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「Development of efficient construction of [11C]carbamate moiety using [11C] COCl2」
https://repo.qst.go.jp/records/71713
https://repo.qst.go.jp/records/71713bf3231ab-9a8a-48db-a7d7-54be512d4376
| Item type | 会議発表用資料 / Presentation(1) | |||||
|---|---|---|---|---|---|---|
| 公開日 | 2015-06-09 | |||||
| タイトル | ||||||
| タイトル | 「Development of efficient construction of [11C]carbamate moiety using [11C] COCl2」 | |||||
| 言語 | ||||||
| 言語 | eng | |||||
| 資源タイプ | ||||||
| 資源タイプ識別子 | http://purl.org/coar/resource_type/c_c94f | |||||
| 資源タイプ | conference object | |||||
| アクセス権 | ||||||
| アクセス権 | metadata only access | |||||
| アクセス権URI | http://purl.org/coar/access_right/c_14cb | |||||
| 著者 |
Fujinaga, Masayuki
× Fujinaga, Masayuki× Ogawa, Masanao× Kumata, Katsushi× Shimoda, Yoko× Kawamura, Kazunori× Zhang, Ming-Rong× 藤永 雅之× 小川 政直× 熊田 勝志× 下田 陽子× 河村 和紀× 張 明栄 |
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| 抄録 | ||||||
| 内容記述タイプ | Abstract | |||||
| 内容記述 | Objectives: [11C]Phosgene ([11C]COCl2) is an important 11C-labeling reagent for synthesizing various radioactive compounds containing a [11C]urea or [11C]carbamate moiety. We have developed several 11C-labeled lignads containing carbamate or unsymmetrical urea moiety using [11C]COCl2 and reported the synthesis of [11C]1 as a novel PET ligand for imaging of fatty acid amide hydrolase using [11C]COCl2 or [11C]CO2 [1]. However, the synthesis of [11C]1 had some problems in poor reactivity and reproducibility. In this study, we developed a method for synthesizing [11C]1-3 via 2 routes, starting from several phenol derivatives and base, to improve the reproducibility and versatility for constructing the [11C]carbamate moiety. Methods: The alkylamine 10 was prepared from commercialy available materials. [11C]1-3 were synthesized by reaction of phenol derivatives with [11C]COCl2 in the presence of various bases, followed by reaction with amine 10, via 2 routes as shown in Scheme 1. Results: In the case of route A, when Et3N, DMAP, pyridine, or DBU was used, [11C]1 was obtained with moderate yield but [11C]2 or [11C]3 could not be obtained because 8 or 9 was formed at low yields. Instead of these bases, when 1,2,2,6,6-pentamethylpiperidine was used, 7-9 were produced in 68%, 88%, and 91% yields, which were determined by analyzing the reaction mixtures using radio-HPLC. However, following reaction of 8 or 9 with 10 did not proceed. In the case of route B, when 1,2,2,6,6-pentamethylpiperidine was used, after [11C]COCl2 was trapped to the reaction mixture, immediate addition of amine 10 to the mixture accomplished the reaction. After the two-steps reaction, it was found that [11C]1-3 were produced with 92%, 82%, and 68% yields in the mixtures. Conclusions: We succeeded in improvement of reaction efficiency of [11C]1-3. These results showed that utilization of 1,2,2,6,6-pentamethylpiperadine was more effective for constructing the [11C]carbamate moiety compared to other bases, such as Et3N, DBU, and DMAP. References: [1] Fujinaga M, et al. (2013) J Label Compd Radiopharm, 56, S92. [2] Kumata K, et al. (2015) ACS Chemical Neuroscience. |
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| 会議概要（会議名, 開催地, 会期, 主催者等） | ||||||
| 内容記述タイプ | Other | |||||
| 内容記述 | 21st International Symposium on Radiopharmaceutical Sciences | |||||
| 発表年月日 | ||||||
| 日付 | 2015-05-30 | |||||
| 日付タイプ | Issued | |||||
