1-(3,4,5-trimethoxyphenyl)-3-[3-methoxyestra-1,3,5(10)-trien-17β-acetate,2-yl]-2-propen-1-one | 1028058-68-5

• 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: 1-(3,4,5-trimethoxyphenyl)-3-[3-methoxyestra-1,3,5(10)-trien-17β-acetate,2-yl]-2-propen-1-one
• 英文别名: [(8R,9S,13S,14S,17S)-3-methoxy-13-methyl-2-[(E)-3-oxo-3-(3,4,5-trimethoxyphenyl)prop-1-enyl]-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] acetate
• CAS: 1028058-68-5
• 化学式: C₃₃H₄₀O₇
• 分子量: 548.676
• InChiKey: JDHUKMFVOCUTKD-WQNLGFIBSA-N

物化性质

• 熔点：
  133-135 °C
• 沸点：
  678.5±55.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(3,4,5-trimethoxyphenyl)-3-[3-methoxyestra-1,3,5(10)-trien-17β-acetate,2-yl]-2-propen-1-one 在 三氟乙酸 作用下， 反应 4.0h， 以23%的产率得到4,5,6-trimethoxy-3-[3-methoxyestra-1,3,5(10)-trien-17β-acetate,2-yl]indan-1-one
  参考文献：
  名称：

  Synthesis of chalcone derivatives on steroidal framework and their anticancer activities☆

  摘要：

  Chalcone derivatives on estradiol framework have been synthesized. Some of the derivatives showed potent anticancer activity against some human cancer cell lines. Compounds 9 and 19 showed potent activity against MCF-7, a hormone dependent breast cancer cell line. Chalcone 7 was further modified to the corresponding indanone derivative (19) using the Nazarov reaction, which showed better activity than the parent compound against the MCF-7 breast cancer cell line. Active anticancer derivatives were also evaluated for osmotic hemolysis using the erythrocyte as a model system. It was observed that chalcone derivatives showing cytotoxicity against cancer cell lines did not affect the fragility of erythrocytes and hence may be considered as non-toxic to normal cells. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.07.012
• 作为产物：
  描述：

  17-Beta-雌二醇 3-甲醚 在 吡啶 、 氢氧化钾 、 三氯氧磷 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 生成 1-(3,4,5-trimethoxyphenyl)-3-[3-methoxyestra-1,3,5(10)-trien-17β-acetate,2-yl]-2-propen-1-one
  参考文献：
  名称：

  Synthesis of chalcone derivatives on steroidal framework and their anticancer activities☆

  摘要：

  Chalcone derivatives on estradiol framework have been synthesized. Some of the derivatives showed potent anticancer activity against some human cancer cell lines. Compounds 9 and 19 showed potent activity against MCF-7, a hormone dependent breast cancer cell line. Chalcone 7 was further modified to the corresponding indanone derivative (19) using the Nazarov reaction, which showed better activity than the parent compound against the MCF-7 breast cancer cell line. Active anticancer derivatives were also evaluated for osmotic hemolysis using the erythrocyte as a model system. It was observed that chalcone derivatives showing cytotoxicity against cancer cell lines did not affect the fragility of erythrocytes and hence may be considered as non-toxic to normal cells. (c) 2007 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2007.07.012

文献信息

• Synthesis of chalcone derivatives on steroidal framework and their anticancer activities☆
  作者：H SAXENA、U FARIDI、J KUMAR、S LUQMAN、M DAROKAR、K SHANKER、C CHANOTIYA、M GUPTA、A NEGI

  DOI：10.1016/j.steroids.2007.07.012

  日期：2007.11

  Chalcone derivatives on estradiol framework have been synthesized. Some of the derivatives showed potent anticancer activity against some human cancer cell lines. Compounds 9 and 19 showed potent activity against MCF-7, a hormone dependent breast cancer cell line. Chalcone 7 was further modified to the corresponding indanone derivative (19) using the Nazarov reaction, which showed better activity than the parent compound against the MCF-7 breast cancer cell line. Active anticancer derivatives were also evaluated for osmotic hemolysis using the erythrocyte as a model system. It was observed that chalcone derivatives showing cytotoxicity against cancer cell lines did not affect the fragility of erythrocytes and hence may be considered as non-toxic to normal cells. (c) 2007 Elsevier Inc. All rights reserved.