¹⁸F-labelled 5-fluorouracil | 823-63-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: ¹⁸F-labelled 5-fluorouracil
• 英文别名: 5-(fluoro-18F)pyrimidine-2,4(1H,3H)-dione；5-(18F)fluoranyl-1H-pyrimidine-2,4-dione
• CAS: 823-63-2
• 化学式: C₄H₃FN₂O₂
• 分子量: 129.08
• InChiKey: GHASVSINZRGABV-SFIIULIVSA-N

物化性质

• 熔点：
  281-283 °C

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,4-di-tert-butoxy-5-(fluoro-18F)pyrimidine 在 盐酸 作用下， 以 水 为溶剂， 反应 0.03h， 生成 ¹⁸F-labelled 5-fluorouracil
  参考文献：
  名称：

  通过金属转移反应，可以从[18F]氟化物合成用于人类PET成像的[18F] 5-氟尿嘧啶。

  摘要：

  Translation of new F-18-fluorination reactions to produce radiotracers for human positron emission tomography (PET) imaging is rare because the chemistry must have useful scope and the process for F-18-labeled tracer production must be robust and simple to execute. The application of transition metal mediators has enabled impactful F-18-fluorination methods, but to date none of these reactions have been applied to produce a human-injectable PET tracer. In this article we present chemistry and process innovations that culminate in the first production from [F-18]fluoride of human doses of [F-18]5-fluorouracil, a PET tracer for cancer imaging in humans. The first preparation of nickel 6-aryl complexes by transmetalation from arylboronic acids or esters was developed and enabled the synthesis of the [F-18]5-fluorouracil precursor. Routine production of >10 mCi doses of [F-18]5-fluorouracil was accomplished with a new instrument for azeotrope-free [F-18]fluoride concentration in a process that leverages the tolerance of water in nickel-mediated F-18-fluorination.

  DOI：

  10.1021/acs.organomet.6b00059

文献信息

• [EN] SOLID-PHASE FLUORINATION OF URACIL AND CYTOSINE<br/>[FR] FLUORATION EN PHASE SOLIDE D'URACILE ET DE CYTOSINE
  申请人：HAMMERSMITH IMANET LTD

  公开号：WO2004056400A1

  公开（公告）日：2004-07-08

  The invention relates to a process for the production of an 18F-labelled tracer which comprises treatment of a solid support-bound precursor of formula (I): SOLID SUPPORT-LINKER-I+ -TRACER (I) Y- wherein the TRACER is of formula (A): or an amine protected derivative thereof, wherein Y- is an anion, preferably trifluoromethylsulphonate (triflate) anion; and R1 is either (i) a group CH-NP1AP2A in which P1A and P2A are each independently hydrogen or a protecting group, or (ii) a carbonyl group; with 18F- to produce the labelled tracer of formula (II) or an amine protected derivative thereof, wherein R1 is as defined for the compound of formula (I).

  本发明涉及一种制备18F标记示踪剂的方法，其中包括对式(I)的固体支持前体进行处理：SOLID SUPPORT-LINKER-I+ -TRACER (I) Y-，其中TRACER的式(A)为：或其氨基保护衍生物，其中Y-是阴离子，优选为三氟甲磺酸盐（三氟甲磺酸盐）阴离子；R1要么是（i）CH-NP1AP2A基团，其中P1A和P2A各自独立地是氢或保护基，要么是（ii）羰基基团；用18F-处理，以产生式(II)的标记示踪剂或其氨基保护衍生物，其中R1如式(I)化合物中所定义。
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  作者：Mirko Diksic、Pasquale Di Raddo

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