3-benzyloxy-14β-(prop-2-en-yl)-des-D-estra-1,3,5(10)-trien-13α-carboxylic acid | 1620902-20-6

• 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: 3-benzyloxy-14β-(prop-2-en-yl)-des-D-estra-1,3,5(10)-trien-13α-carboxylic acid
• CAS: 1620902-20-6
• 化学式: C₂₆H₃₀O₃
• 分子量: 390.522
• InChiKey: HCBIAWPZNHAITH-BIATYSSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.99
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-benzyloxy-14β-(prop-2-en-yl)-des-D-estra-1,3,5(10)-trien-13α-carboxylic acid 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以82%的产率得到3-benzyloxy-16β-bromomethyl-17-oxa-D-homoestra-1,3,5(10)-trien-17a-one
  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
• 作为产物：
  描述：

  16,17-seco-3-benzyloxy-13β-estra-1,3,5(10),16-tetraen-1-al 在 Jones reagent 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以37%的产率得到3-benzyloxy-14β-(prop-2-en-yl)-des-D-estra-1,3,5(10)-trien-13α,9α-carbolactone
  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