1-(((5-(4-nitrophenyl)furan-2-yl)methylene)amino)imidazolidine-2,4-dione-3-13N | 1357058-98-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(((5-(4-nitrophenyl)furan-2-yl)methylene)amino)imidazolidine-2,4-dione-3-13N
• CAS: 1357058-98-0
• 化学式: C₁₄H₁₀N₄O₅
• 分子量: 313.25
• InChiKey: OZOMQRBLCMDCEG-GKTGUEEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.74
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  118.05
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  ethyl 2-{2-[5-(4-nitrophenyl)furfurylidene]hydrazino}acetate 在 氨，N-13 、 N,N-二异丙基乙胺 作用下， 以 水 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 0.6h， 生成 1-(((5-(4-nitrophenyl)furan-2-yl)methylene)amino)imidazolidine-2,4-dione-3-13N
  参考文献：
  名称：

  Radiosynthesis of [13N]dantrolene, a positron emission tomography probe for breast cancer resistant protein, using no-carrier-added [13N]ammonia

  摘要：

  Dantrolene (1) is a substrate for breast cancer resistant protein, which is widely distributed in the blood-brain-barrier, intestine, gall bladder, and liver. PET study with 1 labeled with a positron emitter can be used to visualize BCRP and to elucidate the effect of BCRP on the pharmacokinetics of drugs. The objective of this study was to label 1 using nitrogen-13 (N-13, a positron emitter; half-life: 9.9 min). Using no-carrier-added [N-13]NH3 as the labeling agent, we synthesized [N-13] dantrolene ([N-13] 1) for the first time. The reaction of carbomyl chloride 2b with [N-13]NH3 gave an unsymmetrical urea [N-13]3, followed by cyclization of [N-13]3 to afford [N-13]1. Due to its instability, 2b was prepared in situ by treating amine 5 with triphosgene in a ratio of 4 to 1 and used for subsequent [N-13] ammonolysis without purification. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.077