{"created":"2023-05-15T14:52:31.535026+00:00","id":71713,"links":{},"metadata":{"_buckets":{"deposit":"99c3f03a-aeeb-429c-a956-8f72f8dd6fc4"},"_deposit":{"created_by":1,"id":"71713","owners":[1],"pid":{"revision_id":0,"type":"depid","value":"71713"},"status":"published"},"_oai":{"id":"oai:repo.qst.go.jp:00071713","sets":["10:28"]},"author_link":["705667","705673","705670","705677","705669","705668","705666","705675","705676","705674","705671","705672"],"item_10005_date_7":{"attribute_name":"発表年月日","attribute_value_mlt":[{"subitem_date_issued_datetime":"2015-05-30","subitem_date_issued_type":"Issued"}]},"item_10005_description_5":{"attribute_name":"抄録","attribute_value_mlt":[{"subitem_description":"Objectives: [11C]Phosgene ([11C]COCl2) is an important 11C-labeling reagent for synthesizing various radioactive\ncompounds containing a [11C]urea or [11C]carbamate moiety. We have developed several 11C-labeled lignads\ncontaining carbamate or unsymmetrical urea moiety using [11C]COCl2 and reported the synthesis of [11C]1 as a\nnovel PET ligand for imaging of fatty acid amide hydrolase using [11C]COCl2 or [11C]CO2 [1]. However, the synthesis\nof [11C]1 had some problems in poor reactivity and reproducibility. In this study, we developed a method for\nsynthesizing [11C]1-3 via 2 routes, starting from several phenol derivatives and base, to improve the reproducibility\nand versatility for constructing the [11C]carbamate moiety.\nMethods: The alkylamine 10 was prepared from commercialy available materials. [11C]1-3 were synthesized by\nreaction of phenol derivatives with [11C]COCl2 in the presence of various bases, followed by reaction with amine 10,\nvia 2 routes as shown in Scheme 1.\nResults: In the case of route A, when Et3N, DMAP, pyridine, or DBU was used, [11C]1 was obtained with moderate\nyield but [11C]2 or [11C]3 could not be obtained because 8 or 9 was formed at low yields. Instead of these bases,\nwhen 1,2,2,6,6-pentamethylpiperidine was used, 7-9 were produced in 68%, 88%, and 91% yields, which were\ndetermined by analyzing the reaction mixtures using radio-HPLC. However, following reaction of 8 or 9 with 10 did not\nproceed. In the case of route B, when 1,2,2,6,6-pentamethylpiperidine was used, after [11C]COCl2 was trapped to the\nreaction mixture, immediate addition of amine 10 to the mixture accomplished the reaction. After the two-steps\nreaction, it was found that [11C]1-3 were produced with 92%, 82%, and 68% yields in the mixtures.\nConclusions: We succeeded in improvement of reaction efficiency of [11C]1-3. These results showed that utilization of\n1,2,2,6,6-pentamethylpiperadine was more effective for constructing the [11C]carbamate moiety compared to other\nbases, such as Et3N, DBU, and DMAP.\nReferences: [1] Fujinaga M, et al. (2013) J Label Compd Radiopharm, 56, S92. [2] Kumata K, et al. (2015) ACS\nChemical Neuroscience.","subitem_description_type":"Abstract"}]},"item_10005_description_6":{"attribute_name":"会議概要（会議名, 開催地, 会期, 主催者等）","attribute_value_mlt":[{"subitem_description":"21st International Symposium on Radiopharmaceutical Sciences","subitem_description_type":"Other"}]},"item_access_right":{"attribute_name":"アクセス権","attribute_value_mlt":[{"subitem_access_right":"metadata only access","subitem_access_right_uri":"http://purl.org/coar/access_right/c_14cb"}]},"item_creator":{"attribute_name":"著者","attribute_type":"creator","attribute_value_mlt":[{"creatorNames":[{"creatorName":"Fujinaga, Masayuki"}],"nameIdentifiers":[{"nameIdentifier":"705666","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Ogawa, Masanao"}],"nameIdentifiers":[{"nameIdentifier":"705667","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Kumata, Katsushi"}],"nameIdentifiers":[{"nameIdentifier":"705668","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Shimoda, Yoko"}],"nameIdentifiers":[{"nameIdentifier":"705669","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Kawamura, Kazunori"}],"nameIdentifiers":[{"nameIdentifier":"705670","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"Zhang, Ming-Rong"}],"nameIdentifiers":[{"nameIdentifier":"705671","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"藤永 雅之","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"705672","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"小川 政直","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"705673","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"熊田 勝志","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"705674","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"下田 陽子","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"705675","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"河村 和紀","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"705676","nameIdentifierScheme":"WEKO"}]},{"creatorNames":[{"creatorName":"張 明栄","creatorNameLang":"en"}],"nameIdentifiers":[{"nameIdentifier":"705677","nameIdentifierScheme":"WEKO"}]}]},"item_language":{"attribute_name":"言語","attribute_value_mlt":[{"subitem_language":"eng"}]},"item_resource_type":{"attribute_name":"資源タイプ","attribute_value_mlt":[{"resourcetype":"conference object","resourceuri":"http://purl.org/coar/resource_type/c_c94f"}]},"item_title":"「Development of efficient construction of [11C]carbamate moiety using [11C] COCl2」","item_titles":{"attribute_name":"タイトル","attribute_value_mlt":[{"subitem_title":"「Development of efficient construction of [11C]carbamate moiety using [11C] COCl2」"}]},"item_type_id":"10005","owner":"1","path":["28"],"pubdate":{"attribute_name":"公開日","attribute_value":"2015-06-09"},"publish_date":"2015-06-09","publish_status":"0","recid":"71713","relation_version_is_last":true,"title":["「Development of efficient construction of [11C]carbamate moiety using [11C] COCl2」"],"weko_creator_id":"1","weko_shared_id":-1},"updated":"2023-05-15T19:48:12.988829+00:00"}