- Bright fluorescence through activation of a low absorption fluorophore: The case of a unique naphthalimide-tetrazine dyad
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An original fluorescent dyad has been prepared, featuring a 1,8-naphthalimide chromophore linked to a fluorescent tetrazine. This bichromophore benefits from the good absorption coefficient of the imide, and displays a quasi complete energy transfer to the tetrazine, followed by its fluorescence emission. This allows the preparation of remarkable transparent solutions and solids displaying a strong yellow fluorescence with a long life-time.
- Qing, Zhou,Audebert, Pierre,Clavier, Gilles,Meallet-Renault, Rachel,Miomandre, Fabien,Tang, Jie
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- Synthesis and evaluation of antioxidative properties of a series of organoselenium compounds
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A series of organoselenocyanate compounds 4a-d were synthesized utilizing 1,8-naphthalic anhydride as the building unit. These compounds were evaluated for their antioxidative activities against DMBA-PMA-induced oxidative stress in a two-stage mouse skin carcinogenic model. Compound 4d was found to have the maximum antioxidative property in comparison with the other compounds. Also, the pretreatment group showed better results than the concomitant treatment groups.
- Hossain, Sk. Ugir,Sengupta, Sumitra,Bhattacharya, Sudin
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- Naphthalimide-based fluorescent Zn2+ chemosensors showing PET effect according to their linker length in water
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We have developed naphthalimide-based fluorescent chemosensors that exhibit fluorescence enhancement upon binding Zn2+ ion in 10 mM HEPES buffer (pH 7.4) at 25 °C. The fluorescence enhancement was induced by a PET inhibition process in which electron transfer from the nitrogen lone pair electrons of the Dpa unit to naphthalimide was blocked upon the binding of the sensor to Zn2+. The longer the linker length (n = 1-3) of the sensor, the less the PET efficiency becomes. Among the sensors (1, 2, and 3) examined, 1 shows the highest selectivity and sensitivity for Zn2+ over other transition metal ions and alkali metal ions in water.
- Kim, Soon Young,Hong, Jong-In
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- Naphthalene Imide Conjugates: Formation of Supramolecular Assemblies, and the Encapsulation and Release of Dyes through DNA-Mediated Disassembly
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We report the synthesis of two new amphiphilic conjugates 1 and 2 based on naphthalene di- and monoimide chromophores and the investigation of their photophysical, self-assembly and DNA-binding properties. These conjugates showed aqueous good solubility and exhibited strong interactions with DNA and polynucleotides such as poly(dG.dC)-poly(dG.dC) and poly(dA.dT)-poly(dA.dT). The interaction of these conjugates with DNA was evaluated by photo- and biophysical techniques. These studies revealed that the conjugates interact with DNA through intercalation with association constants in the order of 5-8×104 M-1. Of these two conjugates, bolaamphiphile 1 exhibited a supramolecular assembly that formed vesicles with an approximate diameter of 220 nm in the aqueous medium at a critical aggregation concentration of 0.4 mM, which was confirmed by SEM and TEM. These vesicular structures showed a strong affinity for hydrophobic molecules such as Nile red through encapsulation. Uniquely, when exposed to DNA the vesicles disassembled, and therefore this transformation could be utilised for the encapsulation and release of hydrophobic molecules by employing DNA as a stimulus.
- Shankar, Balaraman H.,Jayaram, Dhanya T.,Ramaiah, Danaboyina
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- Photoprocesses of naphthalene imide and diimide derivatives in aqueous solutions of DNA
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Despite the growing number of redox-active chromophores utilized to photoinduce oligonucleotide cleavage, detailed correlations between the degree of ground-state complexation and product yields have not been developed. To elucidate the specific role of s
- Rogers, Joy E.,Weiss, Sharon J.,Kelly, Lisa A.
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- Controllable three-component luminescence from a 1,8-naphthalimide/Eu(iii) complex: White light emission from a single molecule
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A macrocycle-appended naphthalimide derivative and its Eu(iii) complex show triple luminescence from isolated naphthalimide (blue), aggregated naphthalimide excimers (green) and Eu centres (red) with the balance being sensitive to the degree of aggregation, allowing white light emission to be obtained from a single molecule. The Royal Society of Chemistry 2012.
- Shelton, Alexander H.,Sazanovich, Igor V.,Weinstein, Julia A.,Ward, Michael D.
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- Kinetic analysis for the effect of intramolecular hydrogen bonding on photophysical properties of N-hydroxyalkyl-1, 8-naphthalimides
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N-(2-hydroxyethyl)-, N-(2-methoxyethyl)-, N-(3-hydroxypropyl)-, and N-(3-methoxypropyl)-1, 8- naphthalimide (1, 2a, 2b, 3a, and 3b, respectively) were prepared and their photophysical properties examined. The UV and IR spectra of 2a and 3a indichloromethane showed the presence ofintramolecular hydrogen bonding between the carbonyl group and the hydroxy group. In addition, the fluorescence intensities of 2a and 3a indichloromethane were found to be about two times larger than those of 1, 2b, and 3b. Furthermore, the fluorescence lifetimes of 2a and 3a, determined by picosecond single photon counting, were about two times longer than those of 1, 2b, and 3b. The rate constants of the intersystem crossing (kisca nd 3a, calculated based on the quantum yields of the intersystem crossing (Pisc) determined by the time-resolved thermallensing technique, were about one half of those obtained for 1, 2b, and 3b, while the rate constants of fluorescence emission (k f) and internal conversion (kic) were minimally affected by the presence of intramolecular hydrogen bonding. Enhancement of the fluorescence quantum yield and the lifetime of 2a and 3a was thus explained by a decrease in the efficiency of the intersystem crossing from 1(ππ*)to 3(nπ*), that results from an increase in the energy of the 3(nπ*) level due to the presence of intramolecular hydrogen bonding.
- Matsubayashi, Kazuhiko,Kajimura, Chisato,Shiratori, Hideo,Kubo, Yasuo,Yoshihara, Toshitada,Tobita, Seiji
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- White fluorescence from core-shell silica nanoparticles
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Into the white: Encapsulation of a naphthalimide moiety in the core of silica nanoparticles afforded nanospheres with a strong green excimeric emission. Together with the blue emission of the monomeric naphthalimide and the yellow fluorescence of the tetrazine acceptor on the outer shell, the added contributions provide intense white fluorescence upon 330?nm UV excitation.
- Malinge, Jeremy,Allain, Clemence,Brosseau, Arnaud,Audebert, Pierre
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- Ruthenium(II)-arene complexes with naphthalimide-tagged N,O- and N,N-chelating ligands: Synthesis and biological evaluation
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A new family of ruthenium(II)-arene complexes with naphthalimide functionalized N,O- and N,N-chelating ligands of the general formula [Ru(η6-p-cymene)Cl(L)] (2b-4b) (where: L = 4-[N-(2-((2-hydroxy-5-Br-phenyl)methyl imino)ethyl)]-N-butyl-1,8-na
- Ghebreyessus, Kesete,Peralta, Ashley,Katdare, Meena,Prabhakaran, Krishnan,Paranawithana, Shanthi
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- Modelling and Phenotypic Screening of NAP-6 and 10-Cl-BBQ, AhR Ligands Displaying Selective Breast Cancer Cytotoxicity in Vitro
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To exploit the interaction of the aryl hydrocarbon receptor (AhR) pathway in developing breast-cancer-specific cytotoxic compounds, we examined the breast cancer selectivity and the docking pose of the AhR ligands (Z)-2-(2-aminophenyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione (NAP-6; 5) and 10-chloro-7H-benzo[de]benzo[4,5]imidazo[2,1-a]isoquinolin-7-one (10-Cl-BBQ; 6). While the breast cancer selectivity of 5 in vitro is known, we discuss the SAR around this lead and, by using phenotypic cell-line screening and the MTT assay, show for the first time that 6 also presents with breast cancer selectivity, notably in the triple-negative (TN) receptor breast cancer cell line MDA-MB-468, the ER+ breast cancer cell lines T47D, ZR-75-1 and the HER2+ breast cancer cell line SKBR3 (GI50 values of 0.098, 0.97, 0.13 and 0.21 μM, respectively). Indeed, 6 is 55 times more potent in MDA-MB-468 cells than normal MCF10A breast cells (GI50 of 0.098 vs 5.4 μM) and more than 130 times more potent than in cell lines derived from pancreas, brain and prostate (GI50 of 0.098 vs 10–13 μM). Molecular docking poses of 5 and 6 together with analogue synthesis and phenotypic screening show the importance of the naphthalene moiety, and an ortho-disposed substituent on the N-phenyl moiety for biological activity.
- Baker, Jennifer R.,Pollard, Brett L.,Lin, Andrew J. S.,Gilbert, Jayne,Paula, Stefan,Zhu, Xiao,Sakoff, Jennette A.,McCluskey, Adam
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p. 1499 - 1512
(2021/03/03)
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- Synthesis and: In vitro anti-proliferative evaluation of naphthalimide-chalcone/pyrazoline conjugates as potential SERMs with computational validation
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A series of naphthalimide-chalcone/pyrazoline conjugates was prepared and evaluated for their anti-breast cancer potential against estrogen responsive, i.e. MCF-7 (ER+), and triple-negative, i.e. MDA-MB-231 (ER-), cell lines. The structure-activity-relati
- Awolade, Paul,Kaur, Mandeep,Kumar, Vipan,Oluwakemi, Ebenezer,Pankaj,Saha, Sourav Taru,Shalini,Singh, Parvesh
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p. 15836 - 15845
(2020/05/13)
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- Persistent Room-Temperature Radicals from Anionic Naphthalimides: Spin Pairing and Supramolecular Chemistry
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N-Substituted naphthalimides (NNIs) have been shown to exhibit highly efficient and persistent room-temperature phosphorescence from an NNI-localized triplet excited state, when the N-substitution is a sufficiently strong donor and mediates an intramolecu
- Huang, Wenhuan,Chen, Biao,Zhang, Guoqing
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supporting information
p. 12497 - 12501
(2019/09/10)
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- Potassium ion probe, preparation method and applications thereof
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The invention relates to a potassium ion probe, a preparation method and applications thereof, wherein the potassium ion probe has high selectivity to potassium ions, can emit green fluorescence and detect K concentration, contains hydroxyl so as to be
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Paragraph 0101-0105
(2019/11/21)
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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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- A naphthalimide phosphate potassium salt plant growth regulator and its application
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The invention discloses a naphthalimide potassium phosphate plant growth regulator with a structure represented by a formula I shown in the description. A preparation method for the naphthalimide potassium phosphate plant growth regulator comprises the steps of enabling 1,8-naphthalic anhydride and ethanolamine to react to produce N-(2-hydroxyethyl)-1,8-naphthalimide, then, enabling N-(2-hydroxyethyl)-1,8-naphthalimide to react with phosphorus oxychloride to produce N-(dichlorophosphoryl ethyl)-1,8-naphthalimide, and finally, enabling N-(dichlorophosphoryl ethyl)-1,8-naphthalimide to react with potassium hydroxide to produce the compound represented by the formula I. The compound has very good plant growth regulating activity and plays a remarkable role in promoting rooting, increasing yield and improving quality by root or seed treatment or foliage spray. The compound can be extensively applied to agricultural or forestry production as the plant growth regulator and has the characteristics of low production and use costs, good use effect, safety, no pollution and the like.
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Paragraph 0008; 0022; 0023
(2017/08/25)
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- Acetylsalicylate plant growth regulator
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The invention discloses an acetylsalicylate compound with a structure as shown in a formula I, serving as a plant growth regulator. The compound as shown in the formula I is used for promoting plants to root and sprout and promoting growing development, h
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Paragraph 0033; 0034; 0035; 0036
(2017/07/22)
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- Naphthalimide-substituted 2,4-dichlorocinnamic acid ethyl ester compound and application thereof
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The invention discloses a naphthalimide-substituted 2,4-dichlorocinnamic acid ethyl ester compound having a structure as shown in formula I used as a plant growth regulator. The compound of formula I has excellent germination and rooting promotion, yield
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Paragraph 0012; 0025; 0026; 0027
(2017/07/21)
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- Imide bit or 4 - substituted 1, 8 - naphthalene imide derivatives as PARP inhibitors
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The invention belongs to the field of medical chemistry, discloses use of imide site or 4-substituted 1, 8-naphthyl imide derivatives as PARP (poly adeno-sine diphosphate ribose polymerase) inhibitors, and in particular relates to the use of 1, 8-naphthyl imide derivative as shown in general formula (I), pharmacological or physiologically acceptable salts of the compound as shown in the general formula (I), and pharmaceutical compositions of the compound as shown in the general formula (I), as the PARP (poly adeno-sine diphosphate ribose polymerase) inhibitors. R1 and R2 have the meanings as defined.
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Paragraph 0037; 0038; 0039; 0040
(2017/04/11)
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- Design, synthesis, and identification of a novel napthalamide-isoselenocyanate compound NISC-6 as a dual Topoisomerase-IIα and Akt pathway inhibitor, and evaluation of its anti-melanoma activity
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Synthesis and anti-melanoma activity of novel naphthalimide isoselenocyanate (NISC) and naphthalimide selenourea (NSU) analogs are described. The novel agents were screened for growth inhibition of different human melanoma cell lines including those having BRAFV600E mutation (UACC903, 1205Lu, and A375M) and BRAFWT (CHL-1). In general, the NISC analogs (4a-d) were more effective in inhibiting the cell viability than the NSU analogs (7a-b). Overall, NISC-6 (4d), having a six-carbon alkyl chain, was identified as the most cytotoxic compound in both BRAFV600E mutated and BRAFWT cells. NISC-6 docked strongly into the binding sites of Akt1 and human topoisomerase IIα (Topo-IIα), and the docking results were supported by experimental findings showing NISC-6 to inhibit of both Akt pathway and Topo-IIα activity in a dose dependent manner. Furthermore, NISC-6 effectively induced apoptosis in human melanoma cells, inhibited tumor growth by ~69% in a melanoma mouse xenograft model, and showed excellent compliance with the Lipinski’ rule of five, suggesting both its efficacy and drug-like behavior under physiological conditions.
- Karelia, Deepkamal N.,Sk, Ugir Hossain,Singh, Parvesh,Gowda, A.S. Prakasha,Pandey, Manoj K.,Ramisetti, Srinivasa R.,Amin, Shantu,Sharma, Arun K.
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p. 282 - 295
(2017/05/01)
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- Naphthalenedicarboxamide ethylnaphthalene acetic ester type compound and application thereof
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The invention discloses an Naphthalenedicarboxamide ethylnaphthalene acetic ester type compound with the structure shown as the formula I and a purpose of the compound as a plant growth regulator. The compound shown as the formula I shown as the accompanying drawing has excellent plant growth regulation activity of promoting rooting, increasing the yield and improving the quality; by the modes of seed treatment or root and stem leaf spraying and the like, the compound can be widely applied to rooting, seeding strengthening, yield increase and quality improvement of plants or crops such as grains, cotton, fruit and vegetables, and has the characteristics of use safety, low cost, obvious effect and the like.
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Paragraph 0024; 0025; 0026
(2016/10/08)
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- Naphthalenedicarboxamide ethylhexoate type compound and application thereof
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The invention discloses an Naphthalenedicarboxamide ethylhexoate type compound with the structure shown as the formula I and a purpose of the compound as a plant growth regulator. The compound shown as the formula I shown as the accompanying drawing has excellent plant growth regulation functions of promoting rooting, increasing the yield and improving the quality; by the modes of seed treatment or root and stem leaf spraying and the like, the compound can be widely applied to rooting, seeding strengthening, yield increase and quality improvement of plants or crops such as grains, cotton, fruit and vegetables, and has the characteristics of use safety, low cost, obvious effect and the like.
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Paragraph 0026; 0027; 0028
(2016/10/17)
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- A phenyl [...] hERG potassium ion channel of small molecule fluorescent probe and its application (by machine translation)
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The invention discloses a phenyl furan small molecule fluorescent probe and its application. The general structure of the fluorescent probe shown in formula (I): In the formula, R 1 is halogen, a mono-substituted alkyl or alkoxy substituent base or many ; R 2 to fluorophore; n=1-6 ; ethylene in between with the fluorophore containing 1-6 is connected with the carbon of the alkyl chain. The fluorescence probe molecule can be used to mark hERG potassium ion channel, can be used for hERG the activity of the potassium ion channel inhibitors screening and listing pharmaceutical evaluation of the cardiac toxicity, in addition can also as a tool to medicine hERG potassium ion channel related phannacological, pathology and physiol research. Furthermore, this kind of compound preparation method mild reaction conditions, the raw material is cheap and easy to obtain, operation and after treatment is simple. (by machine translation)
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Paragraph 0057; 0063; 0064
(2016/11/24)
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- 1,8-Naphthalimide derivatives: New leads against dynamin i GTPase activity
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Fragment-based in silico screening against dynamin I (dynI) GTPase activity identified the 1,8-naphthalimide framework as a potential scaffold for the design of new inhibitors targeting the GTP binding pocket of dynI. Structure-based design, synthesis and subsequent optimization resulted in the development of a library of 1,8-naphthalimide derivatives, called the Naphthaladyn series, with compounds 23 and 29 being the most active (IC50 of 19.1 ± 0.3 and 18.5 ± 1.7 μM respectively). Compound 29 showed effective inhibition of clathrin-mediated endocytosis (IC50(CME) 66 μM). The results introduce 29 as an optimised GTP-competitive lead Naphthaladyn compound for the further development of naphthalimide-based dynI GTPase inhibitors.
- Abdel-Hamid, Mohammed K.,Macgregor, Kylie A.,Odell, Luke R.,Chau, Ngoc,Mariana, Anna,Whiting, Ainslie,Robinson, Phillip J.,McCluskey, Adam
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p. 8016 - 8028
(2015/07/27)
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- Development of unsymmetrical dyads as potent noncarbohydrate-based inhibitors against human β-N-acetyl-D-hexosaminidase
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Human β-N-acetyl-D-hexosaminidase has gained much attention due to its roles in several pathological processes and been considered as potential targets for disease therapy. A novel and efficient skeleton, which was an unsymmetrical dyad containing naphthalimide and methoxyphenyl moieties with an alkylamine spacer linkage as a noncarbohydrate-based inhibitor, was synthesized, and the activities were valuated against human β-N-acetyl-D- hexosaminidase. The most potent inhibitor exhibits high inhibitory activity with Ki values of 0.63 μM. The straightforward synthetic manners of these unsymmetrical dyads and understanding of the binding model could be advantageous for further structure optimization and development of new therapeutic agents for Hex-related diseases.
- Guo, Peng,Chen, Qi,Liu, Tian,Xu, Lin,Yang, Qing,Qian, Xuhong
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supporting information
p. 527 - 531
(2013/07/26)
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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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- 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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- 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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- Development of novel naphthalimide derivatives and their evaluation as potential melanoma therapeutics
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Synthesis and anti-melanoma activity of various naphthalimide analogs, rationally modified by introducing isothiocyanate (ITC) and thiourea (TU) functionalities, found in well-known anti-cancer agents, is described. The structure-activity relationship comparison of the novel agents in inhibiting cancer cell growth was evaluated in various melanoma cell lines. Both ITC and TU analogs effectively inhibited cell viability and induced apoptosis in various human melanoma cells. Nitro substitution and increase in alkyl chain length, in general, enhanced the apoptotic activity of ITC derivatives. All the new compounds were well tolerated when injected intraperitoneal (i.p.) in mice at effective doses at which both the ITC and TU derivatives inhibited melanoma tumor growth in mice following i.p. xenograft. The nitro substituted naphthalimide-ITC derivative 3d was found to be the most effective in inducing apoptosis, and in inhibiting melanoma cell and tumor growth.
- Sk, Ugir Hossain,Prakasha Gowda,Crampsie, Melissa A.,Yun, Jong K.,Spratt, Thomas E.,Amin, Shantu,Sharma, Arun K.
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scheme or table
p. 3331 - 3338
(2011/08/06)
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- Molecular recognition of DNA by rigid [n]-polynorbornane-derived bifunctional intercalators: Synthesis and evaluation of their binding properties
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We have exploited the concept of multivalency in the context of DNA recognition, using novel chemistry to synthesize a new type of bis-intercalator with unusual sequence-selectivity. Bis-intercalation has been observed previously, but design principles for de novo construction of such molecules are not known. Our compounds feature two aromatic moieties projecting from a rigid, polynorbornane-based scaffold. The length and character of the backbone as well as the identity of the intercalators were varied, resulting in mono- or divalent recognition of the double helix with varying affinity. Our lead compound proved to be a moderately sequence-selective bis-intercalator with an unwinding angle of 27° and a binding constant of about 8 μM. 9-Aminoacridine rings were preferred over acridine carboxamides or naphthalimides, and a rigid [3]-polynorbornane scaffold was superior to a [5]-polynorbornane. The flexibility of the linker connecting the rings to the scaffold, although less influential, could affect the strength and character of the DNA binding.
- Van Vliet, Liisa D.,Ellis, Tom,Foley, Patrick J.,Liu, Ligong,Pfeffer, Frederick M.,Russell, Richard A.,Warrener, Ronald N.,Hollfelder, Florian,Waring, Michael J.
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p. 2326 - 2340
(2008/02/05)
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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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- Photoinduced electron transfer in covalently linked 1,8-naphthalimide/viologen systems
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A series of polymethylene-linked 1,8-naphthalimide/viologen diads has been synthesized. The number of intervening methylenes was varied from 2 to 6. For comparison, a series of W-alkylpyridiniumyl-1,8-naphthalimide "parent" compounds was prepared and phot
- Le, Thao P.,Rogers, Joy E.,Kelly, Lisa A.
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p. 6778 - 6785
(2007/10/03)
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- Various 2-(substituted piperazinyl)-1H-benz [de]isoquinoline-1,3 (2H) -diones
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Compounds of the following formula and their acid addition salts STR1 Z is STR2 A is straight or branched chain alkylene of 2 to 6 carbons; B is straight chain alkylene of 2 to 4 carbons; X is straight or branched chain alkyl of 1 to 8 carbons, phenyl, benzyl, phenethyl, substituted phenyl, substituted benzyl, or substituted phenethyl, R1 and R2 are located at the 7 or 8 and 5 or 6 position respectively and are independently selected from the group consisting of hydrogen, straight or branched chain alkyl of 1 to 4 carbons, straight or branched chain alkoxy of 1 to 4 carbons, Cl, Br, F, amino, nitro, CF3, and cyano; are disclosed. These compounds possess antiprotozoal activity.
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- Various 2-substituted-1H-benz[de]isoquinoline-1,3(2H)-diones
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Compounds of the following formula and their acid addition salts STR1 A is straight or branched chain alkylene of 2 to 6 carbons; R1 and R2 are located at the 7 or 8 and 5 or 6 position respectively and are independently selected from the group consisting of hydrogen, straight or branched chain alkyl of 1 to 4 carbons, straight or branched chain alkoxy of 1 to 4 carbons, Cl, Br, F, amino, nitro, cyano, and CF3 ; R3 and R4 are independently selected from the group consisting of hydrogen and straight or branched chain alkyl of 1 to 4 carbons; and n is 1, 2, or 3; m is 1 or 2; are disclosed. These compounds possess anti-protozoal activity.
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- 2-(Piperidinyl or tetrahydropyridinyl)-alkyl)-2,3-dihydro-3-hydroxy-1H-benz(DE)isoquinolin-1-ones
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Compounds of the following formula STR1 wherein R1 and R2 are selected from hydrogen, lower alkyl, lower alkoxy, lower alkylthio, halogen, trifluoromethyl, nitro, amino and cyano; Z is selected from STR2 R3 is selected fro
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- Use of 2-(hydroxyalkyl)-1H-benz[de]isoquinoline-1,3(2H)-diones as anti-allergy agents
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Method of treating allergies with a pharmaceutical composition containing as the active ingredient a compound or mixture of compounds of the formula STR1 wherein R1 and R2 are independently selected from hydrogen, halogen, trifluoromethyl, lower alkyl, lower alkoxy, lower alkylthio, nitro, amino, or cyano; and A is a straight or branched chain alkylene of 1 to 8 carbons.
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- 2-[(4-Oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-8-yl)alkyl]-1H-benz[de]isoquinolin-1,3(2H)-diones
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Compounds of the following formula and their acid addition salts STR1 wherein R1 and R2 are selected from hydrogen, lower alkyl, lower alkoxy, lower alkylthio, halogen, trifluoromethyl, amino, nitro and cyano; R3 is hydrogen, lower alkyl or lower alkenyl; R4 is hydrogen, halogen, or lower alkyl; and A is straight or branched chain alkylene are disclosed. These compounds exhibit antidepressant activity. In addition, these compounds are useful as antiinflammatory agents.
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- 2-[(Dihydroisoquinolinyl or dihydroisoindol-2-yl)alkyl]-1H-benz[de]isoquinoline-1,3(2H)-diones
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Compounds of the following formula and their acid addition salts SPC1 Wherein R1, R2, R3, and R4 are independently selected from hydrogen, halogen, lower alkyl, lower alkoxy, lower alkylthio, nitro, cyano, amino and trifluoromethyl; A is a straight or branched chain alkylene of 1 to 8 carbons; and m is 1 or 2 are disclosed. These compounds exhibit antidepressant and anti-anxiety activity. In addition these compounds are useful as antiinflammatory agents.
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- 2-[[4-(2,3-Dihydro-2-oxo-1H-benzimidazol-1-yl)-1-(piperidinyl or 1,2,3,6-tetrahydro-1-pyridinyl)]alkyl]-1H-benz[de]isoquinoline-1,3(2H)-diones
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Compounds of the following formula and their acid addition salts STR1 wherein R1 and R2 are selected from hydrogen, halogen, lower alkyl, lower alkoxy, lower alkylthio, nitro, amino, trifluoromethyl, or cyano; R3 is hydrogen or lower alkyl; R4 and R5 are selected from hydrogen, halogen, lower alkyl, or lower alkoxy; the dashed line indicates the optional presence of a double bond; and A is straight or branched chain alkylene of 1-8 carbons; are disclosed. These compounds exhibit antidepressant activity. In addition, these compounds are useful as antiinflammatory agents.
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- 2-[[4-(Azine or diazine or triazine)-1-piperazinyl]alkyl]-1H-benz[de]isoquinoline-1,3(2H)-diones
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Compounds of the following formula and their acid addition salts SPC1 Wherein R1 and R2 are independently selected from hydrogen, halogen, lower alkyl, lower alkoxy, lower alkylthio, nitro, cyano, amino and trifluoromethyl; A is a straight or branched chain alkylene of 1 to 8 carbons; and R is a 6-membered unsaturated substituted or unsubstituted heterocyclic ring selected from pyridine, diazine and triazine are disclosed. These compounds exhibit antidepressant activity. In addition these compounds are also useful as antiinflammatory agents.
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- 2-[(Substituted-piperidinyl or tetrahydropyridinyl)alkyl]-1H-benz[de]isoquinoline-1,3(2H)-diones
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Compounds of the following formula and their acid addition salts SPC1 Wherein R1 and R2 are independently selected from hydrogen, halogen, lower alkyl, lower alkoxy, lower alkylthio, nitro, cyano, amino and trifluoromethyl; A is a st
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- 2-[(Substituted-piperazinyl)alkyl]-1H-benz[de]isoquinoline-1,3(2H)-diones
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Compounds of the following formula and their acid addition salts SPC1 Wherein R1 and R2 are independently selected from hydrogen, halogen, lower alkyl, lower alkoxy, lower alkylthio, nitro, cyano, amino and trifluoromethyl; A is a st
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- N-(1-(1,3-Dihydro-1,3-dioxo-2H-benz(de)-isoquinolin-2-yl)alkyl)-4-N-piperidinyl)-n-phenylalkylamides
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Compounds of the following formula and their acid addition salts SPC1 Wherein R1 and R2 are independently selected from hydrogen, halogen, lower alkyl, lower alkoxy, lower alkylthio, nitro, cyano, amino and trifluoromethyl; A is a st
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