methyl 18-<125I>iodo-17-octadecenoate | 87640-12-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 18-<125I>iodo-17-octadecenoate
• 英文别名: methyl 18-[125I]iodo-17-octadecenoate
• CAS: 87640-12-8
• 化学式: C₁₉H₃₅IO₂
• 分子量: 420.486
• InChiKey: TXQGEWNJPXEKSL-GFSVPJOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.96
• 重原子数：
  22.0
• 可旋转键数：
  16.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  methyl 18-<125I>iodo-17-octadecenoate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以79%的产率得到18-<125I>iodo-17-octadecenoic acid
  参考文献：
  名称：

  Synthesis and evaluation of radioiodinated (E)-18-iodo-17-octadecenoic acid as a model iodoalkenyl fatty acid for myocardial imaging

  摘要：

  125I-labeled (E)-18-iodo-17-octadecenoic acid (13) has been prepared and evaluated in rats to determine the myocardial uptake and retention and degree of in vivo deiodination of this model iodovinyl-substituted fatty acid, which contains no structural perturbation to inhibit metabolism. This new agent was prepared by NaI-chloramine-T treatment of (17-carbomethoxyheptadec-1-en-1-yl)boronic acid (11) prepared by catecholborane treatment of methyl 17-octadecynoate (10), followed by basic hydrolysis to the free acid (13). The pivotal substrate, 17-octadecynoic acid (9), was prepared by two new routes. The 125I-labeled acid 13 showed high myocardial uptake (1 h, 1.90-2.28% dose/g) with 45% washout after 2 h but lower heart/blood ratios in comparison to analogues containing the tellurium heteroatom. Deiodination was low for the first 2 h after injection (2 h, 61% dose/g). Excellent myocardial images were obtained in a dog with the 123I-labeled agent.

  DOI：

  10.1021/jm00367a021
• 作为产物：
  描述：

  甲基十八碳-17-炔酸酯 在 sodium iodide 、 水 、 chloroamine-T 、 儿萘酚硼烷 作用下， 生成 methyl 18-<125I>iodo-17-octadecenoate
  参考文献：
  名称：

  Synthesis and evaluation of radioiodinated (E)-18-iodo-17-octadecenoic acid as a model iodoalkenyl fatty acid for myocardial imaging

  摘要：

  125I-labeled (E)-18-iodo-17-octadecenoic acid (13) has been prepared and evaluated in rats to determine the myocardial uptake and retention and degree of in vivo deiodination of this model iodovinyl-substituted fatty acid, which contains no structural perturbation to inhibit metabolism. This new agent was prepared by NaI-chloramine-T treatment of (17-carbomethoxyheptadec-1-en-1-yl)boronic acid (11) prepared by catecholborane treatment of methyl 17-octadecynoate (10), followed by basic hydrolysis to the free acid (13). The pivotal substrate, 17-octadecynoic acid (9), was prepared by two new routes. The 125I-labeled acid 13 showed high myocardial uptake (1 h, 1.90-2.28% dose/g) with 45% washout after 2 h but lower heart/blood ratios in comparison to analogues containing the tellurium heteroatom. Deiodination was low for the first 2 h after injection (2 h, 61% dose/g). Excellent myocardial images were obtained in a dog with the 123I-labeled agent.

  DOI：

  10.1021/jm00367a021