2-(1'-propynyl)estradiol | 192062-02-5

• 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-(1'-propynyl)estradiol
• 英文别名: 2-(1'-Propynyl) estradiol；(8R,9S,13S,14S,17S)-13-methyl-2-prop-1-ynyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
• CAS: 192062-02-5
• 化学式: C₂₁H₂₆O₂
• 分子量: 310.436
• InChiKey: VFBWVXKSUXUBTB-OKSLILNBSA-N

物化性质

• 沸点：
  474.5±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1'-propynyl)estradiol 在 环己酮 、 aluminum isopropoxide 作用下， 以 甲苯 为溶剂， 生成
  参考文献：
  名称：

  Antiangiogenic agents

  摘要：

  通过向哺乳动物疾病或状况中施用上述公式化合物的有效量来治疗其特征为不良血管生成的组合物和治疗方法： 其中 R a 从—OCH 3 ，—OCH 2 CH 3 或—CCCH 3 中选择；Z从>C(H)—OH，>C(H)—O-烷基，>C(H)—O-磺酸酯中选择，其中烷基是由1至10个碳组成的线性、支链和/或环烃链。

  公开号：

  US20050203075A1
• 作为产物：
  描述：

  3,17-bis-O-(tert-butyldimethylsilyl)-2-iodo-estradiol 在 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 65.5h， 生成 2-(1'-propynyl)estradiol
  参考文献：
  名称：

  Synthesis of Analogs of 2-Methoxyestradiol with Enhanced Inhibitory Effects on Tubulin Polymerization and Cancer Cell Growth

  摘要：

  A new series of estradiol analogs was synthesized in an attempt to improve on the anticancer activity of 2-methoxyestradiol, a naturally occurring mammalian tubulin polymerization inhibitor. The compounds were evaluated as inhibitors of tubulin polymerization and the binding of [H-3]colchicine to tubulin, as well as for in vitro cytotoxicity in human cancer cell cultures. Overall, the most potent of the new compounds were 2-(2',2',2'-trifluoroethoxy)-6-oximinoestradiol, 2-ethoxy-6-oximinoestradiol, and 2-ethoxy-6-methoximinoestradiol. These agents lacked significant affinity for the estrogen receptor. The cytotoxicities of the compounds correlated in general with their abilities to inhibit tubulin polymerization, thus supporting inhibition of tubulin polymerization as the primary mechanism causing inhibition of cell growth.

  DOI：

  10.1021/jm9700833

文献信息

• The Effect of Exchanging Various Substituents at the 2-Position of 2-Methoxyestradiol on Cytotoxicity in Human Cancer Cell Cultures and Inhibition of Tubulin Polymerization
  作者：Mark Cushman、Arasambattu K. Mohanakrishnan、Melinda Hollingshead、Ernest Hamel

  DOI：10.1021/jm020218r

  日期：2002.10.1

  A new set of estradiol derivatives bearing various substituents at the 2-position were synthesized in order to further elucidate the structural parameters associated with the antitubulin activity and cytotoxicity of 2-substituted estradiols. The potencies of the new compounds as inhibitors of tubulin polymerization were determined, and the cytotoxicities of the analogues in human cancer cell cultures were investigated. The substituents introduced into the 2-position of estradiol included E-3'-hydroxy-1'-propenyl, 2'-hydroxyethoxy, 3-N,N-dimethylaminoethylideneamino, 2'-hydroxyethylineneamino, (beta-3,4,5-trimethoxyphenyl)ethenyl, phenylethynyl, ethynly, 1'-propynyl, and cyano. The substituents conferring the ability to inhibit tubulin polymerization included E-3'-hydroxy-1'-propenyl, 2'-hydroxyethoxy, ethynyl, and 1'-propynyl. The remaining compounds were all inactive as inhibitors of tubulin polymerization when tested at concentrations of up to 40 muM. All of the compounds were cytotoxic in a panel of 55 human cancer cell cultures, and in general, the most cytotoxic compounds were also the most potent as inhibitors of tubulin polymerization. 2-(1'-Propynyl)estradiol displayed significant anticancer activity in the in vivo hollow fiber animal model.
• EP1773349A4
  申请人：——

  公开号：EP1773349A4

  公开（公告）日：2009-07-29
• METHODS AND COMPOSITIONS FOR TREATMENT OF PREECLAMPSIA
  申请人：CHILDREN'S MEDICAL CENTER CORPORATION

  公开号：EP1773349A2

  公开（公告）日：2007-04-18
• METHODS FOR TREATING AND DIAGNOSING COMPLICATIONS OF PREMATURE BIRTH
  申请人：CHILDREN'S MEDICAL CENTER CORPORATION

  公开号：EP1906969A2

  公开（公告）日：2008-04-09
• EP1906969A4
  申请人：——

  公开号：EP1906969A4

  公开（公告）日：2009-07-29