Chinese Journal of Chemistry

Cover image for Vol. 31 Issue 9

Special Issue: Medicinal Chemistry

September, 2013

Volume 31, Issue 9

Pages 1113–1233

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Review
    6. Communications
    7. Full Papers
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      Cover Picture: Insight into the Structural Requirements of Protoporphyrinogen Oxidase Inhibitors: Molecular Docking and CoMFA of Diphenyl Ether, Isoxazole Phenyl, and Pyrazole Phenyl Ether (Chin. J. Chem. 9/2013) (page 1113)

      Shenggang Yang, Gefei Hao, Franck E. Dayan, Patrick J. Tranel and Guangfu Yang

      Version of Record online: 18 SEP 2013 | DOI: 10.1002/cjoc.201390021

      Thumbnail image of graphical abstract

      The cover picture shows that a multistep framework is developed with the ultimate goal of identifying novel herbicides. Protoporphyrinogen oxidase (PPO, EC 1.3.3.4) is one of the most significant targets for herbicide design. Using the crystal structure of tobacco mitochondrial PPO (mtPPO) as template, inhibitors were docked into the active site. The docking pose of each compound was subsequently used in a receptor-based alignment, leading to the development of a significant CoMFA model with r2 value of 0.98 and q2 (cross validation r2) value of 0.63. This novel multistep framework gives insight into the structural characteristics for the binding of inhibitors. In addition, the simplicity of the proposed approach may be particularly applicable in virtual screening procedures. More details are discussed in the article by Yang et al. on page 1153–1158.

  2. Editorial

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Review
    6. Communications
    7. Full Papers
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      Special Issue of "Medicinal Chemistry" (page 1115)

      Renxiao Wang

      Version of Record online: 18 SEP 2013 | DOI: 10.1002/cjoc.201390022

  3. Contents

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Review
    6. Communications
    7. Full Papers
    1. You have free access to this content
  4. Review

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Review
    6. Communications
    7. Full Papers
    1. Molecular Similarity: Methods and Performance (pages 1123–1132)

      Chaoqian Cai, Jiayu Gong, Xiaofeng Liu, Daqi Gao and Honglin Li

      Version of Record online: 16 SEP 2013 | DOI: 10.1002/cjoc.201300390

      Thumbnail image of graphical abstract

      Some important aspects of molecular similarity are reviewed in this paper, including the implementations of various similarity evaluation methods, summaries and characteristics of a number of molecular databases, different performance evaluation metrics, etc.

  5. Communications

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Review
    6. Communications
    7. Full Papers
    1. Synthesis of 4-(2-Phenylhydrazono)-1-(4-phenylthiazol-2-yl)-1H-pyrazol-5(4H)-one Compounds and Characterization of Their Affinities to Anti-apoptotic Bcl-2 Family Proteins (pages 1133–1138)

      Shicheng Shi, Li Han, Mi Zhou, Yangfeng Li, Zhen Liu, Biao Yu and Renxiao Wang

      Version of Record online: 26 JUL 2013 | DOI: 10.1002/cjoc.201300426

      Thumbnail image of graphical abstract

      This class of compounds are not effective binders of anti-apoptotic Bcl-2 family proteins. Their apoptosis-inducing effects are possibly due to BAX activation rather than Bcl-2 inhibition as suggested by a recent study.

    2. Asymmetric Synthesis, Antifungal Activity and Molecular Modeling of Iodiconazole Isomers (pages 1139–1143)

      Yongqiang Zhang, Shengzheng Wang, Zhenyuan Miao, Jianzhong Yao, Wannian Zhang and Chunquan Sheng

      Version of Record online: 26 JUL 2013 | DOI: 10.1002/cjoc.201300430

      Thumbnail image of graphical abstract

      Two isomers of iodiconazole, a novel antifungal agent, were prepared by asymmetric synthesis. Their antifungal activity and binding modes were investigated.

  6. Full Papers

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Review
    6. Communications
    7. Full Papers
    1. Design and Synthesis of Tri-substituted Chiral Pyrrolidin-2-one Derivatives as CCR4 Antagonists (pages 1144–1152)

      Wei Sun, Linjie Tian, Hui Qi, Dan Jiang, Ying Wang, Song Li, Junhai Xiao and Xiaohong Yang

      Version of Record online: 5 JUL 2013 | DOI: 10.1002/cjoc.201300363

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      The structure of CCR4 based on bovine rhodopsin was built through homology modeling. And six tri-substituted chiral pyrrolidin-2-one derivatives have been designed and synthesized as CCR4 antagonists. Several of these compounds show high inhibitory effect in cell assays and higher affinity for the N-terminal of CCR4. Among the compounds, 1c exhibited excellent activity.

    2. Insight into the Structural Requirements of Protoporphyrinogen Oxidase Inhibitors: Molecular Docking and CoMFA of Diphenyl Ether, Isoxazole Phenyl, and Pyrazole Phenyl Ether (pages 1153–1158)

      Shenggang Yang, Gefei Hao, Franck E. Dayan, Patrick J. Tranel and Guangfu Yang

      Version of Record online: 16 SEP 2013 | DOI: 10.1002/cjoc.201300449

      Thumbnail image of graphical abstract

      Protoporphyrinogen oxidase (PPO, EC 1.3.3.4) is one of the most significant action targets for a large and chemically diverse family of inhibitors that may be used as herbicide, bactericide, fungicide, or photosensitizing activator to treat cancer through photodynamic therapy (PDT). Molecular docking and 3D-QSAR CoMFA were combined in a multistep framework with the ultimate goal of identifying important factor contributing to the activity of PPO inhibitors. This novel multistep framework gives insight into the structural characteristics that affect the binding and the inhibitory activity of these analogues on PPO with different kinds of structural framework, and it can be extended to other classes of PPO inhibitors. In addition, the simplicity of the proposed approach may be particularly applicable in virtual screening procedures.

    3. Design, Synthesis, and Biological Evaluation of Novel Dual Inhibitors of Secretory Phospholipase A2 and Sphingomyelin Synthase (pages 1164–1170)

      Xing Gao, Haojun Gong, Peng Men, Lu Zhou and Deyong Ye

      Version of Record online: 3 APR 2013 | DOI: 10.1002/cjoc.201300079

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      The secretory phospholipase A2 (sPLA2) and sphingomyelin (SMS) are the key enzymes to atherosclerosis. In this paper, we combined the single sPLA2 and SMS inhibitors with a carbon chain to get a series of dual inhibitors. The biological evaluation showed these compounds had the moderate inhibition against both enzymes.

    4. Molecular Drug Resistance Prediction for Acetohydroxyacid Synthase Mutants Against Chlorsulfuron Using MB-QSAR (pages 1171–1180)

      Yinwu He, Congwei Niu, Xin Wen and Zhen Xi

      Version of Record online: 16 SEP 2013 | DOI: 10.1002/cjoc.201300417

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      MB-QSAR models were constructed in acetohydroxyacid synthase mutants to predict and elucidate the molecular herbicide resistance against chlorsulfuron.

    5. Triazole and Benzotriazole Derivatives as Novel Inhibitors for p90 Ribosomal S6 Protein Kinase 2: Synthesis, Molecular Docking and SAR Analysis (pages 1192–1198)

      Jun Yuan, Ye Zhong, Shiliang Li, Xue Zhao, Guoqin Luan, Zhenjiang Zhao, Jin Huang, Honglin Li and Yufang Xu

      Version of Record online: 19 JUL 2013 | DOI: 10.1002/cjoc.201300443

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      In the present study, a series of triazole and benzotriazole derivatives as novel p90 ribosomal S6 protein kinase 2 (RSK2) inhibitors were designed and synthesized. The in vitro activities of the 14 compounds against RSK2 were evaluated, among which, compounds 5, 6, 11, 12, 13 and 14 exhibited enzyme IC50 values of 8.91, 2.86, 3.19, 3.05, 4.49 and 2.09 µmol/L respectively. The proposed binding modes were simulated using molecular docking method, and the docking results coupled with the structure-activity relationship (SAR) analysis indicated that all our active compounds bound to the RSK2 ATP binding site at NTKD, and the electron-donating groups on the 4-position of phenyl were the key point for the inhibitory activity.

    6. Synthesis and Biological Evaluation of Quinolinone Compounds as SARS CoV 3CLpro Inhibitors (pages 1199–1206)

      Yuanpei Sun, Ning Zhang, Jian Wang, Yu Guo, Bo Sun, Wei Liu, Honggang Zhou and Cheng Yang

      Version of Record online: 19 JUL 2013 | DOI: 10.1002/cjoc.201300392

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      Quinolinone derivatives were selected via virtual screening, and they were synthesised and tested for SARS CoV 3CLpro enzymatic inhibition in vitro. Compound 23 showed the most potent inhibitory activity (IC50=36.86 nmol/L). The binding model was also discussed using docking studies.

    7. Synthesis and Anti-HIV Activity of a Series of 6-Modified 2′,3′-Dideoxyguanosine and 2′,3′-Didehydro-2′,3′-dideoxyguanosine Analogs (pages 1207–1218)

      Lujia Xie, Xiantao Yang, Delin Pan, Yingli Cao, Mou Cao, Guichun Lin, Zhu Guan, Ying Guo, Lihe Zhang and Zhenjun Yang

      Version of Record online: 16 SEP 2013 | DOI: 10.1002/cjoc.201300440

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      A series of 6-modified 2′,3′-dideoxyguanosine and 2′,3′-didehydro-2′,3′-dideoxyguanosine analogs were synthesized. Anti-HIV activity was investigated in cell-based assay. ddGTP was synthesized as well as D4TTP by a novel "one-pot" method, and the incorporation efficiencies recognized by DNA polymerase and HIV reverse transcriptase (HIV RT) were evaluated.

    8. Catalytic Mechanism of Cytochrome P450 2D6 for 4-Hydroxylation of Aripiprazole: A QM/MM Study (pages 1219–1227)

      Rongwei Shi, Weihua Li, Guixia Liu and Yun Tang

      Version of Record online: 16 SEP 2013 | DOI: 10.1002/cjoc.201300427

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      A hydroxylation reaction mechanism of the antipsychotic drug in the active site of CYP2D6 was studied by ONIOM methods, which describes the conversion of aripiprazole from an active form to an inactive 4-hydroxylated form.

    9. Synthesis, Biological Activity Evaluation and Molecular Modeling Study on the New Isoconessimine Derivatives as Acetylcholinesterase Inhibitors (pages 1228–1233)

      Guofei Jin, Zhongduo Yang, Weiwei Xue, Jie Sheng, Yin Shi and Xiaojun Yao

      Version of Record online: 16 SEP 2013 | DOI: 10.1002/cjoc.201300441

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      A series of 3-N-aryloxyethyl substitutional isoconessimine derivatives were synthesized and evaluated as acetylcholinesterase (AChE) inhibitors. All of the synthesized derivatives exhibited potential anti-acetylcholinesterase activities with IC50 values at micromolar to sub-micromolar range. 7b showed the most potent inhibitory activity with an IC50 of 110 nmol/L. The molecular docking results showed that 7b can be well docked into the active site of acetylcholinesterase.

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