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Organic Electrofluorescent Materials Using Pyridine-Containing Macrocyclic Compounds 被引量:1
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作者 Tingxi LI Long FU Wenwen YU Renhe HUANG 《Journal of Materials Science & Technology》 SCIE EI CAS CSCD 2008年第5期753-756,共4页
Novel pyridine-containing macrocyclic compounds, such as 6,12,19,25-tetramethyl-7,11,20,24-dinitrilo-dibenzo [b,m]1,4,12,15-tetra-azacyclodoc osine (TMCD), were synthesized and used as electron transport layer in or... Novel pyridine-containing macrocyclic compounds, such as 6,12,19,25-tetramethyl-7,11,20,24-dinitrilo-dibenzo [b,m]1,4,12,15-tetra-azacyclodoc osine (TMCD), were synthesized and used as electron transport layer in organic electroluminescent devices. Devices with a structure of glass/indium-tin oxide/arylamine derivative/ tris(quinolinolato)aluminum(Ⅲ) (Alq)/TMCD/LiF/Al exhibited green emission from the Alq layer with external quantum efficiency of 0.84% and luminous efficiency of 1.3 lm/W. The derivatives of TMCD were synthesized and characterized as well. These compounds were also found to be useful as the electron-transporting materials in organic electroluminescent devices. 展开更多
关键词 pyridine-containing macrocyclic compound Organic electroluminescent Electron-transporting material
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CLEMOCHINENOSIDE A, A MACROCYCLIC COMPOUND FROM CLEMATIS CHINENSIS 被引量:2
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《Chinese Chemical Letters》 SCIE CAS CSCD 1992年第2期119-120,共2页
The structure of a new macrocyclic compound, clemochinenoside A obtained from Clematis chinensis was identified by NMR, FAB-MS, NOE and chemical hydrolysis.
关键词 NOE CLEMOCHINENOSIDE A PRO A macrocyclic compound FROM CLEMATIS CHINENSIS
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Synthesis and characterization of macrocyclic compounds with a hydroxyl functional group 被引量:1
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作者 Min Ou Chun Zhu +1 位作者 Qi-Long Zhang Bi-Xue Zhu 《Chinese Chemical Letters》 SCIE CAS CSCD 2013年第10期869-872,共4页
A novel [1+1] Schiff-base macrocyclic compound 3 has been synthesized from precursor 1, 1,3-bis(2'- formylphenoxy)-2-propanol, and precursor 2, resorcinol-bis(4-aminophenyl)ether, via condensation and cyclizacti... A novel [1+1] Schiff-base macrocyclic compound 3 has been synthesized from precursor 1, 1,3-bis(2'- formylphenoxy)-2-propanol, and precursor 2, resorcinol-bis(4-aminophenyl)ether, via condensation and cyclizaction using Ba2+ as template. The macrocycle 3 was further reduced giving saturated macrocycle 4. The structures of 3 and 4 were characterized by elemental analysis, ~H NMR, IR, and MS spectra, and their structures were determined via single crystal X-ray diffraction studies. X-ray diffraction analysis revealed that the macrocyclic compound 3 has a folded conformation, and the corresponding reduced product 4 adopts a twisted and folded conformation due to its flexible nature. ~ 2013 Bi-Xue Zhu. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved. 展开更多
关键词 Schiff base macrocyclic compound Synthesis Structure
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NEW MACROCYCLIC COMPOUND,CLEMOCHINENOSIDE B FROM CLEMATIS CHINENSIS 被引量:1
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作者 Chun Qing SONG Ren Sheng XU State Key Laboratory for New Drug Research,Shanghai Institute of Materia Medica,Academia Sinica,319 Yueyang Rd,Shanghai 200031 《Chinese Chemical Letters》 SCIE CAS CSCD 1993年第6期505-506,共2页
The structure of a new macrocyclic compound,clemochinenoside B, isolated from the root of Clematis chinensis was elucidated by means of NMR,FAB-MS,NOE and chemical hydrolysis.
关键词 NOE NEW macrocyclic compound CLEMOCHINENOSIDE B FROM CLEMATIS CHINENSIS
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Structure Studies on New Types of Macrocyclic Compounds Part V.Crystal Structure of Nickel(II) Complex of 5,12-Diphenyl-7,14-dimethyl-1,4,8,11-tetraazacyclotetradecane-N',N-diacetic Acid
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作者 Lin Yu-Juan(Fujian Institute of Research on the Structure of Matter,Academia Sinica,Fuzhou,350002)Chen Li-Qin Ni Shi-Sheng Xu Ji-De(Department of Chemistry,Anhui University,Hefei,230039) 《Chinese Journal of Structural Chemistry》 SCIE CAS CSCD 1995年第6期44-46,共3页
Crystal structure of nickel(II) complex with a new 14 membered tetraazamacrocyclic ligand 5,12-diphenyl-7,14-dimethyl-1,4,8,11-tetraazacyclotetradecane-N’,N-diacetic acid,Ni[N<sub>4</sub>C<sub>10&... Crystal structure of nickel(II) complex with a new 14 membered tetraazamacrocyclic ligand 5,12-diphenyl-7,14-dimethyl-1,4,8,11-tetraazacyclotetradecane-N’,N-diacetic acid,Ni[N<sub>4</sub>C<sub>10</sub>(CH<sub>2</sub>COO)<sub>2</sub>(C<sub>6</sub>H<sub>5</sub>)<sub>2</sub>]·2H<sub>2</sub>O, M<sub>r</sub>= 589. 38 is reported.It crystallizes in monoclinic P2<sub>1</sub>/c space group with a=12.949(6),b=16.373(3),c=14.232(16),β=98.68(6)°,V=2982.9(7),Z=4,D<sub>c</sub>=1.312 gcm-3,μ=6.953 cm-1,F(000)=1256.0.Finally,the structure was refined to R=0.080,R<sub>w</sub>=0.065 for 2952 reflections.The central nickel ion of the complex forms an octahedron with four nitrogen atoms of the macrocycle and two oxygen atoms of the appended carboxylate groups.Two phenyl planes of the ligand are almost parallel to each other. 展开更多
关键词 CRYSTAL STRUCTURE macrocyclic compound NICKEL COMPLEX
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Synthesis of Tetra-Schiff Base Macrocyclic Compound Containing Benzo-12-crown-4
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作者 Bin SUN Jun Ru CHEN +2 位作者 Hua CHEN Yao Zhong LI Xian Jun LI 《Chinese Chemical Letters》 SCIE CAS CSCD 2002年第6期513-514,共2页
Tetra-Schiff base macrocyclic compound containing benzo-12-crown-4 was synthesized via condensation of 2, 6-diformyl-4-methyl-phenol with 4, 5- diaminobenzo-12C- 4 promoted by proton. The compound was characterized b... Tetra-Schiff base macrocyclic compound containing benzo-12-crown-4 was synthesized via condensation of 2, 6-diformyl-4-methyl-phenol with 4, 5- diaminobenzo-12C- 4 promoted by proton. The compound was characterized by MS, IR 1HNMR spectroscopy and elemental analysis. 展开更多
关键词 Schiff base CROWN macrocyclic compound
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Synthesis and Characterization of a 42-Membered Macrocyclic Compound C_(40)H_(46)N_6O_4 with [2+2] Condensation
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作者 MAZhen LIUShi-Xiong 《Chinese Journal of Structural Chemistry》 SCIE CAS CSCD 北大核心 2003年第5期553-557,共5页
The title compound 1,4,23,26,29,48-hexaaza-6,9:16,19:31,34:41,44-tetrabenzo-12, 15,37,40-tetraoxa-cyclodotetracontane-4,5,18,19,25,26,39,40-octaene 1 (C40H46N6O4) was synthe- sized by [2+2] condensation of diethylenet... The title compound 1,4,23,26,29,48-hexaaza-6,9:16,19:31,34:41,44-tetrabenzo-12, 15,37,40-tetraoxa-cyclodotetracontane-4,5,18,19,25,26,39,40-octaene 1 (C40H46N6O4) was synthe- sized by [2+2] condensation of diethylenetriamine with 4,4?diformyl-diphenoxyethane (dialdehyde) in a mixed solvent of ethanol and tetrahydrofuran. The crystal data are: Mr = 674.83, triclinic, P, a = 5.8249(1), b = 9.4114(8), c = 17.649(2) ? a = 79.310(7), b = 85.397(4), g = 78.970(8), V = 932.1(1) ?, Z = 1, Dc = 1.202 g/cm3, F(000) = 360, m(MoKa) = 0.079 mm-1, R = 0.0486 and wR = 0.1439. The title molecule has a crystallographic center symmetry. The distance between the two secondary amine nitrogen atoms is 18.890(3) ? 展开更多
关键词 crystal structure macrocyclic compound CONDENSATION
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Syntheses and Crystal Structures of Two New Macrocyclic Compounds
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作者 吕昌伟 贾新刚 +1 位作者 吴尧平 刘建 《Chinese Journal of Structural Chemistry》 SCIE CAS CSCD 2013年第1期132-136,共5页
Two new macrocyclic compounds, [Cu2(L)2](ClO4)4·2CH3OH (1) and [Cu(L)](ClO4)2·2H2O (2) (L = 1,3,10,12,15,18-hexaazatetracyclodocosane) were synthesized by condensation reactions involving amine... Two new macrocyclic compounds, [Cu2(L)2](ClO4)4·2CH3OH (1) and [Cu(L)](ClO4)2·2H2O (2) (L = 1,3,10,12,15,18-hexaazatetracyclodocosane) were synthesized by condensation reactions involving amines and formaldehyde in the presence of copper anion. Compound 1 crystallizes in triclinic, space group Pí with a = 10.442(2), b = 14.197(3), c = 17.388(4), α = 91.218(4), β = 90.69(3), γ = 93.756(4)o, V = 2520.4(9)3, Z = 2, F(000) = 1260, Dc = 1.589 Mg/m3, Mr = 1205.92, μ = 1.137 mm-1, λ = 0.71073, the final R = 0.0668 and wR = 0.1573 for 9703 observed reflections with I 2σ(I). Compound 2 crystallizes in monoclinic, space group C2/c with a = 16.911(2), b = 11.4172(15), c = 27.059(4), β = 107.787(2)o, V = 4974.7(12)3, Z = 8, F(000) = 2504, Dc = 1.610 Mg/m3, Mr = 602.92, μ = 1.155 mm-1, λ = 0.71073, the final R = 0.0419 and wR = 0.1131 for 4374 observed reflections with I 2σ(I). 展开更多
关键词 macrocyclic compounds SYNTHESIS crystal structure
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Enhancing self-assembly efficiency of macrocyclic compound into nanotubes by introducing double peptide linkages
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作者 Cheng-Yan Wu Yi-Nan Gao +3 位作者 Zi-Han Zhang Rui Liu Quan Tang Zhong-Lin Lu 《Chinese Chemical Letters》 SCIE CAS CSCD 2024年第11期299-303,共5页
Constructing more stable self-assembled organic nanotubes has been one of the focuses of scientists in recent decades.Hexakis(m-phenylene ethynylene)(m-PE)benzene macrocycles can form stable tubular self-assemblies in... Constructing more stable self-assembled organic nanotubes has been one of the focuses of scientists in recent decades.Hexakis(m-phenylene ethynylene)(m-PE)benzene macrocycles can form stable tubular self-assemblies in nonpolar or weakly polar solvents through theπ-πinteraction of the main skeleton and the hydrogen bonding of the side chain amide.We covalently linked two macrocyclic units at the para position of the macrocycles using two oligo(β-alanine)linkers through an efficient synthetic route.UV-visible spectroscopy,fluorescence spectroscopy,and circular dichroism spectroscopy were employed to demonstrate that the incorporation of two peptide chains significantly enhances the stability of the self-assemblies.Meanwhile,the average open time of the ion channel formed by the macrocyclic dimer in the lipid bilayer was significantly better than that of the ion channel formed by a single macrocycle.This study shows that this strategy effectively improves the efficiency of self-assembly and the stability of its formed self-assemblies,providing a feasible strategy for constructing organic self-assembled nanotubes in highly polar solvents. 展开更多
关键词 macrocyclic compounds Supramolecular assembly Ion transportation Synthetic ion channels Molecular nanotubes
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Syntheses of Macrocyclic Compounds by Photoinduced Electron Transfer Reactions of N-Fuctionalized Tetrachlorophthalimied
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《厦门大学学报(自然科学版)》 CAS CSCD 北大核心 1999年第S1期436-436,共1页
关键词 Syntheses of macrocyclic compounds by Photoinduced Electron Transfer Reactions of N-Fuctionalized Tetrachlorophthalimied
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Structure Studies on New Types of Macrocyclic Compounds Part Ⅵ. Crystal Structure of Copper(Ⅱ) Complex of 5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane-N', N'-diaceticacid
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作者 林玉娟 徐济德 《Chinese Journal of Structural Chemistry》 SCIE CAS CSCD 1996年第5期362-366,共5页
The crystal structure of copper(Ⅱ) complex with a new 14-membered tetraazamacrocyclic ligand 5,5,7,12,12,14-hexamethy1-1,4,8,11-tetraazacyclotetradecane-N'N'-diacetic acid,[CuC16N4H34(CH2COO)(CH2COOH)]·C... The crystal structure of copper(Ⅱ) complex with a new 14-membered tetraazamacrocyclic ligand 5,5,7,12,12,14-hexamethy1-1,4,8,11-tetraazacyclotetradecane-N'N'-diacetic acid,[CuC16N4H34(CH2COO)(CH2COOH)]·ClO4·0. 5HCIO4·1. 5H2O was determined. Crystallographic data: Mr = 639.22,orthorhombic, space group Pcnb with a=11.743(4),b=16.446(2),c=29.611 (4) A,Z=8,V=5726(3) A3, Dc=1.482 g·cm-3, F(000)=1344,μ=9. 64 cm-1,R=0.063,and Rw=0.067 for 2386 reflections with I≥3σ(I). The structure shows an unusual configuration in which two carboxyl groups were bonded to two neighboring nitrogen atoms of the macrocycle, N1 and N4, and six methyl substituents occur on one side of the macrocycle, while two carboxyl groups on the other side, and central copper(Ⅱ) ion forms a five-coordinated geometry. 展开更多
关键词 macrocyclic compound crystal structure copper complex
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Synthesis and Crystal Structure of a New Dinuclear Manganese(Ⅱ) Manganese(Ⅲ) Complex of a Macrocyclic Ligand 被引量:1
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作者 JIANFang-fang XIAOHai-lian XULiang-zhong PANGLei 《Chemical Research in Chinese Universities》 SCIE CAS CSCD 2004年第6期725-728,共4页
A mixed-valence dinuclear manganese complex, [Mn ⅡMn ⅢL](ClO 4)·1/2MeOH, where L is a macrocyclic ligand derived from the cyclocondensation of sodium 2,6-diformyl-4-methylphenolate with N,N-bis(2-aminoethyl)... A mixed-valence dinuclear manganese complex, [Mn ⅡMn ⅢL](ClO 4)·1/2MeOH, where L is a macrocyclic ligand derived from the cyclocondensation of sodium 2,6-diformyl-4-methylphenolate with N,N-bis(2-aminoethyl)-2-hydroxybenzyl amine, was obtained and its structure was determined by X-ray diffraction. The orange crystal is a monoclinic system with space group P2 1/c and lattice parameters a=1.1617(4), b=1.4005(3), c=1.4641(3) nm, β=113.03(2)°, and Z=2. The crystal structure shows that each pendant-arm is bonded in a bidentate fashion to the adjacent metal atom and that both the arms are on the same side of the macrocycle. The two Mn atoms are bridged by two μ 2-phenoxy oxygen atoms of the tetra-imine macrocycle, and each Mn atom, locating in a trigonal prismatic coordination environment(N 3O 3), is six-coordinated by the two imine nitrogen atoms, one tertiary nitrogen atom and a pendant phenol moiety apart from the two oxygen atoms. 展开更多
关键词 Dinuclear manganese complex macrocyclic compound Crystal structure
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Synthesis of Arsamacrocyclic Polyethers
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作者 Xin You CHEN Guo Feng YU Wen Tian TAO (Department of Chemistry. Xiaogan Teachers College,Hubei 432100)(Department of Chemistry, Wuhan University,Wuhan 430072) 《Chinese Chemical Letters》 SCIE CAS CSCD 1999年第8期665-666,共2页
The synthesis of eight new arsamacrocyclic Polyethers was described. The structures of these compounds were characterized by elemental analysis, IR, H-1-NMR and MS.
关键词 macrocyclic compound arsamacrocyclic polyether SYNTHESIS
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Synthesis and Crystal Structure of a Novel(2:2)Macrocyclic Thiocarbohydrazone
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作者 Hao ZHANG Fu Xin XIE +4 位作者 Yu Peng TIAN Xu Hui ZHU Yin Han ZHANG Chun Ying DUAN Shi Sheng NI 《Chinese Chemical Letters》 SCIE CAS CSCD 1998年第1期111-112,共2页
The first reported X-ray crystal structure of a new(2:2)macrocyclic thiocarbohydrazone,effectively derived from thiocarbohydrazide and di(2-formylphenoxy)ethylene is shown.
关键词 Schiff base macrocyclic compound THIOCARBOHYDRAZONE
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含蒽大环化合物的合成及其功能研究进展
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作者 陈南英 罗金荣 +4 位作者 黄春游 陈志林 卢远辉 陶萍芳 黄国保 《化学试剂》 2026年第2期30-40,共11页
超分子化学作为一门新兴的热点交叉学科,其发展总是伴随着新型大环化合物的合成和应用而前进。含蒽大环化合物因其结合了蒽的优异光物理性质和可调的大环空腔,已成为超分子化学和材料科学的前沿领域。通过精妙的分子设计,研究人员已经... 超分子化学作为一门新兴的热点交叉学科,其发展总是伴随着新型大环化合物的合成和应用而前进。含蒽大环化合物因其结合了蒽的优异光物理性质和可调的大环空腔,已成为超分子化学和材料科学的前沿领域。通过精妙的分子设计,研究人员已经开发出多种合成策略,并探索了其在分子识别、刺激响应材料、光电器件和复杂组装体等方面的广泛应用。蒽是一种经典的芳香烃,因其具有较大的疏水刚性平面和较强的富电子共轭体系,使其较高的荧光量子产率,纳秒水平的荧光寿命,高分辨的吸收以及良好的化学稳定性。使其在有机合成、药物分析以及细胞成像领域中展现出优越的应用前景。将蒽单元引入到大环化合物的骨架中,可以结合大环的主客体化学和蒽的功能特性,创造出具有独特光学、电子和识别性能的新型功能材料。综述了最近十年含蒽大环化合物的合成方法及其在分子识别和超分子催化中的最新研究进展。以蒽为“砌块”,深入挖掘蒽在大环结构中所扮演的不可替代的角色,重点强调蒽在大环动态化学中的独特性,及其刚性平面在稳定特定主客体复合物中的关键作用,为今后此类大环化合物的合成及应用提供参考。 展开更多
关键词 大环化合物 合成 功能性 分子识别
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Chiral Amplification and Regulation:Design and Applications of Circularly Polarized Luminescence-Active Materials Derived From Macrocyclic Compounds 被引量:5
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作者 Wei Zhang Mao-Qin Liu Yang Luo 《Aggregate》 2025年第6期20-54,共35页
Chirality is a fundamental property in molecules and biological systems,characterized by asymmetric configurational features.Circularly polarized luminescence(CPL)materials have gained significant attention due to the... Chirality is a fundamental property in molecules and biological systems,characterized by asymmetric configurational features.Circularly polarized luminescence(CPL)materials have gained significant attention due to their unique optical activities,with applications in 3D displays,chiral sensors,asymmetric catalysis,and more.Chiral transfer and amplification typically involve the generation of chirality in the excited state,facilitated by interactions like energy transfer,electron transfer,or chiral induction.Supramolecular self-assembly strategies,particularly macrocyclic compounds,enable chiral amplification by linking chiral and achiral luminescent units through intermolecular interactions.Macrocyclic hosts—cyclodextrins,calix[n]arenes,pillar[n]arenes,chiral cyclophanes,and cucurbit[n]urils—are especially promising due to their stable structures and adjustable cavities for vip encapsulation.These compounds induce unique photophysical properties through host–vip complexation,making them ideal for constructing chiral transfer,amplification,and CPL-active materials.This review summarizes their advancements in multicolor CPL materials,chiral sensing,induction,asymmetric catalysis,and separation,highlighting their potential in supramolecular chiral material design.The challenges and future directions of this field are also discussed,aiming to guide further research and application in supramolecular chiral systems. 展开更多
关键词 chiral amplification chiral transfer circularly polarized luminescence macrocyclic compounds supramolecular assembly
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Synthesis and characterization of new azo containing Schiff base macrocycle 被引量:5
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作者 Saeed Malek-Ahmadi Amir Abdolmaleki 《Chinese Chemical Letters》 SCIE CAS CSCD 2011年第4期439-442,共4页
Fully conjugated Schiff base macrocycle has been prepared through a simple and mild condition,a one-pot cyclization procedure of four-component without using a template.The condensation reaction of related bis(hydrox... Fully conjugated Schiff base macrocycle has been prepared through a simple and mild condition,a one-pot cyclization procedure of four-component without using a template.The condensation reaction of related bis(hydroxybenzaldehyde) with phenylenediamines to prepare a conjugated[2 + 2]Schiff base macrocycle has been investigated and fluorescent[2 + 2]Schiff base macrocycles with N_2O_2 binding pockets has been prepared and characterized by elemental analysis,^1H NMR,IR,fluorescent,UV-visible and MALDI mass spectroscopies. 展开更多
关键词 Schiff base macrocycle Non-template Azo compounds
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Water-soluble supramolecular polymers constructed by macrocycle-based host-vip interactions 被引量:5
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作者 Yanmei Chen Siyu Sun +2 位作者 Dou Lu Yujun Shi Yong Yao 《Chinese Chemical Letters》 SCIE CAS CSCD 2019年第1期37-43,共7页
Supramolecular polymers,which combined of the supramolecular chemistry and polymer science,are constructed from monomers together by reversible noncovalent interactions.Supramolecular polymers in aqueous solution are ... Supramolecular polymers,which combined of the supramolecular chemistry and polymer science,are constructed from monomers together by reversible noncovalent interactions.Supramolecular polymers in aqueous solution are especially important due to their superior biocompatibility and environmental adaptation,which determined they have wide applications in various areas,such as drug delivery,selfhealing,shape memory.Macrocyclic compounds,such as cyclodextrins,calixarenes,cucurbiturils and pillar[n]arenes,are the most used building blocks in the preparation of supramolecular polymers.Macrocycle-based supramolecular polymers,which introduce the host-vip interaction in the system,endow these polymers with interesting and smart physical-chemical properties.In this review,we summarized recent studies about supramolecular polymers in aqueous solution based on macrocyclic compounds. 展开更多
关键词 SUPRAMOLECULAR polymers macrocyclic compounds HOST-vip interaction STIMULI-RESPONSIVE Drug delivery
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A study on some macrocyclic bicopper(Ⅱ) complexes as the model compounds of superoxide dismutase 被引量:5
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作者 QIAN,Wen MEI,Guang-Quan LUO,Qin-HuiState Key Laboratory of Coordination Chemistry,Coordination Chemistry Institute,Nanjing University,Nanjing,Jiangsu 210093,China 《Chinese Journal of Chemistry》 SCIE CAS CSCD 1996年第2期114-122,共9页
24-Membered macrocyclic bicopper(Ⅱ) complexes wth bridging ligand imidzao-late,SCN-,N3-and H2O respectively were synthesized by condensation of diacetylpyridine with 3-oxapentane-1,5-diamine.As the model compounds of... 24-Membered macrocyclic bicopper(Ⅱ) complexes wth bridging ligand imidzao-late,SCN-,N3-and H2O respectively were synthesized by condensation of diacetylpyridine with 3-oxapentane-1,5-diamine.As the model compounds of superoxide dismutase (SOD),the relationship between their SOD activities and properties of bridging ligands and redox potentials of copper(Ⅱ) were studied. 展开更多
关键词 macrocyclic complex bicopper(Ⅱ) superoxide dismutase (SOD) model compound ACTIVITY redox potential
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3-氨基苯并[d]异噁唑类大环ALK抑制剂的设计、合成及活性评价
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作者 周振 刘耀阳 +4 位作者 黎瑶 华炫智 刘洋 杨华丽 程卯生 《沈阳药科大学学报》 2025年第1期52-66,共15页
目的间变性淋巴瘤激酶(anaplastic lymphoma kinase,ALK)的活性失调与多种癌症的发生密切相关。以恩曲替尼为先导化合物,设计并合成一系列3-氨基苯并[d]异噁唑类ALK抑制剂,测试其对ALK阳性的人肺腺癌H2228细胞的抑制活性。方法以邻甲氧... 目的间变性淋巴瘤激酶(anaplastic lymphoma kinase,ALK)的活性失调与多种癌症的发生密切相关。以恩曲替尼为先导化合物,设计并合成一系列3-氨基苯并[d]异噁唑类ALK抑制剂,测试其对ALK阳性的人肺腺癌H2228细胞的抑制活性。方法以邻甲氧基苯甲醛为起始原料,经过还原性C-C偶联、杂环合成和酰胺缩合得到目标化合物A1。以间羟基苯甲酸甲酯和水杨酸甲酯为起始原料,经亲核取代、水解酸化得到中间体5a、5b、13a和13b。以水杨醛及取代水杨醛为起始原料,经过还原性C-C偶联、亲核取代、杂环合成、酰胺缩合、Boc保护与脱保护,以及分子内烯烃复分解反应最终合成得到B、C、D系列大环化合物B1-B4、C1-C4和D1-D7。以恩曲替尼为阳性对照药,使用ALK阳性人肺腺癌H2228细胞株和ALK阴性的人非小细胞肺癌A549细胞株,采用CCK-8法测试目标化合物对细胞株的抑制活性。采用Annexin V-FITC/PI双染流式细胞实验测试化合物B1对H2228肿瘤细胞的凋亡诱导情况。对目标化合物B1和D1进行了ALK酶抑制活性测试。结果与结论合成了16个3-氨基苯并[d]异噁唑类化合物,其中B、C、D系列化合物为大环结构,其结构经核磁共振氢谱和碳谱及高分辨质谱确证。体外H2228肿瘤细胞增殖抑制实验结果表明,化合物B1的抑制活性最佳,IC50=(16.55±3.79)μmol·L^(-1)。细胞凋亡实验表明B1能够浓度依赖性地诱导H2228细胞凋亡。ALK体外酶抑制活性实验中B1和D1的IC50分别为303.7 nmol·L^(-1)和288.0 nmol·L^(-1)。 展开更多
关键词 3-氨基苯并[d]异噁唑 ALK抑制剂 大环化合物
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