Parks, Brandon
(2013)
Synthesis of Pyrrolo[1,3]-Diazepines and Potential Poxvirus Resolvase Inhibitors.
Master's Thesis, University of Pittsburgh.
(Unpublished)
Abstract
This thesis describes our efforts toward the development of a dynamic combinatorial library using pyrrolo[1,3]-diazepines. During our work, I have demonstrated the ability to hydrolyze and recyclize the diazepine core via the condensation of several different aldehydes to afford novel diazepine derivatives. Additionally, I have been able to modulate the electronic and steric properties of the diazepine scaffold through substitution on the pyrrole core. My work towards finding suitable conditions for a thermodynamically controlled dynamic exchange reaction have shown that while hydrolysis of the diazepine scaffold seems to be favored, recyclization of the resulting amine intermediate appears to be disfavored. As a second project I describe our efforts toward the development of a library of pyrimidinone-based potential poxvirus resolvase inhibitors. Utilizing the multi-component Biginelli reaction, I have synthesized a small library of pyrimidinones attached to potential chelating functionalities, including the di-keto acid moiety. Biological testing has resulted in the discovery of a carboxylic acid containing pyrimidinone (MAL1-265) that possesses moderate fowlpox resolvase inhibitory activity (IC50 16 μM).
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Details
| Item Type: |
University of Pittsburgh ETD
|
| Status: |
Unpublished |
| Creators/Authors: |
|
| ETD Committee: |
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| Date: |
1 July 2013 |
| Date Type: |
Publication |
| Defense Date: |
27 March 2013 |
| Approval Date: |
1 July 2013 |
| Submission Date: |
25 April 2013 |
| Access Restriction: |
5 year -- Restrict access to University of Pittsburgh for a period of 5 years. |
| Number of Pages: |
204 |
| Institution: |
University of Pittsburgh |
| Schools and Programs: |
Dietrich School of Arts and Sciences > Chemistry |
| Degree: |
MS - Master of Science |
| Thesis Type: |
Master's Thesis |
| Refereed: |
Yes |
| Uncontrolled Keywords: |
Heterocycle Synthesis, Dynamic Combinatorial Library, Poxvirus Inhibitors |
| Date Deposited: |
01 Jul 2013 18:17 |
| Last Modified: |
01 Jul 2018 05:15 |
| URI: |
http://d-scholarship.pitt.edu/id/eprint/18607 |
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