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Structural investigation of 3,5-disubstituted isoxazoles by 1H-nuclear magnetic resonance

✍ Scribed by Mario Sechi; Luciano Sannia; Maria Orecchioni; Fabrizio Carta; Giuseppe Paglietti; Nouri Neamati

Publisher
Journal of Heterocyclic Chemistry
Year
2003
Tongue
English
Weight
55 KB
Volume
40
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

HIV‐1 integrase (IN) is a very promising and validated target for the development of therapeutic agents against AIDS. In an effort to design and synthesize biological isosteric analogs of β‐diketoacid‐containing inhibitors of IN, we prepared a series of substituted isoxazole carboxylic acids. Several of these compounds inhibited catalytic activities of purified IN at micromolar concentration range. With an aim to prepare a large number of analogues based on the isoxazole pharmacophore we focused our study on a series of 3,5‐disubstituted isoxazole isomers. For a rapid structural analysis we discovered a convenient ^1^H‐nmr method for distinguishing between isomeric structures based on their H‐4 assignments. This “finger print” approach to isomer identification will be useful in combinatorial chemistry settings where a mixture can be further derivatized.

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