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Synthetic Studies of Heterocyclic and Bioactive Agents

Maskrey, Taber (2021) Synthetic Studies of Heterocyclic and Bioactive Agents. Doctoral Dissertation, University of Pittsburgh. (Unpublished)

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This dissertation describes a novel one-pot preparation of bicyclic heterocycles and improved synthetic procedures for the production of compounds possessing established biological activity. A five-component condensation reaction was discovered that follows a mechanistic sequence starting with a Biginelli reaction and ending in a Diels-Alder reaction to form a new class of bicyclic heterocycles. New protocols were developed to synthesize the bioactive compounds Gefitinib and analogs of JP4-039. The FDA approved EGFR inhibitor Gefitinib was synthesized on a pilot-plant scale using a more efficient synthetic sequence and fewer hazardous reagents. A shorter synthetic sequence to ferroptosis inhibitors, JP4-039 and related analogs, was developed with a key vinylogous Mannich reaction utilizing an oxazolidinone auxiliary. The biological activity of new ferroptosis inhibitors was used to generate a structure-activity relationship (SAR) hypothesis.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Maskrey, Tabertal86@pitt.edutal86
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairWipf, Peterpwipf@pitt.edupwipf
Committee MemberKoide, Kazunorikoide@pitt.edukoide
Committee MemberLiu, Pengpengliu@pitt.edupengliu
Committee MemberBayir, Hülyabayihx@ccm.upmc.eduhub22
Date: 3 May 2021
Date Type: Publication
Defense Date: 17 March 2021
Approval Date: 3 May 2021
Submission Date: 15 March 2021
Access Restriction: No restriction; Release the ETD for access worldwide immediately.
Number of Pages: 237
Institution: University of Pittsburgh
Schools and Programs: Dietrich School of Arts and Sciences > Chemistry
Degree: PhD - Doctor of Philosophy
Thesis Type: Doctoral Dissertation
Refereed: Yes
Uncontrolled Keywords: 5-component-condensation reaction, Gefitinib, JP4-039, ferroptosis, vinylogous Mannich reaction
Date Deposited: 03 May 2021 14:46
Last Modified: 03 May 2021 14:46


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