Design, synthesis, and evaluation of conformationally rigid naproxen chiral selectors
Liu, Yuelong
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https://hdl.handle.net/2142/23400
Description
Title
Design, synthesis, and evaluation of conformationally rigid naproxen chiral selectors
Author(s)
Liu, Yuelong
Issue Date
1995
Doctoral Committee Chair(s)
Pirkle, William H.
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Chemistry, Pharmaceutical
Language
eng
Abstract
Conformationally rigid naproxen chiral selector are designed and synthesized based on our chiral recognition hypothesis. When bonded to silica, this type of chiral selectors of rigid conformation are evaluated chromatographically and demonstrate enhanced enantioselectivity towards naproxen and other members of profens, an important group of non-steroidal anti-inflammatory drugs(NSAIDs). The improved enantioselectivity is believed to stem from a highly preorganized disposition of the key functional groups in this type of chiral selectors, which allow for simultaneous optimal use of hydrogen bonding, $\pi$-$\pi$ face-to-face and face-to-edge interactions with but one enantiomer of naproxen. Strong support for our chiral recognition model is obtained from systematic chromatographic studies as well as a series of $\sp1$H$\{\sp1\rm H\}$ nOe experiments on the 1:1 diastereomeric complexes formed between this type of chiral selector and enantiomers of a naproxen-derived amide.
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