Synthesis and biological activity of some new 5′- O-acyl tiazofurin derivatives
Three new 5′- O-acyl tiazofurin derivatives 2– 4 were synthesized and evaluated for their antiproliferative activity against different tumour cell lines as well as for their ability to induce apoptosis in C6 cells in vitro. Apart of the antitumour assays, the cell membrane permeation of 2– 4 and the...
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| Veröffentlicht in: | European journal of medicinal chemistry 2006-04, Vol.41 (4), p.503-512 |
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| container_title | European journal of medicinal chemistry |
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| creator | Pejanović, Vjera Piperski, Vesna Uglješić-Kilibarda, Dragana Tasić, Jelena Dačević, Mirjana Medić-Mijačević, Ljubica Gunić, Esmir Popsavin, Mirjana Popsavin, Velimir |
| description | Three new 5′-
O-acyl tiazofurin derivatives
2–
4 were synthesized and evaluated for their antiproliferative activity against different tumour cell lines as well as for their ability to induce apoptosis in C6 cells in vitro. Apart of the antitumour assays, the cell membrane permeation of
2–
4 and their intracellular metabolism in C6 cells in vitro was also studied in order to evaluate their potential as possible tiazofurin bioisosteres or prodrugs. |
| doi_str_mv | 10.1016/j.ejmech.2006.01.005 |
| format | Article |
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O-acyl tiazofurin derivatives
2–
4 were synthesized and evaluated for their antiproliferative activity against different tumour cell lines as well as for their ability to induce apoptosis in C6 cells in vitro. Apart of the antitumour assays, the cell membrane permeation of
2–
4 and their intracellular metabolism in C6 cells in vitro was also studied in order to evaluate their potential as possible tiazofurin bioisosteres or prodrugs.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2006.01.005</identifier><identifier>PMID: 16519966</identifier><identifier>CODEN: EJMCA5</identifier><language>eng</language><publisher>Oxford: Elsevier Masson SAS</publisher><subject>Animals ; Anticancer agents ; Antineoplastic agents ; Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - pharmacology ; Apoptosis ; Apoptosis - drug effects ; Biological and medical sciences ; Cell Division - drug effects ; Cell Line, Tumor ; Cell Survival - drug effects ; Chemical Phenomena ; Chemistry, Physical ; Cytotoxicity ; DNA, Neoplasm - biosynthesis ; DNA, Neoplasm - genetics ; Drug Screening Assays, Antitumor ; General aspects ; Humans ; In Situ Nick-End Labeling ; Indicators and Reagents ; Magnetic Resonance Spectroscopy ; Medical sciences ; Mice ; Pharmacology. Drug treatments ; Prodrugs ; Ribavirin - analogs & derivatives ; Ribavirin - chemical synthesis ; Ribavirin - pharmacology ; Spectrophotometry, Infrared ; Structure-Activity Relationship ; Tiazofurin derivatives</subject><ispartof>European journal of medicinal chemistry, 2006-04, Vol.41 (4), p.503-512</ispartof><rights>2006 Elsevier SAS</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c390t-fdc631a496793d82553b237e1edfca4d3e4203505e679f12ee6e7e2cfdbbf073</citedby><cites>FETCH-LOGICAL-c390t-fdc631a496793d82553b237e1edfca4d3e4203505e679f12ee6e7e2cfdbbf073</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.ejmech.2006.01.005$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17775616$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16519966$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Pejanović, Vjera</creatorcontrib><creatorcontrib>Piperski, Vesna</creatorcontrib><creatorcontrib>Uglješić-Kilibarda, Dragana</creatorcontrib><creatorcontrib>Tasić, Jelena</creatorcontrib><creatorcontrib>Dačević, Mirjana</creatorcontrib><creatorcontrib>Medić-Mijačević, Ljubica</creatorcontrib><creatorcontrib>Gunić, Esmir</creatorcontrib><creatorcontrib>Popsavin, Mirjana</creatorcontrib><creatorcontrib>Popsavin, Velimir</creatorcontrib><title>Synthesis and biological activity of some new 5′- O-acyl tiazofurin derivatives</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>Three new 5′-
O-acyl tiazofurin derivatives
2–
4 were synthesized and evaluated for their antiproliferative activity against different tumour cell lines as well as for their ability to induce apoptosis in C6 cells in vitro. Apart of the antitumour assays, the cell membrane permeation of
2–
4 and their intracellular metabolism in C6 cells in vitro was also studied in order to evaluate their potential as possible tiazofurin bioisosteres or prodrugs.</description><subject>Animals</subject><subject>Anticancer agents</subject><subject>Antineoplastic agents</subject><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Apoptosis</subject><subject>Apoptosis - drug effects</subject><subject>Biological and medical sciences</subject><subject>Cell Division - drug effects</subject><subject>Cell Line, Tumor</subject><subject>Cell Survival - drug effects</subject><subject>Chemical Phenomena</subject><subject>Chemistry, Physical</subject><subject>Cytotoxicity</subject><subject>DNA, Neoplasm - biosynthesis</subject><subject>DNA, Neoplasm - genetics</subject><subject>Drug Screening Assays, Antitumor</subject><subject>General aspects</subject><subject>Humans</subject><subject>In Situ Nick-End Labeling</subject><subject>Indicators and Reagents</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Pharmacology. Drug treatments</subject><subject>Prodrugs</subject><subject>Ribavirin - analogs & derivatives</subject><subject>Ribavirin - chemical synthesis</subject><subject>Ribavirin - pharmacology</subject><subject>Spectrophotometry, Infrared</subject><subject>Structure-Activity Relationship</subject><subject>Tiazofurin derivatives</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp90E9qGzEUx3FRGho3yQ1KmU27m8mTNJIym0IJ_QeBLOq90EhPjczMKJXGDu6qR_EZegQfpSepjA3ZdaXN5_cQX0LeUGgoUHm9anA1on1oGIBsgDYA4gVZUCVvas5E-5IsgDFeC8bbc_I65xUUIQFekXMqBe06KRdk-X07zQ-YQ67M5Pa7PsQh_gjWDJWxc9iEeVtFv9_lOOJ-N-FTJf7-_lNX97Wx26Gag_kV_TqFqXKYwsaUCeZLcubNkPHq9F6Q5edPy9uv9d39l2-3H-9qyzuYa--s5NS0nVQddzdMCN4zrpCi89a0jmPLgAsQWICnDFGiQma963sPil-Q98ezjyn-XGOe9RiyxWEwE8Z11mXFpGKiwPYIbYo5J_T6MYXRpK2moA8x9UofY-pDTA1Ul1Rl9vZ0f92P6J5Hp3oFvDsBk0sxn8xkQ352Sikh6cF9ODosMTYBk8424GTRhYR21i6G___kH81amGs</recordid><startdate>20060401</startdate><enddate>20060401</enddate><creator>Pejanović, Vjera</creator><creator>Piperski, Vesna</creator><creator>Uglješić-Kilibarda, Dragana</creator><creator>Tasić, Jelena</creator><creator>Dačević, Mirjana</creator><creator>Medić-Mijačević, Ljubica</creator><creator>Gunić, Esmir</creator><creator>Popsavin, Mirjana</creator><creator>Popsavin, Velimir</creator><general>Elsevier Masson SAS</general><general>Elsevier</general><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>20060401</creationdate><title>Synthesis and biological activity of some new 5′- O-acyl tiazofurin derivatives</title><author>Pejanović, Vjera ; Piperski, Vesna ; Uglješić-Kilibarda, Dragana ; Tasić, Jelena ; Dačević, Mirjana ; Medić-Mijačević, Ljubica ; Gunić, Esmir ; Popsavin, Mirjana ; Popsavin, Velimir</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c390t-fdc631a496793d82553b237e1edfca4d3e4203505e679f12ee6e7e2cfdbbf073</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>Animals</topic><topic>Anticancer agents</topic><topic>Antineoplastic agents</topic><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Apoptosis</topic><topic>Apoptosis - drug effects</topic><topic>Biological and medical sciences</topic><topic>Cell Division - drug effects</topic><topic>Cell Line, Tumor</topic><topic>Cell Survival - drug effects</topic><topic>Chemical Phenomena</topic><topic>Chemistry, Physical</topic><topic>Cytotoxicity</topic><topic>DNA, Neoplasm - biosynthesis</topic><topic>DNA, Neoplasm - genetics</topic><topic>Drug Screening Assays, Antitumor</topic><topic>General aspects</topic><topic>Humans</topic><topic>In Situ Nick-End Labeling</topic><topic>Indicators and Reagents</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Pharmacology. Drug treatments</topic><topic>Prodrugs</topic><topic>Ribavirin - analogs & derivatives</topic><topic>Ribavirin - chemical synthesis</topic><topic>Ribavirin - pharmacology</topic><topic>Spectrophotometry, Infrared</topic><topic>Structure-Activity Relationship</topic><topic>Tiazofurin derivatives</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pejanović, Vjera</creatorcontrib><creatorcontrib>Piperski, Vesna</creatorcontrib><creatorcontrib>Uglješić-Kilibarda, Dragana</creatorcontrib><creatorcontrib>Tasić, Jelena</creatorcontrib><creatorcontrib>Dačević, Mirjana</creatorcontrib><creatorcontrib>Medić-Mijačević, Ljubica</creatorcontrib><creatorcontrib>Gunić, Esmir</creatorcontrib><creatorcontrib>Popsavin, Mirjana</creatorcontrib><creatorcontrib>Popsavin, Velimir</creatorcontrib><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>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pejanović, Vjera</au><au>Piperski, Vesna</au><au>Uglješić-Kilibarda, Dragana</au><au>Tasić, Jelena</au><au>Dačević, Mirjana</au><au>Medić-Mijačević, Ljubica</au><au>Gunić, Esmir</au><au>Popsavin, Mirjana</au><au>Popsavin, Velimir</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and biological activity of some new 5′- O-acyl tiazofurin derivatives</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2006-04-01</date><risdate>2006</risdate><volume>41</volume><issue>4</issue><spage>503</spage><epage>512</epage><pages>503-512</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>Three new 5′-
O-acyl tiazofurin derivatives
2–
4 were synthesized and evaluated for their antiproliferative activity against different tumour cell lines as well as for their ability to induce apoptosis in C6 cells in vitro. Apart of the antitumour assays, the cell membrane permeation of
2–
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| fulltext | fulltext |
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| ispartof | European journal of medicinal chemistry, 2006-04, Vol.41 (4), p.503-512 |
| issn | 0223-5234 1768-3254 |
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| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Animals Anticancer agents Antineoplastic agents Antineoplastic Agents - chemical synthesis Antineoplastic Agents - pharmacology Apoptosis Apoptosis - drug effects Biological and medical sciences Cell Division - drug effects Cell Line, Tumor Cell Survival - drug effects Chemical Phenomena Chemistry, Physical Cytotoxicity DNA, Neoplasm - biosynthesis DNA, Neoplasm - genetics Drug Screening Assays, Antitumor General aspects Humans In Situ Nick-End Labeling Indicators and Reagents Magnetic Resonance Spectroscopy Medical sciences Mice Pharmacology. Drug treatments Prodrugs Ribavirin - analogs & derivatives Ribavirin - chemical synthesis Ribavirin - pharmacology Spectrophotometry, Infrared Structure-Activity Relationship Tiazofurin derivatives |
| title | Synthesis and biological activity of some new 5′- O-acyl tiazofurin derivatives |
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