16β-bromo-7α-methylestra-1,3,5(10)-triene-3,17β-diol | 146016-37-7

• 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: 16β-bromo-7α-methylestra-1,3,5(10)-triene-3,17β-diol
• 英文别名: (7R,8R,9S,13S,14S,16S,17R)-16-bromo-7,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
• CAS: 146016-37-7
• 化学式: C₁₉H₂₅BrO₂
• 分子量: 365.31
• InChiKey: ZHJMBYOGCJWPTK-HEKUSSOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  16β-bromo-7α-methylestra-1,3,5(10)-triene-3,17β-diol 在 sodium iodide 作用下， 以 丁酮 为溶剂， 反应 1.0h， 以80%的产率得到16α-iodo-7α-methylestra-1,3,5(10)-triene-3,17β-diol
  参考文献：
  名称：

  7.alpha.-Methyl- and 11.beta.-ethoxy-substitution of iodine-125-labeled [125I]16.alpha.-iodoestradiol: effect on estrogen receptor-mediated target tissue uptake

  摘要：

  The 7alpha-methyl and 11beta-ethoxy derivatives of 16alpha-[I-125]iodoestradiol were prepared via halogen exchange with I-125 of the corresponding 16beta-bromoestradiol precursors. The 16alpha-bromo derivatives were obtained via halogenation of the analogous 17-enol acetate, epimerization to the 16beta-isomer, and hydride reduction. Stereochemical assignments were based on high resolution H-1 NMR. To evaluate the effect of the nature and stereochemistry of the 16-halo substituent on the relative binding affinity for the estrogen receptor, the analogous 16-chloro derivatives were also prepared. The highest binding affinities were observed with the 7alpha-methyl-16alpha-haloestradiols, particularly the bromo and chloro derivatives while the 16alpha-iodo derivatives gave somewhat lower values. Both the 11beta-ethoxy and 7alpha-methyl-16alpha-[I-125]iodoestradiols localize in the uteri of immature female rats via a receptor-mediated process. Rapid blood clearance of the I-125-labeled 7alpha-methyl derivative results in lower I-125 uptake by the uterus as well as nontarget organs as compared to the 11beta-substituted estradiol analogs. However, uterus to blood and nontarget ratios are more favorable for the 7alpha-methyl-16alpha-[I-125]iodoestradiol as compared to the analogous 11beta-ethoxy derivatives suggesting that this compound substituted with I-125 may be useful for the in vivo imaging of estrogen receptor-rich breast tumors by single photon emission computerized tomography.

  DOI：

  10.1021/jm00054a011
• 作为产物：
  描述：

  阿美雌酮 在 sodium tetrahydroborate 、 acetate buffer 、 硫酸 、 溴 、 lithium bromide 作用下， 以 乙醚 、 乙醇 、 溶剂黄146 、 丁酮 为溶剂， 反应 3.25h， 生成 16β-bromo-7α-methylestra-1,3,5(10)-triene-3,17β-diol
  参考文献：
  名称：

  7.alpha.-Methyl- and 11.beta.-ethoxy-substitution of iodine-125-labeled [125I]16.alpha.-iodoestradiol: effect on estrogen receptor-mediated target tissue uptake

  摘要：

  The 7alpha-methyl and 11beta-ethoxy derivatives of 16alpha-[I-125]iodoestradiol were prepared via halogen exchange with I-125 of the corresponding 16beta-bromoestradiol precursors. The 16alpha-bromo derivatives were obtained via halogenation of the analogous 17-enol acetate, epimerization to the 16beta-isomer, and hydride reduction. Stereochemical assignments were based on high resolution H-1 NMR. To evaluate the effect of the nature and stereochemistry of the 16-halo substituent on the relative binding affinity for the estrogen receptor, the analogous 16-chloro derivatives were also prepared. The highest binding affinities were observed with the 7alpha-methyl-16alpha-haloestradiols, particularly the bromo and chloro derivatives while the 16alpha-iodo derivatives gave somewhat lower values. Both the 11beta-ethoxy and 7alpha-methyl-16alpha-[I-125]iodoestradiols localize in the uteri of immature female rats via a receptor-mediated process. Rapid blood clearance of the I-125-labeled 7alpha-methyl derivative results in lower I-125 uptake by the uterus as well as nontarget organs as compared to the 11beta-substituted estradiol analogs. However, uterus to blood and nontarget ratios are more favorable for the 7alpha-methyl-16alpha-[I-125]iodoestradiol as compared to the analogous 11beta-ethoxy derivatives suggesting that this compound substituted with I-125 may be useful for the in vivo imaging of estrogen receptor-rich breast tumors by single photon emission computerized tomography.

  DOI：

  10.1021/jm00054a011

文献信息

• 7.alpha.-Methyl- and 11.beta.-ethoxy-substitution of iodine-125-labeled [125I]16.alpha.-iodoestradiol: effect on estrogen receptor-mediated target tissue uptake
  作者：Hasrat Ali、Jacques Rousseau、Johan E. Van Lier

  DOI：10.1021/jm00054a011

  日期：1993.1

  The 7alpha-methyl and 11beta-ethoxy derivatives of 16alpha-[I-125]iodoestradiol were prepared via halogen exchange with I-125 of the corresponding 16beta-bromoestradiol precursors. The 16alpha-bromo derivatives were obtained via halogenation of the analogous 17-enol acetate, epimerization to the 16beta-isomer, and hydride reduction. Stereochemical assignments were based on high resolution H-1 NMR. To evaluate the effect of the nature and stereochemistry of the 16-halo substituent on the relative binding affinity for the estrogen receptor, the analogous 16-chloro derivatives were also prepared. The highest binding affinities were observed with the 7alpha-methyl-16alpha-haloestradiols, particularly the bromo and chloro derivatives while the 16alpha-iodo derivatives gave somewhat lower values. Both the 11beta-ethoxy and 7alpha-methyl-16alpha-[I-125]iodoestradiols localize in the uteri of immature female rats via a receptor-mediated process. Rapid blood clearance of the I-125-labeled 7alpha-methyl derivative results in lower I-125 uptake by the uterus as well as nontarget organs as compared to the 11beta-substituted estradiol analogs. However, uterus to blood and nontarget ratios are more favorable for the 7alpha-methyl-16alpha-[I-125]iodoestradiol as compared to the analogous 11beta-ethoxy derivatives suggesting that this compound substituted with I-125 may be useful for the in vivo imaging of estrogen receptor-rich breast tumors by single photon emission computerized tomography.