Synthesis and antimicrobial activities of 2-(5-mercapto)-1,3-oxadiazol-2-ylmethyl-1,2,4-triazol-3-one derivatives


DEMİRBAŞ A. , SAHIN D., DEMİRBAŞ N. , Karaoglu S. A. , Bektas H.

TURKISH JOURNAL OF CHEMISTRY, cilt.34, sa.3, ss.347-358, 2010 (SCI İndekslerine Giren Dergi) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 34 Konu: 3
  • Basım Tarihi: 2010
  • Doi Numarası: 10.3906/kim-0911-10
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Sayfa Sayıları: ss.347-358

Özet

The synthesis of 4-amino-2-[(5-mercapto-1,3,4-oxadiazol-2-yl)methyl]-5-(4-methylphenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (2) and 4-amino-2-[(4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)methyl]-5-(4-methylphenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (5) was performed starting from 2-[4-amino-3-(4-methylphenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetohydrazide (1). The treatment of 2 and 5 with 4-fluorobenzaldehyde (for 8) or salicylaldehyde (for 6) afforded the corresponding Schiff bases (6 and 8). The condensation of 5 with phenacyl bromide produced 4-amino-5-(4-methylphenyl)-2-[(6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (7). The alkylation of 2 and 8 was carried out by using methyl iodide in basic media. Compounds 3 and 10a,b were prepared by aminoalkylation of 2 and 8 with 4-fluorophenyl piperazine, morpholine, or 4-methyl piperazine in the presence of formaldehyde. The synthesized compounds were screened for their antimicrobial activities and, with the exception of 2, 4, 7, and 9, were found to possess good or moderate activities against the screened bacterial strains except Candida tropicalis and Candida albicans.

The synthesis of 4-amino-2-[(5-mercapto-1,3,4-oxadiazol-2-yl)methyl]-5-(4-methylphenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (2) and 4-amino-2-[(4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)methyl]-5-(4-methylphenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (5) was performed starting from 2-[4-amino-3-(4-methylphenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]acetohydrazide (1). The treatment of 2 and 5 with 4-fluorobenzaldehyde (for 8) or salicylaldehyde (for 6) afforded the corresponding Schiff bases (6 and 8). The condensation of 5 with phenacyl bromide produced 4-amino-5-(4-methylphenyl)-2-[(6-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl)methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (7). The alkylation of 2 and 8 was carried out by using methyl iodide in basic media. Compounds 3 and 10a,b were prepared by aminoalkylation of 2 and 8 with 4-fluorophenyl piperazine, morpholine, or 4-methyl piperazine in the presence of formaldehyde. The synthesized compounds were screened for their antimicrobial activities and, with the exception of 2, 4, 7, and 9, were found to possess good or moderate activities against the screened bacterial strains except Candida tropicalis and Candida albicans.