HCC. In this study, it is confirmed that 3-nitro-naphthalimide and nitrogen mustard conjugate (NNM-25), a novel compound conjugated by NNM-25, displayed more potent therapeutic action on HCC, both in vivo and in vitro, than amonafide, a naphthalimide drug in clinical trials. More importantly, preliminary toxicological evaluation also supported that NNM-25 exhibited less systemic toxicity than amonafide at the therapeutic dose. The antitumor mechanism of conjugates of naphthalimides with nitrogen mustard remains poorly understood up to now. Here, we first reported that apoptosis might be the terminal fate of cancer cells treated with NNM-25. Inhibition of p53 by siRNA resulted in a significant decrease of NNM-25-induced apoptosis, which corroborated that p53 played a vital role in the cell apoptosis triggered by NNM-25. NNM-25 inhibited the PARP-1 activity, AKT phosphorylation, up-regulated the protein expression of p53, Bad, and mTOR as well as down-regulating the protein expression of Bcl-2 and decreasing mitochondrial membrane potential. It also facilitated cytochrome c release from mitochondria to cytoplasm, activated caspase 8, caspase 9, and caspase 3 in HepG2 cells in vitro, as also authenticated in H22 tumor-bearing mice in vivo. Collectively, the conjugation of naphthalimides with nitrogen mustard provides favorable biological activity and thus is a valuable strategy for future drug design in HCC therapy.

Small molecule modifiers of MicroRNA miR-122 function for the treatment of hepatitis C Virus infection and hepatocellular carcinoma

MicroRNAs are a recently discovered new class of important endogenous regulators of gene function. Aberrant regulation of microRNAs has been linked to various human diseases, most importantly cancer. Small molecule intervention of microRNA misregulation h