Synthesis and anticholinesterase activity of new bispyridinium compounds

✍ Scribed by Fu-Lian Hsu; Radharaman Ray; Offie E. Clark; Shekar Munavalli; William P. Ashman

• Publisher: John Wiley and Sons
• Year: 1992
• Tongue: English
• Weight: 491 KB
• Volume: 81
• Category: Article
• ISSN: 0022-3549
• DOI: 10.1002/jps.2600811211

✦ Synopsis

Synthesis of new bis(1-methylpyridinium) compounds containing a 1,4-diacetylbenzene linkage between the pyridinium moieties from commercially available 2-, 3-, and 4-picoline precursors was accomplished via metallation, reaction of the picolyllithium with 1,4-dicyanobenzene, and subsequent quaternization of the resulting bispyridyl compounds. Acetylcholinesterase inhibitory activity was determined colorimetrically with purified electric eel enzyme. Examination of structure-activity relationships indicated that the 3-substituted pyridinium compound is the most potent isomer, followed by the 2-substituted isomer, and that the 4-substituted analogue is the least active.