92060-89-4

Usage

Organic compound

Contains a benzo[de]isoquinoline-1,3(2H)-dione skeleton

Substituents

2-(2-hydroxyethyl) and 6-nitro

Physical state

Yellow to brown solid

Solubility

Not readily soluble in water

Uses

Precursor or intermediate in the synthesis of pharmaceuticals and other organic compounds

Biological activity

May exhibit biological activity, of interest to pharmaceutical and organic chemistry researchers

Upstream product

• 6642-29-1 4-nitronaphthalic-1,8-anhydride 
• 141-43-5 ethanolamine 
• 602-87-9 4-nitroacenaphthene 
• 83-32-9 acenaphthene 

Downstream Products

• 1353887-81-6 C₂₂H₂₀N₂O₃S 
• 1353887-65-6 C₄₄H₄₅N₅O₄ 
• 1353887-66-7 C₄₈H₄₄N₄O₄S 
• 1353887-61-2 C₄₅H₄₀N₄O₄S 
• 1353887-62-3 C₄₄H₄₂N₄O₄S 

Relevant academic research and scientific papers

Sensor potential of 1,8-naphthalimide and its dyeing ability of cotton fabric

A new 4-(2-N,N-dimethylamino)ethylamino-N-2-hydroxyethyl-1,8-naphthalimide has been synthesized. The photophysical characteristics have been determined in aqueous and acetonitrile solutions. The influence of metal cations (Ni 2+, Zn2+, and Cu2) and protons on the fluorescence intensity has been studied to evaluate the capacities of the newly synthesized 1,8-naphthalimide as a fluorescence sensor. The 1,8- naphthalimide dye has been chemically bonded to a cotton textile fabric in order to obtain a heterogeneous fluorescent sensor for detecting of metal cations and protons.

Pyrophosphate-selective fluorescent chemosensor based on 1,8-Naphthalimide-DPA-Zn(II) Complex and its application for cell imaging

A new zinc(II) complex with a two-dipicolylamine-substituted 1,8-naphthalimide for recognition of pyrophosphate with ratiometrical fluorescence changes in aqueous solution has been synthesized and characterized. Its biological application to monitor the intracellular pyrophosphate (PPi) was successfully demonstrated by the observation that the fluorescence of 1 was enhanced by the presence of the Zn2+ion and was quenched by addition of PPi.

Structural characterization of 1,8-naphthalimides and in?vitro microbiological activity of their Cu(II) and Zn(II) complexes

Two new 1,8-naphthalimide derivatives (NI1 and NI2) have been synthesized and characterized. The photophysical properties of the new compounds have been investigated in organic solvents of different polarity. It has been shown that both compounds are solvent depended. Cu(II) and Zn(II) complexes of NI2 were obtained and characterized by IR-NMR, fluorescence and EPR spectroscopy. The influence of different metal cations on the fluorescence intensity has been investigated in acetonitrile solution. Antimicrobial composite PLA-metal complexes materials have been obtained for the first time. Microbiological activity of both metal complexes has been investigated in?vitro against different Gram-positive and Gram-negative bacteria and two yeasts. The various antimicrobial activities and the minimum inhibitory concentrations (MICs) of both complexes have been determined. The microbiological activity of composite materials PLA-metal complexes in thin polymeric film has also been investigated. The results suggest that the new metal complexes could find application in designing new antimicrobial preparations to control the spread of infections.

Synthesis and photophysical evaluation of a pyridinium 4-amino-1,8- naphthalimide derivative that upon intercalation displays preference for AT-rich double-stranded DNA

The synthesis, characterisation and solid state crystal structure of a cationic 4-amino-1,8-naphthalimide derivative (1) are described. The photophysical properties of 1 are shown to vary with the solvent polarity and H-bonding ability. The fluorescence of 1 is enhanced and blue-shifted in its 1:1 complex with 5′-adenosine-monophosphate while it is partially quenched and red-shifted in its complex with 5′-guanosine-monophosphate. Linear and circular dichroism measurements show that 1 binds to double-stranded DNA by intercalation. Comparative UV-visible and fluorescence studies with double stranded synthetic polynucleotides poly(dA-dT)2 and poly(dG-dC) 2 show that 1 binds much more strongly to the AT polymer; 1 also has a strong preference for A-T rich sequences in natural DNA. Thermal denaturation measurements also reveal a much greater stabilisation of the double-stranded poly(dA-dT)2 than of natural DNA. The Royal Society of Chemistry 2012.

Anticancer activity and topoisomerase II inhibition of naphthalimides with Ω-hydroxylalkylamine side-chains of different lengths

Background: The substituted 1,8-Naphthalimides (1H-benzo[de]isoquinoline-1,3(2H)- diones) are known as DNA intercalators stabilizing DNA-Topoisomerase II complexes. This interaction disrupts the cleavage-relegation equilibrium of Topo II, resulting in formation of broken strands of DNA. Objective: To investigate the influence of type of substituents and substitution positions in 1,8- naphthalimde skeleton on the inhibition of Topoisomerase II activity. Method: The starting 1,8-naphthalimide were prepared from acenaphthene by introduction of appropriate substituents followed by condensation with ω-hydroxylakylamines of different chain length. The substituents were introduced to 1,8-naphthalimide molecule by nucleophilic substitution of leaving groups like nitro or bromo present in 4 or 4,5- positions using the ω- hydroxylalkylamines. The bioactivity of obtained compounds was examined in model cell lines. Results: Antiproliferative activity of selected compounds against HCT 116 human colon cancer cells, human non-small cell lung cells A549 and non-tumorigenic BEAS-2B human bronchial epithelium cells was examined. Several of investigated compounds exhibit a significant activity (IC50 μM to 7 μM) against model cancer cell lines. It was demonstrated that upon treatment with concentration of 200 μM, all derivatives display Topo II inhibitory activity, which may be compared with activity of Amonafide. Conclusion: The replacement of the nitro groups in the chromophore slightly reduces its anticancer activities, whereas the presence of both nitro group and ω-hydroxylalkylamine chain resulted in seriously increased anticancer activity. Obtained compounds showed Topo II inhibitory activity, moreover, influence of the substitution pattern on the ability to inhibit Topo II activity and cancer cells proliferation was observed.

Ratiometric two-photon fluorescent probes for mitochondrial hydrogen sulfide in living cells

Hydrogen sulfide (H2S) is an important signaling molecule with diverse biological roles. Various fluorescent probes for H2S with biological application have been developed. However, two-photon ratiometric imaging of mitochondrial Hs

Design, synthesis and pH sensing properties of novel 1,8-naphtalimide-based bichromophoric system

In this work we report on the design, synthesis and sensor properties of a novel bichromophoric sensor system based on 1,8-naphthalimide fluorophores. The synthesized dyad was configured as a fluorescent wavelength-shifting energy transfer chromophore. The novel donor-acceptor system contains blue emitting 4-methoxy-1,8-naphthalimide donor dye, capable of both absorbing light and efficiently transferring the energy to yellow-green emitting 4-N-methylpiperazinyl-1,8-naphthalimide acceptor. The energy-transfer efficiency in the dyad system was calculated to be more than 99%. The acceptor unit in the donor-acceptor system was also designed as a PET based sensor according to the "fluorophore-spacer-receptor" model. The fluorescence behaviour of the bichromophoric system was investigated as a function of pH. The fluorescence enhancement of the novel dyad in acidic media was more than 29 times indicating the high ability of the system to act as an efficient pH chemosensor.

Novel naphthalimide-benzoic acid conjugates as potential apoptosis-inducing agents: Design, synthesis, and biological activity

A series of novel naphthalimide derivatives with 4-[4-(3,3-diphenylallyl)piperazin-1-yl]benzoic acid as side chain were designed and synthesized. Their antitumor activities were evaluated against a variety of cancer cell lines in vitro. Preliminary results showed that most of the derivatives had cytotoxic activity comparable with that of amonafide, with IC50 values of 10-6-10-5m. Interestingly, compound 12e had the unique antitumor activity against MCF-7 among the cancer cell lines tested. More importantly, flow cytometric analysis indicated that compared with amonafide, the target compounds could effectively induce G2/M arrest and progress to apoptosis in HL-60 cells after double staining with annexin V-FITC and propidium iodide. The present work provided a novel class of naphthalimide-based derivatives with potential apoptosis-inducing and improved antitumor activity for further optimization.

NOVEL SUBSTITUTED 1H-BENZ [DE] ISOQUINOLINE-1, 3 -DIONES

The present invention relates to novel substituted 1H-benz[de]isoquinoline-1,3-diones. This invention particularly relates to novel substituted 1H-benz[de]isoquinoline-1,3-diones particularly N-[2-(Chloroethyl)]- and N-[3-(Chloropropyl)]-naphthalimides and antitumor activity thereof. The present invention also relates to process of preparation of novel substituted 1H-benz[de]isoquinoline-1,3-diones. The present invention further relates to pharmaceutical composition for the treatment of cancer and related diseases.

The Synthesis of Alkylamino-N-alkylnaphthalic-1,8-imides from 2- and 4-nitronaphthalic Anhydrides by Nitro group Displacement

4-Alkylamino-N-alkylnaphthalic-1,8-imides and 2-alkylamino isomers have been synthesised by the reaction of 4-nitro- and 2-nitronaphthalic anhydrides respectively with primary amines in aprotic solvents in which reaction the nitro group in 3-nitronaphthalic anhydride is unreactive. Unsymmetrical compounds in the 2- and 4-series are derived from either the appropriate 4-nitro-N-alkylnaphthalic-1,8-imide or for 4-dilakylamino compounds from 4-nitronaphthalic anhydride by reaction with a secondary amine and then the 4-dialkylaminonaphthalic anhydride with a primary amine.