Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1016/0006-291x(78)91014-8 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
-Acetylcolchinol Methyl Ether (a Natural Product); Suhailamine (a Phantom Natural Product).
J Nat Prod
September 2019
Department of Chemistry, Chemistry Research Laboratory , University of Oxford, Mansfield Road , Oxford OX1 3TA , U.K.
The reported characterization data for the allocolchicinoid alkaloid suhailamine, isolated from and known to have an erroneous structure, have been reanalyzed. This analysis has led to the current proposal that suhailamine has the same structure as -acetylcolchinol methyl ether (NCME), an assertion that is supported by comparison with previously reported data for NCME. Suhailamine is therefore a phantom natural product, while NCME represents a naturally occurring allocolchicinoid rather than a purely synthetic entity.
View Article and Find Full Text PDFTubulin-binding dibenz[c,e]oxepines: Part 2. Structural variation and biological evaluation as tumour vasculature disrupting agents.
Bioorg Med Chem
March 2017
Manchester Pharmacy School, University of Manchester, Oxford Road, Manchester M13 9PT, UK.
5,7-Dihydro-3,9,10,11-tetramethoxybenz[c,e]oxepin-4-ol 1, prepared from a dibenzyl ether precursor via Pd-catalysed intramolecular direct arylation, possesses broad-spectrum in vitro cytotoxicity towards various tumour cell lines, and induces vascular shutdown, necrosis and growth delay in tumour xenografts in mice at sub-toxic doses. The biological properties of 1 and related compounds can be attributed to their ability to inhibit microtubule assembly at the micromolar level, by binding reversibly to the same site of the tubulin αβ-heterodimer as colchicine 2 and the allocolchinol, N-acetylcolchinol 4.
View Article and Find Full Text PDFAsymmetric synthesis of antimicrotubule biaryl hybrids of allocolchicine and steganacin.
Chemistry
August 2007
Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
The asymmetric synthesis of novel axially chiral biaryl compounds 5 a-f containing a seven- or eight-membered heterocyclic medium ring is described. These molecules can be considered to be structural hybrids of allocolchicine- and steganacin-type natural products. The synthesis featured an atropo-diastereoselective biaryl Suzuki coupling in which a benzylic stereocenter efficiently transferred its stereochemical information to the biaryl axis.
View Article and Find Full Text PDFSynthesis of (S)-(-)-N-acetylcolchinol using intramolecular biaryl oxidative coupling.
Org Biomol Chem
June 2006
School of Chemistry, Leeds University, Leeds LS2 9JT, UK.
An asymmetric synthesis of the tubulin polymerisation inhibitor (S)-(-)-N-acetylcolchinol is reported based on an intramolecular biaryl oxidative coupling of a 1,3-diarylpropyl acetamide intermediate using phenyliodonium bis(trifluoroacetate) as the final step. Three syntheses of the penultimate 1,3-diarylpropyl acetamide intermediate (S)-(-)-N-[1-[3-(tert-butyldimethylsilyloxy)phenyl)]-3-(3,4,5-trimethoxyphenyl)propyl] acetamide are described which differ in the means by which the stereogenic centre was introduced.
View Article and Find Full Text PDFSingle dose of the antivascular agent, ZD6126 (N-acetylcolchinol-O-phosphate), reduces perfusion for at least 96 hours in the GH3 prolactinoma rat tumor model.
Neoplasia
November 2004
Department of Basic Medical Sciences, St. George's Hospital Medical School, Tooting, London, UK.
Tumor vasculature is an attractive therapeutic target as it differs structurally from normal vasculature, and the destruction of a single vessel can lead to the death of many tumor cells. The effects of antivascular drugs are frequently short term, with regrowth beginning less than 24 hours posttreatment. This study investigated the duration of the response to the vascular targeting agent, ZD6126, of the GH3 prolactinoma, in which efficacy and dose-response have previously been demonstrated.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!