Chinese Journal of Chemistry

Cover image for Vol. 30 Issue 12

Special Issue: Dedicated to the 60th Anniversary of East China University of Science and Technology

December, 2012

Volume 30, Issue 12

Pages 2729–2881

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communication
    6. Full Papers
    7. Note
    8. Errata
    9. Retraction
    1. You have free access to this content
      Cover Picture: Inhibitors of HIV-1 Integrase-Human LEDGF/p75 Interaction Identified from Natural Products via Virtual Screening (Chin. J. Chem. 12/2012) (page 2729)

      Guoping Hu, Xi Li, Yaozong Li, Xianqiang Sun, Guixia Liu, Weihua Li, Jin Huang, Xu Shen and Yun Tang

      Article first published online: 27 DEC 2012 | DOI: 10.1002/cjoc.201290035

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      The cover picture shows the discovery of inhibitors targeting HIV-1 integrase-human LEDGF/p75 interaction via virtual screening. One of the most challenges for anti-HIV therapy is the rapid emergence of drug resistance. Protein-protein interaction inhibitors bring us hopes to overcome the viral resistance. We conducted a virtual screening combined with bioassays to search such inhibitors from natural product library. Several compounds were discovered to block integrase- LEDGF/p75 interaction with potent activities. These findings could be helpful for anti-HIV drug discovery. More details are discussed in the article by Tang et al. on page 2752–2758.

  2. Editorial

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communication
    6. Full Papers
    7. Note
    8. Errata
    9. Retraction
    1. You have free access to this content
  3. Contents

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communication
    6. Full Papers
    7. Note
    8. Errata
    9. Retraction
    1. Contents: Chin. J. Chem. 12/2012 (pages 2732–2739)

      Article first published online: 27 DEC 2012 | DOI: 10.1002/cjoc.201290037

  4. Communication

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communication
    6. Full Papers
    7. Note
    8. Errata
    9. Retraction
    1. Gold-Catalyzed Direct Indolation of Tetrahydroisoquinolines (pages 2741–2746)

      Yan Zhang, Sha Luo, Bainian Feng and Chengjian Zhu

      Article first published online: 13 DEC 2012 | DOI: 10.1002/cjoc.201201154

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      Nitrogen-containing heterocyclic compounds are important motifs of pharmaceuticals and functional materials, and there has been a growing interest in new synthetic methods for their preparations. In this paper, we report a direct cross-coupling reaction of indole with N-aryl tetrahydroisoquinolines in the presence of gold catalyst. The reaction is compatible with a wide range of substituted indoles, to enable the formation of various alkylated heteroarenes under very mild reaction conditions.

  5. Full Papers

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communication
    6. Full Papers
    7. Note
    8. Errata
    9. Retraction
    1. One-pot Three Component Synthesis of Polyfluoroarylated Arylacetates via VNSAr-SNAr Reaction (pages 2747–2751)

      Yang Xiong, Jingjing Wu, Senhan Xiao and Song Cao

      Article first published online: 13 DEC 2012 | DOI: 10.1002/cjoc.201201044

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      A series of 2-polyfluoroaryl arylacetates were synthesized by a one-pot three-component VNSAr-SNAr reaction of polyfluoroarenes, ethyl 2-chloropropionate, and ortho-substituted nitrobenzenes.

    2. Inhibitors of HIV-1 Integrase-Human LEDGF/p75 Interaction Identified from Natural Products via Virtual Screening (pages 2752–2758)

      Guoping Hu, Xi Li, Yaozong Li, Xianqiang Sun, Guixia Liu, Weihua Li, Jin Huang, Xu Shen and Yun Tang

      Article first published online: 11 DEC 2012 | DOI: 10.1002/cjoc.201200897

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      Natural products were virtually screened against the LEDGF/p75 binding pocket of HIV-1 IN. Bioassays characterized 8 of 24 selected natural products as potent inhibitors. The two most potent inhibitors had IC50 values of 0.56 and 0.69 µmol/L, respectively.

    3. Novel and Efficient Syntheses of Four Useful Shikimate-derived Epoxy Chiral Building Blocks via Cyclic Sulfite Intermediates (pages 2759–2766)

      Na Quan, Liangdeng Nie, Xiaoxin Shi, Ruiheng Zhu and Xia Lü

      Article first published online: 13 DEC 2012 | DOI: 10.1002/cjoc.201201000

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      All of the four stereoisomers of methyl 4,5-epoxy-3-hydroxy-cyclohex-1-ene-carboxylate (1a1d) are useful chiral building blocks. Novel and efficient syntheses of these four epoxy chiral building blocks from naturally abundant (−)-shikimic acid (2) via cyclic sulfite intermediates are described in this article. The compound (3R,4R,5S)-1a was synthesized via four steps from (−)-shikimic acid in 79% overall yield. The compounds (3S,4R,5S)-1b, (3S,4S,5R)-1c and (3R,4S,5R)-1d were synthesized via seven steps from (−)-shikimic acid in 56%, 64% and 65% overall yields, respectively.

    4. Synthesis of 1,3,5-Trisubstituted [4-tert-Butyl 2-(5,5-difluoro-2,2-dimethyl-6-vinyl-1,3-dioxan-4-yl)acetate]pyrazoles via a Pd-Catalyzed C[BOND]H Activation (pages 2767–2773)

      Xiaoguang Wang, Xiang Fang, Xueyan Yang, Meng Ni and Fanhong Wu

      Article first published online: 13 DEC 2012 | DOI: 10.1002/cjoc.201201100

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      The gem-difluoromethylenated acetonide was efficiently synthesized as new precursor of HMG-CoA reductase inhibitor. Straightforward olefination via Pd-catalyzed C4-H activation of 1,3,5-trisubstituted pyrazoles was proceeded smoothly in the presence of Pd(OAc)2 and AgCO3.

    5. Fe3O4 Modified Up-Conversion Luminescent Nanocrystals for Biological Applications (pages 2774–2778)

      Yu Hou, Zifei Yin, Hailiang Xin, Yonghua Su and Huagui Yang

      Article first published online: 30 OCT 2012 | DOI: 10.1002/cjoc.201200854

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      A new and facile two-step synthetic strategy was developed to prepare magnetic Fe3O4 modified single crystalline up-conversion luminescent NaYF4: Yb3+, Er3+ nanocrystals using Fe3O4 nanoparticles as the seeds. Acting as the "nuclei" in the reaction, the presence of Fe3O4 nanoparticles facilitates the formation of up-conversion NaYF4: Yb3+, Er3+ nanocrystals on their surfaces through heterogeneous nucleation process. The uptake and intracellular distribution of as-prepared multifunctional nanocrystals were also investigated in cell-labelling.

    6. Novel Organic Dyes Based on Bulky Tri(triphenylamine)-Substituted Styrene for Dye-Sensitized Solar Cells (pages 2779–2785)

      Zhiyun Zhang, Jinlong Han, Xin Li, Shengyun Cai and Jianhua Su

      Article first published online: 13 DEC 2012 | DOI: 10.1002/cjoc.201201081

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      A novel class of organic D-π-A dyes employing tri(triphenylamine)-substituted styrene as donor was designed and synthesized for dye-sensitized solar cells (DSSCs). The DSSC device based on TF with furan as π-linker achieved a solar-to-electricity conversion efficiency (η) of 4.52%.

    7. Facile Synthesis of 4,5-Disubstituted 2H-1,2,3-Triazoles by Catalyst-free Cycloaddition between Substituted Vinyl Sulfones and Sodium Azide under Ambient Conditions (pages 2786–2790)

      Jinjin Yang, Wei Yin, Renhua Liu and Changhu Chu

      Article first published online: 13 DEC 2012 | DOI: 10.1002/cjoc.201200998

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      A highly efficient method for readily preparing 4,5-disubstituted 2H-1,2,3-triazoles was found. Under ambient conditions, a catalyst free cycloaddition between substituted vinyl sulfones and sodium azide could be completed in a very short time. In this cycloaddition process, sulfonyl group acts as a leaving group, while its ester group was retained.

    8. Investigation of Peptoid Chiral Stationary Phases Terminated with N′-Substituted Phenyl-L-proline/leucine Amide (pages 2791–2797)

      Haibo Wu, Guangjun Song, Xinmiao Liang and Yanxiong Ke

      Article first published online: 13 DEC 2012 | DOI: 10.1002/cjoc.201201041

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      Eight peptoid chiral stationary phases (CSPs) terminated with L-proline or L-leucine amide were prepared and evaluated with 59 racemates. The influence of terminal p-methyl and p-chloro substituents on selectivity was found varied along with the terminal amino acid and peptoid chain length.

    9. A New Synthetic Method of (Z)-4-Aryl-but-2-en-1-ols via Suzuki-Miyaura Cross-Coupling Reaction of 4-Substituted 1,2-Oxaborol-2(5H)-ols with Benzyl Bromides (pages 2798–2804)

      Tao Yu, Xinyan Wu and Jun Yang

      Article first published online: 17 DEC 2012 | DOI: 10.1002/cjoc.201201122

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      Z and E configuration 4-aryl-but-2-en-1-ols were isolated from several terrestrial plants, and (Z)-4-aryl-but-2-en-1-ols were found to have choleretic activity. Strategies have been reported to synthesize (E)-4-aryl-but-2-en-1-ols with high selectivity. However, there is no method to obtain (Z)-4-aryl-but-2-en-1-ols with high selectivity now. We developed a Suzuki-Miyaura cross-coupling reaction of 1,2-oxaborol-2(5H)-ols with benzyl bromides to synthesize (Z)-4-aryl-but-2-en-1-ols, the products were obtained in up to 94% isolated yield.

    10. Preparation of Nanoporous Carbon/Graphene Composites and Its Application in Direct Methanol Fuel Cell (pages 2805–2812)

      Xiuhua Jin, Qinglian Wei, Haojun Huang, Mengxue Wang and Yongmin Huang

      Article first published online: 13 DEC 2012 | DOI: 10.1002/cjoc.201200987

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      The nanoporous carbon/graphene composite (NCGC) has been prepared through a one pot hydrothermal method by using graphene oxide (GO) as raw material, phenol, formaldehyde as carbon resources and triblock copolymer F127 as template. Pt electrocatalyst taking NCGC as support shows better activity and stability than that with XC-72 as support toward methanol oxidation.

    11. Synthesis and Pharmacological Properties of 5-Alkyl Substituted Nicotine Analogs (pages 2813–2818)

      Jing Wang, Xi Li, Qianjia Yuan, Jiangmeng Ren, Jin Huang and Bubing Zeng

      Article first published online: 13 DEC 2012 | DOI: 10.1002/cjoc.201200952

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      An eight-step synthetic route was developed to synthesize a series of nicotine analogs. 17 nicotine analogs were synthesized, among which compounds 10d and 10g exhibited excellent biological activities toward SY-SY5Y and RD.

    12. Aqueous-Phase, Palladium-Catalyzed Heck Reaction: The Significant Role of CN-containing Counter Anion (pages 2819–2822)

      Yueqin Cai, Gonghua Song and Xiaoying Zhou

      Article first published online: 30 OCT 2012 | DOI: 10.1002/cjoc.201200675

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      Water-soluble diol-functionalized imidazolium ionic liquid 1, prepared from 2,2-bis(1-methyl-methylimidazolium)propane-1,3-diol bromide, potassium hydroxide, and malononitrile, was used as an efficient phosphine-free ligand for palladium-catalyzed arylation of aryl halides with acrylates in aqueous phase under mild conditions.

    13. A Highly Sensitive and Selective Colorimetric Chemosensor for F Detection Based on Perylene-3,4:9,10-tetracarboxylic Bisimide (pages 2823–2826)

      Liang Zhang, Limin Wang, Guanjun Zhang, Jianjun Yu, Xiaofei Cai, Mingshuang Teng and Yue Wu

      Article first published online: 17 DEC 2012 | DOI: 10.1002/cjoc.201201116

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      A novel colorimetric chemosensor PBIOSi had been designed and synthesized. The addition of F− to a THF solution of PBIOSi resulted in an obvious color change (from red to green) in a short time because of the specific cleavage of Si[BOND]O bond in PBIOSi by F−.

    14. Ethylenediamine: A Highly Effective Catalyst for One-Pot Synthesis of Aryl Nitroalkenes via Henry Reaction and Dehydration (pages 2827–2833)

      Jianxin Yang, Jing Dong, Xia Lü, Qiang Zhang, Wei Ding and Xiaoxin Shi

      Article first published online: 17 DEC 2012 | DOI: 10.1002/cjoc.201201094

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      Ethylenediamine (H2NCH2CH2NH2) was found to be a highly effective catalyst for the condensation of aryl aldehydes with nitromethane (or nitroethane). When 1–2 mol% of ethylenediamine was used as the catalyst, the one-pot reaction of aryl aldehydes with nitromethane (or nitroethane) by refluxing for 3–10 h efficiently afforded various aryl nitroalkenes 1a1y in 85%–97% yields.

    15. Highly Substituted Cyclopentenes Formation via a Stereoselective Tandem CDC Reaction and Cyclization (pages 2834–2838)

      Yi Li, Li Cao, Xiaoyan Luo and Weiping Deng

      Article first published online: 17 DEC 2012 | DOI: 10.1002/cjoc.201200951

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      A facile iron-catalyzed C(sp3)-C(sp2) bond formation through DDQ-mediated cross-dehydrogenative homo-coupling of (E)-1,2-diarylprop-1-enes for the synthesis of highly aryl-substituted cyclopentenes has been developed.

    16. A Study of Nano Materials and Their Reactions in Liquid Using in situ Wet Cell TEM Technology (pages 2839–2843)

      Xin Chen, Lihui Zhou, Ping Wang, Chongjun Zhao and Xiaoli Miao

      Article first published online: 27 DEC 2012 | DOI: 10.1002/cjoc.201201036

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      An in situ wet cell TEM set up was used to observe electrochemical deposition of nano nickel film in liquid. Interestingly, nickel particle and particle layers appeared in front of the film first and then merged with it.

    17. Degradation of 2,4-DCP by the Immobilized Laccase on the Carrier of Fe3O4@SiO2-NH2 (pages 2849–2860)

      Weiwei Huan, Yuxiang Yang, Bin Wu, Hongming Yuan, Yani Zhang and Xiangnong Liu

      Article first published online: 13 DEC 2012 | DOI: 10.1002/cjoc.201200718

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      Fe3O4@SiO2-NH2 nano-carrier particles with chain structure were successfully prepared. Immobilization of laccase using Fe3O4@SiO2-NH2 as carrier through covalent attachment was carried out. The optimal conditions regarding degradation efficiency was discussed. Magnetic nanoparticles immobilized laccase was easy to operate, separate and recover from the reaction system. Moreover, because of its magnetic, catalytic, and other good characteristics, the immobilized laccase had a faster degradation rate than the free laccase by the "magneto-induced effect" on the laccase; the magnetic carrier Fe3O4@MSS-NH2 could promote the degradation reaction and the activity of immobilized laccase was kept almost unchanged during the course of repeated use.

    18. Synthesis of Conjugated Aryleneethynylenesiloles Dendron (pages 2861–2868)

      Jie Liu, Chenxu Yan, Shanshan Li, Chengyun Wang and Yongjia Shen

      Article first published online: 17 DEC 2012 | DOI: 10.1002/cjoc.201200908

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      According to the different desilylation conditions of trimethylsilyl group and Si(CH3)2 group in silacyclopentadiene unit, aryleneethynylenesiloles dendron was synthesized.

    19. Nanoscale Interfacial Activity of the Natural Lipopeptide, [Asp1, Glu5] Surfactin-C16, and DMPC in Mixed Monolayer (pages 2869–2873)

      Ying Yang, Aihua Zou, Changsheng Song and Bozhong Mu

      Article first published online: 27 SEP 2012 | DOI: 10.1002/cjoc.201200396

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      The monolayer technique combined with atomic force microscopy (AFM) was used to probe the interfacial behavior of DMPC and surfactin-C16 in the mixed monolayer. The two components are partially miscible in some cases. It is proposed that the miscibility is governed by hydrophobic interactions between surfactin-C16 and DMPC, and the ionization states and physical states of surfactin-C16 in the monolayer.

  6. Note

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communication
    6. Full Papers
    7. Note
    8. Errata
    9. Retraction
    1. Pyrene Excimer-based Bis-triazolyl Pyranoglycoligands as Specific Mercury Sensors (pages 2874–2878)

      Xiaopeng He, Juan Xie, Guorong Chen and Kaixian Chen

      Article first published online: 11 DEC 2012 | DOI: 10.1002/cjoc.201200978

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      New C3,4-disubstituted bis-triazolyl glycoligands that feature a glucosyl or galactosyl scaffold incorporating dual pyrenyl groups were synthesized via the CuI-catalyzed azide-alkyne 1,3-dipolar cycloaddition reaction (Cue-AAC). These compounds exert a major emission band corresponding to that of pyrene excimer and respond specifically to mercury with a markedly quenched fluorescence. The epimeric nature of the pyranoglycosyl scaffold is determined influential toward the selectivity of the sensors.

  7. Errata

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communication
    6. Full Papers
    7. Note
    8. Errata
    9. Retraction
    1. You have free access to this content
      Erratum: Immobilization of Glucose Oxidase on Ordered Macroporous Silicas Functionalized with Amino Group (page 2879)

      Quanzhou Wu, Jianfeng He, Jingjia Zhang and Jiming Ou

      Article first published online: 27 DEC 2012 | DOI: 10.1002/cjoc.201290032

      This article corrects:

      Immobilization of Glucose Oxidase on Ordered Macroporous Silicas Functionalized with Amino Group

      Vol. 30, Issue 2, 283–287, Article first published online: 15 FEB 2012

    2. You have free access to this content
      Erratum: Antimicrobial Aromatic Polyketides from Gorgonian-Associated Fungus, Penicillium commune 518 (page 2880)

      Junfeng Wang, Peipei Liu, Yi Wang, Hui Wang, Jing Li, Yibin Zhuang and Weiming Zhu

      Article first published online: 27 DEC 2012 | DOI: 10.1002/cjoc.201290033

      This article corrects:

      Antimicrobial Aromatic Polyketides from Gorgonian-Associated Fungus, Penicillium commune 518

      Vol. 30, Issue 6, 1236–1242, Article first published online: 7 MAY 2012

  8. Retraction

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communication
    6. Full Papers
    7. Note
    8. Errata
    9. Retraction
    1. You have free access to this content
      Retraction: A New Sesquiterpene from Caragana intermediia and Its Anti-Pyricularia oryzae P-2b Activity (page 2881)

      Zhihua Sun, Changqi Hu and Jinyi Wang

      Article first published online: 27 DEC 2012 | DOI: 10.1002/cjoc.201290034

      This article corrects:

      Retraction: A New Sesquiterpene from Caragana intermediia and Its Anti-Pyricularia oryzae P-2b Activity

      Vol. 26, Issue 5, 831–834, Article first published online: 15 MAY 2008

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