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Title:Design, synthesis, and evaluation of conformationally rigid naproxen chiral selectors
Author(s):Liu, Yuelong
Doctoral Committee Chair(s):Pirkle, William H.
Department / Program:Chemistry
Discipline:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Degree:Ph.D.
Genre:Dissertation
Subject(s):Chemistry, Organic
Chemistry, Pharmaceutical
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.
Issue Date:1995
Type:Text
Language:English
URI:http://hdl.handle.net/2142/23400
Rights Information:Copyright 1995 Liu, Yuelong
Date Available in IDEALS:2011-05-07
Identifier in Online Catalog:AAI9543654
OCLC Identifier:(UMI)AAI9543654


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