Skip navigation
Skip navigation

The Synthesis and Tubulin Binding Activity of Thiophene-Based Analogues of Combretastatin A-4

Flynn, Bernard; Flynn, Guy; Hamel, Ernest; Jung, M Katherine

Description

A number of analogues of combretastatin A-4 (1), containing a thiophene ring interposed between the two phenyl groups, have been prepared. The synthesis of these compounds employed a combination of palladium-mediated coupling and iodocyclization techniques. The thiophene compounds 11, 14, 18, and 19 also represent non-benzofused analogues of some recently described tubulin binding benzo[b]thiophenes 3-5. The most active thiophene compounds identified in this study were 11, 14, and 18. Overall...[Show more]

dc.contributor.authorFlynn, Bernard
dc.contributor.authorFlynn, Guy
dc.contributor.authorHamel, Ernest
dc.contributor.authorJung, M Katherine
dc.date.accessioned2015-12-13T23:26:59Z
dc.identifier.issn0960-894X
dc.identifier.urihttp://hdl.handle.net/1885/93097
dc.description.abstractA number of analogues of combretastatin A-4 (1), containing a thiophene ring interposed between the two phenyl groups, have been prepared. The synthesis of these compounds employed a combination of palladium-mediated coupling and iodocyclization techniques. The thiophene compounds 11, 14, 18, and 19 also represent non-benzofused analogues of some recently described tubulin binding benzo[b]thiophenes 3-5. The most active thiophene compounds identified in this study were 11, 14, and 18. Overall they are less active than 1 but exhibit comparable activity to the most active of the benzo[b]thiophenes 3-5. A structure-activity relationship of these compounds is considered.
dc.publisherPergamon-Elsevier Ltd
dc.sourceBioorganic and Medicinal Chemistry Letters
dc.subjectKeywords: benzothiophene derivative; combretastatin A4; palladium; phenyl group; thiophene derivative; article; cell growth; cell strain MCF 7; controlled study; cyclization; drug activity; drug protein binding; drug structure; drug synthesis; growth inhibition; hu
dc.titleThe Synthesis and Tubulin Binding Activity of Thiophene-Based Analogues of Combretastatin A-4
dc.typeJournal article
local.description.notesImported from ARIES
local.description.refereedYes
local.identifier.citationvolume11
dc.date.issued2001
local.identifier.absfor030503 - Organic Chemical Synthesis
local.identifier.ariespublicationMigratedxPub26428
local.type.statusPublished Version
local.contributor.affiliationFlynn, Bernard, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationFlynn, Guy, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationHamel, Ernest, National Institutes of Health
local.contributor.affiliationJung, M Katherine, National Institutes of Health
local.description.embargo2037-12-31
local.bibliographicCitation.startpage2341
local.bibliographicCitation.lastpage2343
local.identifier.doi10.1016/S0960-894X(01)00436-X
dc.date.updated2015-12-12T09:48:34Z
local.identifier.scopusID2-s2.0-0035801759
CollectionsANU Research Publications

Download

File Description SizeFormat Image
01_Flynn_The_Synthesis_and_Tubulin_2001.pdf117.38 kBAdobe PDF    Request a copy


Items in Open Research are protected by copyright, with all rights reserved, unless otherwise indicated.

Updated:  20 July 2017/ Responsible Officer:  University Librarian/ Page Contact:  Library Systems & Web Coordinator