Investigating the cyclization of enediyne analogs using density functional theory

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Investigating the cyclization of enediyne analogs using density functional theory

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dc.contributor.advisor Kerwin, Sean
dc.creator Estep, Dylan
dc.date.accessioned 2012-08-20T14:56:41Z
dc.date.available 2012-08-20T14:56:41Z
dc.date.created 2012
dc.date.issued 2012-08-20
dc.identifier.uri http://hdl.handle.net/2152/17530
dc.description.abstract Enediynes are organic molecules that readily undergo a thermal rearrangement, now commonly known as the Bergman cyclization, to a cyclic para diradical form. Interest in this rearrangement was renewed when it was found to be crucial to the mechanism of cytotoxicity in a variety of natural products containing the enediyne structural moiety. Cyclization of these molecules leads to DNA strand scission and ultimately cell death. Recent efforts by medicinal chemists to discover therapeutically relevant enediyne derivatives have been complemented by computational approaches, which seek to compute energies and energetic barriers to cyclization that can accurately predict the behavior of these molecules in vivo. Here we demonstrate this approach for cis-hex-3-ene-1,5-diyne and two of its analogs using density functional theory, discuss the validity of its predictions, and investigate the effect of basis set on the description of these molecules’ reactivity.
dc.language.iso eng
dc.subject density functional theory
dc.subject computational chemistry
dc.subject rational drug design
dc.subject enediyne
dc.subject natural products
dc.subject cancer
dc.title Investigating the cyclization of enediyne analogs using density functional theory
dc.type Thesis
dc.description.department Pharmacy

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