Synthesis and Anticancer Evaluation of Some New 4-Amino-3-(p-methoxybenzyl)-4,5-dihydro-1,2,4-triazole-5-one Derivatives

BEKİRCAN O., KÜÇÜK M., Kahveci B., Bektas H.

ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, cilt.63, sa.11, ss.1305-1314, 2008 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 63 Sayı: 11
  • Basım Tarihi: 2008
  • Doi Numarası: 10.1515/znb-2008-1109
  • Dergi Adı: ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1305-1314
  • Anahtar Kelimeler: 1,2,4-Triazoles, E/Z Geometrical Isomers, cis/trans Amide Conformers, Benzylidenehydrazides, Anticancer Activity, ANTIMICROBIAL ACTIVITY, CONVENIENT SYNTHESIS, BREAST-CANCER, N-ACYL, TAMOXIFEN, WOMEN
  • Karadeniz Teknik Üniversitesi Adresli: Evet

Özet

4-Amino-3-p-methoxybenzyl-5-oxo-4,5-dihydro-1,2,4-triazol-1-yl-acetic acid ethyl ester (2) was prepared from 4-amino-4,5-dihydro-1H-1,2,4-triazole-5-one (1) and ethyl bromoacetate. Compound 3 was synthesized by the condensation of 2 with hydrazine hydrate. The treatment of compound 3 with various aromatic aldehydes resulted in the formation of arylidene hydrazides as cistrans conformers 4a-g. Thiosemicarbazide derivative 5 was prepared by the reaction Of compound 3 with phenylisothiocyanate. Cyclization of 5 with sodium hydroxide resulted in the formation of compound 6. Treatment of 6 with benzyl bromide gave compound 7. Four of the newly synthesized compounds were screened for their anticancer activity against a panel of 60 cell lines derived from nine cancer types, namely, non-small cell lung, colon, breast, ovarian, leukemia, renal, melanoma, prostate and CNS cancers at a fixed dose of 10 mu M.