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Synthesis of Pyrrolo[1,3]-Diazepines and Potential Poxvirus Resolvase Inhibitors

Parks, Brandon (2013) Synthesis of Pyrrolo[1,3]-Diazepines and Potential Poxvirus Resolvase Inhibitors. Master's Thesis, University of Pittsburgh. (Unpublished)

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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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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Parks, Brandonbwp5@pitt.eduBWP5
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairWipf, Peterwipf@pitt.eduWIPF
Committee MemberNelson, Scott / Gsgnelson@pitt.eduSGNELSON
Committee MemberCurran, Dennis / Pcurran@pitt.eduCURRAN
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


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