(17α,20E)-21-<¹²⁵I>iodo-11β-methoxy-19-norpregna-1,3,5(10),20-tetraene-3,17-diol 3-acetate | 91085-43-7

• 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: (17α,20E)-21-<¹²⁵I>iodo-11β-methoxy-19-norpregna-1,3,5(10),20-tetraene-3,17-diol 3-acetate
• CAS: 91085-43-7
• 化学式: C₂₃H₂₉IO₄
• 分子量: 494.481
• InChiKey: OPEWNPMBVUYXJR-HHVUINNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (17α,20E)-21-<¹²⁵I>iodo-11β-methoxy-19-norpregna-1,3,5(10),20-tetraene-3,17-diol 3-acetate 在 sodium acetate 、 sodium carbonate 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 1.0h， 以80%的产率得到17alpha-碘乙烯基-11beta-甲氧基雌甾二醇
  参考文献：
  名称：

  Synthesis and evaluation of (17.alpha.,20E)-21-[125I]iodo-19-norpregna-1,3,5(10),20-tetraene-3,17-diol and (17.alpha.,20E)-21-[125I]iodo-11.beta.-methoxy-19-norpregna-1,3,5(10),20-tetraene-3,17-diol [17.alpha.-iodovinyl)estradiol derivatives] as high specific activity potential radiopharmaceuticals

  摘要：

  Two 17 alpha-[125I]iodovinyl estradiol derivatives 4b,d possessing high specific activity have been prepared and tested as potential radiopharmaceuticals. The use of the 3-acetyl derivatives 2c,e and the replacement of iodine monochloride with sodium iodide and Chloramine-T in THF/phosphate buffer (pH 7.0) permitted us to synthesize no-carrier-added (17 alpha,20E)-21-[125I]iodo-19-norpregna-1,3,5(10),20-tetraene-3,17-d iol (4b) and (17 alpha,20E)-21-[125I]iodo-11 beta-methoxy-19-norpregna-1,3,5(10),20-tetraene-3,17-diol (4d) with 50% radiochemical yield and high purity. Although the specific activity represents only half of the theoretical value in some cases, this modified approach is a substantial improvement over the previously published method. Our preliminary distribution studies indicate that although both 4b and 4d localize in the tissues known to have a large concentration of estrogen receptors, 4d accumulates in higher amounts in target tissues and provides a high target to nontarget ratio.

  DOI：

  10.1021/jm00376a010
• 作为产物：
  描述：

  ((17α,20E)-3-(acetyloxy)-11β-methoxy-17-hydroxy-19-norpregna-1,3,5(10),20-tetraen-21-yl)boronic acid 在 sodium iodide 、 phosphate buffer pH 7 、 chloroamine-T 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以60%的产率得到(17α,20E)-21-<¹²⁵I>iodo-11β-methoxy-19-norpregna-1,3,5(10),20-tetraene-3,17-diol 3-acetate
  参考文献：
  名称：

  Synthesis and evaluation of (17.alpha.,20E)-21-[125I]iodo-19-norpregna-1,3,5(10),20-tetraene-3,17-diol and (17.alpha.,20E)-21-[125I]iodo-11.beta.-methoxy-19-norpregna-1,3,5(10),20-tetraene-3,17-diol [17.alpha.-iodovinyl)estradiol derivatives] as high specific activity potential radiopharmaceuticals

  摘要：

  Two 17 alpha-[125I]iodovinyl estradiol derivatives 4b,d possessing high specific activity have been prepared and tested as potential radiopharmaceuticals. The use of the 3-acetyl derivatives 2c,e and the replacement of iodine monochloride with sodium iodide and Chloramine-T in THF/phosphate buffer (pH 7.0) permitted us to synthesize no-carrier-added (17 alpha,20E)-21-[125I]iodo-19-norpregna-1,3,5(10),20-tetraene-3,17-d iol (4b) and (17 alpha,20E)-21-[125I]iodo-11 beta-methoxy-19-norpregna-1,3,5(10),20-tetraene-3,17-diol (4d) with 50% radiochemical yield and high purity. Although the specific activity represents only half of the theoretical value in some cases, this modified approach is a substantial improvement over the previously published method. Our preliminary distribution studies indicate that although both 4b and 4d localize in the tissues known to have a large concentration of estrogen receptors, 4d accumulates in higher amounts in target tissues and provides a high target to nontarget ratio.

  DOI：

  10.1021/jm00376a010