2-Pentylestradiol

• 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: 2-Pentylestradiol
• 英文别名: (8R,9S,13S,14S,17S)-13-methyl-2-pentyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol；2-n-Pentyl estradiol；(8R,9S,13S,14S,17S)-13-methyl-2-pentyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
• 化学式: C₂₃H₃₄O₂
• 分子量: 342.522
• InChiKey: QGIBTURYXYIAOG-PAHONEIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 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：

  2-formylestradiol 在 palladium on activated charcoal 氢气 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 25.0 ℃ 、206.84 kPa 条件下， 反应 4.17h， 生成 2-Pentylestradiol
  参考文献：
  名称：

  Synthesis, Antitubulin and Antimitotic Activity, and Cytotoxicity of Analogs of 2-Methoxyestradiol, an Endogenous Mammalian Metabolite of Estradiol That Inhibits Tubulin Polymerization by Binding to the Colchicine Binding Site

  摘要：

  In order to define the structural parameters associated with the antitubulin activity and cytotoxicity of 8-methoxyestradiol, a mammalian metabolite of estradiol, an array of analogs was synthesized and evaluated. The potencies of the new congeners as inhibitors of tubulin polymerization and colchicine binding were determined using tubulin purified from bovine brain, and the cytotoxicities of the new compounds were studied in a variety of cancer cell cultures. Maximum antitubulin activity was observed in estradiols having unbranched chain substituents at the 2-position with three non-hydrogen atoms. 2-Ethoxyestradiol and 2-((E)-1-propenyl)-estradiol were substantially more potent than 2-methoxyestradiol itself. The tubulin polymerization inhibitors in this series displayed significantly higher cytotoxicities in the MDA-MB-435 breast cancer cell line than in the other cell lines studied. The potencies of the analogs as cytotoxic and antimitotic agents in cancer cell cultures correlated with their potencies as inhibitors;of tubulin polymerization, supporting the hypothesis that inhibition of tubulin polymerization is the mechanism of the cytotoxic action of 2-methoxyestradiol and its congeners. Several of the more potent analogs were tested in an estrogen receptor binding assay, and their affinities relative to estradiol were found to be very low.

  DOI：

  10.1021/jm00012a003

文献信息

• Regioselective monoalkylation of 17β-estradiol for the synthesis of cytotoxic estrogens
  作者：Koen Van Gansbeke、Eirik Johansson Solum、Sandra Liekens、Anders Vik、Trond Vidar Hansen

  DOI：10.1016/j.steroids.2017.06.001

  日期：2017.8

  synthesis of estrogens achieved.A convenient one‐pot protocol was used that tolerates air and moist.Analogs of the steroid metabolite 2‐methoxyestradiol were prepared as potential new anti‐cancer agents.Some analogs showed anti‐proliferative effects in the low micromolar range observed in the CEM and HeLa cell lines. ABSTRACT The regioselective synthesis of estrogens and their derivatives continues to

  图形抽象图。没有可用的字幕。亮点实现雌激素的区域选择性合成。使用方便的单锅方案，耐受空气和潮湿。制备类固醇代谢物 2-甲氧基雌二醇的类似物作为潜在的新型抗癌剂。一些类似物在低微摩尔范围内显示出抗增殖作用在 CEM 和 HeLa 细胞系中观察到。摘要 雌激素及其衍生物的区域选择性合成一直受到关注。大多数报道的合成需要多步协议，但总体收率低且缺乏区域选择性。仍然需要新的制备方案。在此，以高度区域选择性的方式合成了 11 个 2-烷基化 17°-雌二醇类似物。这些产品是使用方便的、一锅和高产的方案获得的。
• Synthesis, Antitubulin and Antimitotic Activity, and Cytotoxicity of Analogs of 2-Methoxyestradiol, an Endogenous Mammalian Metabolite of Estradiol That Inhibits Tubulin Polymerization by Binding to the Colchicine Binding Site
  作者：Mark Cushman、Hu-Ming He、John A. Katzenellenbogen、Chii M. Lin、Ernest Hamel

  DOI：10.1021/jm00012a003

  日期：1995.6

  In order to define the structural parameters associated with the antitubulin activity and cytotoxicity of 8-methoxyestradiol, a mammalian metabolite of estradiol, an array of analogs was synthesized and evaluated. The potencies of the new congeners as inhibitors of tubulin polymerization and colchicine binding were determined using tubulin purified from bovine brain, and the cytotoxicities of the new compounds were studied in a variety of cancer cell cultures. Maximum antitubulin activity was observed in estradiols having unbranched chain substituents at the 2-position with three non-hydrogen atoms. 2-Ethoxyestradiol and 2-((E)-1-propenyl)-estradiol were substantially more potent than 2-methoxyestradiol itself. The tubulin polymerization inhibitors in this series displayed significantly higher cytotoxicities in the MDA-MB-435 breast cancer cell line than in the other cell lines studied. The potencies of the analogs as cytotoxic and antimitotic agents in cancer cell cultures correlated with their potencies as inhibitors;of tubulin polymerization, supporting the hypothesis that inhibition of tubulin polymerization is the mechanism of the cytotoxic action of 2-methoxyestradiol and its congeners. Several of the more potent analogs were tested in an estrogen receptor binding assay, and their affinities relative to estradiol were found to be very low.