Construction of New Potential Reactivators of Phosphonylated Acetylcholinesterase. Substitution of F for H in the Nucleus of Pyridinecarboxaldehyde Oximes

摘要

Two new Fluoro-pyridnecarboxaldehyde oxime methiodide (F-PAM) compounds have been synthesized: 3-F-2-PAM and 5-F-2-PAM. These compounds and their unquaternized oxime precursors have been rigorously characterized by elemental analysis, mass spectroscopy, MNR, UV, and pKa determination. Detail spectroscopic interpretations are provided and correlated with analogous data for other PAM compounds. Both F-isomers of 2-PAM are obtained in low yield, 3-F-2-PAM is unstable during titration with NaOH, while 5-F-2-PAM is stable but its pKa is only 0.15 pKa units lower than that of 2-PAM.