| Characterization of an abeo-taxane: brevifoliol and derivatives. | |
| | |
MedLine Citation:
|
PMID: 15165147 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
|
Brevifoliol is a natural diterpene isolated from Taxus baccata Nutt. A series of brevifoliol 1 derivatives, 2-8 and 10, were prepared for characterization and semisynthesis purposes and included the introduction of acetyl, Troc, and TES groups at C-5 and C-13. Derivatives 16-20 of 5-acetylbrevifoliol 2 were obtained via esterification with cinnamic acid, with both 2S-(-)- and 2R-(+)-3-phenyllactic acid, and with N-benzoyl-(2'R,3'S)-3'-phenylisoserine at C-13. Brevifoliol compounds 12, 13, and 15 with either 2S-(-)-phenyllactate moieties at C-5 and C-13 or an N-benzoyl-(2'R,3'S)-3'-phenylisoserinyl at C-13 were also prepared. An abeo-taxane structure for 1 was clearly defined from the (13)C NMR analysis of the 5-acetyl-13-oxo derivative 8 and from the conversion of 1 into 10, a conformationally restrained compound having a C-13, C-15 oxygen bridge. The biological activity of each of these derivatives is being studied. |
| | |
Authors:
|
Steve Tremblay; Chantal Soucy; Neil Towers; Philip J Gunning; Livain Breau |
Related Documents
:
|
19679107 - Metabolism and biological production of resolvins derived from docosapentaenoic acid (d... 17241047 - Stm study on 2d molecular assemblies of luminescent quinacridone derivatives: structure... 8931947 - Structure determination of metabolites isolated from urine and bile after administratio... 1344867 - On hypotensive action of some imidazoline derivatives of sulphonamidated aryloxyalkylca... 15337627 - N6/n3 hypothesis and allergies: biologically plausible, but not confirmed. 12581177 - Intrathecally applied flurbiprofen produces an endocannabinoid-dependent antinociceptio... |
Publication Detail:
|
Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
|
Title: Journal of natural products Volume: 67 ISSN: 0163-3864 ISO Abbreviation: J. Nat. Prod. Publication Date: 2004 May |
Date Detail:
|
Created Date: 2004-05-28 Completed Date: 2004-06-24 Revised Date: 2006-11-15 |
Medline Journal Info:
|
Nlm Unique ID: 7906882 Medline TA: J Nat Prod Country: United States |
Other Details:
|
Languages: eng Pagination: 838-45 Citation Subset: IM |
Affiliation:
|
Département de Chimie, Université du Québec à Montréal, C.P. 8888 Succ. Centre-Ville, Montréal (PQ), Canada, H3C 3P8. |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
|
Catalysis Esterification Molecular Structure Nuclear Magnetic Resonance, Biomolecular Plants, Medicinal / chemistry* Stereoisomerism Structure-Activity Relationship Taxoids / chemical synthesis, chemistry* Taxus / chemistry* |
| Chemical | |
Reg. No./Substance:
|
0/Taxoids; 0/brevifoliol |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Previous Document: Terpene isocyanides, isocyanates, and isothiocyanates from the Okinawan marine sponge Stylissa sp.
Next Document: Glycosidase-inhibiting pyrrolidines and pyrrolizidines with a long side chain in Scilla peruviana.