21-<<(trifluoromethyl)sulfonyl>oxy>-16α-ethyl-19-norpregn-4-ene-3,20-dione | 113975-10-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 21-<<(trifluoromethyl)sulfonyl>oxy>-16α-ethyl-19-norpregn-4-ene-3,20-dione
• CAS: 113975-10-3
• 化学式: C₂₃H₃₁F₃O₅S
• 分子量: 476.557
• InChiKey: MINHDSFVGRWTTJ-BILPMHSYSA-N

物化性质

• 沸点：
  538.5±50.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  77.51
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  21-<<(trifluoromethyl)sulfonyl>oxy>-16α-ethyl-19-norpregn-4-ene-3,20-dione 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 FENP
  参考文献：
  名称：

  21-[18F]fluoro-16.alpha.-ethyl-19-norprogesterone. Synthesis and target tissue selective uptake of a progestin receptor-based radiotracer for positron emission tomography

  摘要：

  We have synthesized 21-[18F]fluoro-16 alpha-ethyl-19-norprogesterone (FENP), a high affinity ligand for the progesterone receptor, labeled with the positron-emitting radionuclide fluorine-18 (t1/2 = 110 min). The synthesis proceeds in two steps from 21-hydroxy-16 alpha-ethyl-19-norprogesterone and involves [18F]fluoride ion displacement of the 21-trifluoromethanesulfonate (21-triflate). This material is purified by HPLC and is obtained in 4-30% overall yield (decay corrected) within 40 min after the end of bombardment to produce [18F]fluoride ion. The effective specific activity, determined by competitive radioreceptor binding assays, is 700-1400 Ci/mmol. In vivo, [18F]FENP demonstrates highly selective, receptor-mediated uptake by the uterus of estrogen-primed rats; the uterus to blood and uterus to muscle ratios were respectively 26 and 16 at 1 h and 71 and 41 at 3 h after injection. The high target tissue selectivity of this uptake suggests that this compound may be useful for the in vivo imaging of progestin target tissues and receptor-rich tumors (such as human breast tumors) by positron emission tomography.

  DOI：

  10.1021/jm00402a019
• 作为产物：
  描述：

  三氟甲磺酸酐 、 16alpha-乙基-21-羟基-19-去甲-4-孕烯-3,20-二酮 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以78%的产率得到21-<<(trifluoromethyl)sulfonyl>oxy>-16α-ethyl-19-norpregn-4-ene-3,20-dione
  参考文献：
  名称：

  21-[18F]fluoro-16.alpha.-ethyl-19-norprogesterone. Synthesis and target tissue selective uptake of a progestin receptor-based radiotracer for positron emission tomography

  摘要：

  We have synthesized 21-[18F]fluoro-16 alpha-ethyl-19-norprogesterone (FENP), a high affinity ligand for the progesterone receptor, labeled with the positron-emitting radionuclide fluorine-18 (t1/2 = 110 min). The synthesis proceeds in two steps from 21-hydroxy-16 alpha-ethyl-19-norprogesterone and involves [18F]fluoride ion displacement of the 21-trifluoromethanesulfonate (21-triflate). This material is purified by HPLC and is obtained in 4-30% overall yield (decay corrected) within 40 min after the end of bombardment to produce [18F]fluoride ion. The effective specific activity, determined by competitive radioreceptor binding assays, is 700-1400 Ci/mmol. In vivo, [18F]FENP demonstrates highly selective, receptor-mediated uptake by the uterus of estrogen-primed rats; the uterus to blood and uterus to muscle ratios were respectively 26 and 16 at 1 h and 71 and 41 at 3 h after injection. The high target tissue selectivity of this uptake suggests that this compound may be useful for the in vivo imaging of progestin target tissues and receptor-rich tumors (such as human breast tumors) by positron emission tomography.

  DOI：

  10.1021/jm00402a019