2051-98-1Relevant articles and documents
Synthesis and application of novel heterocyclic dyes based on 11-Amino-3-Bromo-13H-acenaphtho[1,2-e]pyridazino[3,2-b]-quinazoline-13-one
Patel, Vijay H.,Patel, Manish P.,Patel, Ranjan G.
, p. 599 - 606 (2001)
Synthesized a new fused heterocyclic compound, 11-Amino-3-Bromo-13H-acenaphtho[1,2-e]pyridazino[3,2-b]-quinazoline-13-one and is used to synthesize a novel series of heterocyclic mono azo dyes by coupling with various naphthols. All the dyes were characterized by their percentage yield, melting point, UV-visible spectroscopy, elemental analysis, infrared spectroscopy and dyeing performance on nylon 66 and polyester fibres. The percentage dye bath exhaustion on different fibres has been found to be reasonably good and acceptable. The dyed fibres showed fair to fairly good fastness to light and very good to excellent fastness to washing, rubbing, perspiration and sublimation.
Synthesis of Triphenylethylene-Naphthalimide Conjugates as topoisomerase-IIα inhibitor and HSA binder
Rani, Sudesh,Luxami, Vijay,Paul, Kamaldeep
, p. 1821 - 1831 (2021)
A series of triphenylethylene-naphthalimide (TPE-naph) conjugates was synthesized by a molecular hybridization technique, and their anticancer activity was evaluated in vitro on 60 human cancer cell lines through their cytotoxicity. The ratios of E and Z isomers were determined on the basis of HPLC methodology and NMR spectroscopy. The structure-activity relationship for anticancer activity was deduced on the basis of the nature and bulkiness of the amine attached to the C-4 position of the naphthalene ring. Experimental and molecular modeling studies of the most active TPE-naph conjugate bearing a morpholinyl group showed that it was able to inhibit topoisomerase-II (TOPO-II) as a possible intracellular target. Moreover, the transportation behavior of TPE-naph conjugate towards human serum albumin (HSA) indicated efficient binding affinity. The steady-state and time-dependent fluorescent results suggested that this conjugate quenched HSA significantly through static as well as dynamic quenching. Thus, this report discloses the scope of triphenylethylene-naphthalimide (TPE-naph) conjugates as efficient anticancer agents.
Synthesis of naphthalimide-phenanthro[9,10-d]imidazole derivatives: In vitro evaluation, binding interaction with DNA and topoisomerase inhibition
Luxami, Vijay,Paul, Kamaldeep,Singh, Iqubal
, (2020)
The synthesis and characterization of a series of naphthalimide and phenanthro[9,10-d]imidazole conjugate is described. These compounds are evaluated in vitro for their cytotoxicity towards 60 human cancer cell lines. Derivative 16 shows excellent cytotoxic activity against these cancer cell lines with the range of growth inhibition from ?55.78 to 94.53. The most potent derivative (ethylpiperazine, 16) is further studied to evaluate the interaction with ct-DNA using absorption and emission spectroscopy as well as DNA viscosity measurement. The DNA binding studies indicate that compound 16 is significantly interacted with DNA through groove binding having binding constant value of 7.81 × 104 M?1 alongwith partial intercalation between the base pairs of DNA strands. Further, topoisomerase inhibition study suggests that compound 16 is induced apoptosis and inhibits human topoisomerase (Topo-IIα) as a possible intracellular target. Molecular docking study of compound 16 with ct-DNA shows good docking score.
Blue emitting 1,8-naphthalimides with electron transport properties for organic light emitting diode applications
Ulla, Hidayath,Kiran, M. Raveendra,Garudachari,Ahipa,Tarafder, Kartick,Adhikari, Airody Vasudeva,Umesh,Satyanarayan
, p. 344 - 354 (2017)
In this article, the synthesis, characterization and use of two novel naphthalimides as electron-transporting emitter materials for organic light emitting diode (OLED) applications are reported. The molecules were obtained by substituting electron donating chloro-phenoxy group at the C-4 position. A detailed optical, thermal, electrochemical and related properties were systematically studied. Furthermore, theoretical calculations (DFT) were performed to get a better understanding of the electronic structures. The synthesized molecules were used as electron transporters and emitters in OLEDs with three different device configurations. The devices with the molecules showed blue emission with efficiencies of 1.89?cdA-1, 0.98?lmW?1, 0.71% at 100?cdm-2. The phosphorescent devices with naphthalimides as electron transport materials displayed better performance in comparison to the device without any electron transporting material and were analogous with the device using standard electron transporting material, Alq3. The results demonstrate that the naphthalimides could play a significant part in the progress of OLEDs.
Electron-poor bowl-shaped polycyclic aromatic dicarboximides: Synthesis, crystal structures, and optical and redox properties
Shoyama, Kazutaka,Schmidt, David,Mahl, Magnus,Würthner, Frank
, p. 5328 - 5331 (2017)
Two new bowl-shaped polycyclic aromatic hydrocarbons, based on corannulene and naphthalene dicarboximide, are synthesized by an improved Suzuki-Miyaura cross-coupling and C-H arylation cascade reaction. Crystallographic analyses confirm structural assignments and provide insight into molecular interactions in the solid state. The new bowl-shaped molecules show reversible oxidation and reduction, intense visible range absorption, and high fluorescence quantum yields. These molecules can be considered bowl-shaped congeners of planar perylene dicarboximides.
In vitro and in vivo imaging application of a 1,8-naphthalimide-derived Zn2+ fluorescent sensor with nuclear envelope penetrability
Zhang, Changli,Liu, Zhipeng,Li, Yunling,He, Weijiang,Gao, Xiang,Guo, Zijian
, p. 11430 - 11432 (2013)
A newly developed fluorescent sensor, Naph-BPEA, shows a specific turn-on response to Zn2+ and can be excited by visible light. The in situ nuclear Zn2+ imaging in HeLa and HepG2 cells reveals the nuclear envelope penetrability of the sensor. The specific sensor location in a zebrafish larva was also demonstrated.
Functionalization of poly(amidoamine) dendrimer-based nano-architectures using a naphthalimide derivative and their fluorescent, dyeing and antimicrobial properties on wool fibers
Sadeghi-Kiakhani, Mousa,Safapour, Siyamak
, p. 1005 - 1012 (2016)
Novel naphthalimide-poly(amidoamine) dendrimer fluorescent dyes were synthesized, and their structures were identified and confirmed using different characterization methods such as Fourier transform infrared, 1H NMR, 13C NMR, differential scanning calorimetry, elemental analysis and UV-vis spectroscopy. The spectrophotometric studies demonstrated absorption maxima (λmax) and extinction coefficient (max) values in the ranges of 429-438 nm and 25,635-88,618 L/mol/cm, respectively. The dyeing, fastness and antimicrobial properties of dyed wool fibers were examined. Colorimetric measurements demonstrated a greenish-yellow hue with remarkable fluorescence intensity on dyed wool. Although the fastness properties of naphthalimide dye on wool fibers were poor/moderate, color fastness was appreciably improved through modification of the dye using dendrimers. The results revealed that the newly synthesized dyes are potent antimicrobial agents on wool fibers. Overall, it was deduced that poly(amidoamine) (PAMAM) dendrimers could be exploited as a promising tool in tailoring the different properties of naphthalimide dyes, being suitable for dyeing and antimicrobial finishing agents for wool fibers.
Study on synthesis and fluorescence property of rhodamine–naphthalene conjugate
Qin, Jing-can,Fu, Zhen-hai,Tian, Li-mei,Yang, Zheng-yin
, (2020)
In this study, a novel ligand (HL) consisting of 2-methyl quinoline-4-carboxylic acid, rhodamine and naphthalene moiety, was designed and synthesized, it could be developed a ratiometric fluorescent sensor for selective detection of Al3+ via fluorescence resonance energy transfer (FRET) from naphthalimide moiety to rhodamine moiety. The addition of Al3+ trigger the significant fluorescence enhancement of HL at 550 nm at the expense of the fluorescent emission of HL centered at 524 nm.
Naphthalimide-based optical turn-on sensor for monosaccharide recognition using boronic acid receptor
Seraj, Sanaz,Rouhani, Shohre,Faridbod, Farnoush
, p. 17933 - 17940 (2019)
A highly selective and sensitive fluorescent sensor for the determination of fructose is developed. The fluorescent sensor was prepared by incorporating a new naphthalimide dye with a planar structure as a selectophore and graphene oxide (GO) nanoplatelets as a quencher for rapid optical detection of fructose. The designed probe, made with the high fusion loop-containing dye, along with the GO nanoplatelets, detected fructose over the other monosaccharides very well. The proposed sensor displays a linear response range of 7 × 10-5 to 3 × 10-2 M with a low limit of detection of 23 × 10-6 M in solution at pH 7.4. This sensor shows a good selectivity towards fructose with respect to other saccharides. The proposed sensor was then applied to the determination of fructose in human plasma with satisfactory results.
Synthesis and fluorescence quenching mechanism of novel naphthalimide derivative by nanographene oxide
Rouhani, Shohre,Seraj, Sanaz
, (2021/07/30)
Novel naphthalimide derivative with amine functional group was prepared, and its FTIR and 1H and 13C NMR spectral characteristics were reported. The fluorescence quenching of synthesized dye by nanographene oxide was studied using absorption and fluorescence measurements. From the stern-Volmer analysis, we observed that the quenching was mainly due to the dynamic mechanism. The CV plots indicate that the quenching also went through an electron transfer process. The binding constant (K) and the number of binding sites (n) were calculated based on the fluorescence quenching data. In addition, the free energy change (ΔG) for the electron transfer process was calculated.
