Synthesis of 3-alkyl(aryl)-4-alkylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-ones and 3-alkyl-4-alkylamino-4,5-dihydro-1H-1,2,4-triazol-5-ones as antitumor agents


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DEMIRBAS N. , UGURLUOGLU R., Demirbas A.

BIOORGANIC & MEDICINAL CHEMISTRY, vol.10, no.12, pp.3717-3723, 2002 (Journal Indexed in SCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 10 Issue: 12
  • Publication Date: 2002
  • Doi Number: 10.1016/s0968-0896(02)00420-0
  • Title of Journal : BIOORGANIC & MEDICINAL CHEMISTRY
  • Page Numbers: pp.3717-3723

Abstract

A series of 3-alkyl-4-phenylethylidenamino- (8) and 3-alkyl-4-(3-phenylallylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones (9) was synthesized from the reaction of the corresponding 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (1), with phenylacetaldehyde and cinnamaldehyde, 3-Alkyl-4-(2-phenylethyamino)- (10) and 3-alkyl-4-(3-phenylpropylamino)-4,5dihydro- 1H-1,2,4-triazol-5-ones (11) were obtained from the selective reduction of compounds (8) and (9) with NaBH4. The in vitro antitumor activity of the novel compounds was screened and the highest inhibition of tree tumor cell lines was observed for the compounds containing phenylethylenamino and phenylethylamino groups at position 4 of 1,2,4-triazol ring. (C) 2002 Elsevier Science Ltd. All rights reserved.

A series of 3-alkyl-4-phenylethylidenamino- (8) and 3-alkyl-4-(3-phenylallylidenamino)-4,5-dihydro-1H-1,2,4-triazol-5-ones (9) was synthesized from the reaction of the corresponding 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-ones (1), with phenylacetaldehyde and cinnamaldehyde, 3-Alkyl-4-(2-phenylethyamino)- (10) and 3-alkyl-4-(3-phenylpropylamino)-4,5dihydro- 1H-1,2,4-triazol-5-ones (11) were obtained from the selective reduction of compounds (8) and (9) with NaBH4. The in vitro antitumor activity of the novel compounds was screened and the highest inhibition of tree tumor cell lines was observed for the compounds containing phenylethylenamino and phenylethylamino groups at position 4 of 1,2,4-triazol ring. (C) 2002 Elsevier Science Ltd. All rights reserved.