N-[2-(diethylamino)ethyl][(18)F]-2-fluoroisonicotinamide | 1192242-44-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-[2-(diethylamino)ethyl][(18)F]-2-fluoroisonicotinamide
• 英文别名: N-[2-(diethylamino)ethyl]-2-(18F)fluoranylpyridine-4-carboxamide
• CAS: 1192242-44-6
• 化学式: C₁₂H₁₈FN₃O
• 分子量: 238.294
• InChiKey: IEEJYKAJNFSWNE-HSGWXFLFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  45.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-[2-(diethylamino)ethylaminocarbonyl]pyrid-2-yltrimethylammonium triflate 在 fluorine-18 、 potassium carbonate 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 乙腈 为溶剂， 反应 0.08h， 生成 N-[2-(diethylamino)ethyl][(18)F]-2-fluoroisonicotinamide
  参考文献：
  名称：

  Rapid and efficient synthesis of [18F]fluoronicotinamides, [18F]fluoroisonicotinamides and [18F]fluorobenzamides as potential pet radiopharmaceuticals for melanoma imaging

  摘要：

  为了简化亲核性放射氟化反应以适应自动化需求，使用一步合成法，通过在三甲基铵基烟酰胺、三甲基铵基异烟酰胺和三甲基铵基苯甲酰胺前体上的取代反应，合成了一系列的[18F]氟烟酰胺、[18F]氟异烟酰胺和[18F]氟苯甲酰胺。基于起始的[18F]氟化物，发现在20分钟的合成时间内，放射化学产率和纯度分别大于90%和97%，并且无需高效液相色谱纯化。这种合成方法非常有前景，作为一种快速且简单的方法，用于[18F]氟烟酰胺、[18F]氟异烟酰胺和[18F]氟苯甲酰胺的自动化放射氟化，具有高放射化学产率和非常短的制备时间。版权所有 © 2011 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.1869

文献信息

• Nicotinamide Derivatives
  申请人：Katsifis Andrew

  公开号：US20110178396A1

  公开（公告）日：2011-07-21

  A compound comprising a pyridine carboxamide structure, for use in imaging or treating melanoma, is described. An aromatic ring in the structure is substituted with a radiohalogen atom and the substitution on the amide nitrogen atom is such that the compound binds to melanin.

  描述了一种含有吡啶羧酰胺结构的化合物，用于成像或治疗黑色素瘤。结构中的芳香环被取代为一个放射性卤原子，酰胺氮原子上的取代使得该化合物与黑色素结合。
• Discovery of [¹⁸F]<i>N</i>-(2-(Diethylamino)ethyl)-6-fluoronicotinamide: A Melanoma Positron Emission Tomography Imaging Radiotracer with High Tumor to Body Contrast Ratio and Rapid Renal Clearance
  作者：Ivan Greguric、Stephen R. Taylor、Delphine Denoyer、Patrice Ballantyne、Paula Berghofer、Peter Roselt、Tien Q. Pham、Filomena Mattner、Thomas Bourdier、Oliver C. Neels、Donna S. Dorow、Christian Loc’h、Rodney J. Hicks、Andrew Katsifis

  DOI：10.1021/jm9008423

  日期：2009.9.10

  The high melanoma uptake and rapid body clearance displayed by our series of [I-123]liodonicotinamides prompted the development of [F-18]N-(2-(diethylamino)ethyl)-6-fluoronicotinamide ([F-18]2), a novel radiotracer for PET melanoma imaging. Significantly, unlike fluorobenzoates, [F-18]fluorine incorporation on the nicotinamide ring is one step, facile, and high yielding. [F-18]2 displayed high tumor uptake, rapid body clearance via predominantly renal excretion, and is currently being evaluated in preclinical studies for progression into clinical trials to assess the responsiveness of therapeutic agents.
• Rapid and efficient synthesis of [18F]fluoronicotinamides, [18F]fluoroisonicotinamides and [18F]fluorobenzamides as potential pet radiopharmaceuticals for melanoma imaging
  作者：I. Al Jammaz、B. Al-Otaibi、S. Okarvi、J. Amartey

  DOI：10.1002/jlcr.1869

  日期：2011.5.30

  In an attempt to simplify nucleophilic radiofluorination reactions to be amenable for automation, a series of [18F]fluoronicotinamides, [18F]fluoroisonicotinamides and [18F]fluorobenzamides were synthesized using one-step synthetic approach involving displacement reactions on trimethylammonium-nicotinamide, trimethylammonium-isonicotinamide and trimethylammonium-benzamide precursors. Based on starting [18F]-fluoride, radiochemical yields and purities were found to be greater than 90 and 97%, respectively, within 20 min synthesis time and, without high-performance liquid chromatography purification. This synthetic approach holds great promise as a rapid and simple method for the automated radiofluorination of [18F]fluoronicotinamides, [18F]fluoroisonicotinamides and [18F]fluorobenzamides with high radiochemical yield and very short preparation time. Copyright © 2011 John Wiley & Sons, Ltd.

  为了简化亲核性放射氟化反应以适应自动化需求，使用一步合成法，通过在三甲基铵基烟酰胺、三甲基铵基异烟酰胺和三甲基铵基苯甲酰胺前体上的取代反应，合成了一系列的[18F]氟烟酰胺、[18F]氟异烟酰胺和[18F]氟苯甲酰胺。基于起始的[18F]氟化物，发现在20分钟的合成时间内，放射化学产率和纯度分别大于90%和97%，并且无需高效液相色谱纯化。这种合成方法非常有前景，作为一种快速且简单的方法，用于[18F]氟烟酰胺、[18F]氟异烟酰胺和[18F]氟苯甲酰胺的自动化放射氟化，具有高放射化学产率和非常短的制备时间。版权所有 © 2011 John Wiley & Sons, Ltd.