Synthesis of some new 1,3,4-thiadiazol-2-ylmethyl-1,2,4-triazole derivatives and investigation of their antimicrobial activities


DEMİRBAŞ A., Sahin D., DEMİRBAŞ N., Karaoglu Ş.

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, cilt.44, sa.7, ss.2896-2903, 2009 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 44 Sayı: 7
  • Basım Tarihi: 2009
  • Doi Numarası: 10.1016/j.ejmech.2008.12.005
  • Dergi Adı: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.2896-2903
  • Anahtar Kelimeler: 1,2,4-Triazole, 1,3,4-Thiadiazole, Mannich base, Schiff base, Antimicrobial activity, ANTIBACTERIAL ACTIVITY, MANNICH-BASES, ANTITUMOR ACTIVITIES, AGENTS, OXAZOLIDINONES, INHIBITORS
  • Recep Tayyip Erdoğan Üniversitesi Adresli: Evet

Özet

4-Amino-2-[(5-arylamino-4,5-dihydro-1,3,4-thiadiazol-2-yl)methyl]-5-(4-methylphenyl)-2,4-dihydro-3H-1,2,4-triazol-3-ones(3a-c) were obtained in acidic media via the formation of 2-[(4-amino-3-aryl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)acetyl]-N-arylhydrazinecarbothioamides (2a-c), and then, compound 3b was converted to methylated derivative, 4. The basic treatment of carbothioamide derivatives, 2a-c, afforded 4-amino-2-[(4-aryl-5-sulphanyl-4H-1,2,4-triazol-3-yl)methyl]-5-(4-methylphenyl)-2,4-dihyro-3H-1,2, 4-triazol-3-ones (5a-c). The alkylation reactions of compounds 4H-1,2,4-triazol-3-ylmethyl-5-(4-methylphenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one derivatives (Sa-c) were performed by using methyl iodide or ethyl bromide in the presence of sodium ethoxide, while the treatment of the same intermediates, 5a-c, with aromatic aldehydes produced 2-{[4-(4-aryl)-5-sulphanyl-4H-1,2,4-triazol-3-yl]methyl}-4-(arylmethylene)amino-5-(4-methylphenyl)-2,4-dihydro-3H-1,2,4-triazol-3-ones (8a-d). The synthesis of 4-amino-(or arylideneamino)-5-(4-methylphenyl)-2-{[(4-methylpiperazin-1-yl or morpholin-4-ylethyl)methyl]-4-aryl-5-thioxo-4,5 -dihydro-1H-1,2,4-triazol-3-yl}methyl-2,4-dihydro-3H-1,2,4-triazol-3-ones (7a, b and 9) was performed by a one pot three-component Mannich reaction involving the corresponding compounds, 4-(substituted)amino-4H-1,2,4-triazol-3-ylmethyl-5-(4-methylphenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one derivatives 5a, b and 8a, methylpiperazine or 2-(4-morpholino)ethylamine and formaldehyde. The newly synthesized compounds were well characterized by elemental analyses, IR, (1)H NMR, (13)C NMR and mass spectral studies. They were also screened for their microbial activities. The antimicrobial activity study revealed that some of which 2a, c, 3c, 5a-c, 8a-d showed good activity against a variety of microorganisms. (C) 2008 Elsevier Masson SAS. All rights reserved.