Efficient synthesis of [11C]H-1152, a PET probe specific for Rho-kinases, highly potential targets in diagnostic medicine and drug development
A novel PET probe, [11C]H-1152, specific for Rho-kinases, was synthesized efficiently for the first time based on rapid Pd0-mediated C-[11C]methylation using [11C]methyl iodide and a tributylstannyl precursor, giving the isolated radioactivity of 3.8±1.2 GBq (n=3), specific radioactivity of 97±10 GB...
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| Veröffentlicht in: | Tetrahedron 2012-03, Vol.68 (10), p.2336-2341 |
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| creator | Suzuki, Masaaki Takashima-Hirano, Misato Koyama, Hiroko Yamaoka, Takafumi Sumi, Kengo Nagata, Hiroko Hidaka, Hiroyoshi Doi, Hisashi |
| description | A novel PET probe, [11C]H-1152, specific for Rho-kinases, was synthesized efficiently for the first time based on rapid Pd0-mediated C-[11C]methylation using [11C]methyl iodide and a tributylstannyl precursor, giving the isolated radioactivity of 3.8±1.2 GBq (n=3), specific radioactivity of 97±10 GBq μmol−1 (n=3), and high chemical and radiochemical purities (>99%). The decay-corrected radiochemical yield based on 11CH3I was 63±14%. New potentials of a trifluoroacetyl (TFA) group as a tolerant protecting and facile deprotecting group of a secondary amine were demonstrated by highly selective stannylation (via lithiation of isoquinoline moiety using t-C4H9Li) and ready removal by hydroxide ion leaving the arylstannyl moiety intact, respectively. The role of excess hexamethylphosphoric triamide (HMPA) to realize an efficient stannylation of the isoquinoline lithium species is also discussed briefly.
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| doi_str_mv | 10.1016/j.tet.2012.01.033 |
| format | Article |
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[Display omitted]</description><identifier>ISSN: 0040-4020</identifier><identifier>EISSN: 1464-5416</identifier><identifier>DOI: 10.1016/j.tet.2012.01.033</identifier><identifier>CODEN: TETRAB</identifier><language>eng</language><publisher>Kidlington: Elsevier Ltd</publisher><subject>Chemistry ; C–C Coupling ; Decay ; Diagnostic systems ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings ; HMPA ; Iodides ; Lithiation ; Lithium ; Organic chemistry ; Positron emission tomography (PET) ; Precursors ; Preparations and properties ; Radioactivity ; Rho-kinase H-1152 ; Synthesis (chemistry) ; Tetrahedrons</subject><ispartof>Tetrahedron, 2012-03, Vol.68 (10), p.2336-2341</ispartof><rights>2012 Elsevier Ltd</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c426t-3adb4a4198632827661d68d6efe14c0377c6c618373ea37988111b1e044b6ee93</citedby><cites>FETCH-LOGICAL-c426t-3adb4a4198632827661d68d6efe14c0377c6c618373ea37988111b1e044b6ee93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.tet.2012.01.033$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=25661747$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Suzuki, Masaaki</creatorcontrib><creatorcontrib>Takashima-Hirano, Misato</creatorcontrib><creatorcontrib>Koyama, Hiroko</creatorcontrib><creatorcontrib>Yamaoka, Takafumi</creatorcontrib><creatorcontrib>Sumi, Kengo</creatorcontrib><creatorcontrib>Nagata, Hiroko</creatorcontrib><creatorcontrib>Hidaka, Hiroyoshi</creatorcontrib><creatorcontrib>Doi, Hisashi</creatorcontrib><title>Efficient synthesis of [11C]H-1152, a PET probe specific for Rho-kinases, highly potential targets in diagnostic medicine and drug development</title><title>Tetrahedron</title><description>A novel PET probe, [11C]H-1152, specific for Rho-kinases, was synthesized efficiently for the first time based on rapid Pd0-mediated C-[11C]methylation using [11C]methyl iodide and a tributylstannyl precursor, giving the isolated radioactivity of 3.8±1.2 GBq (n=3), specific radioactivity of 97±10 GBq μmol−1 (n=3), and high chemical and radiochemical purities (>99%). The decay-corrected radiochemical yield based on 11CH3I was 63±14%. New potentials of a trifluoroacetyl (TFA) group as a tolerant protecting and facile deprotecting group of a secondary amine were demonstrated by highly selective stannylation (via lithiation of isoquinoline moiety using t-C4H9Li) and ready removal by hydroxide ion leaving the arylstannyl moiety intact, respectively. The role of excess hexamethylphosphoric triamide (HMPA) to realize an efficient stannylation of the isoquinoline lithium species is also discussed briefly.
[Display omitted]</description><subject>Chemistry</subject><subject>C–C Coupling</subject><subject>Decay</subject><subject>Diagnostic systems</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</subject><subject>HMPA</subject><subject>Iodides</subject><subject>Lithiation</subject><subject>Lithium</subject><subject>Organic chemistry</subject><subject>Positron emission tomography (PET)</subject><subject>Precursors</subject><subject>Preparations and properties</subject><subject>Radioactivity</subject><subject>Rho-kinase H-1152</subject><subject>Synthesis (chemistry)</subject><subject>Tetrahedrons</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNp9kcFuEzEQhlcIJELhAbj5gsShu8zYjncjTigKtFIlEConhCzHO5s4bNbB41TKS_DMOErVIydf_u8fzzdV9RahQUDzYddkyo0ElA1gA0o9q2aoja7nGs3zagagodYg4WX1inkHAIhSzaq_q2EIPtCUBZ-mvCUOLOIgfiIuf93UiHN5LZz4troXhxTXJPhAPhREDDGJ79tY_w6TY-JrsQ2b7XgSh5hLW3CjyC5tKLMIk-iD20yRc-H21JeBEwk39aJPx43o6YHGeNgX7HX1YnAj05vH96r68Xl1v7yp775-uV1-uqu9libXyvVr7TQuOqNkJ1tjsDddb2gg1B5U23rjDXaqVeRUu-g6RFwjgdZrQ7RQV9X7S29Z6s-RONt9YE_j6CaKR7bYam0WAFKXKF6iPkXmRIM9pLB36WQR7Nm93dni3p7dW0Bb3Bfm3WO9Y-_GIbnJB34C5bx8uNVtyX285Kjs-hAoWT7fwhdFiXy2fQz_mfIPXcCYsQ</recordid><startdate>20120311</startdate><enddate>20120311</enddate><creator>Suzuki, Masaaki</creator><creator>Takashima-Hirano, Misato</creator><creator>Koyama, Hiroko</creator><creator>Yamaoka, Takafumi</creator><creator>Sumi, Kengo</creator><creator>Nagata, Hiroko</creator><creator>Hidaka, Hiroyoshi</creator><creator>Doi, Hisashi</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20120311</creationdate><title>Efficient synthesis of [11C]H-1152, a PET probe specific for Rho-kinases, highly potential targets in diagnostic medicine and drug development</title><author>Suzuki, Masaaki ; 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The decay-corrected radiochemical yield based on 11CH3I was 63±14%. New potentials of a trifluoroacetyl (TFA) group as a tolerant protecting and facile deprotecting group of a secondary amine were demonstrated by highly selective stannylation (via lithiation of isoquinoline moiety using t-C4H9Li) and ready removal by hydroxide ion leaving the arylstannyl moiety intact, respectively. The role of excess hexamethylphosphoric triamide (HMPA) to realize an efficient stannylation of the isoquinoline lithium species is also discussed briefly.
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| subjects | Chemistry C–C Coupling Decay Diagnostic systems Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings HMPA Iodides Lithiation Lithium Organic chemistry Positron emission tomography (PET) Precursors Preparations and properties Radioactivity Rho-kinase H-1152 Synthesis (chemistry) Tetrahedrons |
| title | Efficient synthesis of [11C]H-1152, a PET probe specific for Rho-kinases, highly potential targets in diagnostic medicine and drug development |
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