| dc.contributor |
Chemistry |
|
| dc.creator |
Rimoldi, John M. |
|
| dc.date |
2014-03-14T21:20:47Z |
|
| dc.date |
2014-03-14T21:20:47Z |
|
| dc.date |
1993 |
|
| dc.date |
2005-10-10 |
|
| dc.date |
2005-10-10 |
|
| dc.date |
2005-10-10 |
|
| dc.date.accessioned |
2023-02-28T18:21:31Z |
|
| dc.date.available |
2023-02-28T18:21:31Z |
|
| dc.identifier |
etd-10102005-131622 |
|
| dc.identifier |
http://hdl.handle.net/10919/39739 |
|
| dc.identifier |
http://scholar.lib.vt.edu/theses/available/etd-10102005-131622/ |
|
| dc.identifier.uri |
http://localhost:8080/xmlui/handle/CUHPOERS/269719 |
|
| dc.description |
Several C-7 and C-13 diazirinyl taxol analogs have been synthesized as potential photoaffinity-labeled derivatives for studying the nature of the binding site of taxol on polymerized tubulin. One analog has been prepared in both deuterium- and tritium-labeled versions.
Methods were developed to selectively hydrolyze the C-2 benzoate of taxol which have allowed for the preparation of a variety of C-2 modified taxol derivatives. The C-2 taxol analogs were tested in several cell culture assays, and substantial increases in potency were observed with many of these derivatives, suggesting that the C-2 benzoate may play a crucial role in taxol's activity.
Reaction of 2'-tert-butyldimethylsilyl-7-triethylsilyl taxol with Triton B™ selectively hydrolyzed the C-2 benzoate and the C-4 acetate respectively. This is the first disclosure of the C-4 deacetylation of taxol carrying an intact C-13 side chain.
Several oxetane ring opened taxol analogs were synthesized via reaction of taxol with electrophilic reagents. The reaction of these oxetane ring-opened analogs have revealed some interesting rearrangements and functional group transfer reactions. |
|
| dc.description |
Ph. D. |
|
| dc.format |
xi, 250 leaves |
|
| dc.format |
BTD |
|
| dc.format |
application/pdf |
|
| dc.format |
application/pdf |
|
| dc.language |
en |
|
| dc.publisher |
Virginia Tech |
|
| dc.relation |
OCLC# 35838253 |
|
| dc.relation |
LD5655.V856_1993.R576.pdf |
|
| dc.rights |
In Copyright |
|
| dc.rights |
http://rightsstatements.org/vocab/InC/1.0/ |
|
| dc.subject |
LD5655.V856 1993.R576 |
|
| dc.title |
Investigations of the chemistry of taxol |
|
| dc.type |
Dissertation |
|
| dc.type |
Text |
|