17aα-hydroxy-3-methoxy-13α-D-homoestra-1,3,5(10)-trien-16α-yl-p-toluenesulfonate | 544693-39-2

• 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: 17aα-hydroxy-3-methoxy-13α-D-homoestra-1,3,5(10)-trien-16α-yl-p-toluenesulfonate
• CAS: 544693-39-2
• 化学式: C₂₇H₃₄O₅S
• 分子量: 470.63
• InChiKey: LHVHVODBNYDHAJ-BDDGOPHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.99
• 重原子数：
  33.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  17aα-hydroxy-3-methoxy-13α-D-homoestra-1,3,5(10)-trien-16α-yl-p-toluenesulfonate 在 palladium on activated charcoal jones reagent 、 氢气 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 20.0 ℃ 、2.0 MPa 条件下， 反应 25.0h， 生成 3-methoxy-13α-D-homoestra-1,3,5(10)-trien-17a-one
  参考文献：
  名称：

  Synthesis and receptor-binding examinations of the normal and 13-epi-D-homoestrones and their 3-methyl ethers

  摘要：

  An effective epimerization of the normal estrone 3-methyl and 3-benzyl ethers by using o-phenylenediamine and AcOH made the possibility for facile entry into the 13alpha-estrone series. Combination of this synthetic methodology with an isolation step carried out by means of the Girard-P reagent, the corresponding ethers of 13-epi-estrone were obtained in excellent yields. The 3-hydroxy and 3-methoxy D-homoestrone derivatives in both the normal and the 13alpha-estrone series were then synthesized and tested in vitro in a radioligand-binding assay. The estrogen receptor recognizes these compounds, but their relative binding affinities (RBAs) are lower than that of the reference compound 3,17beta-estradiol. The progesterone receptor-binding affinities of the four D-homo derivatives were also tested showing low values for 13alpha-D-homoestrone and its 3-methyl ether. Pharmacologically, these 13alpha-D-homoestrone derivatives are estrogen receptor-selective molecules. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(02)00181-2
• 作为产物：
  描述：

  对甲苯磺酸 、 3-methoxy-16,17-seco-13α-estra-1,3,5(10),16-tetraen-17-al 以 二氯甲烷 为溶剂， 反应 24.0h， 以89%的产率得到17aα-hydroxy-3-methoxy-13α-D-homoestra-1,3,5(10)-trien-16α-yl-p-toluenesulfonate
  参考文献：
  名称：

  Synthesis and receptor-binding examinations of the normal and 13-epi-D-homoestrones and their 3-methyl ethers

  摘要：

  An effective epimerization of the normal estrone 3-methyl and 3-benzyl ethers by using o-phenylenediamine and AcOH made the possibility for facile entry into the 13alpha-estrone series. Combination of this synthetic methodology with an isolation step carried out by means of the Girard-P reagent, the corresponding ethers of 13-epi-estrone were obtained in excellent yields. The 3-hydroxy and 3-methoxy D-homoestrone derivatives in both the normal and the 13alpha-estrone series were then synthesized and tested in vitro in a radioligand-binding assay. The estrogen receptor recognizes these compounds, but their relative binding affinities (RBAs) are lower than that of the reference compound 3,17beta-estradiol. The progesterone receptor-binding affinities of the four D-homo derivatives were also tested showing low values for 13alpha-D-homoestrone and its 3-methyl ether. Pharmacologically, these 13alpha-D-homoestrone derivatives are estrogen receptor-selective molecules. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(02)00181-2