Synthesis of 1‐[(1 R )‐1‐(6‐fluoro‐1,3‐benzothiazol‐2‐yl)ethyl]‐3‐substituted phenyl ureas and their inhibition activity to acetylcholinesterase and butyrylcholinesterase

A series of novel 1‐[(1 R )‐1‐(6‐fluoro‐1,3‐benzothiazol‐2‐yl)ethyl]‐3‐substituted phenyl ureas were synthesized by the condensation of (1 R )‐1‐(6‐fluoro‐1,3‐benzothiazol‐2‐yl)ethanamine with substituted phenyl isocyanates under mild conditions. Their structures were confirmed 1 H, 13 C, and 19 F NMR spectra, and elemental analyses. The optical activities were confirmed by optical rotation measurements. The inhibition activity of 1‐[(1 R )‐1‐(6‐fluoro‐1,3‐benzothiazol‐2‐yl)ethyl]‐3‐substituted phenyl ureas to acetylcholinesterase (ACHE) and butyrylcholinesterase (BCHE) was also tested. Preliminary bioassay indicated that the target ureas displayed excellent acetylcholinesterase and butyrylcholinesterase inhibition activity. J. Heterocyclic Chem., 2011.