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 (SCI-Expanded, Scopus)

  • Publication Type: Article / Article
  • Volume: 10 Issue: 12
  • Publication Date: 2002
  • Doi Number: 10.1016/s0968-0896(02)00420-0
  • Journal Name: BIOORGANIC & MEDICINAL CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.3717-3723
  • Karadeniz Technical University Affiliated: Yes

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.