k Microwave assisted synthesis of novel hybrid tacrine-sulfonamide derivatives and investigation of their antioxidant and anticholinesterase activities

Ulus R., Kurt B. , Gazioglu I. , Kaya M.

BIOORGANIC CHEMISTRY, vol.70, pp.245-255, 2017 (Journal Indexed in SCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 70
  • Publication Date: 2017
  • Doi Number: 10.1016/j.bioorg.2017.01.005
  • Title of Journal : BIOORGANIC CHEMISTRY
  • Page Numbers: pp.245-255


A novel series of tacrine derivatives containing sulfonamide group were synthesized and their inhibitory effects on acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) were evaluated. The result showed that all the synthesized tacrine-sulfonamides (VIIIa-o) exhibited inhibitory activity on both cholinesterases. VIIIg showed the highest inhibitory activity on AChE IC50 = 0.009 mu M. This value is 220-fold greater than that of galantamine (IC50 = 2.054 mu M) and 6-fold greater than tacrine (IC50 = 0.055 mu M). VIIIf displayed the strongest inhibition of BuChE (IC50 = 2.250 mu M), which is close to donepezil (IC50 = 2.680 mu M) and 8-fold greater than that of galantamine (IC50 = 18.130 mu M) Furthermore, all of the synthesized tacrine derivatives showed higher inhibition of BuChE than that of galantamine. In addition, the cupric reducing antioxidant capacities (CUPRAC) and ABTS cation radical scavenging abilities of the synthesized compounds were investigated for the antioxidant activity. Among them, VIIIb (IC50 = 94.390 +/- 2.310 mu M) showed significantly better ABTS cation radical scavenging ability than all of the new synthesized compounds. (C) 2017 Published by Elsevier Inc.