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Synthesis of some new hybride molecules containing several azole moieties and investigation of their biological activities

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Abstract

1,2,4-Triazole-3-one prepared from tryptamine was converted to the corresponding carbothioamides by several steps. Their treatment with ethyl bromoacetate or 4-chlorophenacyl bromide produced the corresponding 5-oxo-1,3-thiazolidine or 3-(4-chlorophenyl)-1,3-thiazole derivatives. Acetohydrazide derivative that was obtained starting from tryptamine, was converted to the corresponding Schiff basis and sulfonamide by the treatment with suitable aldehydes and benzensulphonyl chloride, respectively. 2-[(4-Amino-5-thioxo-4,5-dihydro-1H-1,2,4-triazole-3-yl)methyl]-4-[2-(1H-indole-3-yl)ethyl]-5-methyl-2,4-dihydro-3H-1,2,4-triazole-3-one was synthesized starting from hydrazide via the formation of the corresponding 1,3,4-oxadiazole compound, while the other bitriazole compounds were obtained by intramolecular cyclisation of carbothioamides in basic media. The treatment of 1,2,4-triazole or 1,3,4-oxadiazole compound with several amines generated the corresponding Mannich bases. Ethyl (2-amino-1,3-thiazole-4-yl)acetate was converted to the corresponding 1,3,4-oxadiazole derivative, arylidenehydrazides, 1,2,4-triazole-3-one and 5-oxo-1,3-oxazolidine derivatives by several steps. The structural assignments of new compounds were based on their elemental analysis and spectral (FT IR, 1H NMR, 13C NMR and LC-MS) data. The antimicrobial, antilipase and antiurease activity studies revealed that some of the synthesized compounds showed antimicrobial, antilipase and/or antiurease activity.

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Authors and Affiliations

  1. Department of Forest Industrial Engineering, Artvin Çoruh University, Artvin, 08000, Turkey

    Sule Ceylan

  2. Department of Chemistry, Karadeniz Technical University, Trabzon, 61080, Turkey

    Hacer Bayrak, Ahmet Demirbas & Neslihan Demirbas

  3. Department of Biology, Recep Tayyip Erdogan University, Rize, 5300, Turkey

    Serdar Ulker & Sengul Alpay-Karaoglu

Authors
  1. Sule Ceylan
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  2. Hacer Bayrak
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  3. Ahmet Demirbas
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  4. Serdar Ulker
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  5. Sengul Alpay-Karaoglu
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  6. Neslihan Demirbas
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Correspondence to Neslihan Demirbas.

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Ceylan, S., Bayrak, H., Demirbas, A. et al. Synthesis of some new hybride molecules containing several azole moieties and investigation of their biological activities. Russ J Bioorg Chem 40, 314–329 (2014). https://doi.org/10.1134/S1068162014030145

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  • DOI: https://doi.org/10.1134/S1068162014030145

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