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Unformatted text preview: potent than the other isomer, since the lack of rotation around the bond prevents rotational inter-conversion between the two forms. This means that one isomer may be able to achieve the necessary conformation to bind a target molecule (such as an enzyme or receptor), while the other isomer may not be able to bind at all or may be an inferior binding partner. For example, chlorprothixine is a first generation antipsychotic drug that was first used to treat schizophrenia and other disorders in the 1950’s. The drug functions by blocking certain receptors in neurons, which requires binding of the drug to the receptor. Research has shown that cis-chlorprothixene is biologically active, while the trans form is almost completely inactive. In fact, the trans isomer is considered a contaminant in the drug formulation. S Cl H NMe 2 S Cl H Me 2 N cis-chlorprothiexine trans-chlorprothiexine J. Med. Chem. 1993 , 36, 2219-2227....
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This note was uploaded on 03/02/2012 for the course CHEM 5111 taught by Professor Vogel during the Fall '08 term at MIT.
- Fall '08