Convenient synthesis of fused heterocyclic 1,3,5-triazines from some N-acyl imidates and heterocyclic amines as anticancer and antioxidant agents

Bekircan O., Kuxuk M., Kahveci B., Kolaylı S.

ARCHIV DER PHARMAZIE, cilt.338, sa.8, ss.365-372, 2005 (SCI-Expanded) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 338 Sayı: 8
  • Basım Tarihi: 2005
  • Doi Numarası: 10.1002/ardp.200400964
  • Dergi Adı: ARCHIV DER PHARMAZIE
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.365-372
  • Anahtar Kelimeler: fused heterocycle, N-acyl imidate, 1,3,5-triazine, anticancer, antioxidant, NATIONAL-CANCER-INSTITUTE, ANTITUMOR-ACTIVITY, BIOLOGICAL EVALUATION, DRUG DISCOVERY, IN-VITRO, DERIVATIVES, INHIBITORS, PYRAZOLO<1,5-A>-1,3,5-TRIAZINES, PYRAZOLO<1,5-C>-AS-TRIAZINES, AMIDINES
  • Karadeniz Teknik Üniversitesi Adresli: Evet

Özet

N-Acyl imidates (2), reacting with 5-amino pyrazole (3), 2-aminobenzimidazole (4), 3-amino-1,2,4-triazole (5), 3,5-diamino-1,2,4-triazole (6), and 5-aminotetrazole (7) give pyrazolo[1,5-a][1,3,5]triazine (8), benzo [4,5]imidazo [1,2-a] [1,3,5]triazine (9), [1,2,4]triazolo [2,3-a][1,3,5]triazine (10), [1,2,4]triazolo[2,3-a][1,3,5]triazin-5-ylamine (12), and tetrazolo-[1,5-a][1,3,5]triazine (14) derivatives, respectively The synthesized compounds were characterized on the basis of IR, H-1-NMR, C-13-NMR, and mass spectral data and elemental analyses results. Five of the newly synthesized compounds, 8a, 9a, 10a, 12a, and 14a, were selected by National Cancer Institute and screened for their anticancer activity against three cancer cell lines MCF7, NCI-H460, and SF-268, where 12a exhibited moderate antiproliferation potential. 12a was, thus, further tested for anticancer activity against 60 human cancer cell lines and showed moderate growth inhibition potency. 12a showed a high growth inhibitory activity against A498 renal cancer cell line. All of the newly synthesized Compounds 8-10, 12 and 14 were tested for their antioxidant capacity where they exhibited very high activity, even higher than the widely used reference antioxidants butylated hydroxytoluene and 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox (R)) Compound 12a also showed the highest antioxidant activity.