Electrochemical sulfonylation of thiols with sulfonyl hydrazides: a metal- and oxidant-free protocol for the synthesis of thiosulfonates
An efficient electrochemical transformation of structurally diverse sulfonyl hydrazides and thiols into thiosulfonates in the presence of ammonium iodide as redox catalyst and electrolyte in acetonitrile at ambient temperature is reported. Transition metal- and oxidant-free conditions are the striki...
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| Veröffentlicht in: | Green chemistry : an international journal and green chemistry resource : GC 2018, Vol.2 (19), p.4428-4432 |
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| container_title | Green chemistry : an international journal and green chemistry resource : GC |
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| creator | Mo, Zu-Yu Swaroop, Toreshettahally R Tong, Wei Zhang, Yu-Zhen Tang, Hai-Tao Pan, Ying-Ming Sun, Hong-Bin Chen, Zhen-Feng |
| description | An efficient electrochemical transformation of structurally diverse sulfonyl hydrazides and thiols into thiosulfonates in the presence of ammonium iodide as redox catalyst and electrolyte in acetonitrile at ambient temperature is reported. Transition metal- and oxidant-free conditions are the striking features of this protocol. The
in vitro
cytotoxicity of all compounds is evaluated by MTT assay against four human cancer cell lines. The results reveal that
3ac
and
3ag
exhibit potential inhibitory activity against tumor cells. Furthermore,
3ag
inhibits cell migration ability and tubulin polymerization in T-24 cells, leading to cell cycle arrest and apoptosis.
We have developed a new metal- and oxidant-free method for the synthesis of anticancer thiosulfonates
via
sulfonylation of thiols. |
| doi_str_mv | 10.1039/c8gc02143k |
| format | Article |
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in vitro
cytotoxicity of all compounds is evaluated by MTT assay against four human cancer cell lines. The results reveal that
3ac
and
3ag
exhibit potential inhibitory activity against tumor cells. Furthermore,
3ag
inhibits cell migration ability and tubulin polymerization in T-24 cells, leading to cell cycle arrest and apoptosis.
We have developed a new metal- and oxidant-free method for the synthesis of anticancer thiosulfonates
via
sulfonylation of thiols.</description><identifier>ISSN: 1463-9262</identifier><identifier>EISSN: 1463-9270</identifier><identifier>DOI: 10.1039/c8gc02143k</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Acetonitrile ; Ambient temperature ; Ammonium ; Apoptosis ; Cancer ; Cell adhesion & migration ; Cell cycle ; Cell migration ; Cytotoxicity ; Electrochemistry ; Electrolytic cells ; Green chemistry ; Hydrazides ; Iodides ; Metals ; Polymerization ; Thiols ; Toxicity ; Tubulin ; Tumor cell lines ; Tumor cells</subject><ispartof>Green chemistry : an international journal and green chemistry resource : GC, 2018, Vol.2 (19), p.4428-4432</ispartof><rights>Copyright Royal Society of Chemistry 2018</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c318t-47a34f682e3b452ab3a069a5b10a7f49d582dd3f6f4373585c57db93685d9cd33</citedby><cites>FETCH-LOGICAL-c318t-47a34f682e3b452ab3a069a5b10a7f49d582dd3f6f4373585c57db93685d9cd33</cites><orcidid>0000-0001-7531-0458 ; 0000-0002-3625-7647</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,4009,27902,27903,27904</link.rule.ids></links><search><creatorcontrib>Mo, Zu-Yu</creatorcontrib><creatorcontrib>Swaroop, Toreshettahally R</creatorcontrib><creatorcontrib>Tong, Wei</creatorcontrib><creatorcontrib>Zhang, Yu-Zhen</creatorcontrib><creatorcontrib>Tang, Hai-Tao</creatorcontrib><creatorcontrib>Pan, Ying-Ming</creatorcontrib><creatorcontrib>Sun, Hong-Bin</creatorcontrib><creatorcontrib>Chen, Zhen-Feng</creatorcontrib><title>Electrochemical sulfonylation of thiols with sulfonyl hydrazides: a metal- and oxidant-free protocol for the synthesis of thiosulfonates</title><title>Green chemistry : an international journal and green chemistry resource : GC</title><description>An efficient electrochemical transformation of structurally diverse sulfonyl hydrazides and thiols into thiosulfonates in the presence of ammonium iodide as redox catalyst and electrolyte in acetonitrile at ambient temperature is reported. Transition metal- and oxidant-free conditions are the striking features of this protocol. The
in vitro
cytotoxicity of all compounds is evaluated by MTT assay against four human cancer cell lines. The results reveal that
3ac
and
3ag
exhibit potential inhibitory activity against tumor cells. Furthermore,
3ag
inhibits cell migration ability and tubulin polymerization in T-24 cells, leading to cell cycle arrest and apoptosis.
We have developed a new metal- and oxidant-free method for the synthesis of anticancer thiosulfonates
via
sulfonylation of thiols.</description><subject>Acetonitrile</subject><subject>Ambient temperature</subject><subject>Ammonium</subject><subject>Apoptosis</subject><subject>Cancer</subject><subject>Cell adhesion & migration</subject><subject>Cell cycle</subject><subject>Cell migration</subject><subject>Cytotoxicity</subject><subject>Electrochemistry</subject><subject>Electrolytic cells</subject><subject>Green chemistry</subject><subject>Hydrazides</subject><subject>Iodides</subject><subject>Metals</subject><subject>Polymerization</subject><subject>Thiols</subject><subject>Toxicity</subject><subject>Tubulin</subject><subject>Tumor cell lines</subject><subject>Tumor cells</subject><issn>1463-9262</issn><issn>1463-9270</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNpFkU1LxDAQhosouK5evAsBb0I1adKk9SZlXcUFL3ouaT5s1myzJlm0_gJ_tl2r62kG5uGZ4Z0kOUXwEkFcXoniRcAMEfy6l0wQoTgtMwb3dz3NDpOjEJYQIsQomSRfM6tE9E60amUEtyBsrHZdb3k0rgNOg9gaZwN4N7HdDUHbS88_jVThGnCwUpHbFPBOAvdhJO9iqr1SYO1ddMJZoJ0fPAqEvhtKMOFPPAp5VOE4OdDcBnXyW6fJ8-3sqbpLF4_z--pmkQqMipgSxjHRtMgUbkie8QZzSEueNwhypkkp8yKTEmuqCWY4L3KRM9mUmBa5LIXEeJqcj97huLeNCrFeuo3vhpV1hrYpYcboQF2MlPAuBK90vfZmxX1fI1hvk66rYl79JP0wwGcj7IPYcf-fwN9aOX2c</recordid><startdate>2018</startdate><enddate>2018</enddate><creator>Mo, Zu-Yu</creator><creator>Swaroop, Toreshettahally R</creator><creator>Tong, Wei</creator><creator>Zhang, Yu-Zhen</creator><creator>Tang, Hai-Tao</creator><creator>Pan, Ying-Ming</creator><creator>Sun, Hong-Bin</creator><creator>Chen, Zhen-Feng</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7ST</scope><scope>7U6</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>JG9</scope><orcidid>https://orcid.org/0000-0001-7531-0458</orcidid><orcidid>https://orcid.org/0000-0002-3625-7647</orcidid></search><sort><creationdate>2018</creationdate><title>Electrochemical sulfonylation of thiols with sulfonyl hydrazides: a metal- and oxidant-free protocol for the synthesis of thiosulfonates</title><author>Mo, Zu-Yu ; Swaroop, Toreshettahally R ; Tong, Wei ; Zhang, Yu-Zhen ; Tang, Hai-Tao ; Pan, Ying-Ming ; Sun, Hong-Bin ; Chen, Zhen-Feng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c318t-47a34f682e3b452ab3a069a5b10a7f49d582dd3f6f4373585c57db93685d9cd33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Acetonitrile</topic><topic>Ambient temperature</topic><topic>Ammonium</topic><topic>Apoptosis</topic><topic>Cancer</topic><topic>Cell adhesion & migration</topic><topic>Cell cycle</topic><topic>Cell migration</topic><topic>Cytotoxicity</topic><topic>Electrochemistry</topic><topic>Electrolytic cells</topic><topic>Green chemistry</topic><topic>Hydrazides</topic><topic>Iodides</topic><topic>Metals</topic><topic>Polymerization</topic><topic>Thiols</topic><topic>Toxicity</topic><topic>Tubulin</topic><topic>Tumor cell lines</topic><topic>Tumor cells</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mo, Zu-Yu</creatorcontrib><creatorcontrib>Swaroop, Toreshettahally R</creatorcontrib><creatorcontrib>Tong, Wei</creatorcontrib><creatorcontrib>Zhang, Yu-Zhen</creatorcontrib><creatorcontrib>Tang, Hai-Tao</creatorcontrib><creatorcontrib>Pan, Ying-Ming</creatorcontrib><creatorcontrib>Sun, Hong-Bin</creatorcontrib><creatorcontrib>Chen, Zhen-Feng</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Environment Abstracts</collection><collection>Sustainability Science Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Materials Research Database</collection><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mo, Zu-Yu</au><au>Swaroop, Toreshettahally R</au><au>Tong, Wei</au><au>Zhang, Yu-Zhen</au><au>Tang, Hai-Tao</au><au>Pan, Ying-Ming</au><au>Sun, Hong-Bin</au><au>Chen, Zhen-Feng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Electrochemical sulfonylation of thiols with sulfonyl hydrazides: a metal- and oxidant-free protocol for the synthesis of thiosulfonates</atitle><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle><date>2018</date><risdate>2018</risdate><volume>2</volume><issue>19</issue><spage>4428</spage><epage>4432</epage><pages>4428-4432</pages><issn>1463-9262</issn><eissn>1463-9270</eissn><abstract>An efficient electrochemical transformation of structurally diverse sulfonyl hydrazides and thiols into thiosulfonates in the presence of ammonium iodide as redox catalyst and electrolyte in acetonitrile at ambient temperature is reported. Transition metal- and oxidant-free conditions are the striking features of this protocol. The
in vitro
cytotoxicity of all compounds is evaluated by MTT assay against four human cancer cell lines. The results reveal that
3ac
and
3ag
exhibit potential inhibitory activity against tumor cells. Furthermore,
3ag
inhibits cell migration ability and tubulin polymerization in T-24 cells, leading to cell cycle arrest and apoptosis.
We have developed a new metal- and oxidant-free method for the synthesis of anticancer thiosulfonates
via
sulfonylation of thiols.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/c8gc02143k</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0001-7531-0458</orcidid><orcidid>https://orcid.org/0000-0002-3625-7647</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1463-9262 |
| ispartof | Green chemistry : an international journal and green chemistry resource : GC, 2018, Vol.2 (19), p.4428-4432 |
| issn | 1463-9262 1463-9270 |
| language | eng |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Acetonitrile Ambient temperature Ammonium Apoptosis Cancer Cell adhesion & migration Cell cycle Cell migration Cytotoxicity Electrochemistry Electrolytic cells Green chemistry Hydrazides Iodides Metals Polymerization Thiols Toxicity Tubulin Tumor cell lines Tumor cells |
| title | Electrochemical sulfonylation of thiols with sulfonyl hydrazides: a metal- and oxidant-free protocol for the synthesis of thiosulfonates |
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