17β-hydroxy-3-benzyloxy-13α-estra-1,3,5(10)-trien-16α-ylmethyl acetate | 544693-46-1

• 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: 17β-hydroxy-3-benzyloxy-13α-estra-1,3,5(10)-trien-16α-ylmethyl acetate
• 英文别名: 3-benzyloxy-16α-acetoxymethyl-13α-estra-1,3,5(10)-trien-17β-ol
• CAS: 544693-46-1
• 化学式: C₂₈H₃₄O₄
• 分子量: 434.576
• InChiKey: DHZIMTLLTHXNCD-RJWVBVEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 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：

  17β-hydroxy-3-benzyloxy-13α-estra-1,3,5(10)-trien-16α-ylmethyl acetate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以5.4 g的产率得到3-benzyloxy-16α-hydroxymethyl-13α-estra-1,3,5(10)-trien-17β-ol
  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：

  3-benzyloxy-13α-estra-1,3,5(10)-trien-17-one 在 钾硼氢 、 sodium methylate 作用下， 以 甲醇 、 苯 为溶剂， 反应 59.0h， 生成 17β-hydroxy-3-benzyloxy-13α-estra-1,3,5(10)-trien-16α-ylmethyl acetate
  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

文献信息

• Stereoselective synthesis of the four 16-hydroxymethyl-3-methoxy- and 16-hydroxymethyl-3-benzyloxy-13 α -estra-1,3,5(10)-trien-17-ol isomers and their antiproliferative activities
  作者：Anita Kiss、Erzsébet Mernyák、János Wölfling、Izabella Sinka、István Zupkó、Gyula Schneider

  DOI：10.1016/j.steroids.2018.02.008

  日期：2018.6

  yielded a mixture of two diastereomeric diols, the 16α-hydroxymethyl,17β-hydroxy and 16β-hydroxymethyl,17α-hydroxy isomers (17a-20a) in a ratio of 6:1. We describe a straightforward synthetic route to transform the isomers with trans functional groups attached to ring D (17a-20a) into isomers with cis functional groups (25a-28a). We determined the in vitro antiproliferative activities of compounds 17a-20a

  16-羟基亚甲基-3-甲氧基-13α-estra-1,3,5（10）-trien-17-one（14）和16-羟基亚甲基-3-苄氧基-13α-estra-1,3,5的还原（10）-三烯-17-（16）以6∶1的比例产生两种非对映体二醇的混合物，即16α-羟甲基，17β-羟基和16β-羟甲基，17α-羟基异构体（17a-20a）。我们描述了一种简单的合成路线，以将具有与环D（17a-20a）连接的反式官能团的异构体转变为具有顺式官能团（25a-28a）的异构体。我们通过MTT测定法针对一组人类贴壁癌细胞系HeLa，A2780，MCF-7，T47D，MDA-MB-231和MDA-MB-测定了化合物17a-20a和25a-28a的体外抗增殖活性361。