2896-24-4Relevant academic research and scientific papers
The first example of an azaphenalene profluorescent nitroxide
Blinco, James P.,McMurtrie, John C.,Bottle, Steven E.
, p. 4638 - 4641 (2007)
The synthesis of the first example of an azaphenalene-based fused aromatic nitroxide TMAO, [1,1,3,3-tetramethyl-2,3-dihydro-2-azaphenalen-2-yloxyl, (5)], is described. This novel nitroxide possesses some of the structural rigidity of the isoindoline class of nitroxides, as well as some properties akin to TEMPO nitroxides. Additionally, the integral aromatic ring imparts fluorescence that is switched on by radical scavenging reactions of the nitroxide, which makes it a sensitive probe for polymer degradation. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Synthesis, spectroscopic and structural characterization and solution stability of ruthenium sandwich complexes containing 1,8-naphthalimide ligands
Pioli, Marianna,Loffi, Cecilia,Mazzeo, Paolo Pio,Bacchi, Alessia,Pelagatti, Paolo
, (2020)
Two different N-substituted naphthalimide ligands 1 (bearing a phenyl on the imide nitrogen) and 2 (bearing a benzyl on the imide nitrogen) have been synthesized and reacted with the cationic organometallic fragment [Cp*Ru(ACN)3]PF6. Ligand 1 brings to the formation of a sandwich complex (3Naph) where Ru is positioned on the naphthalene platform, while the N-imide phenyl substituent is not involved in coordination. This has been proven by single-crystal X-ray diffraction analysis conducted on crystals of 3Naph, revealing the first sandwich complex structurally characterized containing a naphthaleneimide ligand η6-coordinated to a metal. Ligand 2 shows instead a different behavior, leading to the formation of two isomeric complexes (4Naph and 4Bz), where Ru is placed on the naphthalene platform and on the N-imide benzyl substituent, in a rough 1:1 ratio. Complex 3Naph results very labile in coordinating solvents, such as acetonitrile, where it undergoes a fast and quantitative ligand solvolysis, with formation of free 1 and [Cp*Ru(ACN)3]PF6. In the cases of complexes 4, only complex 4Naph undergoes a fast and quantitative ligand solvolysis once dissolved in acetonitrile, whereas complex 4Bz results more stable.
Discovery and Characterization of Novel Naphthalimide Analogs as Potent Multitargeted Directed Ligands against Alzheimer's Disease
Chapman, James,Gao, Jie
, (2020/06/26)
Current therapeutic drugs for Alzheimer's disease (AD) can only offer limited symptomatic benefits and do not halt disease progression. Multitargeted directed ligands (MTDLs) have been considered to be a feasible way to treat AD due to the multiple neuropathological processes in AD. Previous studies proposed that compounds containing two aromatic groups connected by a carbon chain should act as effective amyloid β (Aβ) aggregation inhibitors although the optimal length of the carbon chain has not been explored. In the current study, a series of naphthalimide analogs were designed and synthesized based on the proposed structure and multiple bioactivities beneficial to the AD treatment were reported. In vitro studies showed that compound 8, which has two aromatic groups connected by a two-carbon chain, exhibited significant inhibition of Aβ aggregation through the prevention of elongation and association of Aβ fibril growth. Furthermore, this compound also displayed antioxidative activities and neuroprotection from Aβ monomer induced toxicity in primary cortical neurons. The results of the present study highlight a novel naphthalimide-based compound 8 as a promising MTDL against AD. Its structural elements can be further explored for enhanced therapeutic capabilities.
Target Enzyme-Activated Two-Photon Fluorescent Probes: A Case Study of CYP3A4 Using a Two-Dimensional Design Strategy
Ning, Jing,Wang, Wei,Ge, Guangbo,Chu, Peng,Long, Feida,Yang, Yongliang,Peng, Yulin,Feng, Lei,Ma, Xiaochi,James, Tony D.
supporting information, p. 9959 - 9963 (2019/06/24)
The rapid development of fluorescent probes for monitoring target enzymes is still a great challenge owing to the lack of efficient ways to optimize a specific fluorophore. Herein, a practical two-dimensional strategy was designed for the development of an isoform-specific probe for CYP3A4, a key cytochrome P450 isoform responsible for the oxidation of most clinical drugs. In first dimension of the design strategy, a potential two-photon fluorescent substrate (NN) for CYP3A4 was effectively selected using ensemble-based virtual screening. In the second dimension, various substituent groups were introduced into NN to optimize the isoform-selectivity and reactivity. Finally, with ideal selectivity and sensitivity, NEN was successfully applied to the real-time detection of CYP3A4 in living cells and zebrafish. These findings suggested that our strategy is practical for developing an isoform-specific probe for a target enzyme.
Mechanochemical N-alkylation of imides
Bri?, Anamarija,Dud, Mateja,Margeti?, Davor
supporting information, p. 1745 - 1752 (2017/09/27)
The mechanochemical N-alkylation of imide derivatives was studied. Reactions under solvent-free conditions in a ball mill gave good yields and could be put in place of the classical solution conditions. The method is general and can be applied to various imides and alkyl halides. Phthalimides prepared under ball milling conditions were used in a mechanochemical Gabriel synthesis of amines by their reaction with 1,2-diaminoethane.
Water-solvent method for the synthesis of N-substituted and N-,4-disubstituted 1,8-naphthalimides under microwave irradiation
Zhang, Ye,Feng, Shao-Bo,Wang, Kai,Yi, Xiang-Hui,Wang, Heng-Shan,Pan, Ying-Ming
experimental part, p. 3042 - 3052 (2012/08/14)
A preparation of a series of N-and N-,4-substituted 1,8-naphthalimides using water as solvent under microwave irradiation, which proceeded via efficient and green reaction of 1,8-naphthalic anhydride derivatives with different amines, is described.
Solvent-free synthesis of 1,8-naphthalimide derivatives under microwaves irradiation
Wu, Qiang,Qin, Wen
scheme or table, p. 4713 - 4714 (2012/02/15)
A solvent-free synthesis of a series of 1,8-naphthalimide derivatives, which proceeds via facile, economical and efficient reaction of primary amine with 1,8-naphthalic anhydride derivatives under microwave irradiation, was described.
Microwave-assisted synthesis and evaluation of naphthalimides derivatives as free radical scavengers
Zhang, Ye,Feng, Shaobo,Wu, Qiang,Wang, Kai,Yi, Xianghui,Wang, Hengshan,Pan, Yingming
experimental part, p. 752 - 759 (2012/05/20)
A facile and efficient microwave-assisted reaction of 1,8-naphthalic anhydride derivatives with primary amines, leading to the synthesis of 1,8-naphthalimides, has been developed. Subsequently, the free radical scavenging properties of the 1,8-naphthalimide derivatives were evaluated against 2,2-diphenyl-1-picrylhydrazyl (DPPH). The results showed that the scavenging activities of compounds 2a, NBNA, 3b, and 3c were more efficient than that of the common synthetic antioxidant 2,6-diterbutyl- 4-methylphenol (BHT), with IC50 values of 61.9, 54.0, 42.2, and 43.1 μM, respectively. The imide groups introduced at position 4 as well as the nitro functionality at position 3 of the naphthalene moiety were the major contributors to the free radical scavenging activities. Springer Science+Business Media, LLC 2010.
Synthesis and antidepressant-like activity evaluation of sulphonamides and sulphonyl-hydrazones
De Oliveira, Kely Navakoski,Costa, Philipe,Santin, José Roberto,Mazzambani, Leonor,Bürger, Cristiani,Mora, Cristiano,Nunes, Ricardo José,De Souza, Márcia Maria
experimental part, p. 4295 - 4306 (2011/08/21)
In this study a series of sulphonamides and sulphonyl hydrazones of maleimide, naphthalimide and phthalimide derivatives was synthesized. The antidepressant effect of these compounds was evaluated by the forced-swimming test in mice. The behavioural parameter observed in this test is a reduction in the immobility time, which is indicative of antidepressant activity. All compounds, except 8, 11 and 24, were active as antidepressants. The most active compound was the sulphonyl-hydrazone 10 which showed an activity of around 72.02% at 60 mg/kg, it thus being more active than imipramine (10 mg/kg, ip), a commercial antidepressant. Other important results were obtained for the benzylnaphthalimide derivatives, the sulphonamides 21 and 22 showing activity of 64% at 10 mg/kg, also being more active than imipramine. These results indicate that the sulphonamides and sulphonyl-hydrazone cyclic imide derivatives are potential compounds for use in the designing of new candidates for the treatment of depression.
Ionic liquids accelerate access to N-substituted-1,8-naphthalimides
MacGregor, Kylie A.,McCluskey, Adam
experimental part, p. 767 - 769 (2011/03/18)
The synthesis of N-substituted-1,8-naphthalimides is accelerated in the presence of the room temperature ionic liquid [BMIM][NO3]. Reaction times are reduced from 18 h in volatile organic compounds (VOCs) (PhCH 3, EtOH and THF) to 20 min in the ionic liquid [BMIM][NO 3]. The reaction yields are typically increased to >85% and the products are isolated by ethanol-mediated precipitation direct from the ionic liquid, requiring no further purification. Crown Copyright
