Archiv der Pharmazie

Cover image for Archiv der Pharmazie

November 2012

Volume 345, Issue 11

Pages 841–917

  1. Contents

    1. Top of page
    2. Contents
    3. Review Article
    4. Full Papers
    1. Archiv der Pharmazie 11/2012

      Article first published online: 2 NOV 2012 | DOI: 10.1002/ardp.201290011

  2. Review Article

    1. Top of page
    2. Contents
    3. Review Article
    4. Full Papers
    1. Functionalized 1,4-Benzothiazine: A Versatile Scaffold with Diverse Biological Properties (pages 841–851)

      Olayinka Oyewale Ajani

      Article first published online: 14 AUG 2012 | DOI: 10.1002/ardp.201200140

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      1,4-Benzothiazines are heterocyclic compounds with wide biological properties, which qualify them as excellent scaffolds in therapeutic and medicinal research. Many derivatives have been synthesized as target structures in novel drug development. The known widespread applications of the 1,4-benzothiazine scaffolds are presented.

  3. Full Papers

    1. Top of page
    2. Contents
    3. Review Article
    4. Full Papers
    1. Synthesis and Characterization of Thiazolo- and Thiazinomorphinans and Their Intermediate Products as Novel Opioid-Active Derivatives (pages 852–858)

      Attila Sipos, Valeria Follia, Sándor Berényi, Sándor Antus, Helmut Schmidhammer and Mariana Spetea

      Article first published online: 10 AUG 2012 | DOI: 10.1002/ardp.201200176

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      A new procedure was elaborated for the synthesis of potentially opioid-active thiazolo- and thiazinomorphinans. These derivatives and some intermediates related with the synthesis were tested in opioid receptor binding studies. Two compounds showed remarkable µ opioid activities and specificities.

    2. Synthesis and Evaluation of a Series of Piperidine-2,6-dione-piperazine (piperidine) Derivatives as Multireceptor Atypical Antipsychotics (pages 859–869)

      Yin Chen, Xiangqing Xu, Xin Liu, Bi-Feng Liu and Guisen Zhang

      Article first published online: 8 AUG 2012 | DOI: 10.1002/ardp.201200023

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      The discovery and synthesis of novel, potential antipsychotic piperidine-2,6-dione derivatives combining potent dopamine D2, D3 and serotonin 5-HT1A, 5-HT2A, 5-HT2C receptor properties are described. The structure–activity relationships that led to the promising derivative 1-(4-(4-(6-fluorobenzo[d]isoxazol-3-yl)piperidin-1-yl)butyl)-4-(4-chlorophenyl)-piperidine-2,6-dione 5 are reported.

    3. Synthesis and Discovery of Novel Pyrazole Carboxamide Derivatives as Potential Osteogenesis Inducers (pages 870–877)

      Hong-Shui Lv, Qian-Qian Han, Xiao-Ling Ding, Ji-Liang Zhou, Pi-Shan Yang, Jun-Ying Miao and Bao-Xiang Zhao

      Article first published online: 26 JUL 2012 | DOI: 10.1002/ardp.201200180

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      A series of novel N-aryl-3-aryl-1-arylmethyl-1H-pyrazole-5-carboxamide derivatives 4al were synthesized and used to induce mouse osteoblast precursors (MC3T3-E1 cells) into osteoblasts. The induction was assessed by alkaline phosphatase (ALP) activity and expression of the bone sialoprotein (BSP) gene. Compounds 4ad, 4g, 4h, and 4k led to increased ALP activity and compound 4h was the most effective in inducing osteogenesis. The mRNA expression of BSP, a marker of osteogenesis, was up-regulated by compound 4h.

    4. Trimethyl-4-oxo-4,5,6,7-tetrahydroindazole-1-acetic Acid: A New Lead Compound with Selective COX-2 Inhibitory Activity (pages 878–883)

      Hamdy M. Abdel-Rahman and Keriman Ozadali

      Article first published online: 21 AUG 2012 | DOI: 10.1002/ardp.201200193

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      Tetrahydroindazole-1-acetic acid derivatives were designed and synthesized by a new one-step pathway and evaluated for their COX-1/COX-2 inhibitory activities. 2-(3,6,6-Trimethyl-4-oxo-4,5,6,7-tetrahydroindazol-1-yl)acetic acid 4 emerged as the most potent COX-2 inhibitor. Docking studies of compound 4 in the active site of COX-2 demonstrated its potential binding mode to the enzyme.

    5. Carbodiimides in the Synthesis of Enamino- and α-Aminophosphonates as Peptidomimetics of Analgesic/Antiinflammatory and Anticancer Agents (pages 884–895)

      Wafaa M. Abdou, Reham F. Barghash and Mohamed S. Bekheit

      Article first published online: 29 AUG 2012 | DOI: 10.1002/ardp.201200142

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      Carbodiimide was allowed to react with different phosphorus nucleophiles. The resulting heterocumulenes were reacted with dialkylhydrogenphosphonates and tris-(dialkyl)aminophosphines. Horner–Emmons reagents were applied to the same carbodiimide to obtain more phosphorylated N-heterocycles. The analgesic, antiinflammatory, and antitumor activities of the newly synthesized compounds were investigated.

    6. Synthesis and Antitubercular Activity Evaluation of Novel Unsymmetrical Cyclohexane-1,2-diamine Derivatives (pages 896–901)

      Beena, Seema Joshi, Nitin Kumar, Saqib Kidwai, Ramandeep Singh and Diwan S. Rawat

      Article first published online: 4 SEP 2012 | DOI: 10.1002/ardp.201200219

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      Unsymmetrical cyclohexane-1,2-diamine derivatives were synthesized and evaluated for their activity against Mycobacterium tuberculosis H37Rv. Eight compounds (11h, 13a, 13e, 13f, 14a, 14c, 14d, and 15d) were found to be active at or below 6.25 µM, with negligible toxicity to human red blood cells at a concentration much higher than MIC99. Compound 13a was found to be non-hemolytic at up to 500 µg/mL.

    7. Computational Modeling, Synthesis, and Antioxidant Potential of Novel Phenylcarbamoylbenzoic Acid Analogs in Combating Oxidative Stress (pages 902–910)

      Waleed A. Bayoumi, Magda A. Elsayed, Hany N. Baraka and Laila Abou-zeid

      Article first published online: 24 AUG 2012 | DOI: 10.1002/ardp.201200183

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      A series of new phenylcarbamoylbenzoic acid analogs were designed, synthesized, and evaluated for their in vitro antioxidant activity, aiming to find a lead for the treatment of oxidative stress. Molecular modeling studies revealed that compounds 8c and 9a selectively bind to the crucial amino acid residues in the active site of 3MNG. The in vitro antioxidant activity was determined using the ABTS antioxidant assay. Compounds 8c, 9a, and 9b showed high antioxidant activity and are thus promising as potent antioxidant leads.

    8. Synthesis and Antimicrobial Activity of Novel Heterocyclic Sulfamoyl-phenyl-carboximidamides Derived from Clinically Applied Sulfonamides (pages 911–917)

      Katarzyna Gobis, Henryk Foks, Katarzyna Wiśniewska, Maria Dąbrowska-Szponar, Ewa Augustynowicz-Kopeć and Agnieszka Napiórkowska

      Article first published online: 7 AUG 2012 | DOI: 10.1002/ardp.201200160

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      A series of novel heterocyclic sulfamoyl-phenyl-carboximidamides were synthesized via condensation of clinically applied sulfonamides with heterocyclic methyl carbimidates. The new structures were confirmed by IR and NMR spectra as well as elemental analyses. All the compounds were screened for their antimicrobial activity. N′-(4-(N-(Thiazol-2-yl)sulfamoyl)phenyl)pyrazine-2-carboximidamide (16) was found to be as potent as the clinically applied sulfamethoxypyridazine.

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