602-87-9Relevant articles and documents
Synthesis and characterization of novel monoazo N-ester-1,8-naphthalimide disperse dyestuffs
Gharanjig, Kamaladin,Arami, Mokhtar,Rouhani, Shohre,Bahrami, Hajir,Movassagh, Barahman,Mahmoodi, Niyaz Mohammad
, p. 1021 - 1028 (2007)
Five novel monoazo disperse dyestuffs based on N-ester-1,8-naphthalimide were synthesized. Acenaphthene was nitrated, then oxidized to 4-nitro-1,8-naphthalic anhydride. 4-Nitro-1,8-naphthalic anhydride was reacted with methyl and ethyl glycinate in alcoholic media, followed with reduction. 4-Amino-N-methyl and ethyl glycinate-1,8-naphthalimide were obtained. These products were diazotized and coupled with appropriate aromatic amines to give bluish-red or violet dyestuffs. All intermediates and dyestuffs were purified and characterized by 1H-NMR, FTIR, DSC, UV-VIS and Elemental Analysis. Dispersion of dyestuffs was prepared in water and applied to polyester fabrics. The dyed fabrics showed that four of the synthesized dyestuffs were suitable for coloring polyester fibers, producing deep bluish red with very good build up properties.
A substituent constant analysis of the interaction of substituted naphthalene monoimides with DNA
Stevenson,Yen,Yang,Boykin,Wilson
, p. 1677 - 1682 (1984)
In a continuing analysis of substituent effects in intercalator-DNA interactions, an unsubstituted naphthalene monoimide, 1, with a 3-(dimethylamino)propyl group on the imide nitrogen has been prepared along with 3- and 4-nitro- (2 and 3) and 3- and 4-amino- (4 and 5) substituted derivatives. These derivatives allow an evaluation of the importance of the Hammett substituent constant and of the substituent position on the binding of naphthelene monoimides to DNA. Viscosity and spectrophotomeric analyses indicate that all five compounds bind to DNA by intercalation. The 4-nitro compound gives a smaller viscosity increase and binds only approximately one-third as strongly as the 3-nitro derivatives. It is postulated that this difference is due to significant angle that the 4-nitro group makes with the intercalated monoimide ring system. The 3-NO2 group can assume a coplanar configuration with the monoimide ring system, allowing more favorable interactions with DNA base pairs, larger viscosity increases, and stronger binding to DNA. The binding constants of the 3-substutited monoimides are in the order 2 > 4 > 1 and, thus, do not follow a substituent constant pattern. The T(m) values from thermal melting of DNA, on the other hand, are in the oder 2 > 1 > 4, suggesting that the enthalpy contributions are significantly different for the binding of the three compounds to DNA. van't Hoff plots support this finding and indicate that both enthalpy and entropy contribute significantly to the binding free energy of 1 and 2 while the binding of 4 is primarily an enthalpic process. Plots of T(m) and 65°C log K values as a function of substituent constant for 1, 2, and 4 are linear. CPK model building studies suggest that 4 can form a hydrogen bond with the 5' diester oxygen of the sugar-phosphate backbone of DNA in an intercalation complex. This would lead to more favorable energetics of binding but a loss of mobility and/or available binding configurations with a resulting enthalpy-entropy compensation in the binding free energy of 4. This series of compounds dramatically illustrates the steric and hydrogen bonding complexity that can arise in attempts to design drugs to favorably interact with a DNA intercalation site as a potential bioreceptor.
A naphthalimide-polyamine conjugate preferentially accumulates in hepatic carcinoma metastases as a lysosome-targeted antimetastatic agent
Ma, Jing,Li, Linrong,Yue, Kexin,Zhang, Zhansheng,Su, Shihao,Chen, Yutong,Yu, Lu,Zhang, Pengfei,Ma, Ruijuan,Li, Yingguang,Ma, Yinxia,Jia, Huinan,Wang, Chaojie,Wang, Jiajia,Xie, Songqiang
, (2021/05/10)
Disseminated tumors lead to approximately 90% of cancer-associated deaths especially for hepatocellular carcinoma (HCC), indicating the imperative need of antimetastatic drugs and the ineffectiveness of current therapies. Recently polyamine derivatives have been identified as a promising prospect in dealing with metastatic tumors. Herein, a novel class of naphthalimide-polyamine conjugates 8a-8d, 13a-13c, 17 and 21 were synthesized and the mechanism was further determined. The polyamine conjugate 13b displayed remarkably elevated anti-tumor and anti-metastatic effects (76.01% and 75.02%) than the positive control amonafide (46.91% and 55.77%) at 5 mg/kg in vivo. The underlying molecular mechanism indicated that in addition to induce DNA damage by up-regulating p53 and γH2AX, 13b also targeted lysosome to modulate polyamine metabolism and function in a totally different way from that of amonafide. Furthermore, the HMGB1/p62/LC3II/LC3I and p53/SSAT/β-catenin pathways were mainly involved in the inhibition of 13b-induced HCC metastasis by targeting polyamine transporters (PTs) overexpressed in HCC. At last, 13b down-regulated the concentrations of Put, Spd and Spm by modulating polyamine metabolism key enzymes SSAT and PAO, which favored the suppression of fast growing tumor cells. Taken together, our study implies a promising strategy for naphthalimide conjugates to treat terminal cancer of HCC by targeting autophagy and tumor microenvironment with reduced toxicities and notable activities.
Synthesis and dyeing performance of some amphiphilic naphthalimide azo disperse dyes on polyester fabrics
Ameuru, Umar Salami,Yakubu, Mohammed Kabir,Bello, Kasali Ademola,Nkeonye, Peter Obinna,Halimehjani, Azim Ziyaei
, p. 1253 - 1264 (2020/11/26)
A series of monoazo disperse dyes were synthesized by coupling diazotized 4-amino-N-dodecyl-1,8-naphthalimide with N,N-dialkyl anilines and naphthol derivatives. The synthesized intermediates and the dyes were characterized using FTIR, 1H-NMR, 13C-NMR, mass spectroscopy and elemental analysis (CHN). Visible absorption spectra of the dyes were examined in solvents of different polarities. The electronic absorption spectra cover a wavelength (λmax) range of 515-535 nm in DMF at uniformly absorption intensity between 1.59-3.00×104L mol-1cm-1. The dyes gave deep and bright intense hues of light violet, maroon, pink and neon red on polyester fabrics. The dyes generally showed good washing and perspiration rating but poor to moderate light fastness properties on woven polyester fabric and could be recommended for commercial outlets.
Preparation method of 1,8-disubstituted naphthalene series polycyclic aromatic hydrocarbon mononitration derivative
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Paragraph 0040-0051, (2019/08/06)
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.
