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

BEKİRCAN O., Mentese E., Ulkerc S.

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, vol.69, pp.969-981, 2014 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 69
  • Publication Date: 2014
  • Doi Number: 10.5560/znb.2014-4126
  • Journal Name: ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.969-981
  • Keywords: Acetohydrazide Derivatives, 1,2,4-Triazoles, 1,2,4-Triazole-5-thiones, Lipase and alpha-Glucosidase Inhibitor Activities, Anti-mycobacterial Activity, MYCOBACTERIUM-TUBERCULOSIS COMPLEX, ALPHA-GLUCOSIDASE INHIBITORS, ANTIMICROBIAL ACTIVITIES, 1,2,4-TRIAZOLE DERIVATIVES, HYDRAZONE DERIVATIVES, BIOLOGICAL EVALUATION, ANTICANCER EVALUATION, OBESITY, AGENTS, THERAPY
  • Recep Tayyip Erdoğan University Affiliated: Yes

Abstract

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, H-1 NMR, C-13 NMR spectroscopy, elemental analysis and mass spectial studies. The compounds were tested for their anti-lipase, anti-alpha-glucosidase and anti-mycobacterial activities. Compounds 6b and 8c exhibited excellent anti-lipase activity, and compound 8d showed excellent anti-alpha-glucosidase activity. Compounds 3 and 4 exhibited good anti-tuberculosis activity.