Archiv der Pharmazie

Cover image for Archiv der Pharmazie

July 2012

Volume 345, Issue 7

Pages 509–583

  1. Contents

    1. Top of page
    2. Contents
    3. Full Papers
    1. Archiv der Pharmazie 7/2012

      Version of Record online: 4 JUL 2012 | DOI: 10.1002/ardp.201290007

  2. Full Papers

    1. Top of page
    2. Contents
    3. Full Papers
    1. Design, Synthesis and Evaluation of Novel 2-(Aminoalkyl)-isoindoline-1,3-dione Derivatives as Dual-Binding Site Acetylcholinesterase Inhibitors (pages 509–516)

      Michalina Ignasik, Marek Bajda, Natalia Guzior, Michaela Prinz, Ulrike Holzgrabe and Barbara Malawska

      Version of Record online: 30 MAR 2012 | DOI: 10.1002/ardp.201100423

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      A new series of 2-(diethylaminoalkyl)-isoindoline-1,3-dione derivatives intended as dual-binding site cholinesterase inhibitors were designed using molecular modeling. They were evaluated as inhibitors of acetylcholinesterase, butyrylcholinesterase, and the formation of β-amyloid (Aβ) plaques. The most promising selective AChE inhibitors are compounds 10 (IC50 = 1.2 µM) and 11 (IC50 = 1.1 µM), with 6–7 methylene chains, which also inhibit Aβ fibril formation.

    2. Synthesis and Evaluation of 5-Benzylidenethiazolidine-2,4-dione Derivatives for the Treatment of Non-Alcoholic Fatty Liver Disease (pages 517–524)

      Liang Ma, Jinying Chen, Xiaolin Liang, Caifei Xie, Chongyang Deng, Li Huang, Aihua Peng, Yuanquan Wei and Lijuan Chen

      Version of Record online: 25 APR 2012 | DOI: 10.1002/ardp.201100413

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      A series of 5-benzylidenethiazolidine-2,4-dione derivatives were synthesized and evaluated by measuring the expression of adiponectin protein in 3T3-L1 adipocytes. Oral administration of 3V at a dosage of 25 mg/kg effectively improved the serum levels of biochemical markers in the HF/HC-induced NAFLD rat model. 3V was identified as a potent hepatoprotective agent against NAFLD by reducing fat deposition.

    3. 2′-Chloro-4′-aminoflavone Derivatives Selectively Targeting Hepatocarcinoma Cells: Convenient Synthetic Process, G2/M Cell Cycle Arrest and Apoptosis Triggers (pages 525–534)

      Feng Jin, Nannan Zhang, Chunyan Tan, Dan Gao, Cunlong Zhang, Feng Liu, Zhe Chen, Chunmei Gao, Hongxia Liu, Shangfu Li and Yuyang Jiang

      Version of Record online: 30 MAR 2012 | DOI: 10.1002/ardp.201100383

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      A series of 2′-chloro-4′-nitroflavone derivatives and 2′-chloro-4′-aminoflavone derivatives were synthesized. Most compounds exhibited potent in vitro anti-tumor ability toward HepG2 cells, but very little effect on MCF-7 and K562 cells. The representative compound 4e displayed very weak toxicity against two human normal liver cells lines, QSG7701 and HL7702; the most active compound 4c (IC50 = 2 µM) arrested the cell cycle at the G2/M phase and induced apoptosis of HepG2 cells.

    4. Synthesis, Cytotoxic Properties and Tubulin Polymerization Inhibitory Activity of Novel 2-Pyrazoline Derivatives (pages 535–548)

      Mohamed Abdel-Aziz, Omar M. Aly, Sabine S. Khan, Kamalika Mukherjee and Susan Bane

      Version of Record online: 16 MAY 2012 | DOI: 10.1002/ardp.201100471

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      Novel 1-(3′,4′,5′-trimethoxybenzoyl)-3,5-diarylpyrazoline derivatives were synthesized and evaluated for their cytotoxic properties on different cancer cell lines and their tubulin polymerization inhibitory activity. The cytotoxicity of compounds 6d and 6e can be attributed to their ability to interfere with microtubule assembly. Molecular modeling studies involving compound 6e revealed hydrogen-bonding and hydrophobic interactions with several amino acids in the colchicine binding site of β-tubulin.

    5. Design and One-Pot and Microwave-Assisted Synthesis of 2-Amino/5-Aryl-1,3,4-oxadiazoles Bearing a Benzimidazole Moiety as Antioxidants (pages 549–556)

      İlgar Kerimov, Gülgün Ayhan-Kılcıgil, Elçin Deniz Özdamar, Benay Can-Eke, Tülay Çoban, Süheyla Özbey and Canan Kazak

      Version of Record online: 30 MAR 2012 | DOI: 10.1002/ardp.201100440

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      Two new series of 2-amino-1,3,4-oxadiazoles and 5-aryl-1,3,4-oxadiazoles carrying a benzimidazole moiety were synthesized and their antioxidant properties were investigated in vitro. 2-[(2-(4-Chlorophenyl)-1H-benzo[d]imidazole-1-yl)methyl]-5-(4-fluorophenyl)-1,3,4-oxadiazole (9) was found to be the most active compound in all three in vitro systems.

    6. Synthesis, Antitumor, and Antibacterial Activity of Bis[4,5-diarylimidazol-2-ylidene]methane Derivatives (pages 557–564)

      Wukun Liu, Xiaohua Chen and Ronald Gust

      Version of Record online: 30 MAR 2012 | DOI: 10.1002/ardp.201100474

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      To investigate whether the gold in cationic [bis(1,3-diethyl-4,5-diarylimidazol-2-ylidene)]Au(I) bromide complexes is crucial for their antitumor activity, the imidazole ligands were connected by a methylene bridge. In comparison with the gold complexes, the methylene derivatives showed drastically reduced cell growth inhibitory properties. However, the growth of bacteria was significantly inhibited by bis[1,3-diethyl-4,5-bis(4-methoxyphenyl)imidazol-2-ylidene]methane dibromide (4), opening a new application of this compound type.

    7. Synthesis and Anticonvulsant Activities of Some Triazolothiadiazole Derivatives (pages 565–573)

      Xian-Qing Deng, Zheng-Qi Dong, Ming-Xia Song, Bing Shu, Shi-Ben Wang and Zhe-Shan Quan

      Version of Record online: 25 APR 2012 | DOI: 10.1002/ardp.201100326

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      The anticonvulsant activities of 6-substituted-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives (4a4x) and their partially dehydrogenated products 5,6-dihydro-6-substituted-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives (5a5n) were evaluated. Most compounds in the series of 4a4x exhibited potent anticonvulsant activity in the maximal electroshock test. 6-(4-Chlorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole (4h) emerged as the most promising candidate on the basis of its favorable ED50 value of 23.7 mg/kg and PI value of 10.8.

    8. Heterocycles 27. Microwave Assisted Synthesis and Antitumour Activity of Novel Phenothiazinyl-Thiazolyl-Hydrazine Derivatives (pages 574–583)

      Adriana Ignat, Tamas Lovasz, Mihai Vasilescu, Eva Fischer-Fodor, Corina Bianca Tatomir, Castelia Cristea, Luminiţa Silaghi-Dumitrescu and Valentin Zaharia

      Version of Record online: 25 APR 2012 | DOI: 10.1002/ardp.201100355

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      Microwave assisted synthesis afforded excellent yields of new phenothiazinyl-thiazolyl-hydrazine derivatives. Their cytotoxicity was tested in vitro based on spectrometric methods.