The Effect of Ortho Substitution on the Hydrolysis of Benzoylcholine

Abstract
A series of mono- and di-ortho-substituted benzoylcholine compounds has been prepared and the rates of hydroxide ion and cholinesterase catalysed hydrolysis has been determined for each compound. The anti-acetylcholinesterase activities of the compounds have also been determined. It has been found that some of the compounds are stable to esterase catalysed hydrolysis and that the groups which confer stability do not prevent the formation of enzyme substrate complexes. The most suitable groups for ester stabilisation, when used as ortho substituents, are alkyl and iodo as mono substituents and most groups, except hydroxy, as di-ortho substituents.