Thiocamptothecin
The synthesis and the X-ray structure of 16a-thiocamptothecin (TCPT), the thiopyridone analog of camptothecin (CPT), are accomplished. The crystal contains two structurally identical, yet independent molecules. Both of them are connected to other molecules via two intermolecular hydrogen bonds. S-Me...
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| Veröffentlicht in: | Journal of medicinal chemistry 2008-05, Vol.51 (10), p.3040-3044 |
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| container_end_page | 3044 |
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| container_issue | 10 |
| container_start_page | 3040 |
| container_title | Journal of medicinal chemistry |
| container_volume | 51 |
| creator | Samorì, Cristian Guerrini, Andrea Varchi, Greta Zunino, Franco Beretta, Giovanni Luca Femoni, Cristina Bombardelli, Ezio Fontana, Gabriele Battaglia, Arturo |
| description | The synthesis and the X-ray structure of 16a-thiocamptothecin (TCPT), the thiopyridone analog of camptothecin (CPT), are accomplished. The crystal contains two structurally identical, yet independent molecules. Both of them are connected to other molecules via two intermolecular hydrogen bonds. S-Methylation of TCPT leads to the cleavage of the C-ring. The cytotoxic activity of TCPT was evaluated against different human tumor cell lines using CPT as reference compound. |
| doi_str_mv | 10.1021/jm8001982 |
| format | Article |
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The crystal contains two structurally identical, yet independent molecules. Both of them are connected to other molecules via two intermolecular hydrogen bonds. S-Methylation of TCPT leads to the cleavage of the C-ring. The cytotoxic activity of TCPT was evaluated against different human tumor cell lines using CPT as reference compound.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm8001982</identifier><identifier>PMID: 18419110</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Biological and medical sciences ; Camptothecin - analogs & derivatives ; Camptothecin - chemical synthesis ; Camptothecin - chemistry ; Camptothecin - pharmacology ; Cell Line, Tumor ; Crystallography, X-Ray ; DNA Damage ; DNA Topoisomerases, Type I - chemistry ; General aspects ; Humans ; Medical sciences ; Models, Molecular ; Pharmacology. 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Med. Chem</addtitle><description>The synthesis and the X-ray structure of 16a-thiocamptothecin (TCPT), the thiopyridone analog of camptothecin (CPT), are accomplished. The crystal contains two structurally identical, yet independent molecules. Both of them are connected to other molecules via two intermolecular hydrogen bonds. S-Methylation of TCPT leads to the cleavage of the C-ring. The cytotoxic activity of TCPT was evaluated against different human tumor cell lines using CPT as reference compound.</description><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Camptothecin - analogs & derivatives</subject><subject>Camptothecin - chemical synthesis</subject><subject>Camptothecin - chemistry</subject><subject>Camptothecin - pharmacology</subject><subject>Cell Line, Tumor</subject><subject>Crystallography, X-Ray</subject><subject>DNA Damage</subject><subject>DNA Topoisomerases, Type I - chemistry</subject><subject>General aspects</subject><subject>Humans</subject><subject>Medical sciences</subject><subject>Models, Molecular</subject><subject>Pharmacology. Drug treatments</subject><subject>Thiones - chemical synthesis</subject><subject>Thiones - chemistry</subject><subject>Thiones - pharmacology</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpt0M9LwzAUB_AgiptT0H_Am4KH6ntJ2qRHGf4aBQWnBy8hTRPW2a4zaUH_eysr28VDeId8-PK-j5AzhGsEijfLWgJgKukeGWNMIeIS-D4ZA1Aa0YSyETkKYQkADCk7JCOUHFNEGJPT-aJsjK7XbdMurClXx-TA6SrYk2FOyNv93Xz6GGXPD0_T2yzSTGIbachtoiU3cWETkUDqRAGIhYgZGhS2QMhdTF2Su9QlnEspjcNCs8JKTm3BJuRyk7v2zVdnQ6vqMhhbVXplmy4oASLm_evh1QYa34TgrVNrX9ba_ygE9Vdfbev39nwI7fLaFjs59O3BxQB0MLpyXq9MGbaOAuMpT3jvoo0rQ2u_t__af6pEMBGr-curEu-zTHxgpma7XG2CWjadX_W3-2fBX8VFepU</recordid><startdate>20080522</startdate><enddate>20080522</enddate><creator>Samorì, Cristian</creator><creator>Guerrini, Andrea</creator><creator>Varchi, Greta</creator><creator>Zunino, Franco</creator><creator>Beretta, Giovanni Luca</creator><creator>Femoni, Cristina</creator><creator>Bombardelli, Ezio</creator><creator>Fontana, Gabriele</creator><creator>Battaglia, Arturo</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20080522</creationdate><title>Thiocamptothecin</title><author>Samorì, Cristian ; Guerrini, Andrea ; Varchi, Greta ; Zunino, Franco ; Beretta, Giovanni Luca ; Femoni, Cristina ; Bombardelli, Ezio ; Fontana, Gabriele ; Battaglia, Arturo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a381t-a0be6a84c5de67609f7d011d7531c17ed10bf52f6bf9f644888cf1da3de842ed3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Camptothecin - analogs & derivatives</topic><topic>Camptothecin - chemical synthesis</topic><topic>Camptothecin - chemistry</topic><topic>Camptothecin - pharmacology</topic><topic>Cell Line, Tumor</topic><topic>Crystallography, X-Ray</topic><topic>DNA Damage</topic><topic>DNA Topoisomerases, Type I - chemistry</topic><topic>General aspects</topic><topic>Humans</topic><topic>Medical sciences</topic><topic>Models, Molecular</topic><topic>Pharmacology. Drug treatments</topic><topic>Thiones - chemical synthesis</topic><topic>Thiones - chemistry</topic><topic>Thiones - pharmacology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Samorì, Cristian</creatorcontrib><creatorcontrib>Guerrini, Andrea</creatorcontrib><creatorcontrib>Varchi, Greta</creatorcontrib><creatorcontrib>Zunino, Franco</creatorcontrib><creatorcontrib>Beretta, Giovanni Luca</creatorcontrib><creatorcontrib>Femoni, Cristina</creatorcontrib><creatorcontrib>Bombardelli, Ezio</creatorcontrib><creatorcontrib>Fontana, Gabriele</creatorcontrib><creatorcontrib>Battaglia, Arturo</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Samorì, Cristian</au><au>Guerrini, Andrea</au><au>Varchi, Greta</au><au>Zunino, Franco</au><au>Beretta, Giovanni Luca</au><au>Femoni, Cristina</au><au>Bombardelli, Ezio</au><au>Fontana, Gabriele</au><au>Battaglia, Arturo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Thiocamptothecin</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>2008-05-22</date><risdate>2008</risdate><volume>51</volume><issue>10</issue><spage>3040</spage><epage>3044</epage><pages>3040-3044</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>The synthesis and the X-ray structure of 16a-thiocamptothecin (TCPT), the thiopyridone analog of camptothecin (CPT), are accomplished. The crystal contains two structurally identical, yet independent molecules. Both of them are connected to other molecules via two intermolecular hydrogen bonds. S-Methylation of TCPT leads to the cleavage of the C-ring. The cytotoxic activity of TCPT was evaluated against different human tumor cell lines using CPT as reference compound.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>18419110</pmid><doi>10.1021/jm8001982</doi><tpages>5</tpages></addata></record> |
| fulltext | fulltext |
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| ispartof | Journal of medicinal chemistry, 2008-05, Vol.51 (10), p.3040-3044 |
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| language | eng |
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| subjects | Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Biological and medical sciences Camptothecin - analogs & derivatives Camptothecin - chemical synthesis Camptothecin - chemistry Camptothecin - pharmacology Cell Line, Tumor Crystallography, X-Ray DNA Damage DNA Topoisomerases, Type I - chemistry General aspects Humans Medical sciences Models, Molecular Pharmacology. Drug treatments Thiones - chemical synthesis Thiones - chemistry Thiones - pharmacology |
| title | Thiocamptothecin |
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