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Chemical Probes for the Treatment of Castration-Resistant Prostate Cancer and Necrotizing Enterocolitis

Eyer, Benjamin R. (2013) Chemical Probes for the Treatment of Castration-Resistant Prostate Cancer and Necrotizing Enterocolitis. Master's Thesis, University of Pittsburgh. (Unpublished)

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This thesis describes the synthesis of several small molecules, structurally related to SID3712502, which have shown promise as inhibitors of castration-resistant prostate cancer by preventing nuclear translocation of the androgen receptor. This thesis also describes the preparation of a small library of α- and β-glycoslyated analogs of N-acetylglucosamine and N-acetylgalactosamine, which were prepared from an oxazoline intermediate or by an acid catalyzed isomerization with the desired glycosyl acceptors. The configuration of the lead compound, C34, was confirmed by synthesis and NMR studies. Four glucosamine analogs and two galactosamine analogs showed promising in vitro anti-inflammatory effects. These analogs were shown to be probes for reducing cytokine over-expression through inhibition of TLR4 and able to reduce the gross disease of necrotizing enterocolitis.


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Item Type: University of Pittsburgh ETD
Status: Unpublished
CreatorsEmailPitt UsernameORCID
Eyer, Benjamin
ETD Committee:
TitleMemberEmail AddressPitt UsernameORCID
Committee ChairWipf, Peterpwipf@pitt.eduPWIPF
Committee MemberFloreancig, Paulflorean@pitt.eduFLOREAN
Committee MemberHorne, Sethhorne@pitt.eduHORNE
Date: 30 June 2013
Date Type: Publication
Defense Date: 15 February 2013
Approval Date: 30 June 2013
Submission Date: 21 February 2013
Access Restriction: 5 year -- Restrict access to University of Pittsburgh for a period of 5 years.
Number of Pages: 106
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: CRPC, AR, NEC, Toll-like receptor 4 (TLR4), Medicinal Chemistry
Date Deposited: 30 Jun 2013 16:55
Last Modified: 30 Jun 2018 05:15


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