Wang, Chenbo
(2010)
Synthetic Studies on Haouamine A and Other Biologically Active Heterocycles.
Doctoral Dissertation, University of Pittsburgh.
(Unpublished)
Abstract
The first section of this dissertation describes the synthesis of a tethered macrocyclic ring system based on the natural product westiellamide. As expected, this system was shown to increase the affinity and ease of complexation to Ag(I) ions as confirmed by NMR and fluorescence Ag(I) titration studies.The second section describes the synthesis of a new series of heterocyclic inhibitors of the BoNT serotype A metalloprotease based on the therapeutic lead NSC 240898. Preliminary structure-activity relationship studies afford detailed insights into the steric and lectrostaticproperties of the pharmacophore of this molecular scaffold. Four of the newly synthesized inhibitors exhibited elevated inhibition against BoNT/A LC when compared to the lead agent.The third section describes an approach towards the total synthesis of haouamine A. A promising route to the marine alkaloid was established, including a highly efficient Suzuki crosscouplingreaction, aldol condensation and aromatization reaction. Several late-stage intermediates were analyzed by X-ray diffraction to provide valuable information about the relationships between conformation and reactivity.
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Details
| Item Type: |
University of Pittsburgh ETD
|
| Status: |
Unpublished |
| Creators/Authors: |
|
| ETD Committee: |
|
| Date: |
28 June 2010 |
| Date Type: |
Completion |
| Defense Date: |
16 December 2009 |
| Approval Date: |
28 June 2010 |
| Submission Date: |
4 January 2010 |
| Access Restriction: |
No restriction; Release the ETD for access worldwide immediately. |
| 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: |
medicinal chemistry; natural products; total synthesis |
| Other ID: |
http://etd.library.pitt.edu/ETD/available/etd-01042010-113545/, etd-01042010-113545 |
| Date Deposited: |
10 Nov 2011 19:30 |
| Last Modified: |
15 Nov 2016 13:35 |
| URI: |
http://d-scholarship.pitt.edu/id/eprint/6260 |
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