Long-acting anticholinesterases for myasthenia gravis: synthesis and activities of quaternary phenylcarbamates of neostigmine, pyridostigmine and physostigmine.

Bioorganic & Medicinal Chemistry
Qian-Sheng YuNigel H Greig

Abstract

The N-monophenylcarbamate analogues of neostigmine methyl sulfate (6) and pyridostigmine bromide (8) together with their precursors (5), (7), and the N(1)-methylammonium analogues of (-)-phenserine (12), (-)-tolserine (14), (-)-cymserine (16) and (-)-phenethylcymserine (18) were synthesized to produce long-acting peripheral inhibitors of acetylcholinesterase or butyrylcholinesterase. Evaluation of their cholinesterase inhibition against human enzyme ex vivo demonstrated that, whereas compounds 5-8 possessed only marginal activity, 12, 14, 16 and 18 proved to be potent anticholinesterases. An extended duration of cholinesterase inhibition was determined in rodent, making them of potential interest as long-acting agents for myasthenia gravis.

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Citations

Mar 6, 2013·Muscle & Nerve·Saraguaci Hernandez-Oliveira e SilvaLéa Rodrigues-Simioni
May 15, 2015·Neurotoxicology and Teratology·Audrey FischerEmily English
Dec 3, 2014·Journal of Pharmaceutical and Biomedical Analysis·Marie VandeputJean-Michel Kauffmann
May 24, 2013·International Journal of Molecular Sciences·Miroslav Pohanka, Petr Dobes
May 12, 2012·Journal of Environmental Monitoring : JEM·Sara RodriguesBruno Nunes
Jul 2, 2019·Molecular Medicine Reports·Kamlesh Sharma

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