2-Ethoxy-3-Benzyloxy-17β-Benzylaminoestra-1,3,5(10)-Triene | 192062-26-3

• 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-Ethoxy-3-Benzyloxy-17β-Benzylaminoestra-1,3,5(10)-Triene
• 英文别名: 2-ethoxy-3-(benzyloxy)-17β-(benzylamino)estra-1,3,5(10)-triene；2-Ethoxy-3-Benzyloxy-17beta-Benzylaminoestra-1,3,5(10)-Triene；(8R,9S,13S,14S,17S)-N-benzyl-2-ethoxy-13-methyl-3-phenylmethoxy-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-amine
• CAS: 192062-26-3
• 化学式: C₃₄H₄₁NO₂
• 分子量: 495.705
• InChiKey: QBYXYJZKEYIADY-XCYRHCRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Ethoxy-3-Benzyloxy-17β-Benzylaminoestra-1,3,5(10)-Triene 在 palladium dihydroxide 氢气 作用下， 以 四氢呋喃 为溶剂， 23.0 ℃ 、344.73 kPa 条件下， 反应 27.0h， 生成 2-ethoxy-3-hydroxy-17β-aminoestra-1,3,5(10)-triene
  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
• 作为产物：
  描述：

  3-benzyloxy-2-ethoxy-estra-1,3,5(10)-triene-17β-ol 在 manganese(IV) oxide 、 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 122.0h， 生成 2-Ethoxy-3-Benzyloxy-17β-Benzylaminoestra-1,3,5(10)-Triene
  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

• 2-alkoxy estradiols and derivatives thereof
  申请人：The United States of America as represented by the Department of Health

  公开号：US06136992A1

  公开（公告）日：2000-10-24

  Compounds represented by the following structural formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are as defined in the specification. The compounds are disclosed as useful in the treatment of various forms of cancer.

  以下结构式所代表的化合物：##STR1## 其中R.sub.1，R.sub.2和R.sub.3如规范中所定义。这些化合物被披露为治疗各种癌症形式有用的化合物。
• US6136992A
  申请人：——

  公开号：US6136992A

  公开（公告）日：2000-10-24
• Synthesis of Analogs of 2-Methoxyestradiol with Enhanced Inhibitory Effects on Tubulin Polymerization and Cancer Cell Growth
  作者：Mark Cushman、Hu-Ming He、John A. Katzenellenbogen、Ravi K. Varma、Ernest Hamel、Chii M. Lin、Siya Ram、Yesh P. Sachdeva

  DOI：10.1021/jm9700833

  日期：1997.7.1

  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.