Synthesis of some 3,4-disubstituted-6,7-dihydro-imidazo[2,1-b][1,3]thiazole and 3,4-disubstituted-7,8-dihydro-6H-imidazo[2,1-b][1,3]thiazine derivatives and evaluation of their cytotoxicities against F2408 and 5RP7 cells

MERİÇ A., Incesu Z., Hatipoglu I.

MEDICINAL CHEMISTRY RESEARCH, sa.1, ss.30-41, 2008 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Basım Tarihi: 2008
  • Doi Numarası: 10.1007/s00044-008-9090-7
  • Dergi Adı: MEDICINAL CHEMISTRY RESEARCH
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.30-41
  • Anahtar Kelimeler: fused azole heterocycles, bridgehead nitrogen, 6,7-dihydro-imidazo[2,1-b][1,3]thiazoles, 7,8-dihydro-6H-imidazo[2,1-b][1,3]thiazines, WEITERE TUMORHEMMENDE VERBINDUNGSKLASSEN, BRIDGEHEAD NITROGEN ATOM, HETEROCYCLIC-SYSTEMS, EFFEKTE
  • Anadolu Üniversitesi Adresli: Evet

Özet

This article describes the synthesis of 3,4-disubstituted-6,7-dihydro-imidazo[2,1-b][1,3]thiazoles and 3,4-disubstituted-7,8-dihydro-6H-imidazo[2,1-b][1,3]thiazines, having substituted or nonsubstituted phenyl rings at the 5,6 and 2,3 positions, respectively, their cytotoxic effects through noncancer (F2408) and cancer (5RP7) cells, and their detailed H-1- and C-13-nuclear magnetic resonance (NMR) spectral characterization. The title compounds were obtained by the cyclization of 4,5-diaryl-imidazole-2-thione and dihaloalkane (i.e., 1,2-dihaloethane or 1,3-dihalopropane), in the presence of potassium carbonate (K2CO3) in N,N-dimethyl formamide (DMF). 4,5-Diaryl-imidazole-2-thione was prepared by condensation of alpha-hydroxyketones (acyloins), which were obtained by treating aldehydes with cyanide, with thioureas in AcOH. The structure of imidazo[2,1-b][1,3]thiazole and imidazo[2,1-b][1,3]thiazine derivatives was confirmed by infrared (IR), H-1-NMR, and C-13-NMR. The cytotoxicities of the synthesized compounds on both of noncancer (F2408) and cancer (5RP7) cells were measured by 3-(4,5-dimethyl-thiazollyl-2)-2,5-diphenyltetrazolium (MTT) assay. In the presence of only lower doses of compounds 9 and 11, bearing methyl or methoxy substituents on the phenyl ring of imidazo[2,1-b][1,3]thiazole scaffold, the cytotoxic effect was higher on 5RP7 cells than control cells after 24 h.