3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-19-nor-17α-pregn-9-ene-21-carbonitrile | 216372-24-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-19-nor-17α-pregn-9-ene-21-carbonitrile
• CAS: 216372-24-6
• 化学式: C₃₁H₄₂N₂O₄
• 分子量: 506.685
• InChiKey: BABVZZGSSKBXDY-NJPSTFMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  37.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  85.95
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-19-nor-17α-pregn-9-ene-21-carbonitrile 在 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以67.6%的产率得到3-[(8S,11R,13S,14S,17R)-11-[4-(dimethylamino)phenyl]-17-hydroxy-13-methyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]propanenitrile
  参考文献：
  名称：

  New 11β-aryl-substituted steroids exhibit both progestational and antiprogestational activity

  摘要：

  The syntheses of three 11 beta-aryl-19-norpregna-4,9-dien-3-one derivatives with 17-spirolactone and 17 beta-hydroxy-17 alpha-cyanoethyl substitutions are described. The progesterone agonist/antagonist activities of the new compounds are investigated using a recently developed tissue culture system,that relies on the progesterone agonist up-regulation of the prostate-specific antigen (PSA) gene in female breast tumor cell lines. Two of the newly synthesized compounds exhibit mixed agonistic/antagonistic progestational activity. (Steroids 63:523-530, 1998) (C) 1998 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(98)00060-9
• 作为产物：
  描述：

  (5alpha,10alpha)-5,10-环氧-雌甾-9(11)-烯-3,17-二酮环3-(1,2-乙二基缩醛) 在 sodium hydride 、 二甲基亚砜 、 lithium diisopropylamide mono(tetrahydrofuran) 、 copper(l) chloride 作用下， 反应 13.58h， 生成 3,3-ethylenedioxy-5α,17β-dihydroxy-11β-[4-(N,N-dimethylamino)phenyl]-19-nor-17α-pregn-9-ene-21-carbonitrile
  参考文献：
  名称：

  New 11β-aryl-substituted steroids exhibit both progestational and antiprogestational activity

  摘要：

  The syntheses of three 11 beta-aryl-19-norpregna-4,9-dien-3-one derivatives with 17-spirolactone and 17 beta-hydroxy-17 alpha-cyanoethyl substitutions are described. The progesterone agonist/antagonist activities of the new compounds are investigated using a recently developed tissue culture system,that relies on the progesterone agonist up-regulation of the prostate-specific antigen (PSA) gene in female breast tumor cell lines. Two of the newly synthesized compounds exhibit mixed agonistic/antagonistic progestational activity. (Steroids 63:523-530, 1998) (C) 1998 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(98)00060-9