16α-bromo-3-acetoxy-18-methyl-estra-1,3,5(10)-trien-17-one | 259212-89-0

• 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: 16α-bromo-3-acetoxy-18-methyl-estra-1,3,5(10)-trien-17-one
• CAS: 259212-89-0
• 化学式: C₂₁H₂₅BrO₃
• 分子量: 405.332
• InChiKey: LLJFXRUWPDSAFH-YRIDSSQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  16α-bromo-3-acetoxy-18-methyl-estra-1,3,5(10)-trien-17-one 在 sodium tetrahydroborate 、 乙醇 、 硫酸 、 lithium bromide 作用下， 以 乙醇 、 丁酮 为溶剂， 反应 1.5h， 生成 16β-bromo-18-methyl-estra-1,3,5(10)-trien-3,17β-diol
  参考文献：
  名称：

  (17α,20E/Z)-iodovinyl- and 16α-iodo-18-homoestradiol derivatives: synthesis and evaluation for estrogen receptor imaging

  摘要：

  Three new I-125-radioiodinated estrogens featuring a 13 beta-ethyl instead of the natural 13-methyl group, i.e. 18-homoestradiols, were synthesized and evaluated as potential estrogen receptor imaging agents. The 16 alpha-iodo-18-methylestradiol and the I-125-labeled analog were synthesized from the corresponding 16 beta-bromo analog by the halogen-exchange method. The cis-bromohydrin precursor was obtained by bromination of an estrone enolacetate, followed by epimerization and reduction. The isomeric (17 alpha,20E/Z)-iodovinyl-18-methylestradiols were prepared via the vinyltin intermediates. Treatment of 18-methyl-17 alpha-ethynylestradiol with tri-n-butyltin hydride, in the presence of azobisisobutyronitrile as catalyst and heating at 90-100 degrees C afforded the (17 alpha,20E)-tri-n-butylstannyl isomer as the major product. Changing the catalyst for triethyl borane, at room temperature, mainly gave the 20Z-isomer. The nea I-125-labeled analogs were obtained from their corresponding tin intermediates upon treatment with [I-125]NaI in the presence of H2O2. The 16 alpha-[I-125]iodo- and isomeric (17 alpha,20E/Z)-[I-125]iodovinyl-18-methylestradiols were evaluated for estrogen receptor-mediated uterine uptake in immature female rats. Homologation of the C13-methyl group did improve the uterine uptake of the iodovinyl derivatives, but also increased blood retention, resulting in lower target uptake ratios. In the case of the 16 alpha-iodo analog uterine retention decreased upon C13-homologation. (C) 2000 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(99)00084-7
• 作为产物：
  描述：

  levonorgestrel 在 溴 、 对甲苯磺酸 、 溶剂黄146 、 silver carbonate 、 lithium bromide 、 copper(ll) bromide 作用下， 以 乙醚 、 acetate buffer 、 甲苯 、 乙腈 为溶剂， 反应 3.5h， 生成 16α-bromo-3-acetoxy-18-methyl-estra-1,3,5(10)-trien-17-one
  参考文献：
  名称：

  (17α,20E/Z)-iodovinyl- and 16α-iodo-18-homoestradiol derivatives: synthesis and evaluation for estrogen receptor imaging

  摘要：

  Three new I-125-radioiodinated estrogens featuring a 13 beta-ethyl instead of the natural 13-methyl group, i.e. 18-homoestradiols, were synthesized and evaluated as potential estrogen receptor imaging agents. The 16 alpha-iodo-18-methylestradiol and the I-125-labeled analog were synthesized from the corresponding 16 beta-bromo analog by the halogen-exchange method. The cis-bromohydrin precursor was obtained by bromination of an estrone enolacetate, followed by epimerization and reduction. The isomeric (17 alpha,20E/Z)-iodovinyl-18-methylestradiols were prepared via the vinyltin intermediates. Treatment of 18-methyl-17 alpha-ethynylestradiol with tri-n-butyltin hydride, in the presence of azobisisobutyronitrile as catalyst and heating at 90-100 degrees C afforded the (17 alpha,20E)-tri-n-butylstannyl isomer as the major product. Changing the catalyst for triethyl borane, at room temperature, mainly gave the 20Z-isomer. The nea I-125-labeled analogs were obtained from their corresponding tin intermediates upon treatment with [I-125]NaI in the presence of H2O2. The 16 alpha-[I-125]iodo- and isomeric (17 alpha,20E/Z)-[I-125]iodovinyl-18-methylestradiols were evaluated for estrogen receptor-mediated uterine uptake in immature female rats. Homologation of the C13-methyl group did improve the uterine uptake of the iodovinyl derivatives, but also increased blood retention, resulting in lower target uptake ratios. In the case of the 16 alpha-iodo analog uterine retention decreased upon C13-homologation. (C) 2000 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(99)00084-7