Synthesis and Anticholinesterase Activity and Cytotoxicity of Novel Amide Derivatives

ALTINTOP M. D., KAPLANCIKLI Z. A., ÖZDEMİR A., Turan-Zitouni G., TEMEL H. E., AKALIN ÇİFTÇİ G.

ARCHIV DER PHARMAZIE, vol.345, no.2, pp.112-116, 2012 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 345 Issue: 2
  • Publication Date: 2012
  • Doi Number: 10.1002/ardp.201100124
  • Journal Name: ARCHIV DER PHARMAZIE
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Index Chemicus (IC)
  • Page Numbers: pp.112-116
  • Keywords: Amide, Anticholinesterase activity, Cytotoxicity, Thiadiazole, ALZHEIMERS-DISEASE, CHOLINESTERASE-INHIBITORS, ANTI-BACTERIAL, PHENOTHIAZINE
  • Bilecik Şeyh Edebali University Affiliated: No

Abstract

In the present study, some amide derivatives were synthesized and their potential anticholinesterase properties were investigated. N-(Benzothiazol-2-yl)-2-[(5-amino/methyl-1,3,4-thiadiazol-2-yl)thio]acetamide derivatives were obtained by nucleophilic substitution of 2-chloro-N-(benzothiazole-2-yl)acetamide derivatives with appropriate 1,3,4-thiadiazole-2-thioles. The chemical structures of the compounds were elucidated by 1H-NMR, 13C-NMR and FAB+-MS spectral data and elemental analyses. Each amide derivative was evaluated for its ability to inhibit AChE and BuChE using a modification of Ellman's spectrophotometric method. The compounds were also investigated for their cytotoxic properties using MTT assay. 2-(5-Amino-1,3,4-thiadiazol-2-yl)thio-N-(benzothiazol-2-yl)acetamide derivatives have anticholinesterase activity, whereas 2-(5-methyl-1,3,4-thiadiazol-2-yl)thio-N-(benzothiazol-2-yl)acetamide derivatives have no inhibitory effect on enzyme activity. Among these compounds, it is clear that compound IIh is the most potent derivative.