Synthesis and Anti-HIV Activity of [ddN]-[ddN] Dimers and Benzimidazole Nucleoside Dimers
In an attempt to combine the HIV‐inhibitory capacity of different 2′,3′‐dideoxynucleoside (ddN) analogs, we have designed and synthesized several dimers of [AZT]‐[AZT] and [AZT]‐[d4T]. In addition, we also synthesized the dimers of 1‐(1H‐benzimidazol‐1‐yl)‐1‐deoxy‐β‐D‐ribofuranose. The in vitro anti...
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| Veröffentlicht in: | Chemistry & biodiversity 2009-12, Vol.6 (12), p.2200-2208 |
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| creator | Li, Guo-Rui Liu, Jun Pan, Qin Song, Zhi-Bin Luo, Feng-Ling Wang, Shao-Ru Zhang, Xiao-Lian Zhou, Xiang |
| description | In an attempt to combine the HIV‐inhibitory capacity of different 2′,3′‐dideoxynucleoside (ddN) analogs, we have designed and synthesized several dimers of [AZT]‐[AZT] and [AZT]‐[d4T]. In addition, we also synthesized the dimers of 1‐(1H‐benzimidazol‐1‐yl)‐1‐deoxy‐β‐D‐ribofuranose. The in vitro anti‐HIV activity of these compounds on a pseudotype virus, pNL4‐3.Luc.R‐E‐, in the 293T cells has been determined. Among these compounds, 2,2′‐(propane‐1,3‐diyl)bis[1‐(β‐D‐ribofuranosyl)‐1H‐benzimidazole] (3) showed the highest anti‐HIV activity with similar effect as AZT. |
| doi_str_mv | 10.1002/cbdv.200800281 |
| format | Article |
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In addition, we also synthesized the dimers of 1‐(1H‐benzimidazol‐1‐yl)‐1‐deoxy‐β‐D‐ribofuranose. The in vitro anti‐HIV activity of these compounds on a pseudotype virus, pNL4‐3.Luc.R‐E‐, in the 293T cells has been determined. Among these compounds, 2,2′‐(propane‐1,3‐diyl)bis[1‐(β‐D‐ribofuranosyl)‐1H‐benzimidazole] (3) showed the highest anti‐HIV activity with similar effect as AZT.</description><identifier>ISSN: 1612-1872</identifier><identifier>EISSN: 1612-1880</identifier><identifier>DOI: 10.1002/cbdv.200800281</identifier><identifier>PMID: 20020452</identifier><language>eng</language><publisher>Zürich: WILEY-VCH Verlag</publisher><subject>Anti-HIV activity ; Anti-HIV Agents - chemical synthesis ; Anti-HIV Agents - chemistry ; Anti-HIV Agents - pharmacology ; Azidothymidine (AZT) ; Benzimidazole nucleosides ; Benzimidazoles - chemical synthesis ; Benzimidazoles - chemistry ; Benzimidazoles - pharmacology ; Cell Line ; Dideoxynucleosides - chemical synthesis ; Dideoxynucleosides - chemistry ; Dideoxynucleosides - pharmacology ; Dimerization ; HIV Core Protein p24 - metabolism ; Human immunodeficiency virus ; Humans ; Nucleosides ; Nucleosides - chemical synthesis ; Nucleosides - chemistry ; Nucleosides - pharmacology ; Zidovudin ; Zidovudine - chemistry</subject><ispartof>Chemistry & biodiversity, 2009-12, Vol.6 (12), p.2200-2208</ispartof><rights>Copyright © 2009 Verlag Helvetica Chimica Acta AG, Zürich</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3291-c940fe306e67e953093618e3ef8d7c2d381e5471ba4ca3de2bbc48a1bc4856ea3</citedby><cites>FETCH-LOGICAL-c3291-c940fe306e67e953093618e3ef8d7c2d381e5471ba4ca3de2bbc48a1bc4856ea3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcbdv.200800281$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcbdv.200800281$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20020452$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Li, Guo-Rui</creatorcontrib><creatorcontrib>Liu, Jun</creatorcontrib><creatorcontrib>Pan, Qin</creatorcontrib><creatorcontrib>Song, Zhi-Bin</creatorcontrib><creatorcontrib>Luo, Feng-Ling</creatorcontrib><creatorcontrib>Wang, Shao-Ru</creatorcontrib><creatorcontrib>Zhang, Xiao-Lian</creatorcontrib><creatorcontrib>Zhou, Xiang</creatorcontrib><title>Synthesis and Anti-HIV Activity of [ddN]-[ddN] Dimers and Benzimidazole Nucleoside Dimers</title><title>Chemistry & biodiversity</title><addtitle>Chemistry & Biodiversity</addtitle><description>In an attempt to combine the HIV‐inhibitory capacity of different 2′,3′‐dideoxynucleoside (ddN) analogs, we have designed and synthesized several dimers of [AZT]‐[AZT] and [AZT]‐[d4T]. In addition, we also synthesized the dimers of 1‐(1H‐benzimidazol‐1‐yl)‐1‐deoxy‐β‐D‐ribofuranose. The in vitro anti‐HIV activity of these compounds on a pseudotype virus, pNL4‐3.Luc.R‐E‐, in the 293T cells has been determined. Among these compounds, 2,2′‐(propane‐1,3‐diyl)bis[1‐(β‐D‐ribofuranosyl)‐1H‐benzimidazole] (3) showed the highest anti‐HIV activity with similar effect as AZT.</description><subject>Anti-HIV activity</subject><subject>Anti-HIV Agents - chemical synthesis</subject><subject>Anti-HIV Agents - chemistry</subject><subject>Anti-HIV Agents - pharmacology</subject><subject>Azidothymidine (AZT)</subject><subject>Benzimidazole nucleosides</subject><subject>Benzimidazoles - chemical synthesis</subject><subject>Benzimidazoles - chemistry</subject><subject>Benzimidazoles - pharmacology</subject><subject>Cell Line</subject><subject>Dideoxynucleosides - chemical synthesis</subject><subject>Dideoxynucleosides - chemistry</subject><subject>Dideoxynucleosides - pharmacology</subject><subject>Dimerization</subject><subject>HIV Core Protein p24 - metabolism</subject><subject>Human immunodeficiency virus</subject><subject>Humans</subject><subject>Nucleosides</subject><subject>Nucleosides - chemical synthesis</subject><subject>Nucleosides - chemistry</subject><subject>Nucleosides - pharmacology</subject><subject>Zidovudin</subject><subject>Zidovudine - chemistry</subject><issn>1612-1872</issn><issn>1612-1880</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkDlPwzAYhi0E4l4ZUTamFF9xnLG0lCKhIsQlhJDl2F-EIUeJU6D8elJSKjaW75Ce9x0ehA4I7hGM6bFJ7XuPYizbR5I1tE0EoSGREq-v7phuoR3vXxaIxHITbbUBinlEt9HD9bxsnsE7H-jSBv2yceH4_C7om8a9u2YeVFnwaO3kKfyZwdAVUHfsCZRfrnBWf1U5BJOZyaHyzsKS2UMbmc497C_3Lrodnd4MxuHF5dn5oH8RGkYTEpqE4wwYFiBiSCKGEyaIBAaZtLGhlkkCEY9JqrnRzAJNU8OlJosZCdBsFx11vdO6epuBb1ThvIE81yVUM69izkWCEyH_JxmnWFAWtWSvI01deV9Dpqa1K3Q9VwSrhXe18K5W3tvA4bJ6lhZgV_iv6BZIOuDD5TD_p04NToZ3f8vDLut8A5-rrK5flYhZHKn7yZm6Gkaj4WjMFWXf_DSdAg</recordid><startdate>200912</startdate><enddate>200912</enddate><creator>Li, Guo-Rui</creator><creator>Liu, Jun</creator><creator>Pan, Qin</creator><creator>Song, Zhi-Bin</creator><creator>Luo, Feng-Ling</creator><creator>Wang, Shao-Ru</creator><creator>Zhang, Xiao-Lian</creator><creator>Zhou, Xiang</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</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><scope>7TM</scope><scope>7U9</scope><scope>H94</scope></search><sort><creationdate>200912</creationdate><title>Synthesis and Anti-HIV Activity of [ddN]-[ddN] Dimers and Benzimidazole Nucleoside Dimers</title><author>Li, Guo-Rui ; Liu, Jun ; Pan, Qin ; Song, Zhi-Bin ; Luo, Feng-Ling ; Wang, Shao-Ru ; Zhang, Xiao-Lian ; Zhou, Xiang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3291-c940fe306e67e953093618e3ef8d7c2d381e5471ba4ca3de2bbc48a1bc4856ea3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Anti-HIV activity</topic><topic>Anti-HIV Agents - chemical synthesis</topic><topic>Anti-HIV Agents - chemistry</topic><topic>Anti-HIV Agents - pharmacology</topic><topic>Azidothymidine (AZT)</topic><topic>Benzimidazole nucleosides</topic><topic>Benzimidazoles - chemical synthesis</topic><topic>Benzimidazoles - chemistry</topic><topic>Benzimidazoles - pharmacology</topic><topic>Cell Line</topic><topic>Dideoxynucleosides - chemical synthesis</topic><topic>Dideoxynucleosides - chemistry</topic><topic>Dideoxynucleosides - pharmacology</topic><topic>Dimerization</topic><topic>HIV Core Protein p24 - metabolism</topic><topic>Human immunodeficiency virus</topic><topic>Humans</topic><topic>Nucleosides</topic><topic>Nucleosides - chemical synthesis</topic><topic>Nucleosides - chemistry</topic><topic>Nucleosides - pharmacology</topic><topic>Zidovudin</topic><topic>Zidovudine - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Guo-Rui</creatorcontrib><creatorcontrib>Liu, Jun</creatorcontrib><creatorcontrib>Pan, Qin</creatorcontrib><creatorcontrib>Song, Zhi-Bin</creatorcontrib><creatorcontrib>Luo, Feng-Ling</creatorcontrib><creatorcontrib>Wang, Shao-Ru</creatorcontrib><creatorcontrib>Zhang, Xiao-Lian</creatorcontrib><creatorcontrib>Zhou, Xiang</creatorcontrib><collection>Istex</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><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>AIDS and Cancer Research Abstracts</collection><jtitle>Chemistry & biodiversity</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Guo-Rui</au><au>Liu, Jun</au><au>Pan, Qin</au><au>Song, Zhi-Bin</au><au>Luo, Feng-Ling</au><au>Wang, Shao-Ru</au><au>Zhang, Xiao-Lian</au><au>Zhou, Xiang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Anti-HIV Activity of [ddN]-[ddN] Dimers and Benzimidazole Nucleoside Dimers</atitle><jtitle>Chemistry & biodiversity</jtitle><addtitle>Chemistry & Biodiversity</addtitle><date>2009-12</date><risdate>2009</risdate><volume>6</volume><issue>12</issue><spage>2200</spage><epage>2208</epage><pages>2200-2208</pages><issn>1612-1872</issn><eissn>1612-1880</eissn><abstract>In an attempt to combine the HIV‐inhibitory capacity of different 2′,3′‐dideoxynucleoside (ddN) analogs, we have designed and synthesized several dimers of [AZT]‐[AZT] and [AZT]‐[d4T]. In addition, we also synthesized the dimers of 1‐(1H‐benzimidazol‐1‐yl)‐1‐deoxy‐β‐D‐ribofuranose. The in vitro anti‐HIV activity of these compounds on a pseudotype virus, pNL4‐3.Luc.R‐E‐, in the 293T cells has been determined. Among these compounds, 2,2′‐(propane‐1,3‐diyl)bis[1‐(β‐D‐ribofuranosyl)‐1H‐benzimidazole] (3) showed the highest anti‐HIV activity with similar effect as AZT.</abstract><cop>Zürich</cop><pub>WILEY-VCH Verlag</pub><pmid>20020452</pmid><doi>10.1002/cbdv.200800281</doi><tpages>9</tpages></addata></record> |
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| subjects | Anti-HIV activity Anti-HIV Agents - chemical synthesis Anti-HIV Agents - chemistry Anti-HIV Agents - pharmacology Azidothymidine (AZT) Benzimidazole nucleosides Benzimidazoles - chemical synthesis Benzimidazoles - chemistry Benzimidazoles - pharmacology Cell Line Dideoxynucleosides - chemical synthesis Dideoxynucleosides - chemistry Dideoxynucleosides - pharmacology Dimerization HIV Core Protein p24 - metabolism Human immunodeficiency virus Humans Nucleosides Nucleosides - chemical synthesis Nucleosides - chemistry Nucleosides - pharmacology Zidovudin Zidovudine - chemistry |
| title | Synthesis and Anti-HIV Activity of [ddN]-[ddN] Dimers and Benzimidazole Nucleoside Dimers |
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