Synthesis of Some Novel Norbornene-Fused Pyridazines as Potent Inhibitors of Carbonic Anhydrase and Acetylcholinesterase

Kocak R., Akin E. T., Kalin P., Talaz O., SARAÇOĞLU N., DAŞTAN A., ...Daha Fazla

JOURNAL OF HETEROCYCLIC CHEMISTRY, cilt.53, sa.6, ss.2049-2056, 2016 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 53 Sayı: 6
  • Basım Tarihi: 2016
  • Doi Numarası: 10.1002/jhet.2558
  • Dergi Adı: JOURNAL OF HETEROCYCLIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Sayfa Sayıları: ss.2049-2056
  • Ankara Üniversitesi Adresli: Hayır

Özet

The reaction of benzocyclic norbornene derivatives with tetrazines provided the 1,3-dihydropyridazine derivatives as a single product. The dihydropyridazine derivatives have been dehydrogenated with phenyliodine bis(trifluoroacetate) to yield the corresponding pyridazines in a high yield. Two stable diazines, primary product of corresponding 1,4-dihydropyridazine, were also isolated. Structures were then determined by H-1-NMR, and C-13-NMR beside to elemental analyses. The novel pyridazine derivatives (8-9) efficiently inhibited the cytosolic human carbonic anhydrase isoenzymes I and II (hCA I and II). In addition, these novel pyridazine derivatives (8-9) were evaluated for their in vitro acetylcholinesterase inhibitory activity. Ligand-receptor interactions are tested using molecular docking simulations. Obtained docking scores are in good agreement with in vitro results.