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Synthesis and Computational Binding Studies of Cannabinoid Analogues; Simple Computational Methods of Predicting Asymmetric Reactions

  • Author(s): Gutierrez, Michael
  • Advisor(s): Marsella, Michael J
  • et al.
Abstract

With the increased interest in the great therapeutic potential of cannabinoids also comes the need in finding more efficient methods for the facile synthesis of these compounds.

While most synthetic methodologies for the phytocannabinoids involve olivetol in some way, the synthetic pathways presented in this thesis utilize nonaromatic olivetol precurors in conjunction with a tandem Knoevenagel/Diels-Alder or Knoevenagel/oxo-6pi-cyclization to provide access to both natural and unnatural cannabinoids.

These compounds as well as analogues that could potentially be made by the methods provided in this thesis were also computationally screened for their affinity for the CB1 receptor. In addition to this in silico screening, one particular analogue was biologically screened and preliminary studies demonstrated a therapeutic potential towards ALS.

The second project presented in this thesis describes a computationally inexpensive, yet highly accurate, method towards predicting the asymmetric induction of certain reactions. This method examines the electrostatic potential mapped onto the surface of a molecule at the reactive site and at the same time allows for the examination of sterics, if applicable.

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