[¹¹C]cyanogen bromide | 153226-48-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: [¹¹C]cyanogen bromide
• 英文别名: bromoformonitrile
• CAS: 153226-48-3
• 化学式: CBrN
• 分子量: 104.911
• InChiKey: ATDGTVJJHBUTRL-BJUDXGSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  3
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  对羟基苯乙胺 、 [¹¹C]cyanogen bromide 在 borate buffer 作用下， 以 乙醇 为溶剂， 生成 2-(4-hydroxyphenyl)ethyl(11C)cyanamide
  参考文献：
  名称：

  Radiolabeled Phenethylguanidines:  Novel Imaging Agents for Cardiac Sympathetic Neurons and Adrenergic Tumors

  摘要：

  The norepinephrine transporter (NET) substrates [I-123]-m-iodobenzylguanidine (MIBG) and [C-11]-m-hydroxyephedrine (HED) are used as markers of cardiac sympathetic neurons and adrenergic tumors (pheochromocytoma, neuroblastoma). However, their rapid NET transport rates limit their ability to provide accurate measurements of cardiac nerve density. [C-11]Phenethylguanidine ([C-11]1a) and 12 analogues ([C-11]1b-m) were synthesized and evaluated as radiotracers with improved kinetics for quantifying cardiac nerve density. In isolated rat hearts, neuronal uptake rates of [C-11]1a-m ranged from 0.24 to 1.96 mL min(-1) (g wet wt)(-1), and six compounds had extremely long neuronal retention times (clearance T-1/2 > 20 h) due to efficient vesicular storage. Positron emission tomography (PET) studies in nonhuman primates with [C-11]1e, N-[C-11]guanyl-m-octopamine, which has a slow NET transport rate, showed improved myocardial kinetics compared to HED. Compound [C-11]1c, [C-11]-p-hydroxyphenethylguanidine, which has a rapid NET transport rate, avidly accumulated into rat pheochromocytoma xenograft tumors in mice. These encouraging findings demonstrate that radiolabeled phenethylguanidines deserve further investigation as radiotracers of cardiac sympathetic innervation and adrenergic tumors.

  DOI：

  10.1021/jm061398y
• 作为产物：
  描述：

  [11C]methane 在 铂 亚锑氢化物 、 氨 、 pyridinium hydrobromide perbromide 作用下， 生成 [¹¹C]cyanogen bromide
  参考文献：
  名称：

  Westerberg, Goeran; Langstroem, Bengt, Journal of labelled compounds and radiopharmaceuticals, 1997, vol. 40, p. 328 - 329

  摘要：

  DOI：

文献信息

• Fully Automated Radiosynthesis of [¹¹C]Guanidines for Cardiac PET Imaging
  作者：Austin Y. Zhao、Allen F. Brooks、David M. Raffel、Jenelle Stauff、Janna Arteaga、Peter J. H. Scott、Xia Shao

  DOI：10.1021/acsmedchemlett.0c00479

  日期：2020.11.12

  challenging, and historical methods lack compatibility with modern automated radiochemistry synthesis platforms and current Good Manufacturing Practice (cGMP) requirements. To address this challenge, we report a new automated method for radiolabeling guanidines with carbon-11. The method was used to prepare a series of [11C]guanidines in good radiochemical yield (8–76% by radio-HPLC) and was found to have broad

  放射性标记的胍如间碘苄基胍(MIBG) 在核医学中用作诊断显像剂和放射治疗剂，多年来，已经开发了许多将放射性核素掺入胍中的方法。在开发用于心脏交感神经密度的新型正电子发射断层扫描 (PET) 放射性示踪剂的项目中，我们有理由准备 [ 11]C]3F-PHPOG。然而，很快就发现用碳 11 对胍支架进行放射性标记仍然具有挑战性，而且历史方法缺乏与现代自动放射化学合成平台和当前良好生产规范 (cGMP) 要求的兼容性。为了应对这一挑战，我们报告了一种用碳 11 对胍进行放射性标记的新自动化方法。该方法用于制备一系列具有良好放射化学产率（放射性 HPLC 为 8-76%）的 [ 11 C] 胍，并发现其具有广泛的底物范围和对未保护的 OH 和 NH 官能团的耐受性。该方法用于合成[ 11C]3F-PHPOG 用于临床前成像，以及放射性示踪剂临床前使用的适用性通过新西兰白兔的初步心脏 PET 得到证明，该
• Synthesis of ¹¹C-Labeled Guanidines in Supercritical Ammonia
  作者：Gunilla B. Jacobson、Göran Westerberg、Karin E. Markides、Bengt Långström

  DOI：10.1021/ja960667e

  日期：1996.1.1

  11C-labeled cyanamides to 11C-labeled guanidines was achieved in both supercritical ammonia and aqueous ammonia solutions. The latter method gave low and irreproducible yields as compared to performing the reactions in an automated supercritical fluid synthesis (SFS) system (designed for use with supercritical ammonia). Using the SFS system, total radiochemical yields of 11C-labeled guanidines of 30−85%

  描述了在超临界氨中合成十个 11C 标记的芳香族和脂肪族胍。相应的胺首先通过与[11C]溴化氰反应转化为氰胺。脂肪胺的 11C 标记的氰胺的产率很高（70-98%），而芳香胺的产率取决于环上的官能团，吸电子硝基的产率从 0% 到 90%为给电子甲氧基。在超临界氨和氨水溶液中都实现了 11C 标记的氰胺向 11C 标记的胍的转化。与在自动超临界流体合成 (SFS) 系统（设计用于超临界氨）中进行反应相比，后一种方法的产率低且不可重复。使用 SFS 系统，
• Synthesis of sodium [11C]thiocyanate using [11C]cyanogen bromide
  作者：Göran Westerberg、Bengt Långström

  DOI：10.1002/jlcr.2580340608

  日期：1994.6

  method for the preparation of sodium (11C]thiocyanate from [11C]cyanogen bromide and sodium sulfide is described. Sodium [11C]thiocyanate was obtained in 94% decay-corrected radiochemical yield with a specific radioactivity of 122 GBq μmol−1 (3.3 Ci μmol−1) in a synthesis time of 21 minutes. The sodium [11C]thiocyanate was used in the synthesis of ethyl-, isopropyl-, and benzyl [11C]thiocyanate in 78, 71

  描述了一种从 [11C] 溴化氰和硫化钠制备 (11C]硫氰酸钠的方法。[11C]硫氰酸钠的衰减校正放射化学产率为 94%，比放射性为 122 GBq μmol-1 (3.3 Ci μmol−1)，合成时间为 21 分钟。[11C]硫氰酸钠用于合成乙基-、异丙基-和苄基[11C]硫氰酸酯，放射化学产率分别为 78%、71% 和 84%。
• [11C]cyanogen bromide in the synthesis of 1,3-di(2-tolyl)-[11C]guanidine
  作者：Göran Westerberg、Wiebke Kärger、Hirotaka Onoe、Bengt Långström

  DOI：10.1002/jlcr.2580340802

  日期：1994.8

  11C-labelled in a one-pot procedure using [11C]cyanogen bromide as the key intermediate. Synthesis time was 31–33 min counted from the end of bombardment, affording 1,3-di(2-tolyl)-[11C]guanidine (6) in 87 % decay-corrected radiochemical yield counted from [11C]cyanogen bromide. The specific radioactivity of the product at the end of synthesis was 118 GBq μmol−1 (3.2 Ci μmol−1). Autoradiographic studies on slide-mounted

  使用[ 11 C]溴化氰作为关键中间体，以一锅法对标题化合物进行 11 C 标记。从轰击结束算起，合成时间为 31-33 分钟，得到 1,3-二(2-甲苯基)-[11C] 胍 (6)，从 [11C] 溴化氰算起，衰减校正的放射化学产率为 87%。合成结束时产物的比放射性为 118 GBq μmol-1 (3.2 Ci μmol-1)。对载玻片安装的大鼠脑切片进行放射自显影研究显示胍 (6) 的特异性结合，但当静脉注射到恒河猴时，脑摄取非常低，表明 1,3-二(2-甲苯基)-[11C]胍没有穿过血脑屏障。
• Jacobson, G. B.; Gustavsson, S. A.; Markides, K. E., Journal of labelled compounds and radiopharmaceuticals, 1997, vol. 40, p. 793 - 795
  作者：Jacobson, G. B.、Gustavsson, S. A.、Markides, K. E.、Langstroem, B.

  DOI：——

  日期：——