3-benzyloxy-16β-bromomethyl-17-oxa-D-homoestra-1,3,5(10)-triene | 1620902-22-8

• 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-16β-bromomethyl-17-oxa-D-homoestra-1,3,5(10)-triene
• CAS: 1620902-22-8
• 化学式: C₂₆H₃₁BrO₂
• 分子量: 455.435
• InChiKey: GNIPQZCAXBOZET-KPJVPSPYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.51
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  16,17-seco-3-benzyloxy-13β-estra-1,3,5(10),16-tetraen-1-al 在 N-溴代丁二酰亚胺(NBS) 、 钾硼氢 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-benzyloxy-16β-bromomethyl-17-oxa-D-homoestra-1,3,5(10)-triene
  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