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

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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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

Keywords

  • 1,2,4-triazole
  • 1,3,4-oxadiazole
  • 1,3-thiazolidinone
  • 1,3,4-thiadiazole
  • piperazine
  • biological activity