Date of Degree
PhD (Doctor of Philosophy)
Gregory K. Friestad
First Committee Member
Second Committee Member
Third Committee Member
Fourth Committee Member
This thesis consists of two parts, both on synthetic chemistry with medicinal and biological relevance. Part one aims to develop methods for the preparation of quinazoline derivatives. A streamlined method for the preparation of 6-substituted-4-methyl-2-quinazolyl-guanidines and their respective amides has been presented here, using inexpensive and readily available starting materials such as para-bromoaniline, dicyandiamide (DCDA), and other reagents that are well-established for reactions such as Heck coupling, Suzuki coupling, and Ullman coupling reactions. In part two a novel methodology was developed for the specific incorporation of a masked N,O-acetal at the peptide bond between glycine and other amino acids including phenylalanine, alanine, valine, leucine, isoleucine, aspartate, glutamate, and the aromatic amino acids tyrosine and tryptophan. This methodology opens the door to linking a wide variety of derivatives, including carboxylic acids, to a specific peptide bond within a oligopeptide fragment. Such derivatives can be useful in the development of natural products containing these specific linkages or in the development of oligopeptides tagged at specific locations with a biodegradable and traceless linker useful in identifying and reacting with their peptide ligands.
xi, 242 pages
Includes bibliographical references (pages 139-146).
Copyright © 2018 Sherif M. S. Ibrahim
Ibrahim, Sherif M. S.. "Quinazolin-2-yl-guanidines for treatment of neuropsychiatric disorders and the oxidative preparation of N,O-acetals linked to the amide bond of peptides." PhD (Doctor of Philosophy) thesis, University of Iowa, 2018.