Inhibitors of human purine nucleoside phosphorylase. Synthesis, purine nucleoside phosphorylase inhibition, and T-cell cytotoxicity of 2,5-diaminothiazolo[5,4-d]pyrimidin-7(6H)-one and 2,5-diaminothiazolo[4,5-d]pyrimidin-7(6H)-one. Two thio isosteres of 8-aminoguanine
8-Aminoguanine is a potent inhibitor of purine nucleoside phosphorylase (PNP) and also a substrate of PNP. Two thio isosteres of 8-aminoguanine, 2,5-diaminothiazolo[5,4-d]pyrimidin-7(6H)-one (2) and 2,4-diaminothiazolo[4,5-d]pyrimidin-7(6H)-one (3), which cannot be substrates of PNP, were synthesize...
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| Veröffentlicht in: | Journal of medicinal chemistry 1986-09, Vol.29 (9), p.1804-1806 |
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| container_issue | 9 |
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| container_title | Journal of medicinal chemistry |
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| creator | SIRCAR, J. C SUTO, M. J SCOTT, M. E DONG, M. K GILBERTSEN, R. B |
| description | 8-Aminoguanine is a potent inhibitor of purine nucleoside phosphorylase (PNP) and also a substrate of PNP. Two thio isosteres of 8-aminoguanine, 2,5-diaminothiazolo[5,4-d]pyrimidin-7(6H)-one (2) and 2,4-diaminothiazolo[4,5-d]pyrimidin-7(6H)-one (3), which cannot be substrates of PNP, were synthesized and evaluated for their inhibitory activity against PNP. They were found to be weak inhibitors of PNP and to be noncytotoxic for MOLT-4 T-cells in culture. |
| doi_str_mv | 10.1021/jm00159a045 |
| format | Article |
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Synthesis, purine nucleoside phosphorylase inhibition, and T-cell cytotoxicity of 2,5-diaminothiazolo[5,4-d]pyrimidin-7(6H)-one and 2,5-diaminothiazolo[4,5-d]pyrimidin-7(6H)-one. Two thio isosteres of 8-aminoguanine</title><source>MEDLINE</source><source>ACS Publications</source><creator>SIRCAR, J. C ; SUTO, M. J ; SCOTT, M. E ; DONG, M. K ; GILBERTSEN, R. B</creator><creatorcontrib>SIRCAR, J. C ; SUTO, M. J ; SCOTT, M. E ; DONG, M. K ; GILBERTSEN, R. B</creatorcontrib><description>8-Aminoguanine is a potent inhibitor of purine nucleoside phosphorylase (PNP) and also a substrate of PNP. Two thio isosteres of 8-aminoguanine, 2,5-diaminothiazolo[5,4-d]pyrimidin-7(6H)-one (2) and 2,4-diaminothiazolo[4,5-d]pyrimidin-7(6H)-one (3), which cannot be substrates of PNP, were synthesized and evaluated for their inhibitory activity against PNP. 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C</creatorcontrib><creatorcontrib>SUTO, M. J</creatorcontrib><creatorcontrib>SCOTT, M. E</creatorcontrib><creatorcontrib>DONG, M. K</creatorcontrib><creatorcontrib>GILBERTSEN, R. B</creatorcontrib><title>Inhibitors of human purine nucleoside phosphorylase. Synthesis, purine nucleoside phosphorylase inhibition, and T-cell cytotoxicity of 2,5-diaminothiazolo[5,4-d]pyrimidin-7(6H)-one and 2,5-diaminothiazolo[4,5-d]pyrimidin-7(6H)-one. Two thio isosteres of 8-aminoguanine</title><title>Journal of medicinal chemistry</title><addtitle>J Med Chem</addtitle><description>8-Aminoguanine is a potent inhibitor of purine nucleoside phosphorylase (PNP) and also a substrate of PNP. Two thio isosteres of 8-aminoguanine, 2,5-diaminothiazolo[5,4-d]pyrimidin-7(6H)-one (2) and 2,4-diaminothiazolo[4,5-d]pyrimidin-7(6H)-one (3), which cannot be substrates of PNP, were synthesized and evaluated for their inhibitory activity against PNP. They were found to be weak inhibitors of PNP and to be noncytotoxic for MOLT-4 T-cells in culture.</description><subject>Cell Division - drug effects</subject><subject>Cells, Cultured</subject><subject>Chemical Phenomena</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Guanine - analogs & derivatives</subject><subject>Guanine - chemical synthesis</subject><subject>Guanine - pharmacology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</subject><subject>Humans</subject><subject>Organic chemistry</subject><subject>Pentosyltransferases - antagonists & inhibitors</subject><subject>Preparations and properties</subject><subject>Purine-Nucleoside Phosphorylase - antagonists & inhibitors</subject><subject>Structure-Activity Relationship</subject><subject>T-Lymphocytes - cytology</subject><subject>T-Lymphocytes - drug effects</subject><issn>0022-2623</issn><issn>1520-4804</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1986</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFks1r3DAQxdWSkm6Tnnou6FBCC6vt6MuyjyWkTSCQQ7anUhbJkmsFW3Ismdb96-tNlp4COQiB5jfv8WaE0DsKGwqMfr7rAaisNAj5Eq2oZEBECeIIrQAYI6xg_DV6k9IdAHDK-DE65lDRksvVi9Or0HrjcxwTjg1up14HPEyjDw6Hqe5cTN46PLQxLWecO53cBt_OIbcu-bR-jsX-Ud_HsMY6WLwltes6XM855vjH1z7Pe2O2lsR63fsQc-v139jFH3ItiP05zKPvvfWBqI_F5ScSF7e90FMdYv_2VMcGb39HvHAR-xRTdqN7yFuSB4Ffkw5LilP0qtFdcm8P9wn6_vVie35Jrm--XZ1_uSYDlZBJYVhjpJaVrXRV8kIJwY3iTtUVCApl2RQgmAEomLWW1kIZZoyziirnCtnwE3T2qDuM8X5yKe96n_Zj0cHFKe2UAlBCwgK-P4CT6Z3dDUswPc67w_qW-odDXadad82oQ-3Tf6xcfgGnnP8DBIistA</recordid><startdate>198609</startdate><enddate>198609</enddate><creator>SIRCAR, J. C</creator><creator>SUTO, M. J</creator><creator>SCOTT, M. E</creator><creator>DONG, M. K</creator><creator>GILBERTSEN, R. B</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>198609</creationdate><title>Inhibitors of human purine nucleoside phosphorylase. Synthesis, purine nucleoside phosphorylase inhibition, and T-cell cytotoxicity of 2,5-diaminothiazolo[5,4-d]pyrimidin-7(6H)-one and 2,5-diaminothiazolo[4,5-d]pyrimidin-7(6H)-one. Two thio isosteres of 8-aminoguanine</title><author>SIRCAR, J. C ; SUTO, M. J ; SCOTT, M. E ; DONG, M. K ; GILBERTSEN, R. B</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p150t-6b2fb5a59d9a98367443b73e7c9041088f6042b0062ddd1c47b2bbed717ee65f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1986</creationdate><topic>Cell Division - drug effects</topic><topic>Cells, Cultured</topic><topic>Chemical Phenomena</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Guanine - analogs & derivatives</topic><topic>Guanine - chemical synthesis</topic><topic>Guanine - pharmacology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</topic><topic>Humans</topic><topic>Organic chemistry</topic><topic>Pentosyltransferases - antagonists & inhibitors</topic><topic>Preparations and properties</topic><topic>Purine-Nucleoside Phosphorylase - antagonists & inhibitors</topic><topic>Structure-Activity Relationship</topic><topic>T-Lymphocytes - cytology</topic><topic>T-Lymphocytes - drug effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>SIRCAR, J. C</creatorcontrib><creatorcontrib>SUTO, M. J</creatorcontrib><creatorcontrib>SCOTT, M. E</creatorcontrib><creatorcontrib>DONG, M. K</creatorcontrib><creatorcontrib>GILBERTSEN, R. B</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>MEDLINE - Academic</collection><jtitle>Journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>SIRCAR, J. C</au><au>SUTO, M. J</au><au>SCOTT, M. E</au><au>DONG, M. K</au><au>GILBERTSEN, R. B</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Inhibitors of human purine nucleoside phosphorylase. Synthesis, purine nucleoside phosphorylase inhibition, and T-cell cytotoxicity of 2,5-diaminothiazolo[5,4-d]pyrimidin-7(6H)-one and 2,5-diaminothiazolo[4,5-d]pyrimidin-7(6H)-one. Two thio isosteres of 8-aminoguanine</atitle><jtitle>Journal of medicinal chemistry</jtitle><addtitle>J Med Chem</addtitle><date>1986-09</date><risdate>1986</risdate><volume>29</volume><issue>9</issue><spage>1804</spage><epage>1806</epage><pages>1804-1806</pages><issn>0022-2623</issn><eissn>1520-4804</eissn><coden>JMCMAR</coden><abstract>8-Aminoguanine is a potent inhibitor of purine nucleoside phosphorylase (PNP) and also a substrate of PNP. Two thio isosteres of 8-aminoguanine, 2,5-diaminothiazolo[5,4-d]pyrimidin-7(6H)-one (2) and 2,4-diaminothiazolo[4,5-d]pyrimidin-7(6H)-one (3), which cannot be substrates of PNP, were synthesized and evaluated for their inhibitory activity against PNP. They were found to be weak inhibitors of PNP and to be noncytotoxic for MOLT-4 T-cells in culture.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>3091835</pmid><doi>10.1021/jm00159a045</doi><tpages>3</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-2623 |
| ispartof | Journal of medicinal chemistry, 1986-09, Vol.29 (9), p.1804-1806 |
| issn | 0022-2623 1520-4804 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_77007450 |
| source | MEDLINE; ACS Publications |
| subjects | Cell Division - drug effects Cells, Cultured Chemical Phenomena Chemistry Exact sciences and technology Guanine - analogs & derivatives Guanine - chemical synthesis Guanine - pharmacology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Humans Organic chemistry Pentosyltransferases - antagonists & inhibitors Preparations and properties Purine-Nucleoside Phosphorylase - antagonists & inhibitors Structure-Activity Relationship T-Lymphocytes - cytology T-Lymphocytes - drug effects |
| title | Inhibitors of human purine nucleoside phosphorylase. Synthesis, purine nucleoside phosphorylase inhibition, and T-cell cytotoxicity of 2,5-diaminothiazolo[5,4-d]pyrimidin-7(6H)-one and 2,5-diaminothiazolo[4,5-d]pyrimidin-7(6H)-one. Two thio isosteres of 8-aminoguanine |
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