Publication Date
2006
Document Type
Thesis
Committee Members
Daniel Ketcha (Advisor)
Degree Name
Master of Science (MS)
Abstract
Carbonic anhydrases (CAs) are metalloenzymes that catalyze the reversible interconversion of CO2 and bicarbonate. We recently initiated a screen of a broad range of indoles and pyrroles possessing acyl-, carboxyl-, amido-, sulfonyl-, sulfamyl- and oxime- functionalities as potential inhibitors of á-CA II isozyme. As slight inhibition was observed in the case of 2-carboxamido-1-(phenylsulfonyl)pyrrole, and aware that pyrrole carboxamide derived sulfonamides had been previously demonstrated to possess CA inhibition, we sought to prepare a series of 1-(phenylsulfonyl)pyrrole-2-carboxamides but lacking a sulfonamide moiety to ascertain if the activity in our case might be due to a hitherto unrecognized pyrrole pharmacophore. To this end, we examined synthetic routes to such derivatives and found optimal results when employing a microwave-assisted, polymer-supported amidation reaction of 1-(phenylsulfonyl)pyrrole-2-carboxylic acid. Additionally, we examined the microwave-assisted Beckmann rearrangement of the oximes of acyl-1-(phenylsulfonyl)pyrroles and observed optimal results using montmorillonite as catalyst under solventless conditions.
Page Count
116
Department or Program
Department of Chemistry
Year Degree Awarded
2006
Copyright
Copyright 2006, all rights reserved. This open access ETD is published by Wright State University and OhioLINK.
