Chemistry:Encyprate
Encyprate is a monoamine oxidase inhibitor (MAOI) agent that was developed for use in the treatment of depression. It is an irreversible inhibitor of the MAO enzyme because it is agent that can form covalent bonds with the active site. As such, it is sometimes referred to as a “suicide inactivator” of MAO. It was invented by Bruce Horrom of Abbott in the 1960s by structure activity studies on pargyline.[1] Although it is not known to have ever been used in the clinic, it is an example of the heritage of agents that were developed at that time.
Synthesis
The condensation between cyclopropylamine [765-30-0] (1) and benzaldehyde [100-52-7] (2) gives N-benzylidenecyclopropylamine [3187-77-7] (3). The reduction of the Schiff-base gives N-benzylcyclopropylamine [13324-66-8] (4). Urethane formation with ethyl chloroformate [541-41-3] (5) completes the synthesis of encyprate (6).[2][3]
References
- ↑ "Structure-activity relations in the pargyline series". Annals of the New York Academy of Sciences 107 (3): 891–898. July 1963. doi:10.1111/j.1749-6632.1963.tb13332.x. PMID 13979700. Bibcode: 1963NYASA.107..891S.
- ↑ Horrom BW, Martin WB, US patent 3083226, issued 1963
- ↑ The organic chemistry of drug synthesis. New York: Wiley. 1977. p. 27. ISBN 0-470-10750-2. https://books.google.com/books?id=N6OAhuiHqiIC&pg=PA27.
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