3-benzyloxy-17aβ-hydroxy-D-homoestra-1,3,5(10),16-tetraene | 1620902-19-3

• 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: 3-benzyloxy-17aβ-hydroxy-D-homoestra-1,3,5(10),16-tetraene
• 英文别名: (1S,4aS,4bR,10bS,12aS)-12a-methyl-8-phenylmethoxy-4,4a,4b,5,6,10b,11,12-octahydro-1H-chrysen-1-ol
• CAS: 1620902-19-3
• 化学式: C₂₆H₃₀O₂
• 分子量: 374.523
• InChiKey: VWCXKEAWJZPXGD-JMTTVTNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-benzyloxy-13β-D-homoestra-1,3,5(10),16-tetraen-17a-one 在 钾硼氢 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以95%的产率得到3-benzyloxy-17aβ-hydroxy-D-homoestra-1,3,5(10),16-tetraene
  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

• Syntheses and antiproliferative effects of d-homo- and d-secoestrones
  作者：Erzsébet Mernyák、Johanna Szabó、Ildikó Bacsa、Judit Huber、Gyula Schneider、Renáta Minorics、Noémi Bózsity、István Zupkó、Mónika Varga、Zsolt Bikádi、Eszter Hazai、János Wölfling

  DOI：10.1016/j.steroids.2014.05.015

  日期：2014.9

  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.