New thiophene-1,2,4-triazole-5(3)-ones: Highly bioactive thiosemicarbazides, structures of Schiff bases and triazole-thiols

ÜNVER Y., SANCAK K., ÇELİK F., BIRINCI E., KÜÇÜK M., Soylu S., ...Daha Fazla

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, cilt.84, ss.639-650, 2014 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 84
  • Basım Tarihi: 2014
  • Doi Numarası: 10.1016/j.ejmech.2014.01.014
  • Dergi Adı: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.639-650
  • Anahtar Kelimeler: Schiff base, Thiosemicarbazide, 1,2,4-Triazole/thiol, Antioxidant, Antimicrobial, POTENTIAL ANTIDEPRESSANT, ANTIMICROBIAL EVALUATION, ANTIOXIDANT, 2,4-DIHYDRO-3H-1,2,4-TRIAZOLE-3-THIONES, SEMICARBAZONES, DERIVATIVES, DESIGN, AGENTS
  • Karadeniz Teknik Üniversitesi Adresli: Evet

Özet

Key compound 2-(4-amino-5-oxo-3-(thiophene-2-ylmethyl)-4,5-dihydro-1,2,4-tiazole-1-yl) acetohydrazide (3) was synthesized by reacting hydrazine hydrate with ethyl-2-(4-amino-5-oxo-3-(thiophene2-ylmethyl)-4,5-dihydro-1,2,4-tiazole-1yl)acetate (2), obtained in basic media from 4-amino-5-(thiophene-2-ylmethyl)-2H-1,2,4-triazole-3(4H)-one (I). Compound 3 was converted to thiosemicarbazide derivatives (4a-d) and Schiff base derivatives 6a-e and 7a-e. The treatment of compound 4 with NaOH gave 4-amino-24(4-(4-aryl)-5-mercapto-4H-1,2,4-triazole-3-ypmethyl)-5-(thiophene-2-ylmethyl)-2H-1,2,4-triazole-3(4H)-ones (5a-d). All newly compounds, well characterized by elemental analyses, IR, H-1 NMR, C-13 NMR and mass spectral studies were tested for their antioxidant and antimicrobial activities. Thiosemicarbazide derivatives (4a-d) were highly active in two antioxidant tests with 69.0-88.2% DPPH. scavenging and 503-1257 mu M TEAC values, while the others showed lower or no activity. The results of the two antioxidant tests correlated well. Moreover, Thiosemicarbazide derivatives (4a-d) also showed antibacterial activity against Staphylococcus aureus, Bacillus cereus, and Mycobacterium smegmatis. Thiosemicarbazide group deserves attention in the synthesis of bioactive compounds. (C) 2014 Elsevier Masson SAS. All rights reserved.