Synthesis of some new 1-acylthiosemicarbazides, 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazole-3-thiones and their anti-inflammatory activities

ŞAHİN G., PALASKA E., KELİCEN UĞUR E. P., Demirdamar R., Altinok G.

Arzneimittel-Forschung/Drug Research, vol.51, no.6, pp.478-484, 2001 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 51 Issue: 6
  • Publication Date: 2001
  • Doi Number: 10.1055/s-0031-1300066
  • Journal Name: Arzneimittel-Forschung/Drug Research
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.478-484
  • Keywords: 1,2,4-Triazol-5-thione, antiinflammatory activity, synthesis, ulcerogenic activity, 1,3,4-Oxadiazole, anti-inflammatory activity, synthesis, ulcerogenic activity, 1,3,4-Thiadiazole, anti-inflammatory activity, synthesis, ulcerogenic activity, Thiosemicarbazide, anti-inflammatory activity, synthesis, ulcerogenic activity
  • Hacettepe University Affiliated: Yes

Abstract

Sixteen 1-(1-naphthyloxy)acetyl-4-substituted-3-thiosemicarbazides, 2-substituted amino-5-(1-naphthyloxy)methyl-1,3,4-oxadiazoles, 2- substitutedamino-5-(1-naphthyloxy) methyl-1,3,4-thiadiazoles and 3-(1-naphthyloxy)methyl-4-substituted-1,2,4-triazole-5-thiones were synthesized. The structures of the compounds have been elucidated by UV, IR, 1H-NMR, 13C-NMR spectra and elemental analysis. The anti-inflammatory activities of the compounds were evaluated by carregeenan induced hind paw edema and air-pouch inflammation tests in mice. In carrageenan induced hind paw edema test, compounds 1a, 1d, 3d, 4a showed equivalent or higher activity compared to naproxen and phenylbutazone. In the air-pouch inflammatory model, compounds 1a, 1b, 1d, 2c, 3c, 3d, 4a and 4d showed marked anti-inflammatory activity. The ED50 values of these compounds ranged between 24-36 mg/kg. Side effects of the compounds on gastrointestinal system and kidneys were examined and none of the compound showed significant side effects.