Synthesis of novel 4-alkylidene- and 4-alkylamino-5-oxo-4,5-dihydro-[1,2,4]triazole derivatives and investigation of their antitumor activities


Demirbas N., Ugurluoglu R.

TURKISH JOURNAL OF CHEMISTRY, cilt.28, ss.559-571, 2004 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 28 Konu: 5
  • Basım Tarihi: 2004
  • Dergi Adı: TURKISH JOURNAL OF CHEMISTRY
  • Sayfa Sayıları: ss.559-571

Özet

A series of novel 3-alkyl-4-cyclohexylmethylenamino-5-oxo-4,5-dihydro-[1,2,4]triazoles (6a-e) and 3-alkyl-4-hexylidenamino-5-oxo-4,5-dihydro-[1,2,4]triazoles (7b-e) were synthesized from the reaction of corresponding 3-alkyl-4-amino-5-oxo-4,5-dihydro-[1,2,4]triazoles (1) with cyclohexancarboxaldehyde and capronaldehyde. The acetylation of compounds 6e and 7b resulted in the formation of 1-acetyl-4-cyclohexylmethylenamino-5-oxo-3-(p-tolyl)-4,5-dihydro-[1,2,4]triazole (10) and 3-benzyl-4-hexylidenamino5-oxo-4,5-dihydro-[1,2,4]triazole (11). 3-Alkyl-4-cyclohexylmethylamino-5-oxo-4,5-dihydro-[1,2,4]triazoles (8a-e) and 3-alkyl-4-hexylamino-5-oxo-4,5-dihydro-[1,2,4]triazoles (9b-e) were obtained from the selective reduction of compounds 6a-e and 7b-e with NaBH4. The in vitro antitumor activity of some selected compounds was screened by the National Cancer Institute (USA) against several human tumor cell lines, and compounds 8c, 9d and 11c were found to be active.