The neurotransmitter dopamine regulates cognition and promotes reinforcing behaviors.  The dopamine transporter (DAT) protein moves dopamine back into neurons and is responsible for regulating synaptic dopamine levels.   Dysfunctions in dopamine levels are associated with conditions such as Parkinson's disease, schizophrenia, and addiction.   DAT inhibitors prevent DATs from regulating dopamine levels and prevent termination of neurotransmission.  DAT inhibitors are interesting pharmaceutical targets to treat psychiatric and neurodegenerative diseases and addiction.  Modafinil, a known DAT inhibitor, is a cognitive enhancer and wake-promoting agent approved by the U.S. Food and Drug Administration.  We have synthesized a modafinil analogue, 2-(benzylsulfinyl)acetamide, as a novel potential DAT inhibitor. Additionally, six derivatives of this parent compound have been synthesized: 3-chloro-, 3-bromo-, 3-methoxy-, 3-nitro-, 4-bromo, and 4-chloro-2-(benzylsulfinyl)acetamide.  Two more derivatives, 4-methoxy and 4-nitro-2-(benzylsulfinyl)acetamide are underway.  These DAT inhibitors can be used to further understand the dopamine-signaling pathway, and hopefully provide pharmaceutical treatments for Parkinson's disease, schizophrenia, and addiction.

Synthesis of modafinil analog 2-(benzylsulfinyl)acetamide and its derivatives: A series of potential dopamine transporter inhibitors

244th National Meeting (2012)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.