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Z. Naturforsch. 2014,
69b, 969 – 981
doi:10.5560/ZNB.2014-4126
Synthesis and Pharmacological Activities of Some New 2-[1-Heptyl-3-(4-methoxybenzyl)-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl]acetohydrazide Derivatives
1 Department of Chemistry, Faculty of Science, Karadeniz Technical University, 61080 Trabzon, Turkey
2 Department of Chemistry, Faculty of Arts and Sciences, Recep Tayyip Erdogan University, 53100 Rize, Turkey
3 Department of Biology, Faculty of Arts and Sciences, Recep Tayyip Erdogan University, 53100 Rize, Turkey
Reprint requests to Associate Prof. Dr. Olcay Bekircan. Tel. +90-462-3774296 (office); +90-5056153107 (mobile). E-mail:
obekircan@gmail.com
Received June 11, 2014 / published online October 12, 2014
In the present investigation, the key intermediate acetohydrazide derivative 5 was synthesized starting from 3-(4-methoxybenzyl)-4-amino-4,5-dihydro-1,2,4-triazol-5-one (1) by a four-step reaction. Thiosemicarbazides 6a–f and arylidenehydrazide derivatives 8a–d were obtained from compound 5. The cyclization of compounds 6a–f in the presence of NaOH resulted in the formation of compounds 7a–f. The compounds were characterized by IR, 1H NMR, 13C NMR spectroscopy, elemental analysis and mass spectral studies. The compounds were tested for their anti-lipase, anti-α-glucosidase and anti-mycobacterial activities. Compounds 6b and 8c exhibited excellent anti-lipase activity, and compound 8d showed excellent anti-α-glucosidase
activity. Compounds 3 and 4 exhibited good anti-tuberculosis activity.
Key words: Acetohydrazide Derivatives, 1,2,4-Triazoles, 1,2,4-Triazole-5-thiones, Lipase and α-Glucosidase Inhibitor Activities, Anti-mycobacterial Activity