Investigation on the synthesis of new 3-[4-(arylalkoxy)phenylethyl]-2-thioxo-1,3-thiazolidin-4-ones and their biological evaluation against cancer cells
Herein, we report on the 5-step synthesis of new 3-[4-(arylalkoxy)phenylethyl]-2-thioxo-1,3-thiazolidin-4-ones without 5-arylidene fragments starting from tyramine The construction involved protection with Boc2O, regioselective O -alkylation, deprotection with 6 M HCl, neutralization, and finally re...
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| Veröffentlicht in: | Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2017-03, Vol.53 (3), p.341-349 |
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| container_title | Chemistry of heterocyclic compounds (New York, N.Y. 1965) |
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| creator | Dago, Camille Déliko Ambeu, Christelle N’ta Coulibaly, Wacothon Karime Békro, Yves-Alain Mamyrbekova-Bekro, Janat A. Le Guével, Rémy Corlu, Anne Bazureau, Jean-Pierre |
| description | Herein, we report on the 5-step synthesis of new 3-[4-(arylalkoxy)phenylethyl]-2-thioxo-1,3-thiazolidin-4-ones without 5-arylidene fragments starting from tyramine The construction involved protection with Boc2O, regioselective
O
-alkylation, deprotection with 6 M HCl, neutralization, and finally reaction of bis(carboxymethyl)trithiocarbonate under microwave irradiation. The intermediates and the
N
-substituted rhodanine have been also evaluated for their
in vitro
inhibition of cell proliferation (Huh7, Caco 2, MDA-MB231, HCT 116, PC3, NCI-H727, HaCat). Two compounds have shown a selective potent activity against HCT116 cell line. |
| doi_str_mv | 10.1007/s10593-017-2056-2 |
| format | Article |
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O
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N
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in vitro
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O
-alkylation, deprotection with 6 M HCl, neutralization, and finally reaction of bis(carboxymethyl)trithiocarbonate under microwave irradiation. The intermediates and the
N
-substituted rhodanine have been also evaluated for their
in vitro
inhibition of cell proliferation (Huh7, Caco 2, MDA-MB231, HCT 116, PC3, NCI-H727, HaCat). Two compounds have shown a selective potent activity against HCT116 cell line.</description><subject>Alkylation</subject><subject>Cancer</subject><subject>Chemical Sciences</subject><subject>Chemistry</subject><subject>Chemistry and Materials Science</subject><subject>Organic Chemistry</subject><subject>Pharmacy</subject><subject>Synthesis</subject><issn>0009-3122</issn><issn>1573-8353</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNp1kl2L1DAUhosoOK7-AO8C3rhg1nw0TXs5LOvuwoA3eiUSTpO0zZpJxqYzbv0l-3NNqfgBSgInCc97zpvDKYqXlFxQQuTbRIloOCZUYkZEhdmjYkOF5Ljmgj8uNoSQBnPK2NPiWUp3-SppXW6Kh9twsmlyPUwuBpT3NFiU5pBDcgnFDgX7DXH8qcSvYZw9-C_xfj4_DDbM3k7D7D9jhqfBxfuI6Ru-HOF79M64gEscg00IglnSuhG1LvrYOw0e2RP441oVenAhTUhD0HZE2nqfnhdPOvDJvvgZz4qP764-XN7g3fvr28vtDuuSygnXwkhTVbIEWrPGWC0IMdB0puJ128hOc1O10nIuSgBWaSNLXgnZtbRlQE3Nz4rzNe8AXh1Gt8-fVBGcutnu1PJGqKgrUtETzeyrlT2M8esxt03dxeMYsj1F60bk0kSw31QP3ioXujiNoPcuabXNTEMbIkimLv5B5WXs3uncts7l978EdBXoMaY02u6XW0rUMgNqnYFsWKplBtRiha2alNnQ2_EPw_8V_QAUKrN7</recordid><startdate>20170301</startdate><enddate>20170301</enddate><creator>Dago, Camille Déliko</creator><creator>Ambeu, Christelle N’ta</creator><creator>Coulibaly, Wacothon Karime</creator><creator>Békro, Yves-Alain</creator><creator>Mamyrbekova-Bekro, Janat A.</creator><creator>Le Guével, Rémy</creator><creator>Corlu, Anne</creator><creator>Bazureau, Jean-Pierre</creator><general>Springer US</general><general>Springer</general><general>Springer Nature B.V</general><general>Springer Verlag</general><scope>AAYXX</scope><scope>CITATION</scope><scope>1XC</scope></search><sort><creationdate>20170301</creationdate><title>Investigation on the synthesis of new 3-[4-(arylalkoxy)phenylethyl]-2-thioxo-1,3-thiazolidin-4-ones and their biological evaluation against cancer cells</title><author>Dago, Camille Déliko ; Ambeu, Christelle N’ta ; Coulibaly, Wacothon Karime ; Békro, Yves-Alain ; Mamyrbekova-Bekro, Janat A. ; Le Guével, Rémy ; Corlu, Anne ; Bazureau, Jean-Pierre</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c417t-85d7d6674a1829dec500da9fd638b97fc3d6b7e3354aa26cd743657fb1b2a1d83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Alkylation</topic><topic>Cancer</topic><topic>Chemical Sciences</topic><topic>Chemistry</topic><topic>Chemistry and Materials Science</topic><topic>Organic Chemistry</topic><topic>Pharmacy</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dago, Camille Déliko</creatorcontrib><creatorcontrib>Ambeu, Christelle N’ta</creatorcontrib><creatorcontrib>Coulibaly, Wacothon Karime</creatorcontrib><creatorcontrib>Békro, Yves-Alain</creatorcontrib><creatorcontrib>Mamyrbekova-Bekro, Janat A.</creatorcontrib><creatorcontrib>Le Guével, Rémy</creatorcontrib><creatorcontrib>Corlu, Anne</creatorcontrib><creatorcontrib>Bazureau, Jean-Pierre</creatorcontrib><collection>CrossRef</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dago, Camille Déliko</au><au>Ambeu, Christelle N’ta</au><au>Coulibaly, Wacothon Karime</au><au>Békro, Yves-Alain</au><au>Mamyrbekova-Bekro, Janat A.</au><au>Le Guével, Rémy</au><au>Corlu, Anne</au><au>Bazureau, Jean-Pierre</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Investigation on the synthesis of new 3-[4-(arylalkoxy)phenylethyl]-2-thioxo-1,3-thiazolidin-4-ones and their biological evaluation against cancer cells</atitle><jtitle>Chemistry of heterocyclic compounds (New York, N.Y. 1965)</jtitle><stitle>Chem Heterocycl Comp</stitle><date>2017-03-01</date><risdate>2017</risdate><volume>53</volume><issue>3</issue><spage>341</spage><epage>349</epage><pages>341-349</pages><issn>0009-3122</issn><eissn>1573-8353</eissn><abstract>Herein, we report on the 5-step synthesis of new 3-[4-(arylalkoxy)phenylethyl]-2-thioxo-1,3-thiazolidin-4-ones without 5-arylidene fragments starting from tyramine The construction involved protection with Boc2O, regioselective
O
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N
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in vitro
inhibition of cell proliferation (Huh7, Caco 2, MDA-MB231, HCT 116, PC3, NCI-H727, HaCat). Two compounds have shown a selective potent activity against HCT116 cell line.</abstract><cop>New York</cop><pub>Springer US</pub><doi>10.1007/s10593-017-2056-2</doi><tpages>9</tpages></addata></record> |
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| subjects | Alkylation Cancer Chemical Sciences Chemistry Chemistry and Materials Science Organic Chemistry Pharmacy Synthesis |
| title | Investigation on the synthesis of new 3-[4-(arylalkoxy)phenylethyl]-2-thioxo-1,3-thiazolidin-4-ones and their biological evaluation against cancer cells |
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