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Synthesis and reversal effect of a novel N-substituted phthalimidesugar on doxorubicin resistant of human breast cancer cells
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作者 易文渊 李敏 +5 位作者 杨亚平 吕卓远 徐波 韩冬 李中军 崔景荣 《Journal of Chinese Pharmaceutical Sciences》 CAS 2008年第4期319-323,共5页
Thalidomide (α-N-phthalimido-glutarimide, TLD) is a kind of anti-angiogenic and anti-inflammatory drug, and showed effects in the treatment of several disease entities. In this study, the biological effects of a no... Thalidomide (α-N-phthalimido-glutarimide, TLD) is a kind of anti-angiogenic and anti-inflammatory drug, and showed effects in the treatment of several disease entities. In this study, the biological effects of a novel N-sugar substituted phthalimide (STA-35) on the regulation of multidrug resistance (MDR) to doxorubicin (ADR) were investigated. The proliferation of cancer cells was detected by a SRB assay. The activity of P-glycoprotein (P-gp) was determined by a Flow cytometry. The expression of P-gp was measured by western blotting. The results showed that STA-35 inhibited the proliferation of human breast cancer cell line MCF-7 and its ADR resistant cell line MCF-7/ADR, and the relative resistance was only 1.19. Meanwhile, STA-35 could sensitize the cytotoxicity of ADR in MCF-7/ADR cells. In addition, we found that STA-35 reduced the activity of P-gp by suppressing the P-gp expression, which was indicated by the increase in the accumulation of rhodamine 123 in MCF-7/ADR cells. These results suggested a promising application of STA-35 as the MDR reversing agent. The underlying mechanism of the effects might be attributed to the inhibition of P-gp. 展开更多
关键词 Multidrug resistance THALIDOMIDE PHTHALIMIDE P-GLYCOPROTEIN
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Ionic liquid [bmim][BF_4] acts as solvent and promoter for synthesis of halo-containing N-arylphthalimides
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作者 Dong Chu Chen Hong Qi Ye Hao Wu 《Chinese Chemical Letters》 SCIE CAS CSCD 2007年第1期27-29,共3页
A new synthetic process of N-arylphthalimide and halo-containing N-arylphthalimides through the reaction between phthalic anhydride and aromatic amines bearing halo groups in [bmim][BF4] was described, ionic liquid [b... A new synthetic process of N-arylphthalimide and halo-containing N-arylphthalimides through the reaction between phthalic anhydride and aromatic amines bearing halo groups in [bmim][BF4] was described, ionic liquid [bmim][BF4] acted as the dual role of solvent and promoter. 展开更多
关键词 Phthalic anhydride Aromatic amines phthalimides Ionic liquid [bmim]BF4
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The Synthesis of Arylsulfonylphthalimides and Their Reactions with Several Amines in Acetonitrile
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作者 Seyhan Ozturk Halil Kutuk 《International Journal of Organic Chemistry》 2011年第4期202-206,共5页
In this study, several N-(p-substituted-arylsulfonyl)phthalimides (1a-e) were synthesized. The synthesized compounds were then examined with respect to their substitution reactions with t-butylamine, diethylamine, cyc... In this study, several N-(p-substituted-arylsulfonyl)phthalimides (1a-e) were synthesized. The synthesized compounds were then examined with respect to their substitution reactions with t-butylamine, diethylamine, cyclohexylamine, and trans-1,2-diaminocyclohexane in acetonitrile. In order to determine the mechanism, substituent effect, activation entropy, and nucleophile effect were used as criteria. 展开更多
关键词 Arylsulfonyl phthalimides Mechanism SUBSTITUENT Effect Activation Entropy
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2,4,6-Trichloro-1,3,5-triazine/dimethylformamide as an efficient reagent for one-pot conversion of alcohols into N-alkylphthalimides 被引量:3
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作者 Babak Mokhtari Roya Azadi Aseieh Azhdari 《Chinese Chemical Letters》 SCIE CAS CSCD 2010年第2期171-174,共4页
An efficient and mild method for the direct conversion of alcohols into N-alkylphthalimides using 2,4,6-trichloro-1,3,5-triazine and dimethylformamide was described.The reaction was preceded via(alcoxymethylene) dimet... An efficient and mild method for the direct conversion of alcohols into N-alkylphthalimides using 2,4,6-trichloro-1,3,5-triazine and dimethylformamide was described.The reaction was preceded via(alcoxymethylene) dimethylammonium chloride intermediate and produced corresponding N-alkylphthalimides in good-to-excellent yields. 展开更多
关键词 Alcohol Potassium phthalimide 2 4 6-Trichloro-1 3 5-triazine DIMETHYLFORMAMIDE N-alkylphthalimide
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Fragmentation of Some Substituted Phthalimides on Electron Impact Ionization
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作者 WEI Junhua DONG Dewen +2 位作者 LIU Zhiqiang LIU Shuying JIN Danhong 《Chemical Research in Chinese Universities》 SCIE CAS CSCD 1999年第2期99-103,共5页
IntroductionTheeliminationsofCOandCO2fromthemolecularionsofphthalimideanditsN-methyl,N-phenylderivativesinma... IntroductionTheeliminationsofCOandCO2fromthemolecularionsofphthalimideanditsN-methyl,N-phenylderivativesinmassspectrometrywer... 展开更多
关键词 Substituted phthalimide Mass spectrometry Electron impact Electron impact
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Photoredox Synthesis of Thio-Functionalized Cyclic Ethers Using N-Sulfenyl Phthalimides as a Thiyl-Radical Precursor
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作者 Maojian Lu Rong-Bin Liang +2 位作者 Can-Ming Zhu Qing-Xiao Tong Jian-Ji Zhong 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2023年第15期1823-1828,共6页
Comprehensive Summary A visible-light mediated exclusively regioselective synthesis of 2,2-disubstituted thio-functionalized tetrahydrofurans,tetrahydro-pyrans and oxepanes has been described through an operationally ... Comprehensive Summary A visible-light mediated exclusively regioselective synthesis of 2,2-disubstituted thio-functionalized tetrahydrofurans,tetrahydro-pyrans and oxepanes has been described through an operationally simple and mild photoredox protocol.Thiyl radical generated from N-phenylsulfenyl phthalimide by photoredox catalysis was proven to be the key reactive intermediate in this reaction. 展开更多
关键词 Photoredox catalysis Cyclic ethers Thio-functionalization Thiyl radical Sulfenylating reagent N-Sulfenyl phthalimides Synthetic methods CYCLOADDITION Reaction mechanisms
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Tunable System for Electrochemical Reduction of Ketones and Phthalimides 被引量:2
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作者 Yaxin Wang Jianyou Zhao +2 位作者 Tianjiao Qiao Jian Zhang Gong Chen 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2021年第12期3297-3302,共6页
Herein,we report an efficient,tunable system for electrochemical reduction of ketones and phthalimides at room temperature without the need for stoichiometric external reductants.By utilizing NaN_(3) as the electrolyt... Herein,we report an efficient,tunable system for electrochemical reduction of ketones and phthalimides at room temperature without the need for stoichiometric external reductants.By utilizing NaN_(3) as the electrolyte and graphite felt as both the cathode and the anode,we were able to selectively reduce the carbonyl groups of the substrates to alcohols,pinacols,or methylene groups by judiciously choosing the solvent and an acidic additive.The reaction conditions were compatible with a diverse array of functional groups,and phthalimides could undergo one-pot reductive cyclization to afford products with indolizidine scaffolds.Mechanistic studies showed that the reactions involved electron,proton,and hydrogen atom transfers.Importantly,an N_(3)/HN_(3) cycle operated as a hydrogen atom shuttle,which was critical for reduction of the carbonyl groups to methylene groups. 展开更多
关键词 ELECTROCHEMISTRY REDUCTION KETONES phthalimides Radical reactions
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Water-Promoted Ring-Opening Reactions of N-Substituted Saccharins and Phthalimides by Amines
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作者 Lisha Bai Xuan Zhang Ning Ma 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2014年第9期871-877,共7页
The reactions of N-substituted saccharins and phthalimides with amines were promoted by water.Various o-sulfamoyl benzamides and N,N′-disubstituted phthalamides were prepared in moderate to good yields.These reaction... The reactions of N-substituted saccharins and phthalimides with amines were promoted by water.Various o-sulfamoyl benzamides and N,N′-disubstituted phthalamides were prepared in moderate to good yields.These reactions have prominent advantages,such as short reaction time,less by-products and simple isolation of the products.Water can probably stabilize the reaction intermediates and facilitate precipitation of the ring-opening products.When steric hindrance arose,hydrolytic compounds,either free acid or salts of the acids,were obtained.Possible reason for the formation of amine salts of o-sulfamoyl benzoic acids was proposed. 展开更多
关键词 SULFONAMIDES HYDROLYSIS RING-OPENING saccharins phthalimides
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Synthesis and in vitro Fungicidal Activity of a Series of Novel N-(Heterocycly)phthalimides
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作者 Ban, Shurong Chen, Wenbin Xi, Zhen 《Chinese Journal of Chemistry》 SCIE CAS CSCD 2011年第3期515-520,共6页
A series of novel phthalimides was prepared and tested for antifungal activity in vitro against seven phytopa- thogenic fungi: Rhizoctonia solani, Fusarium oxysporum f.sp. cucumerinum Owen., Botrytis cinerea, Fulvia ... A series of novel phthalimides was prepared and tested for antifungal activity in vitro against seven phytopa- thogenic fungi: Rhizoctonia solani, Fusarium oxysporum f.sp. cucumerinum Owen., Botrytis cinerea, Fulvia fulva, Sclerotinia sclerotiorum de Bary, Phytophthora capsici, Botryosphaeria berengeriama. The results showed that those compounds holding the structure of 6-methylpyridin-2-yl exhibited good activity against Phytophthora capsici and Botrytis cinerea. 展开更多
关键词 phthalimides SYNTHESIS biological activity antifungal agents
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Synthesis,biochemical evaluation and computational simulations of new cytochrome bc1 complex inhibitors based on N-(4-aryloxyphenyl)phthalimides
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作者 Hua Cheng Yan Fu +6 位作者 Qing Chang Ni Zhang Mengwei Bu Yan Niu Qiongyou Wu Cheng Chen Francis Verpoort 《Chinese Chemical Letters》 SCIE CAS CSCD 2018年第12期1897-1900,共4页
The cytochrome bc1complex(the bc1complex or complex Ⅲ) is an attractive target for the discovery of numerous pharmaceuticals and pesticides. In order to identify new lead structures for this target, a new series of m... The cytochrome bc1complex(the bc1complex or complex Ⅲ) is an attractive target for the discovery of numerous pharmaceuticals and pesticides. In order to identify new lead structures for this target, a new series of molecules, N-(4-aryloxyphenyl)phthalimides, were designed and synthesized in a straightforward manner. Our design strategy was to introduce a 4-aryloxyphenyl group, a fragment which exhibited promising bc1complex-inhibiting properties, into the aryl group of the valuable N-arylphthalimide backbone. Afterward, the biochemical evaluation of the newly synthesized compounds was carried out,and the results implied that several compounds demonstrated good activities against succinatecytochrome reductase(SCR, a mixture of mitochondrial complex Ⅱ and the bc1complex). Further studies confirmed that 3e’, a representative compound in this paper, was identified as an inhibitor of the bc1complex. Furthermore, computational simulations were also performed to better understand binding of 3e’ to the enzyme complex, which indicated that 3e’ should bind to the Qosite of the bc1complex.Consequently, we harbor the idea that this paper can provide a solid platform for synthesis and discovery of other bc1complex inhibitors. 展开更多
关键词 Cytochrome bc_1 complex Inhibitor N-(4-Aryloxyphenyl)phthalimide SYNTHESIS Biochemical evaluation Computational simulation
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Synthesis, Characterization and Antiepileptic Activity of Some New N-Substituted Phthalimide Analogs
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作者 Omran N. R. Fhid Shaban E. A. Saad +6 位作者 Talal H. Zeglam Asma Eswayah Tariq Elmoug Esra Alnnas Yousra Haroon Ahmed A. Eldep Abdelhamed Ebzabez 《Journal of Life Sciences》 2014年第4期373-377,共5页
The present study was designed to investigate the anticonvulsant effect of series phthalimides possessing an N-aromatic amines moiety substituted at position 2 (2-7). The compounds synthesized using phthalic anhydri... The present study was designed to investigate the anticonvulsant effect of series phthalimides possessing an N-aromatic amines moiety substituted at position 2 (2-7). The compounds synthesized using phthalic anhydride and various amines in reflux synthesizer. The chemical structures of the titled compound were confirmed by physical and spectra analysis. All the synthesized compounds were evaluated in vivo for antiepileptic activity by using standard experimental models. Compounds: 2-(3H-1, 2, 4-Triazole-3-y) isoindoline-1, 3-dione (2), Ethyl-4(1, 3-dioxoisoindoline-2-yl) benzoate 3 and 2-(4-nitrophenyl) isoindoline-1,3dione (7) were found significantly (P 〈 0.01-0.00001) delayed the onset and antagonized picrotoxin-induced seizures. 展开更多
关键词 phthalimides anticonvulsant activity reflux synthesizer.
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Synthesis and Structural Analysis of Novel Norspermidine Derivatives
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作者 Bogumil Brycki Iwona Kowalczyk +2 位作者 Justyna Werner Tomasz Pospieszny Anna Koziróg 《International Journal of Organic Chemistry》 2017年第2期106-139,共34页
A series of new norspermidine derivatives, both nonionic and cationic, have been obtained. Structures of the synthesized compounds have been estab-lished by FTIR, 1H NMR, 13C NMR, 2D NMR, mass spectrometry and element... A series of new norspermidine derivatives, both nonionic and cationic, have been obtained. Structures of the synthesized compounds have been estab-lished by FTIR, 1H NMR, 13C NMR, 2D NMR, mass spectrometry and elemental analyses. Physicochemical and anti-microbial properties have been discussed. 展开更多
关键词 Polyamines Norspermidine phthalimides Quaternary Ammonium Salts Antimicrobial Activity FTIR ^(1)H NMR ^(13)C NMR 2D NMR MS
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Synthesis and cytotoxic activity of heterocycle-substituted phthalimide derivatives 被引量:1
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作者 Ya Jun Yang Ya Nan Yang +4 位作者 Jian Shuang Jiang Zi Ming Feng Hong Yan Liu Xian Dao Pan Pei Cheng Zhang 《Chinese Chemical Letters》 SCIE CAS CSCD 2010年第8期902-904,共3页
A series of heterocycle-substituted phthalimide derivatives were synthesized.Structurally diverse derivatives with heterocyclic rings,including furan,imidazo[1,2-a]pyridine,1,3,4-thiadiazine,imidazo[2,1-b][1,3,4]thiad... A series of heterocycle-substituted phthalimide derivatives were synthesized.Structurally diverse derivatives with heterocyclic rings,including furan,imidazo[1,2-a]pyridine,1,3,4-thiadiazine,imidazo[2,1-b][1,3,4]thiadiazine,pyrazole,1,2,4-triazolo[3,4- b][1,3,4]thiadiazine,thiazole and thiazoline,were obtained by the reactions ofα-bromoketone intermediate with various nucleophiles containing oxygen,nitrogen and sulfur atom.Their cytotoxic activity was also evaluated against five human cancer cell lines in vitro. 展开更多
关键词 PHTHALIMIDE HETEROCYCLE α-Bromoketone Cytotoxic activity
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PHOTO-CIDNP STUDIES OF PHTHALIMIDE DERIVATIVES IN THE PRESENCE OF TRIETHYLAMINE 被引量:1
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作者 Ling Jiang CHENG~(1,2) Han Cheng YUAN~3 Hua Pin PU~4 Bao Zhen YAN~3 Er Cheng LI~2 Jian Hua XU~4 Jin Shi MA~1 Guang Zhi XU~2 1 Institute of Photographic Chemistry,Chinese Academy Of Sciences,Beijing 100101 2 Institute of Chemistry,Chinese Academy of Sciences,Beijing 100080 3 Department of Applied Chemistry,Beijing Institute of Chemical Technology,Beijing 100029 4 Department of Chemistry,Nanjing University,Nanjing,Jiangsu 210008 《Chinese Chemical Letters》 SCIE CAS CSCD 1993年第4期331-334,共4页
The photoreactivity of some phthalimides was tested by CIDNP studies on the reactions with triethylamine.
关键词 CIDNP PHOTO-CIDNP STUDIES OF PHTHALIMIDE DERIVATIVES IN THE PRESENCE OF TRIETHYLAMINE
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An Unusual Reductive Ring-opening Reaction of Phthalimide with Sodium Hydride in DMF
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作者 XiangBaoMENG HuiLI QingLI ZhongJunLI 《Chinese Chemical Letters》 SCIE CAS CSCD 2004年第7期777-778,共2页
An unusual reductive ring-opening reaction of phthalimide with sodium hydride in anhydrous DMF was observed for the first time. The presumed mechanism was described in detail.
关键词 PHTHALIMIDE BENZYLATION reduction ring-opening.
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Synthesis of á-aminonitrile through Anodic Cyanation of N-benzylpiperidine
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作者 Zhao Ping , Yin Ying-wu1,2, 1 ? 1. Department of Chemistry, Tsinghua University, Beijing 100084, China 2. 4F TH-UNIS Building II, Beijing TH-UNIS Insight Co., Ltd. Beijing, China 《合成化学》 CAS CSCD 2004年第z1期44-44,共1页
关键词 MICHAEL addition phthalimide acrylonitrile β -alanine phase transfer catalysis.
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Synthesis of Novel Non-Nucleoside HIV-1 Reverse Transcriptase Inhibitors-1-(3-Phthalimido-2-oxobutyl)-4-Substituted-phenylpiperazines
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作者 Xin CHEN Lin WANG +3 位作者 Zhi Zhong ZHAO Xing Quan ZHANG Xiang Hong CHEN Hong Shan CHEN(Institute of Materia Medica, Chinese Academy of Medical Sciences & Peking Union Medical College, Beijing 100050 Institute of Medicinal Biotechnology, Chinese Academy of M 《Chinese Chemical Letters》 SCIE CAS CSCD 2000年第7期571-572,共2页
We have designed and synthesized a series of new phthalimidopiperazines, biological activity test show that the target compounds(Ic, Ie, ii) can inhibit HIV-I RT with IC50 20.0, 43.8, and 63.7 mu M, respectively.
关键词 PIPERAZINE PHTHALIMIDE HIV1-RT inhibitor
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Synthesis, Spectral Characterization and Ligation of <i>N</i>-[2-(Phenylseleno)ethyl]phthalimide
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作者 Rupali Rastogi Sanjay Kumar Srivastava +1 位作者 Shikha Asolia Raymond J. Butcher 《Journal of Crystallization Process and Technology》 2013年第1期31-34,共4页
PhSe-Na+ generated in situ by reduction of PhSeSePh, with sodium borohydride on reaction with N-(2-bromoethyl) phthalimide in N2 atmosphere results in the formation of N-[2-(phenylseleno)ethyl]phthalimide (L1). The ti... PhSe-Na+ generated in situ by reduction of PhSeSePh, with sodium borohydride on reaction with N-(2-bromoethyl) phthalimide in N2 atmosphere results in the formation of N-[2-(phenylseleno)ethyl]phthalimide (L1). The title compound has been characterized by elemental analysis, FT-IR, 1H and 13C NMR techniques. The crystal structure of L1 has been solved by direct methods and refined by full-matrix least squares. The ligand L1 crystallize in the monoclinic space group. Selenium forms two Se-C linkages, one is due to Se-Calkyl and the other one to Se-Caryl. Further, the ligation reaction of L1 with complex 1 is also explored whose identities are characterized by spectroscopic techniques. 展开更多
关键词 PHTHALIMIDE Selenium MONOCLINIC Phenylseleno Sodium BOROHYDRIDE
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Photoinduced generation of alkyl and phthalimide nitrogen radicals from N-hydroxyphthalimide esters for the synthesis of benzophenone-type bioisosteres
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作者 Fei Li Jianyang Dong +7 位作者 Huijuan Liao Jiayi Dang Xuechen Zhou Yuying Wang Chenya Wang Qin Jiang Gang Li Dong Xue 《Science China Chemistry》 SCIE EI CAS CSCD 2024年第10期3389-3396,共8页
N-Hydroxyphthalimide(NHPI)esters have emerged as powerful sources of alkyl radicals generated by single-electron transfer,but homolysis of NHPI ester to produce an alkyl radical and a phthalimide nitrogen radical is s... N-Hydroxyphthalimide(NHPI)esters have emerged as powerful sources of alkyl radicals generated by single-electron transfer,but homolysis of NHPI ester to produce an alkyl radical and a phthalimide nitrogen radical is still in its infancy.In this study,we developed a light-induced method for generation of alkyl and phthalimide nitrogen radicals from NHPI esters and subsequent reactions of the radicals with[1.1.1]propellane and aryl aldehydes for rapid generation of bicycle[1.1.1]pentane ketones.This method does not require metals or photosensitizers,features a broad substrate scope(90 examples)and excellent functional group tolerance,and can be used for the functionalization of structurally complex natural products and drugs.Mechanistic investigations indicate that the reaction involves photoinduced homolytic cleavage of the Cs_(2)CO_(3)-NHPI ester complex to produce alkyl and phthalimide nitrogen radicals and subsequent hydrogen atom transfer between the phthalimide nitrogen radical and the aldehyde to generate an acyl radical. 展开更多
关键词 phthalimide nitrogen radicals aryl aldehydes hydrogen atom transfer bicycle[1.1.1]pentane ketones BIOISOSTERES
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Chlorinated phthalimide polymer donor as ultra-wide bandgap and deep HOMO guest for achieving highly efficient polymer solar cells
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作者 Weichao Zhang Jianhua Huang +8 位作者 Xiaoyu Lv Ming Zhang Wanru Liu Tianzi Xu Jun Ning Alata Hexig Feng Liu Aiju Xu Chuanlang Zhan 《Chinese Chemical Letters》 SCIE CAS CSCD 2023年第4期501-506,共6页
Quaternary approach has been receiving more and more attention due to its effectiveness in improving solar cell performance, while synthesis/selection of the fourth component is yet a key issue. Herein, we report a ch... Quaternary approach has been receiving more and more attention due to its effectiveness in improving solar cell performance, while synthesis/selection of the fourth component is yet a key issue. Herein, we report a chlorinated phthalimide based donor polymer(namely Ph I-Cl) having an ultra-wide bandgap(2.10 e V) and a deep HOMO(-5.58 e V) level. Addition of Ph I-Cl as the third component of PM6:Y6 and the fourth of PM6:Y6:PC71BM increases both hole and electron mobilities and gives rise to more balanced charge carriers mobilities. Both the short-circuit current-density and fill-factor are increased and open-circuit voltage is well maintained, delivering 17.0% and 18.1% efficiencies, respectively. These results demonstrate that chlorination on the side thiophene of phthalimide-based donor polymer is a way to make deep HOMO and ultra-wide bandgap donor polymer guest used for highly efficient ternary and quaternary strategies. 展开更多
关键词 Phthalimide polymer donor Quaternary strategy Polymer solar cell Wide bandgap Fullerene-free
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