eprintid: 18607
rev_number: 16
userid: 2068
dir: disk0/00/01/86/07
datestamp: 2013-07-01 18:17:07
lastmod: 2018-07-01 05:15:05
status_changed: 2013-07-01 18:17:07
type: thesis_degree
metadata_visibility: show
contact_email: brandonparks10@gmail.com
item_issues_count: 0
eprint_status: archive
creators_name: Parks, Brandon
creators_email: bwp5@pitt.edu
creators_id: BWP5
title: Synthesis of Pyrrolo[1,3]-Diazepines and Potential Poxvirus Resolvase Inhibitors
ispublished: unpub
divisions: sch_as_chemistry
full_text_status: public
keywords: Heterocycle Synthesis, Dynamic Combinatorial Library, Poxvirus Inhibitors
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).
date: 2013-07-01
date_type: published
pages: 204
institution: University of Pittsburgh
refereed: TRUE
etdcommittee_type: committee_chair
etdcommittee_type: committee_member
etdcommittee_type: committee_member
etdcommittee_name: Wipf, Peter
etdcommittee_name: Nelson, Scott / G
etdcommittee_name: Curran, Dennis / P
etdcommittee_email: wipf@pitt.edu
etdcommittee_email: sgnelson@pitt.edu
etdcommittee_email: curran@pitt.edu
etdcommittee_id: WIPF
etdcommittee_id: SGNELSON
etdcommittee_id: CURRAN
etd_defense_date: 2013-03-27
etd_approval_date: 2013-07-01
etd_submission_date: 2013-04-25
etd_release_date: 2013-07-01
etd_access_restriction: 5_year
etd_patent_pending: FALSE
thesis_type: thesis
degree: MS
citation:   Parks, Brandon  (2013) Synthesis of Pyrrolo[1,3]-Diazepines and Potential Poxvirus Resolvase Inhibitors.  Master's Thesis, University of Pittsburgh.    (Unpublished)  
document_url: http://d-scholarship-dev.library.pitt.edu/18607/4/b_parks_ETD.pdf