SYNTHESIS OF SOME NEW HYBRIDE MOLECULES CONTAINING SEVERAL AZOLE MOIETIES AND INVESTIGATION OF THEIR BIOLOGICAL ACTIVITIES

© 2014 Sule Ceylan*, Hacer Bayrak**, Ahmet Demirbas**, Serdar Ulker***, Sengul Alpay-Karaoglu***, Neslihan Demirbas**^{, #}

^#Phone: +90 462 377425; fax: +90 462 325-31-96; e-mail: neslihan@ktu.edu.tr

*Artvin Çoruh University, Department of Forest Industrial Engineering, Artvin, 08000 Turkey
**Karadeniz Technical University Department of Chemistry, Trabzon, 61080 Turkey
***Recep Tayyip Erdogan University, Department of Biology, Rize, 5300 Turkey

Received November 7, 2013; in final form, December 5, 2013

1,2,4-Triazole-3-one prepared from tryptamine was converted to the corresponding carbotioamides 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.

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

Биоорг. химия 2014, 40 (3): 341-356