- The first example of an azaphenalene profluorescent nitroxide
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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.
- Blinco, James P.,McMurtrie, John C.,Bottle, Steven E.
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- Synthesis, spectroscopic and structural characterization and solution stability of ruthenium sandwich complexes containing 1,8-naphthalimide ligands
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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.
- Pioli, Marianna,Loffi, Cecilia,Mazzeo, Paolo Pio,Bacchi, Alessia,Pelagatti, Paolo
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- Discovery and Characterization of Novel Naphthalimide Analogs as Potent Multitargeted Directed Ligands against Alzheimer's Disease
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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.
- Chapman, James,Gao, Jie
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- Target Enzyme-Activated Two-Photon Fluorescent Probes: A Case Study of CYP3A4 Using a Two-Dimensional Design Strategy
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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.
- Ning, Jing,Wang, Wei,Ge, Guangbo,Chu, Peng,Long, Feida,Yang, Yongliang,Peng, Yulin,Feng, Lei,Ma, Xiaochi,James, Tony D.
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supporting information
p. 9959 - 9963
(2019/06/24)
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- Mechanochemical N-alkylation of imides
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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.
- Bri?, Anamarija,Dud, Mateja,Margeti?, Davor
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supporting information
p. 1745 - 1752
(2017/09/27)
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- Water-solvent method for the synthesis of N-substituted and N-,4-disubstituted 1,8-naphthalimides under microwave irradiation
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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.
- Zhang, Ye,Feng, Shao-Bo,Wang, Kai,Yi, Xiang-Hui,Wang, Heng-Shan,Pan, Ying-Ming
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experimental part
p. 3042 - 3052
(2012/08/14)
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- Solvent-free synthesis of 1,8-naphthalimide derivatives under microwaves irradiation
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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.
- Wu, Qiang,Qin, Wen
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scheme or table
p. 4713 - 4714
(2012/02/15)
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- Microwave-assisted synthesis and evaluation of naphthalimides derivatives as free radical scavengers
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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.
- Zhang, Ye,Feng, Shaobo,Wu, Qiang,Wang, Kai,Yi, Xianghui,Wang, Hengshan,Pan, Yingming
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experimental part
p. 752 - 759
(2012/05/20)
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- Synthesis and antidepressant-like activity evaluation of sulphonamides and sulphonyl-hydrazones
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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.
- De Oliveira, Kely Navakoski,Costa, Philipe,Santin, José Roberto,Mazzambani, Leonor,Bürger, Cristiani,Mora, Cristiano,Nunes, Ricardo José,De Souza, Márcia Maria
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experimental part
p. 4295 - 4306
(2011/08/21)
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- Ionic liquids accelerate access to N-substituted-1,8-naphthalimides
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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
- MacGregor, Kylie A.,McCluskey, Adam
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experimental part
p. 767 - 769
(2011/03/18)
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- Evaluation of apoptotic effect of cyclic imide derivatives on murine B16F10 melanoma cells
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Cyclic imides are a large class of compounds obtained by organic synthesis including several sub-classes (succinimides maleimide, glutarimide, phthalimides naphtalimides, and its derivatives). Recently, some cyclic imide derivatives have shown important results as potential antitumor agents, as a Mitonafide and Amonafide. Based on this fact, we have studied antitumoral properties of nine cyclic imide derivatives, four of which are unpublished compounds, against Murine Melanoma Cells (B16F10). Initially, the MTT assay was used to select the compound with the best cytotoxic potential. After this selection, the compound 2-benzyl-1H-benzo[de]isoquinoline-1,3(2H)-dione (4), which showed the best cytotoxic effects, was evaluated by flow cytometry, and a significant increase was observed in the proportion of cells in the subG0/G1, S and G2/M phases accompanied by a significant decrease in the G0/G1 phases. Then the mechanism involved on the death route (necrosis or apoptosis) was evaluated the by bromide and acridine orange method and by an Annexin V-FITC Apoptosis Detection kit. These results confirm that the percentage of B16F10 cells observed in the sub G0/G1 phase were undergoing apoptosis. The biological effects observed in the current study for the cyclic imide derivatives suggested promising applications, especially for the prototype compound 4.
- Machado, Karina Elisa,De Oliveira, Kely Navakoski,Santos-Bubniak, Lorena,Licínio, Marley Aparecida,Nunes, Ricardo José,Santos-Silva, Maria Cláudia
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scheme or table
p. 6285 - 6291
(2011/12/14)
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- Facile synthesis of 1,8-naphthalimides in palladium-catalysed aminocarbonylation of 1,8-diiodo-naphthalene
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1,8-Diiodo-naphthalene was aminocarbonylated with various primary and secondary amines in the presence of palladium(0) complexes formed in situ from palladium(II) acetate and triphenylphosphine. In the case of primary amines, depending on the amine to substrate ratio, two types of products have been obtained in highly chemoselective reaction: dicarboxamides and N-substituted imides have been formed at high and low amine to substrate ratio, respectively. The reaction tolerates the ester functionality, so that amino acid esters could serve as N-nucleophiles and in this way, naphthalimides possessing stereogenic centre in the N-substituent could be synthesised.
- Takács, Attila,ács, Péter,Kollár, László
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p. 983 - 987
(2008/09/18)
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- N-alkylation of imides using phase transfer catalysts under solvent-free conditions
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(Chemical Equation Presented) N-Alkylation of imides in the reaction of imides and alkylhalides, catalyzed by PT catalysts under solvent-free conditions, has been developed. The reaction occurs in the presence of K 2CO3, and in many cases it takes place spontaneously. In the N-benzylation reaction, it has been recognized that TBAB (tetrabutylammonium bromide) and TBATFB (tetrabutylammonium tetrafluoroborate) show highest catalytic effect. Versatility and synthetic capacity of the solvent-free alkylation has been confirmed by N-benzylation and N-ethylation of various imides. The developed procedure gives easy access to N-(ω-bromoalkyl) imides.
- Jaskowska, Jolanta,Kowalski, Piotr
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scheme or table
p. 1371 - 1375
(2009/04/07)
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- PROFLUORESCENT NITROXIDE COMPOUNDS
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A polymeric system which includes a polymeric material and a pro-fluorescent nitroxide compound or a fluorescent spin adduct thereof, the compound having at least one 5 to 10 membered heterocyclic ring comprising a nitroxide moiety or a fluorescent spin adduct thereof and an aryl or heteroaryl group fused therewith, wherein the compound includes at least one fluorophore; with the proviso that when the heterocyclic ring has 5 carbon atoms, the aryl group cannot be an unsubstituted phenanthrene.
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Page/Page column 56
(2010/11/28)
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- Photoinduced energy and electron transfer in 1,8-naphthalimide-corrole dyads
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A series of corrole-1,8-naphthalimide dyads has been synthesized. The dyads were assembled in a convergent fashion from two fragments via a corrole forming reaction. Central to the success of the synthetic strategy was the preparation of suitably functionalized derivatives of naphthalene-1,8-carboxymide. Six different dyads possessing either a different linker (a meta-phenylene or a para-phenylmethylene) or a corrole with different substituents at the 5 and 15 positions were prepared. A photophysical and spectroscopic characterization of the dyads and the reference models show that whereas upon selective excitation of the corrole component no photo-induced process occurs, excitation of the naphthalimide unit results in very efficient energy or electron transfer processes. The electron transfer contributes to the quenching process with a ratio between 0% and 85% depending on the nature of the corrole accepting unit. The processes are discussed in the frame of current theories. This is the first report of stable corrole-based dyads with interesting photo-activity at ambient temperature. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.
- Tasior, Mariusz,Gryko, Daniel T.,Cembor, Marek,Jaworski, Jan S.,Ventura, Barbara,Flamigni, Lucia
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p. 247 - 259
(2008/02/02)
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- A "green" route to perylene dyes: Direct coupling reactions of 1,8-naphthalimide and related compounds under mild conditions using a "new" base complex reagent, t-BuOK/DBN
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The direct coupling reactions of 1,8-naphthalimide compounds efficiently occurred at 130 or 170 °C without the intervention of the leuco form dyes in the presence of base complex reagent, t-BuOK/1,5-diazabicyclo[4.3.0]non-5-ene (DBN), to give the corresponding perylene dyes in good yields with >95% purities. A possible mechanistic speculation for these oxidative coupling reactions is briefly discussed.
- Sakamoto,Pac
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- Efficient one-pot synthesis of N-substituted phthalimides/naphthalimides from azides and anhydrides by iodotrimethylsilane
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N-Substituted phthalimides and naphthalimides have been obtained in good to excellent yields, employing chlorotrimethylsilane and sodium iodide (in situ generation of iodotrimethylsilane) from corresponding azides and anhydrides under mild conditions.
- Kamal, Ahmed,Laxman,Laxman,Rao, N. Venugopal
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p. 8733 - 8734
(2007/10/03)
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- Naphthalimido derivatives as antifolate thymidylate synthase inhibitors
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A new series of N-(substituted)benzyl-1,8-naphthalimides 4, structurally related to the previously reported thymidylate synthase (TS) inhibitor naphthaleins 3, were synthesized and compounds tested for their inhibition of several species of TS. Moreover, their in vitro cytotoxicity together with antimycotic and antibacterial properties were assayed. While no activity was detected in the antibacterial tests, the m-nitro (4ae) and the p-nitro (4af) derivatives were found able to partially inhibit TS at low micromolar concentrations. Introduction of nitro or (substituted)-amino groups in position 4 of the naphthalic ring always led to less active compounds.
- Costi,Tondi,Rinaldi,Barlocco,Cignarella,Santi,Musiu,Pudu,Vacca,La Colla
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p. 1011 - 1016
(2007/10/03)
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- Inhibitors of Bllod Platelet Aggregation. Activity of Some 1H-Benzisoquinolinecarboximidamides on the in Vivo Blood Platelet Aggregation Induced by Collagen
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A series of 33-1H-benzisoquinolinecarboximidamides has been prepared and tested in the rat after intraperitoneal (ip) and/or oral (po) administration for their ability to inhibit the in vivo blood platelet aggregation induced by colagen.In this aggregation test, a considerable number of active compounds were found.Fourteen compounds were active when administred ip , five of which also exhibited significant po activity.One compound was toxic after ip administration but was found to be active after po administration without apparent toxicity.Itis thought that the solubility of the drug in water is an important factor for the resorption after oral administration and, hence, for its oral activity.
- Beetz, Tom,Meuleman, Dick G.,Wieringa, Joop H.
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p. 714 - 719
(2007/10/02)
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