L-.beta.-(2S,4S)- and L-.alpha.-(2S,4R)-dioxolanyl nucleosides as potential anti-HIV agents: asymmetric synthesis and structure-activity relationships
In order to study the structure-activity relationships of L-(2S,4S)- and L-(2S,4R)-dioxolanyl nucleoside as potential anti-HIV agents, various enantiomerically pure L-(2S,4S)- and (2S,4R)-dioxolanylpyrimidine and -purine nucleosides have been synthesized and evaluated against HIV-1 in human peripher...
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| Veröffentlicht in: | Journal of medicinal chemistry 1993-03, Vol.36 (5), p.519-528 |
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| creator | Kim, Hea O Schinazi, Raymond F Shanmuganathan, Kirupathevy Jeong, Lak S Beach, J. Warren Nampalli, Satyanarayana Cannon, Deborah L Chu, Chung K |
| description | In order to study the structure-activity relationships of L-(2S,4S)- and L-(2S,4R)-dioxolanyl nucleoside as potential anti-HIV agents, various enantiomerically pure L-(2S,4S)- and (2S,4R)-dioxolanylpyrimidine and -purine nucleosides have been synthesized and evaluated against HIV-1 in human peripheral blood mononuclear (PBM) cells. The enantiomerically pure key intermediate 8 has been synthesized in six steps from 1,6-anhydro-beta-L-gulose (2), and compound 8 was condensed with 5-substituted pyrimidines, 6-chloropurine, and 2,6-disubstituted purine to obtain various dioxolanylpyrimidine and -purine nucleosides, respectively. Among the compound synthesized, 5-fluorocytosine derivative 29 was found to exhibit the most potent anti-HIV activity (EC50 = 0.0012 microM) although it was toxic (IC50 = 10.0 microM). The order of anti-HIV potency of pyrimidine analogues was as follows: 5-fluorocytosine (beta-isomer) > cytosine (beta-isomer) > 5-fluorocytosine (alpha-isomer) > 5-iodocytosine (beta-isomer) > cytosine (alpha-isomer) > 5-bromocytosine (beta-isomer) > thymine (beta-isomer) > 5-methylcytosine (alpha-isomer) > 5-iodocytosine (alpha-isomer) > 5-chlorocytosine (beta-isomer). The anti-HIV potency of purine analogues was found to be in the following decreasing order: 2,6-diaminopurine (beta-isomer) > 2-chloroadenine (alpha-isomer) > 2-fluoroadenine (beta-isomer) > adenine (beta-isomer) > 2-amino-6-chloropurine (alpha-isomer) > 2-amino-6-chloropurine (beta-isomer) > guanine (beta-isomer) > 2-fluoroadenine (alpha-isomer) > adenine (alpha-isomer) > 2,6-diaminopurine (alpha-isomer) > N6-methyladenine (beta-isomer). It is interesting to note that the alpha-5-fluorocytosine analogue exhibited an excellent anti-HIV activity (EC50 = 0.063 microM) without cytotoxicity up to 100 microM in PBM cell. |
| doi_str_mv | 10.1021/jm00057a001 |
| format | Article |
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Warren ; Nampalli, Satyanarayana ; Cannon, Deborah L ; Chu, Chung K</creator><creatorcontrib>Kim, Hea O ; Schinazi, Raymond F ; Shanmuganathan, Kirupathevy ; Jeong, Lak S ; Beach, J. Warren ; Nampalli, Satyanarayana ; Cannon, Deborah L ; Chu, Chung K</creatorcontrib><description>In order to study the structure-activity relationships of L-(2S,4S)- and L-(2S,4R)-dioxolanyl nucleoside as potential anti-HIV agents, various enantiomerically pure L-(2S,4S)- and (2S,4R)-dioxolanylpyrimidine and -purine nucleosides have been synthesized and evaluated against HIV-1 in human peripheral blood mononuclear (PBM) cells. The enantiomerically pure key intermediate 8 has been synthesized in six steps from 1,6-anhydro-beta-L-gulose (2), and compound 8 was condensed with 5-substituted pyrimidines, 6-chloropurine, and 2,6-disubstituted purine to obtain various dioxolanylpyrimidine and -purine nucleosides, respectively. Among the compound synthesized, 5-fluorocytosine derivative 29 was found to exhibit the most potent anti-HIV activity (EC50 = 0.0012 microM) although it was toxic (IC50 = 10.0 microM). The order of anti-HIV potency of pyrimidine analogues was as follows: 5-fluorocytosine (beta-isomer) > cytosine (beta-isomer) > 5-fluorocytosine (alpha-isomer) > 5-iodocytosine (beta-isomer) > cytosine (alpha-isomer) > 5-bromocytosine (beta-isomer) > thymine (beta-isomer) > 5-methylcytosine (alpha-isomer) > 5-iodocytosine (alpha-isomer) > 5-chlorocytosine (beta-isomer). The anti-HIV potency of purine analogues was found to be in the following decreasing order: 2,6-diaminopurine (beta-isomer) > 2-chloroadenine (alpha-isomer) > 2-fluoroadenine (beta-isomer) > adenine (beta-isomer) > 2-amino-6-chloropurine (alpha-isomer) > 2-amino-6-chloropurine (beta-isomer) > guanine (beta-isomer) > 2-fluoroadenine (alpha-isomer) > adenine (alpha-isomer) > 2,6-diaminopurine (alpha-isomer) > N6-methyladenine (beta-isomer). It is interesting to note that the alpha-5-fluorocytosine analogue exhibited an excellent anti-HIV activity (EC50 = 0.063 microM) without cytotoxicity up to 100 microM in PBM cell.</description><identifier>ISSN: 0022-2623</identifier><identifier>EISSN: 1520-4804</identifier><identifier>DOI: 10.1021/jm00057a001</identifier><identifier>PMID: 8496934</identifier><identifier>CODEN: JMCMAR</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Antiviral Agents - chemical synthesis ; Antiviral Agents - chemistry ; Antiviral Agents - pharmacology ; Carbohydrates. Nucleosides and nucleotides ; Cell Line ; Cell Survival - drug effects ; Chemistry ; Cytosine - analogs & derivatives ; Cytosine - chemical synthesis ; Cytosine - chemistry ; Cytosine - pharmacology ; Dioxolanes - chemical synthesis ; Dioxolanes - chemistry ; Dioxolanes - pharmacology ; Exact sciences and technology ; HIV-1 - drug effects ; human immunodeficiency virus ; Humans ; Molecular Structure ; Nucleosides, nucleotides and oligonucleotides ; Organic chemistry ; Preparations and properties ; Purines - chemical synthesis ; Purines - chemistry ; Purines - pharmacology ; Pyrimidines - chemical synthesis ; Pyrimidines - chemistry ; Pyrimidines - pharmacology ; Structure-Activity Relationship</subject><ispartof>Journal of medicinal chemistry, 1993-03, Vol.36 (5), p.519-528</ispartof><rights>1993 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a395t-1d528923a0bcbb1087582f057c7b34b8dbd41a97cd1028b6ba011ead188cf4743</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jm00057a001$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jm00057a001$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,778,782,2754,27063,27911,27912,56725,56775</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=4661621$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/8496934$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kim, Hea O</creatorcontrib><creatorcontrib>Schinazi, Raymond F</creatorcontrib><creatorcontrib>Shanmuganathan, Kirupathevy</creatorcontrib><creatorcontrib>Jeong, Lak S</creatorcontrib><creatorcontrib>Beach, J. Warren</creatorcontrib><creatorcontrib>Nampalli, Satyanarayana</creatorcontrib><creatorcontrib>Cannon, Deborah L</creatorcontrib><creatorcontrib>Chu, Chung K</creatorcontrib><title>L-.beta.-(2S,4S)- and L-.alpha.-(2S,4R)-dioxolanyl nucleosides as potential anti-HIV agents: asymmetric synthesis and structure-activity relationships</title><title>Journal of medicinal chemistry</title><addtitle>J. Med. Chem</addtitle><description>In order to study the structure-activity relationships of L-(2S,4S)- and L-(2S,4R)-dioxolanyl nucleoside as potential anti-HIV agents, various enantiomerically pure L-(2S,4S)- and (2S,4R)-dioxolanylpyrimidine and -purine nucleosides have been synthesized and evaluated against HIV-1 in human peripheral blood mononuclear (PBM) cells. The enantiomerically pure key intermediate 8 has been synthesized in six steps from 1,6-anhydro-beta-L-gulose (2), and compound 8 was condensed with 5-substituted pyrimidines, 6-chloropurine, and 2,6-disubstituted purine to obtain various dioxolanylpyrimidine and -purine nucleosides, respectively. Among the compound synthesized, 5-fluorocytosine derivative 29 was found to exhibit the most potent anti-HIV activity (EC50 = 0.0012 microM) although it was toxic (IC50 = 10.0 microM). The order of anti-HIV potency of pyrimidine analogues was as follows: 5-fluorocytosine (beta-isomer) > cytosine (beta-isomer) > 5-fluorocytosine (alpha-isomer) > 5-iodocytosine (beta-isomer) > cytosine (alpha-isomer) > 5-bromocytosine (beta-isomer) > thymine (beta-isomer) > 5-methylcytosine (alpha-isomer) > 5-iodocytosine (alpha-isomer) > 5-chlorocytosine (beta-isomer). The anti-HIV potency of purine analogues was found to be in the following decreasing order: 2,6-diaminopurine (beta-isomer) > 2-chloroadenine (alpha-isomer) > 2-fluoroadenine (beta-isomer) > adenine (beta-isomer) > 2-amino-6-chloropurine (alpha-isomer) > 2-amino-6-chloropurine (beta-isomer) > guanine (beta-isomer) > 2-fluoroadenine (alpha-isomer) > adenine (alpha-isomer) > 2,6-diaminopurine (alpha-isomer) > N6-methyladenine (beta-isomer). It is interesting to note that the alpha-5-fluorocytosine analogue exhibited an excellent anti-HIV activity (EC50 = 0.063 microM) without cytotoxicity up to 100 microM in PBM cell.</description><subject>Antiviral Agents - chemical synthesis</subject><subject>Antiviral Agents - chemistry</subject><subject>Antiviral Agents - pharmacology</subject><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Cell Line</subject><subject>Cell Survival - drug effects</subject><subject>Chemistry</subject><subject>Cytosine - analogs & derivatives</subject><subject>Cytosine - chemical synthesis</subject><subject>Cytosine - chemistry</subject><subject>Cytosine - pharmacology</subject><subject>Dioxolanes - chemical synthesis</subject><subject>Dioxolanes - chemistry</subject><subject>Dioxolanes - pharmacology</subject><subject>Exact sciences and technology</subject><subject>HIV-1 - drug effects</subject><subject>human immunodeficiency virus</subject><subject>Humans</subject><subject>Molecular Structure</subject><subject>Nucleosides, nucleotides and oligonucleotides</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>Purines - chemical synthesis</subject><subject>Purines - chemistry</subject><subject>Purines - pharmacology</subject><subject>Pyrimidines - chemical synthesis</subject><subject>Pyrimidines - chemistry</subject><subject>Pyrimidines - pharmacology</subject><subject>Structure-Activity Relationship</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1993</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkU9v1DAQxS0EKkvhxBkpB1RagRfbSeyEG6pKW2kloFu4WhPHYb3kHx4HNV-Ez4vLLisOnEZ67-en8RtCnnO25Ezwt9uOMZYrYIw_IAueC0azgmUPyYIxIaiQIn1MniBuI5ZykR6RoyIrZZlmC_JrRZeVDbCkp2L9Jluf0QT6OokqtOPmr3xzRms33A0t9HOb9JNp7YCutpgAJuMQbB8ctPFlcPTq-msC36KC76I7d50N3pkE5z5sLDr8k4_BTyZM3lIwwf10YU68bSG4oceNG_EpedRAi_bZfh6TLx8ubs-v6Orj5fX5-xWFtMwD5XUuilKkwCpTVZwVKi9EE7swqkqzqqirOuNQKlPHoopKVsA4t1DzojBNprL0mJzsckc__JgsBt05NLaNH7XDhJrLvCyUkhF8vQONHxC9bfToXQd-1pzp-yvof64Q6Rf72KnqbH1g97VH_-XeBzTQNh564_CAZVJyKe5j6A5zGOzdwQb_XUuVqlzfflprkfMb-ZkpfRn5VzseDOrtMPk-dvffBX8Dmmip1A</recordid><startdate>199303</startdate><enddate>199303</enddate><creator>Kim, Hea O</creator><creator>Schinazi, Raymond F</creator><creator>Shanmuganathan, Kirupathevy</creator><creator>Jeong, Lak S</creator><creator>Beach, J. Warren</creator><creator>Nampalli, Satyanarayana</creator><creator>Cannon, Deborah L</creator><creator>Chu, Chung K</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>7T7</scope><scope>7TM</scope><scope>7U9</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>H94</scope><scope>P64</scope></search><sort><creationdate>199303</creationdate><title>L-.beta.-(2S,4S)- and L-.alpha.-(2S,4R)-dioxolanyl nucleosides as potential anti-HIV agents: asymmetric synthesis and structure-activity relationships</title><author>Kim, Hea O ; Schinazi, Raymond F ; Shanmuganathan, Kirupathevy ; Jeong, Lak S ; Beach, J. Warren ; Nampalli, Satyanarayana ; Cannon, Deborah L ; Chu, Chung K</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a395t-1d528923a0bcbb1087582f057c7b34b8dbd41a97cd1028b6ba011ead188cf4743</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1993</creationdate><topic>Antiviral Agents - chemical synthesis</topic><topic>Antiviral Agents - chemistry</topic><topic>Antiviral Agents - pharmacology</topic><topic>Carbohydrates. Nucleosides and nucleotides</topic><topic>Cell Line</topic><topic>Cell Survival - drug effects</topic><topic>Chemistry</topic><topic>Cytosine - analogs & derivatives</topic><topic>Cytosine - chemical synthesis</topic><topic>Cytosine - chemistry</topic><topic>Cytosine - pharmacology</topic><topic>Dioxolanes - chemical synthesis</topic><topic>Dioxolanes - chemistry</topic><topic>Dioxolanes - pharmacology</topic><topic>Exact sciences and technology</topic><topic>HIV-1 - drug effects</topic><topic>human immunodeficiency virus</topic><topic>Humans</topic><topic>Molecular Structure</topic><topic>Nucleosides, nucleotides and oligonucleotides</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>Purines - chemical synthesis</topic><topic>Purines - chemistry</topic><topic>Purines - pharmacology</topic><topic>Pyrimidines - chemical synthesis</topic><topic>Pyrimidines - chemistry</topic><topic>Pyrimidines - pharmacology</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kim, Hea O</creatorcontrib><creatorcontrib>Schinazi, Raymond F</creatorcontrib><creatorcontrib>Shanmuganathan, Kirupathevy</creatorcontrib><creatorcontrib>Jeong, Lak S</creatorcontrib><creatorcontrib>Beach, J. Warren</creatorcontrib><creatorcontrib>Nampalli, Satyanarayana</creatorcontrib><creatorcontrib>Cannon, Deborah L</creatorcontrib><creatorcontrib>Chu, Chung K</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>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Virology and AIDS Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>AIDS and Cancer Research Abstracts</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kim, Hea O</au><au>Schinazi, Raymond F</au><au>Shanmuganathan, Kirupathevy</au><au>Jeong, Lak S</au><au>Beach, J. Warren</au><au>Nampalli, Satyanarayana</au><au>Cannon, Deborah L</au><au>Chu, Chung K</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>L-.beta.-(2S,4S)- and L-.alpha.-(2S,4R)-dioxolanyl nucleosides as potential anti-HIV agents: asymmetric synthesis and structure-activity relationships</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J. Med. Chem</addtitle><date>1993-03</date><risdate>1993</risdate><volume>36</volume><issue>5</issue><spage>519</spage><epage>528</epage><pages>519-528</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>In order to study the structure-activity relationships of L-(2S,4S)- and L-(2S,4R)-dioxolanyl nucleoside as potential anti-HIV agents, various enantiomerically pure L-(2S,4S)- and (2S,4R)-dioxolanylpyrimidine and -purine nucleosides have been synthesized and evaluated against HIV-1 in human peripheral blood mononuclear (PBM) cells. The enantiomerically pure key intermediate 8 has been synthesized in six steps from 1,6-anhydro-beta-L-gulose (2), and compound 8 was condensed with 5-substituted pyrimidines, 6-chloropurine, and 2,6-disubstituted purine to obtain various dioxolanylpyrimidine and -purine nucleosides, respectively. Among the compound synthesized, 5-fluorocytosine derivative 29 was found to exhibit the most potent anti-HIV activity (EC50 = 0.0012 microM) although it was toxic (IC50 = 10.0 microM). The order of anti-HIV potency of pyrimidine analogues was as follows: 5-fluorocytosine (beta-isomer) > cytosine (beta-isomer) > 5-fluorocytosine (alpha-isomer) > 5-iodocytosine (beta-isomer) > cytosine (alpha-isomer) > 5-bromocytosine (beta-isomer) > thymine (beta-isomer) > 5-methylcytosine (alpha-isomer) > 5-iodocytosine (alpha-isomer) > 5-chlorocytosine (beta-isomer). The anti-HIV potency of purine analogues was found to be in the following decreasing order: 2,6-diaminopurine (beta-isomer) > 2-chloroadenine (alpha-isomer) > 2-fluoroadenine (beta-isomer) > adenine (beta-isomer) > 2-amino-6-chloropurine (alpha-isomer) > 2-amino-6-chloropurine (beta-isomer) > guanine (beta-isomer) > 2-fluoroadenine (alpha-isomer) > adenine (alpha-isomer) > 2,6-diaminopurine (alpha-isomer) > N6-methyladenine (beta-isomer). It is interesting to note that the alpha-5-fluorocytosine analogue exhibited an excellent anti-HIV activity (EC50 = 0.063 microM) without cytotoxicity up to 100 microM in PBM cell.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>8496934</pmid><doi>10.1021/jm00057a001</doi><tpages>10</tpages></addata></record> |
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| ispartof | Journal of medicinal chemistry, 1993-03, Vol.36 (5), p.519-528 |
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| subjects | Antiviral Agents - chemical synthesis Antiviral Agents - chemistry Antiviral Agents - pharmacology Carbohydrates. Nucleosides and nucleotides Cell Line Cell Survival - drug effects Chemistry Cytosine - analogs & derivatives Cytosine - chemical synthesis Cytosine - chemistry Cytosine - pharmacology Dioxolanes - chemical synthesis Dioxolanes - chemistry Dioxolanes - pharmacology Exact sciences and technology HIV-1 - drug effects human immunodeficiency virus Humans Molecular Structure Nucleosides, nucleotides and oligonucleotides Organic chemistry Preparations and properties Purines - chemical synthesis Purines - chemistry Purines - pharmacology Pyrimidines - chemical synthesis Pyrimidines - chemistry Pyrimidines - pharmacology Structure-Activity Relationship |
| title | L-.beta.-(2S,4S)- and L-.alpha.-(2S,4R)-dioxolanyl nucleosides as potential anti-HIV agents: asymmetric synthesis and structure-activity relationships |
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