Towards novel S-DABOC inhibitors: Synthesis, biological investigation, and molecular modeling studies
A small family of S-DABO cytosine analogs ( S-DABOCs) has been synthesized and biologically evaluated as HIV-1 inhibitor both on wild type and drug-resistant mutants. An interesting compound ( 5d) has been identified which showed a predicted pharmacokinetic profile similar to that of anti-HIV drugs...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2008-11, Vol.18 (21), p.5777-5780 |
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| container_end_page | 5780 |
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| container_issue | 21 |
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| container_title | Bioorganic & medicinal chemistry |
| container_volume | 18 |
| creator | Radi, Marco Angeli, Lucilla Franchi, Luigi Contemori, Lorenzo Maga, Giovanni Samuele, Alberta Zanoli, Samantha Armand-Ugon, Mercedes Gonzalez, Emmanuel Llano, Anuska Esté, Jose A. Botta, Maurizio |
| description | A small family of
S-DABO cytosine analogs (
S-DABOCs) has been synthesized and biologically evaluated as HIV-1 inhibitor both on wild type and drug-resistant mutants. An interesting compound (
5d) has been identified which showed a predicted pharmacokinetic profile similar to that of anti-HIV drugs on the market. Molecular modeling studies have been finally performed in order to rationalize the results.
A small family of
S-DABO cytosine analogs (
S-DABOCs) has been synthesized and biologically evaluated as HIV-1 inhibitor both on wild type (wt) and drug-resistant mutants leading to the identification of an interesting compound (
5d). Molecular modeling studies have been finally performed in order to rationalize the results. |
| doi_str_mv | 10.1016/j.bmcl.2008.09.070 |
| format | Article |
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S-DABO cytosine analogs (
S-DABOCs) has been synthesized and biologically evaluated as HIV-1 inhibitor both on wild type and drug-resistant mutants. An interesting compound (
5d) has been identified which showed a predicted pharmacokinetic profile similar to that of anti-HIV drugs on the market. Molecular modeling studies have been finally performed in order to rationalize the results.
A small family of
S-DABO cytosine analogs (
S-DABOCs) has been synthesized and biologically evaluated as HIV-1 inhibitor both on wild type (wt) and drug-resistant mutants leading to the identification of an interesting compound (
5d). Molecular modeling studies have been finally performed in order to rationalize the results.</description><identifier>ISSN: 0960-894X</identifier><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3405</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmcl.2008.09.070</identifier><identifier>PMID: 18842407</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Anti-HIV Agents - chemical synthesis ; Anti-HIV Agents - chemistry ; Anti-HIV Agents - pharmacology ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antiviral agents ; Biological and medical sciences ; Cytosine - analogs & derivatives ; Cytosine - chemical synthesis ; Cytosine - chemistry ; Cytosine - pharmacology ; HIV-1 ; HIV-1 - drug effects ; Human immunodeficiency virus 1 ; Medical sciences ; Microbial Sensitivity Tests ; Models, Molecular ; Molecular modeling ; Mutant ; NNRTIs ; Pharmacology. Drug treatments ; Reverse Transcriptase ; S-DABOCs</subject><ispartof>Bioorganic & medicinal chemistry, 2008-11, Vol.18 (21), p.5777-5780</ispartof><rights>2008 Elsevier Ltd</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c416t-30a66c18ffd35bd37429a10b83f737ebbc9e8e0ff3082b734737c2572aff5c723</citedby><cites>FETCH-LOGICAL-c416t-30a66c18ffd35bd37429a10b83f737ebbc9e8e0ff3082b734737c2572aff5c723</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0960894X0801144X$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3536,27903,27904,65309</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20814404$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18842407$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Radi, Marco</creatorcontrib><creatorcontrib>Angeli, Lucilla</creatorcontrib><creatorcontrib>Franchi, Luigi</creatorcontrib><creatorcontrib>Contemori, Lorenzo</creatorcontrib><creatorcontrib>Maga, Giovanni</creatorcontrib><creatorcontrib>Samuele, Alberta</creatorcontrib><creatorcontrib>Zanoli, Samantha</creatorcontrib><creatorcontrib>Armand-Ugon, Mercedes</creatorcontrib><creatorcontrib>Gonzalez, Emmanuel</creatorcontrib><creatorcontrib>Llano, Anuska</creatorcontrib><creatorcontrib>Esté, Jose A.</creatorcontrib><creatorcontrib>Botta, Maurizio</creatorcontrib><title>Towards novel S-DABOC inhibitors: Synthesis, biological investigation, and molecular modeling studies</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem Lett</addtitle><description>A small family of
S-DABO cytosine analogs (
S-DABOCs) has been synthesized and biologically evaluated as HIV-1 inhibitor both on wild type and drug-resistant mutants. An interesting compound (
5d) has been identified which showed a predicted pharmacokinetic profile similar to that of anti-HIV drugs on the market. Molecular modeling studies have been finally performed in order to rationalize the results.
A small family of
S-DABO cytosine analogs (
S-DABOCs) has been synthesized and biologically evaluated as HIV-1 inhibitor both on wild type (wt) and drug-resistant mutants leading to the identification of an interesting compound (
5d). Molecular modeling studies have been finally performed in order to rationalize the results.</description><subject>Anti-HIV Agents - chemical synthesis</subject><subject>Anti-HIV Agents - chemistry</subject><subject>Anti-HIV Agents - pharmacology</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antiviral agents</subject><subject>Biological and medical sciences</subject><subject>Cytosine - analogs & derivatives</subject><subject>Cytosine - chemical synthesis</subject><subject>Cytosine - chemistry</subject><subject>Cytosine - pharmacology</subject><subject>HIV-1</subject><subject>HIV-1 - drug effects</subject><subject>Human immunodeficiency virus 1</subject><subject>Medical sciences</subject><subject>Microbial Sensitivity Tests</subject><subject>Models, Molecular</subject><subject>Molecular modeling</subject><subject>Mutant</subject><subject>NNRTIs</subject><subject>Pharmacology. Drug treatments</subject><subject>Reverse Transcriptase</subject><subject>S-DABOCs</subject><issn>0960-894X</issn><issn>0968-0896</issn><issn>1464-3405</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kU1v1DAQhi0EotvCH-CAcoFemjCOncRBXMryKVXqoUXiZjnOeOuVY7d2sqj_Hq92BbeePLKedzR6H0LeUKgo0PbDthom7aoaQFTQV9DBM7KivOUl49A8JyvoWyhFz3-fkNOUtgCUA-cvyQkVgtccuhXB2_BHxTEVPuzQFTfll8vP1-vC-js72DnE9LG4efTzHSabLorBBhc2ViuXiR2m2W7UbIO_KJQfiyk41ItTMU8jOus3RZqX0WJ6RV4Y5RK-Pr5n5Ne3r7frH-XV9fef68urUnPaziUD1baaCmNG1gwj63jdKwqDYKZjHQ6D7lEgGMNA1EPHeP7VddPVyphGdzU7I-eHvfcxPCz5PjnZpNE55TEsSeYIpUxwnsn3T5K0Z6wF0WSwPoA6hpQiGnkf7aTio6Qg9xrkVu41yL0GCb3MGnLo7XH7Mkw4_o8ce8_AuyOgUm7TROW1Tf-4GgTl2VXmPh04zK3tLEaZtEWvcbQR9SzHYJ-64y_Gl6Y_</recordid><startdate>20081101</startdate><enddate>20081101</enddate><creator>Radi, Marco</creator><creator>Angeli, Lucilla</creator><creator>Franchi, Luigi</creator><creator>Contemori, Lorenzo</creator><creator>Maga, Giovanni</creator><creator>Samuele, Alberta</creator><creator>Zanoli, Samantha</creator><creator>Armand-Ugon, Mercedes</creator><creator>Gonzalez, Emmanuel</creator><creator>Llano, Anuska</creator><creator>Esté, Jose A.</creator><creator>Botta, Maurizio</creator><general>Elsevier Ltd</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>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>20081101</creationdate><title>Towards novel S-DABOC inhibitors: Synthesis, biological investigation, and molecular modeling studies</title><author>Radi, Marco ; Angeli, Lucilla ; Franchi, Luigi ; Contemori, Lorenzo ; Maga, Giovanni ; Samuele, Alberta ; Zanoli, Samantha ; Armand-Ugon, Mercedes ; Gonzalez, Emmanuel ; Llano, Anuska ; Esté, Jose A. ; Botta, Maurizio</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c416t-30a66c18ffd35bd37429a10b83f737ebbc9e8e0ff3082b734737c2572aff5c723</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Anti-HIV Agents - chemical synthesis</topic><topic>Anti-HIV Agents - chemistry</topic><topic>Anti-HIV Agents - pharmacology</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antiviral agents</topic><topic>Biological and medical sciences</topic><topic>Cytosine - analogs & derivatives</topic><topic>Cytosine - chemical synthesis</topic><topic>Cytosine - chemistry</topic><topic>Cytosine - pharmacology</topic><topic>HIV-1</topic><topic>HIV-1 - drug effects</topic><topic>Human immunodeficiency virus 1</topic><topic>Medical sciences</topic><topic>Microbial Sensitivity Tests</topic><topic>Models, Molecular</topic><topic>Molecular modeling</topic><topic>Mutant</topic><topic>NNRTIs</topic><topic>Pharmacology. Drug treatments</topic><topic>Reverse Transcriptase</topic><topic>S-DABOCs</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Radi, Marco</creatorcontrib><creatorcontrib>Angeli, Lucilla</creatorcontrib><creatorcontrib>Franchi, Luigi</creatorcontrib><creatorcontrib>Contemori, Lorenzo</creatorcontrib><creatorcontrib>Maga, Giovanni</creatorcontrib><creatorcontrib>Samuele, Alberta</creatorcontrib><creatorcontrib>Zanoli, Samantha</creatorcontrib><creatorcontrib>Armand-Ugon, Mercedes</creatorcontrib><creatorcontrib>Gonzalez, Emmanuel</creatorcontrib><creatorcontrib>Llano, Anuska</creatorcontrib><creatorcontrib>Esté, Jose A.</creatorcontrib><creatorcontrib>Botta, Maurizio</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>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Radi, Marco</au><au>Angeli, Lucilla</au><au>Franchi, Luigi</au><au>Contemori, Lorenzo</au><au>Maga, Giovanni</au><au>Samuele, Alberta</au><au>Zanoli, Samantha</au><au>Armand-Ugon, Mercedes</au><au>Gonzalez, Emmanuel</au><au>Llano, Anuska</au><au>Esté, Jose A.</au><au>Botta, Maurizio</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Towards novel S-DABOC inhibitors: Synthesis, biological investigation, and molecular modeling studies</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2008-11-01</date><risdate>2008</risdate><volume>18</volume><issue>21</issue><spage>5777</spage><epage>5780</epage><pages>5777-5780</pages><issn>0960-894X</issn><issn>0968-0896</issn><eissn>1464-3405</eissn><eissn>1464-3391</eissn><abstract>A small family of
S-DABO cytosine analogs (
S-DABOCs) has been synthesized and biologically evaluated as HIV-1 inhibitor both on wild type and drug-resistant mutants. An interesting compound (
5d) has been identified which showed a predicted pharmacokinetic profile similar to that of anti-HIV drugs on the market. Molecular modeling studies have been finally performed in order to rationalize the results.
A small family of
S-DABO cytosine analogs (
S-DABOCs) has been synthesized and biologically evaluated as HIV-1 inhibitor both on wild type (wt) and drug-resistant mutants leading to the identification of an interesting compound (
5d). Molecular modeling studies have been finally performed in order to rationalize the results.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>18842407</pmid><doi>10.1016/j.bmcl.2008.09.070</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0960-894X |
| ispartof | Bioorganic & medicinal chemistry, 2008-11, Vol.18 (21), p.5777-5780 |
| issn | 0960-894X 0968-0896 1464-3405 1464-3391 |
| language | eng |
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| source | MEDLINE; Elsevier ScienceDirect Journals |
| subjects | Anti-HIV Agents - chemical synthesis Anti-HIV Agents - chemistry Anti-HIV Agents - pharmacology Antibiotics. Antiinfectious agents. Antiparasitic agents Antiviral agents Biological and medical sciences Cytosine - analogs & derivatives Cytosine - chemical synthesis Cytosine - chemistry Cytosine - pharmacology HIV-1 HIV-1 - drug effects Human immunodeficiency virus 1 Medical sciences Microbial Sensitivity Tests Models, Molecular Molecular modeling Mutant NNRTIs Pharmacology. Drug treatments Reverse Transcriptase S-DABOCs |
| title | Towards novel S-DABOC inhibitors: Synthesis, biological investigation, and molecular modeling studies |
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