D-homoestradiol-17aβ | 6714-05-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: D-homoestradiol-17aβ
• 英文别名: 3,17aβ-dihydroxy-D-homoestra-1,3,5(10)-triene；D-Homooestradiol-3,17aβ；D-Homoestradiol；D-Homooestradiol；(4bS)-2.7t-Dihydroxy-6at-methyl-(4brH.10acH.10btH)-4b.5.6.6a.7.8.9.10.10a.10b.11.12-dodecahydro-chrysen；D-Homo-oestratrien-(1.3.5(10))-diol-(3.17aβ)；D-Homo-oestratrien-(A)-diol-(3.17aβ)；D-homo-estratriene-(A)-diol-(3.17aβ)；(1S,4aS,4bR,10bS,12aS)-12a-methyl-2,3,4,4a,4b,5,6,10b,11,12-decahydro-1H-chrysene-1,8-diol
• CAS: 6714-05-2
• 化学式: C₁₉H₂₆O₂
• 分子量: 286.414
• InChiKey: JJKPSTJJBVJKKQ-GFEQUFNTSA-N

物化性质

• 沸点：
  458.9±45.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 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

• 作为产物：
  描述：

  3-hydroxy-13β-D-homoestra-1,3,5(10)-trien-17a-one 在 钾硼氢 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以85%的产率得到D-homoestradiol-17aβ
  参考文献：
  名称：

  Syntheses and antiproliferative effects of d-homo- and d-secoestrones

  摘要：

  Substituted and/or heterocyclic d-homoestrone derivatives were synthetized via the intramolecular cyclization of a δ-alkenyl-d-secoaldehyde, -d-secoalcohol or -d-secocarboxylic acid of estrone 3-benzyl ether. The d-secoalcohol was modified at three sites in the molecule. The in vitro antiproliferative activities of the new d-homo- and d-secoestrone derivatives were determined on HeLa, MCF-7, A431 and A2780 cells through use of MTT assay. d-Homoalcohols 3 and 5 displayed cell line-selective cytostatic effects against ovarian and cervical cell lines, respectively. Two d-secoestrones (6 and 12c) proved to be effective, with IC50 values comparable with those of the reference agent cisplatin. A selected compound (6) was tested by tubulin polymerization assay and its cancer specificity was additionally determined by using noncancerous human fibroblast cells.

  DOI：

  10.1016/j.steroids.2014.05.015

文献信息

• Goldberg; Studer, <1941>295,300
  作者：Goldberg、Studer

  DOI：——

  日期：——