Synthesis and properties of 1-(3'-dihydroxyboryl-2',3'-dideoxyribosyl)pyrimidines
Nucleoside analogues having a boronic acid in place of the 3-hydroxyl group of deoxyribose have been synthesized. The synthesis of 3'-dihydroxyboryl-2',3'-dideoxyribose was based on asymmetric homologation of boronic esters with (dihalomethyl)lithium, beginning from a (silyloxymethyl)...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2012-12, Vol.10 (47), p.9349-9358 |
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| container_issue | 47 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Kim, Byung Ju Zhang, Jinhua Tan, Shenglan Matteson, Donald S Prusoff, William H Cheng, Yung-Chi |
| description | Nucleoside analogues having a boronic acid in place of the 3-hydroxyl group of deoxyribose have been synthesized. The synthesis of 3'-dihydroxyboryl-2',3'-dideoxyribose was based on asymmetric homologation of boronic esters with (dihalomethyl)lithium, beginning from a (silyloxymethyl)boronic ester. A change of chiral director is required before introduction of the second stereocenter, and the direct displacement of (S,S)-1,2-dicyclohexyl-1,2-ethanediol by (1S,2S,3R,5S)-pinanediol was used for this purpose. Coupling of the pinanediol ester of the 1-acetoxy-3-dioxyboryl-5-tert-butylsilyloxy deoxyribose analogue with silylated pyrimidine bases was accomplished with trimethylsilyl bromide. The boronic acid nucleoside analogues were not cytotoxic toward Hep G2 (human hepatocarcinoma) cells. Decomposition occurred over a period of several hours at 37 °C, pH 7.4, with liberation of free pyrimidine base. |
| doi_str_mv | 10.1039/c2ob26756j |
| format | Article |
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The synthesis of 3'-dihydroxyboryl-2',3'-dideoxyribose was based on asymmetric homologation of boronic esters with (dihalomethyl)lithium, beginning from a (silyloxymethyl)boronic ester. A change of chiral director is required before introduction of the second stereocenter, and the direct displacement of (S,S)-1,2-dicyclohexyl-1,2-ethanediol by (1S,2S,3R,5S)-pinanediol was used for this purpose. Coupling of the pinanediol ester of the 1-acetoxy-3-dioxyboryl-5-tert-butylsilyloxy deoxyribose analogue with silylated pyrimidine bases was accomplished with trimethylsilyl bromide. The boronic acid nucleoside analogues were not cytotoxic toward Hep G2 (human hepatocarcinoma) cells. Decomposition occurred over a period of several hours at 37 °C, pH 7.4, with liberation of free pyrimidine base.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/c2ob26756j</identifier><identifier>PMID: 23108312</identifier><language>eng</language><publisher>England</publisher><subject>Antineoplastic Agents - chemical synthesis ; Antineoplastic Agents - chemistry ; Antineoplastic Agents - pharmacology ; Boronic Acids - chemistry ; Cell Line, Tumor ; Cell Survival - drug effects ; Humans ; Liver Neoplasms - drug therapy ; Molecular Structure ; Nucleosides - chemical synthesis ; Nucleosides - chemistry ; Pyrimidines - chemical synthesis ; Pyrimidines - chemistry ; Pyrimidines - pharmacology ; Pyrimidines - therapeutic use</subject><ispartof>Organic & biomolecular chemistry, 2012-12, Vol.10 (47), p.9349-9358</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c287t-fae5d63ea62d8776bfb314e92531cacad7bc298476ac619fdbb8a7d20bcc76f13</citedby><cites>FETCH-LOGICAL-c287t-fae5d63ea62d8776bfb314e92531cacad7bc298476ac619fdbb8a7d20bcc76f13</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23108312$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kim, Byung Ju</creatorcontrib><creatorcontrib>Zhang, Jinhua</creatorcontrib><creatorcontrib>Tan, Shenglan</creatorcontrib><creatorcontrib>Matteson, Donald S</creatorcontrib><creatorcontrib>Prusoff, William H</creatorcontrib><creatorcontrib>Cheng, Yung-Chi</creatorcontrib><title>Synthesis and properties of 1-(3'-dihydroxyboryl-2',3'-dideoxyribosyl)pyrimidines</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>Nucleoside analogues having a boronic acid in place of the 3-hydroxyl group of deoxyribose have been synthesized. The synthesis of 3'-dihydroxyboryl-2',3'-dideoxyribose was based on asymmetric homologation of boronic esters with (dihalomethyl)lithium, beginning from a (silyloxymethyl)boronic ester. A change of chiral director is required before introduction of the second stereocenter, and the direct displacement of (S,S)-1,2-dicyclohexyl-1,2-ethanediol by (1S,2S,3R,5S)-pinanediol was used for this purpose. Coupling of the pinanediol ester of the 1-acetoxy-3-dioxyboryl-5-tert-butylsilyloxy deoxyribose analogue with silylated pyrimidine bases was accomplished with trimethylsilyl bromide. The boronic acid nucleoside analogues were not cytotoxic toward Hep G2 (human hepatocarcinoma) cells. Decomposition occurred over a period of several hours at 37 °C, pH 7.4, with liberation of free pyrimidine base.</description><subject>Antineoplastic Agents - chemical synthesis</subject><subject>Antineoplastic Agents - chemistry</subject><subject>Antineoplastic Agents - pharmacology</subject><subject>Boronic Acids - chemistry</subject><subject>Cell Line, Tumor</subject><subject>Cell Survival - drug effects</subject><subject>Humans</subject><subject>Liver Neoplasms - drug therapy</subject><subject>Molecular Structure</subject><subject>Nucleosides - chemical synthesis</subject><subject>Nucleosides - chemistry</subject><subject>Pyrimidines - chemical synthesis</subject><subject>Pyrimidines - chemistry</subject><subject>Pyrimidines - pharmacology</subject><subject>Pyrimidines - therapeutic use</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkE1Lw0AYhBdRbK1e_AGSW6u4uu9uspscpfgFBRH1HPaTpqTZuJuC-fdGW-tphuFhGAahcyA3QFhxq6lXlIuMrw7QGFIhMMlYcbj3lIzQSYwrQqAQPD1GI8qA5AzoGL2-9U23tLGKiWxM0gbf2tBVNibeJYBnbIpNtexN8F-98qGvMZ1e_4bGDlGolI99fdkObl2ZqrHxFB05WUd7ttMJ-ni4f58_4cXL4_P8boE1zUWHnbSZ4cxKTk0uBFdOMUhtQTMGWmpphNK0yFPBpeZQOKNULoWhRGktuAM2QbNt77D5c2NjV66rqG1dy8b6TSwBRC4oyygf0KstqoOPMVhXtsNcGfoSSPlzYfl_4QBf7Ho3am3NHv37jH0DpOVs-g</recordid><startdate>20121221</startdate><enddate>20121221</enddate><creator>Kim, Byung Ju</creator><creator>Zhang, Jinhua</creator><creator>Tan, Shenglan</creator><creator>Matteson, Donald S</creator><creator>Prusoff, William H</creator><creator>Cheng, Yung-Chi</creator><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>20121221</creationdate><title>Synthesis and properties of 1-(3'-dihydroxyboryl-2',3'-dideoxyribosyl)pyrimidines</title><author>Kim, Byung Ju ; Zhang, Jinhua ; Tan, Shenglan ; Matteson, Donald S ; Prusoff, William H ; Cheng, Yung-Chi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c287t-fae5d63ea62d8776bfb314e92531cacad7bc298476ac619fdbb8a7d20bcc76f13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Antineoplastic Agents - chemical synthesis</topic><topic>Antineoplastic Agents - chemistry</topic><topic>Antineoplastic Agents - pharmacology</topic><topic>Boronic Acids - chemistry</topic><topic>Cell Line, Tumor</topic><topic>Cell Survival - drug effects</topic><topic>Humans</topic><topic>Liver Neoplasms - drug therapy</topic><topic>Molecular Structure</topic><topic>Nucleosides - chemical synthesis</topic><topic>Nucleosides - chemistry</topic><topic>Pyrimidines - chemical synthesis</topic><topic>Pyrimidines - chemistry</topic><topic>Pyrimidines - pharmacology</topic><topic>Pyrimidines - therapeutic use</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kim, Byung Ju</creatorcontrib><creatorcontrib>Zhang, Jinhua</creatorcontrib><creatorcontrib>Tan, Shenglan</creatorcontrib><creatorcontrib>Matteson, Donald S</creatorcontrib><creatorcontrib>Prusoff, William H</creatorcontrib><creatorcontrib>Cheng, Yung-Chi</creatorcontrib><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>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kim, Byung Ju</au><au>Zhang, Jinhua</au><au>Tan, Shenglan</au><au>Matteson, Donald S</au><au>Prusoff, William H</au><au>Cheng, Yung-Chi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and properties of 1-(3'-dihydroxyboryl-2',3'-dideoxyribosyl)pyrimidines</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2012-12-21</date><risdate>2012</risdate><volume>10</volume><issue>47</issue><spage>9349</spage><epage>9358</epage><pages>9349-9358</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>Nucleoside analogues having a boronic acid in place of the 3-hydroxyl group of deoxyribose have been synthesized. The synthesis of 3'-dihydroxyboryl-2',3'-dideoxyribose was based on asymmetric homologation of boronic esters with (dihalomethyl)lithium, beginning from a (silyloxymethyl)boronic ester. A change of chiral director is required before introduction of the second stereocenter, and the direct displacement of (S,S)-1,2-dicyclohexyl-1,2-ethanediol by (1S,2S,3R,5S)-pinanediol was used for this purpose. Coupling of the pinanediol ester of the 1-acetoxy-3-dioxyboryl-5-tert-butylsilyloxy deoxyribose analogue with silylated pyrimidine bases was accomplished with trimethylsilyl bromide. The boronic acid nucleoside analogues were not cytotoxic toward Hep G2 (human hepatocarcinoma) cells. Decomposition occurred over a period of several hours at 37 °C, pH 7.4, with liberation of free pyrimidine base.</abstract><cop>England</cop><pmid>23108312</pmid><doi>10.1039/c2ob26756j</doi><tpages>10</tpages></addata></record> |
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| ispartof | Organic & biomolecular chemistry, 2012-12, Vol.10 (47), p.9349-9358 |
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| source | MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Antineoplastic Agents - pharmacology Boronic Acids - chemistry Cell Line, Tumor Cell Survival - drug effects Humans Liver Neoplasms - drug therapy Molecular Structure Nucleosides - chemical synthesis Nucleosides - chemistry Pyrimidines - chemical synthesis Pyrimidines - chemistry Pyrimidines - pharmacology Pyrimidines - therapeutic use |
| title | Synthesis and properties of 1-(3'-dihydroxyboryl-2',3'-dideoxyribosyl)pyrimidines |
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