Synthesis of 2′,3′-Dideoxy- and 3′-Azido-2′,3′-dideoxy-pyridazine Nucleosides as Potential Antiviral Agents
The synthesis of 4-methoxy-, 4-amino-3-chloro-, and 4-amino-1-(2,3-dideoxy-B-D-glycero-pentofuranosyl)pyridazin-6-one nucleosides, 6,19 and 20 is described. The synthesis of 3,4-dichloropyridazin-6-one (10) was accomplished in 44% overall yield using bromomaleic anhydride (17) as the starting materi...
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| Veröffentlicht in: | Nucleosides & nucleotides 1994-03, Vol.13 (1-3), p.459-479 |
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| creator | Kasnar, Biserka Wise, Dean S. Kucera, Louis S. Drach, John C. Townsend, Leroy B. |
| description | The synthesis of 4-methoxy-, 4-amino-3-chloro-, and 4-amino-1-(2,3-dideoxy-B-D-glycero-pentofuranosyl)pyridazin-6-one nucleosides, 6,19 and 20 is described. The synthesis of 3,4-dichloropyridazin-6-one (10) was accomplished in 44% overall yield using bromomaleic anhydride (17) as the starting material. The condensation of the silylated base of 10 with the halogenose 12 in the presence of trimethylsilyl triflate as a catalyst afforded a mixture of3,4-dichloro-1-(3,5-di-O-p-toluoyl-2-deoxy-B-D-erythro-pentofuranosyl)pyrridazin-6-one (13) in 67% and its α-anomer 14 in 12% yield, respectively. A series of 3′-sulfonate esters were prepared to explore the synthesis of 3-chloro-4-hydroxy-1-(3-azido-2,3-dideoxy-B-D-erythro-pentofuranosyl) pyridazin-6-one (32) via 6,3-anhydronucleoside analogues. Compounds 15, 19 and 20 were evaluated against human immunodeficiency virus, human cytomegalovirus, and herpes simplex virus type 1 but were inactive. |
| doi_str_mv | 10.1080/15257779408013255 |
| format | Article |
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The synthesis of 3,4-dichloropyridazin-6-one (10) was accomplished in 44% overall yield using bromomaleic anhydride (17) as the starting material. The condensation of the silylated base of 10 with the halogenose 12 in the presence of trimethylsilyl triflate as a catalyst afforded a mixture of3,4-dichloro-1-(3,5-di-O-p-toluoyl-2-deoxy-B-D-erythro-pentofuranosyl)pyrridazin-6-one (13) in 67% and its α-anomer 14 in 12% yield, respectively. A series of 3′-sulfonate esters were prepared to explore the synthesis of 3-chloro-4-hydroxy-1-(3-azido-2,3-dideoxy-B-D-erythro-pentofuranosyl) pyridazin-6-one (32) via 6,3-anhydronucleoside analogues. Compounds 15, 19 and 20 were evaluated against human immunodeficiency virus, human cytomegalovirus, and herpes simplex virus type 1 but were inactive.</description><identifier>ISSN: 0732-8311</identifier><identifier>EISSN: 2332-3892</identifier><identifier>DOI: 10.1080/15257779408013255</identifier><identifier>CODEN: NUNUD5</identifier><language>eng</language><publisher>Monticello, NY: Taylor & Francis Group</publisher><subject>Carbohydrates. 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The synthesis of 3,4-dichloropyridazin-6-one (10) was accomplished in 44% overall yield using bromomaleic anhydride (17) as the starting material. The condensation of the silylated base of 10 with the halogenose 12 in the presence of trimethylsilyl triflate as a catalyst afforded a mixture of3,4-dichloro-1-(3,5-di-O-p-toluoyl-2-deoxy-B-D-erythro-pentofuranosyl)pyrridazin-6-one (13) in 67% and its α-anomer 14 in 12% yield, respectively. A series of 3′-sulfonate esters were prepared to explore the synthesis of 3-chloro-4-hydroxy-1-(3-azido-2,3-dideoxy-B-D-erythro-pentofuranosyl) pyridazin-6-one (32) via 6,3-anhydronucleoside analogues. Compounds 15, 19 and 20 were evaluated against human immunodeficiency virus, human cytomegalovirus, and herpes simplex virus type 1 but were inactive.</description><subject>Carbohydrates. Nucleosides and nucleotides</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Nucleosides, nucleotides and oligonucleotides</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0732-8311</issn><issn>2332-3892</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1994</creationdate><recordtype>article</recordtype><recordid>eNp1UMlOwzAQtRBIlMIHcMuBIwGvdSJxqcoqVYAEnKOJFzBK48pugfTEN_FJfAkuZTkgLjNvZt6b0TyEdgk-ILjAh0RQIaUseSoIo0KsoR5ljOasKOk66mGZcMEI2URbMT5iLGhZ8h6a33Tt7MFEFzNvM_r--rbPUsiPnTb-pcszaHX22RkunPb5L0N_MaZdcBoWrjXZ5Vw1xsc0iBnE7NrPTDtz0GTDlJ5cWKL71IrbaMNCE83OV-6ju9OT29F5Pr46uxgNx7kikrLcMqxKXtOCcqs10XqQXgTBtZS1MEoMQCkQtqCFBiwB28FA1SAl5VzXhSlZH5HVXhV8jMHYahrcBEJXEVwtfav--JY0eyvNFKKCxgZolYs_Qo4lJ4Ql2tGK5lrrwwSefWh0NYOu8eFbw_6_8gH1P4UP</recordid><startdate>19940301</startdate><enddate>19940301</enddate><creator>Kasnar, Biserka</creator><creator>Wise, Dean S.</creator><creator>Kucera, Louis S.</creator><creator>Drach, John C.</creator><creator>Townsend, Leroy B.</creator><general>Taylor & Francis Group</general><general>Dekker</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19940301</creationdate><title>Synthesis of 2′,3′-Dideoxy- and 3′-Azido-2′,3′-dideoxy-pyridazine Nucleosides as Potential Antiviral Agents</title><author>Kasnar, Biserka ; Wise, Dean S. ; Kucera, Louis S. ; Drach, John C. ; Townsend, Leroy B.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c1723-f30c94b2824fdd1dd6777a54d77b5ec56acca5f828da07a0f66cba77244db8e93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1994</creationdate><topic>Carbohydrates. Nucleosides and nucleotides</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Nucleosides, nucleotides and oligonucleotides</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>online_resources</toplevel><creatorcontrib>Kasnar, Biserka</creatorcontrib><creatorcontrib>Wise, Dean S.</creatorcontrib><creatorcontrib>Kucera, Louis S.</creatorcontrib><creatorcontrib>Drach, John C.</creatorcontrib><creatorcontrib>Townsend, Leroy B.</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>Nucleosides & nucleotides</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kasnar, Biserka</au><au>Wise, Dean S.</au><au>Kucera, Louis S.</au><au>Drach, John C.</au><au>Townsend, Leroy B.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 2′,3′-Dideoxy- and 3′-Azido-2′,3′-dideoxy-pyridazine Nucleosides as Potential Antiviral Agents</atitle><jtitle>Nucleosides & nucleotides</jtitle><date>1994-03-01</date><risdate>1994</risdate><volume>13</volume><issue>1-3</issue><spage>459</spage><epage>479</epage><pages>459-479</pages><issn>0732-8311</issn><eissn>2332-3892</eissn><coden>NUNUD5</coden><abstract>The synthesis of 4-methoxy-, 4-amino-3-chloro-, and 4-amino-1-(2,3-dideoxy-B-D-glycero-pentofuranosyl)pyridazin-6-one nucleosides, 6,19 and 20 is described. The synthesis of 3,4-dichloropyridazin-6-one (10) was accomplished in 44% overall yield using bromomaleic anhydride (17) as the starting material. The condensation of the silylated base of 10 with the halogenose 12 in the presence of trimethylsilyl triflate as a catalyst afforded a mixture of3,4-dichloro-1-(3,5-di-O-p-toluoyl-2-deoxy-B-D-erythro-pentofuranosyl)pyrridazin-6-one (13) in 67% and its α-anomer 14 in 12% yield, respectively. A series of 3′-sulfonate esters were prepared to explore the synthesis of 3-chloro-4-hydroxy-1-(3-azido-2,3-dideoxy-B-D-erythro-pentofuranosyl) pyridazin-6-one (32) via 6,3-anhydronucleoside analogues. Compounds 15, 19 and 20 were evaluated against human immunodeficiency virus, human cytomegalovirus, and herpes simplex virus type 1 but were inactive.</abstract><cop>Monticello, NY</cop><pub>Taylor & Francis Group</pub><doi>10.1080/15257779408013255</doi><tpages>21</tpages></addata></record> |
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| subjects | Carbohydrates. Nucleosides and nucleotides Chemistry Exact sciences and technology Nucleosides, nucleotides and oligonucleotides Organic chemistry Preparations and properties |
| title | Synthesis of 2′,3′-Dideoxy- and 3′-Azido-2′,3′-dideoxy-pyridazine Nucleosides as Potential Antiviral Agents |
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