Synthesis and biological evaluation of 2,3-diarylthiophene analogues of combretastatin A-4Electronic supplementary information (ESI) available. See DOI: 10.1039/c5md00028a
A series of novel 2,3-diarylthiophene analogues of combretastatin A-4 (CA-4) were designed with a rigid thiophene moiety to retain the cis -olefin configuration of CA-4 and were subsequently synthesised. All of the target compounds were evaluated for their in vitro anti-proliferative activities. Amo...
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| creator | Wang, Zhan Yang, Qingkun Bai, Zhaoshi Sun, Jun Jiang, Xuewei Song, Hongrui Wu, Yingliang Zhang, Weige |
| description | A series of novel 2,3-diarylthiophene analogues of combretastatin A-4 (CA-4) were designed with a rigid thiophene moiety to retain the
cis
-olefin configuration of CA-4 and were subsequently synthesised. All of the target compounds were evaluated for their
in vitro
anti-proliferative activities. Among these compounds,
5f
and
8d
exhibited superior potency against different tumour cell lines with IC
50
values at sub-micromolar levels. Moreover, compound
8d
significantly inhibited tubulin polymerisation to microtubules and caused microtubule destabilisation. In addition, a molecular modelling study of compound
8d
was performed to clarify its binding mode at the colchicine site in the tubulin dimer and to provide a basis for further structure-guided design of novel CA-4 analogues.
A series of novel 2,3-diarylthiophene analogues of combretastatin A-4 were synthesised and evaluated for their
in vitro
anti-proliferative activities. |
| doi_str_mv | 10.1039/c5md00028a |
| format | Article |
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cis
-olefin configuration of CA-4 and were subsequently synthesised. All of the target compounds were evaluated for their
in vitro
anti-proliferative activities. Among these compounds,
5f
and
8d
exhibited superior potency against different tumour cell lines with IC
50
values at sub-micromolar levels. Moreover, compound
8d
significantly inhibited tubulin polymerisation to microtubules and caused microtubule destabilisation. In addition, a molecular modelling study of compound
8d
was performed to clarify its binding mode at the colchicine site in the tubulin dimer and to provide a basis for further structure-guided design of novel CA-4 analogues.
A series of novel 2,3-diarylthiophene analogues of combretastatin A-4 were synthesised and evaluated for their
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anti-proliferative activities.</description><identifier>ISSN: 2040-2503</identifier><identifier>EISSN: 2040-2511</identifier><identifier>DOI: 10.1039/c5md00028a</identifier><language>eng</language><creationdate>2015-05</creationdate><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Wang, Zhan</creatorcontrib><creatorcontrib>Yang, Qingkun</creatorcontrib><creatorcontrib>Bai, Zhaoshi</creatorcontrib><creatorcontrib>Sun, Jun</creatorcontrib><creatorcontrib>Jiang, Xuewei</creatorcontrib><creatorcontrib>Song, Hongrui</creatorcontrib><creatorcontrib>Wu, Yingliang</creatorcontrib><creatorcontrib>Zhang, Weige</creatorcontrib><title>Synthesis and biological evaluation of 2,3-diarylthiophene analogues of combretastatin A-4Electronic supplementary information (ESI) available. See DOI: 10.1039/c5md00028a</title><description>A series of novel 2,3-diarylthiophene analogues of combretastatin A-4 (CA-4) were designed with a rigid thiophene moiety to retain the
cis
-olefin configuration of CA-4 and were subsequently synthesised. All of the target compounds were evaluated for their
in vitro
anti-proliferative activities. Among these compounds,
5f
and
8d
exhibited superior potency against different tumour cell lines with IC
50
values at sub-micromolar levels. Moreover, compound
8d
significantly inhibited tubulin polymerisation to microtubules and caused microtubule destabilisation. In addition, a molecular modelling study of compound
8d
was performed to clarify its binding mode at the colchicine site in the tubulin dimer and to provide a basis for further structure-guided design of novel CA-4 analogues.
A series of novel 2,3-diarylthiophene analogues of combretastatin A-4 were synthesised and evaluated for their
in vitro
anti-proliferative activities.</description><issn>2040-2503</issn><issn>2040-2511</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNqFj0FLxDAQhYMouLh78S6MNwW7pk0Xut5EK-7JQ72XaTq1kTQpSbqwv8k_aWRFD4J7mgfvex8MY-cpX6ZcrG_lamg551mBR2yW8Zwn2SpNj38yF6ds4f17ZLjIimKdz9hHtTOhJ688oGmhUVbbNyVRA21RTxiUNWA7yG5E0ip0Ox16ZceeDMUBRngi_wVIOzSOAvoQNwbuk7zUJIOzRknw0zhqGsiEaABlOuuGvfqqrDbXgFtUGhtNS6iI4PFlcwd_v5qzkw61p8X3PWMXT-Xrw3PivKxHp4Yor39xcbi__K-vx7YTny6iayo</recordid><startdate>20150513</startdate><enddate>20150513</enddate><creator>Wang, Zhan</creator><creator>Yang, Qingkun</creator><creator>Bai, Zhaoshi</creator><creator>Sun, Jun</creator><creator>Jiang, Xuewei</creator><creator>Song, Hongrui</creator><creator>Wu, Yingliang</creator><creator>Zhang, Weige</creator><scope/></search><sort><creationdate>20150513</creationdate><title>Synthesis and biological evaluation of 2,3-diarylthiophene analogues of combretastatin A-4Electronic supplementary information (ESI) available. See DOI: 10.1039/c5md00028a</title><author>Wang, Zhan ; Yang, Qingkun ; Bai, Zhaoshi ; Sun, Jun ; Jiang, Xuewei ; Song, Hongrui ; Wu, Yingliang ; Zhang, Weige</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-rsc_primary_c5md00028a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Zhan</creatorcontrib><creatorcontrib>Yang, Qingkun</creatorcontrib><creatorcontrib>Bai, Zhaoshi</creatorcontrib><creatorcontrib>Sun, Jun</creatorcontrib><creatorcontrib>Jiang, Xuewei</creatorcontrib><creatorcontrib>Song, Hongrui</creatorcontrib><creatorcontrib>Wu, Yingliang</creatorcontrib><creatorcontrib>Zhang, Weige</creatorcontrib></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Zhan</au><au>Yang, Qingkun</au><au>Bai, Zhaoshi</au><au>Sun, Jun</au><au>Jiang, Xuewei</au><au>Song, Hongrui</au><au>Wu, Yingliang</au><au>Zhang, Weige</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and biological evaluation of 2,3-diarylthiophene analogues of combretastatin A-4Electronic supplementary information (ESI) available. See DOI: 10.1039/c5md00028a</atitle><date>2015-05-13</date><risdate>2015</risdate><volume>6</volume><issue>5</issue><spage>971</spage><epage>976</epage><pages>971-976</pages><issn>2040-2503</issn><eissn>2040-2511</eissn><abstract>A series of novel 2,3-diarylthiophene analogues of combretastatin A-4 (CA-4) were designed with a rigid thiophene moiety to retain the
cis
-olefin configuration of CA-4 and were subsequently synthesised. All of the target compounds were evaluated for their
in vitro
anti-proliferative activities. Among these compounds,
5f
and
8d
exhibited superior potency against different tumour cell lines with IC
50
values at sub-micromolar levels. Moreover, compound
8d
significantly inhibited tubulin polymerisation to microtubules and caused microtubule destabilisation. In addition, a molecular modelling study of compound
8d
was performed to clarify its binding mode at the colchicine site in the tubulin dimer and to provide a basis for further structure-guided design of novel CA-4 analogues.
A series of novel 2,3-diarylthiophene analogues of combretastatin A-4 were synthesised and evaluated for their
in vitro
anti-proliferative activities.</abstract><doi>10.1039/c5md00028a</doi><tpages>6</tpages></addata></record> |
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| source | Royal Society Of Chemistry Journals; Alma/SFX Local Collection |
| title | Synthesis and biological evaluation of 2,3-diarylthiophene analogues of combretastatin A-4Electronic supplementary information (ESI) available. See DOI: 10.1039/c5md00028a |
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